Compounds > 2-(1-hexyloxyethyl)-2-devinyl pyropheophorbide-a
Page last updated: 2024-12-08

2-(1-hexyloxyethyl)-2-devinyl pyropheophorbide-a

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Description

2-(1-hexyloxyethyl)-2-devinyl pyropheophorbide-a, often shortened to **HPPH**, is a synthetic derivative of chlorophyll. It's a complex molecule with a fascinating structure and a significant role in several research areas.

Here's a breakdown:

**What it is:**

* **Pyropheophorbide-a:** This is the core structure of the molecule, a porphyrin ring system similar to heme in hemoglobin but with a different side chain.
* **Devinyl:** This indicates that a vinyl group (CH=CH2) has been removed from the molecule.
* **2-(1-hexyloxyethyl):** This describes a specific modification at the 2-position of the pyropheophorbide-a molecule. A hexyloxyethyl group (CH3(CH2)5CH(CH3)O-) is attached to the 2-position, which changes the molecule's properties.

**Why it's important for research:**

HPPH is a highly valuable tool in various fields, primarily due to its unique photophysical properties:

1. **Photodynamic Therapy (PDT):**
* **Strong absorption in the red region:** HPPH absorbs strongly in the near-infrared (NIR) region of the electromagnetic spectrum. This is crucial for PDT because tissues are more transparent to NIR light, allowing deeper penetration and better treatment efficacy.
* **Singlet oxygen generation:** When HPPH absorbs light, it becomes excited and produces singlet oxygen, a highly reactive species that can damage cancer cells and kill them.
* **Clinical trials:** HPPH is currently in clinical trials for various cancer types, demonstrating its promising potential as a cancer therapy.

2. **Bioimaging:**
* **Fluorescence:** HPPH exhibits strong fluorescence, making it a useful probe for fluorescence imaging techniques.
* **Targeted imaging:** HPPH can be conjugated with specific antibodies or targeting molecules, enabling the visualization and monitoring of specific cellular processes and disease targets.

3. **Photosensitization:**
* **Light-activated reactions:** HPPH can be used to initiate a variety of light-activated reactions, such as polymerization and crosslinking.
* **Novel materials:** This property is exploited in the development of new materials with unique properties, such as photosensitive polymers and photoresponsive surfaces.

**Overall, 2-(1-hexyloxyethyl)-2-devinyl pyropheophorbide-a (HPPH) is a versatile molecule with diverse applications in medicine, imaging, and materials science. Its unique photophysical properties make it a valuable tool for researchers working on developing new treatments, diagnostics, and technologies.**

2-(1-hexyloxyethyl)-2-devinyl pyropheophorbide-a: a photodynamic sensitizer; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID148160
CHEMBL ID500853
CHEMBL ID5170755
SCHEMBL ID12722713
SCHEMBL ID20834922
MeSH IDM0223314

Synonyms (27)

Synonym
2-(1-hexyloxyethyl)-2-devinyl pyropheophorbide-a
149402-51-7
hpph
CHEMBL500853
unii-dob7y3rsx0
dob7y3rsx0 ,
3-phorbinepropanoic acid, 14-ethyl-9-(1-(hexyloxy)ethyl)-4,8,13,18-tetramethyl-20-oxo-
14-ethyl-9-(1-(hexyloxy)ethyl)-4,8,13,18-tetramethyl-20-oxo-3-phorbinepropanoic acid
3-phorbinepropanoic acid, 14-ethyl-9-[1-(hexyloxy)ethyl]-4,8,13,18-tetramethyl-20-oxo-, (3s,4s)-
SCHEMBL12722713
CHEMBL5170755
HY-13722
CS-0007752
2-(1-hexyloxyethyl)-2-devinylpyropheophorbide-a
2-(1-hexyloxyethyl)-2-devinylpyropheophorbide a
3-phorbinepropanoic acid, 14-ethyl-9-(1-(hexyloxy)ethyl)-4,8,13,18-tetramethyl-20-oxo-, (3s,4s)-
Q4596815
3-[(21s,22s)-11-ethyl-16-(1-hexoxyethyl)-4-hydroxy-12,17,21,26-tetramethyl-7,23,24,25-tetrazahexacyclo[18.2.1.15,8.110,13.115,18.02,6]hexacosa-1,4,6,8(26),9,11,13(25),14,16,18(24),19-undecaen-22-yl]propanoic acid
EX-A2655
DB15243
SCHEMBL20834922
photochlorphotochlor
AC-35598
ZFA40251
DTXSID501028872
PD121997
AKOS040741843

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" The objective of this study was to determine the pharmacokinetic parameters of this drug prior to institution of a clinical trial in canine patients with various cancers."( Pharmacokinetics of pyropheophorbide-a-hexyl ether in the dog.
Casteel, SW; Frazier, D; McCaw, DL; Payne, JT; Rogers, K; Tompson, RV, 1996)		0.29
" Pharmacokinetic parameters were calculated for each dog."( Pharmacokinetics of pyropheophorbide-a-hexyl ether in the dog.
Casteel, SW; Frazier, D; McCaw, DL; Payne, JT; Rogers, K; Tompson, RV, 1996)		0.29
" The mean half-life was calculated to be 26."( Pharmacokinetics of pyropheophorbide-a-hexyl ether in the dog.
Casteel, SW; Frazier, D; McCaw, DL; Payne, JT; Rogers, K; Tompson, RV, 1996)		0.29
" Upon collecting time-dependent fluorescence images at the tissue surface overlying both normal and diseased tissue volumes, and fitting these images to a pharmacokinetic model describing the uptake (wash-in) and release (wash-out) of fluorescent dye, the pharmacokinetics of fluorescent dye was spatially determined."( Pharmacokinetics of ICG and HPPH-car for the detection of normal and tumor tissue using fluorescence, near-infrared reflectance imaging: a case study.
Gurfinkel, M; Gust, JD; Hawrysz, DJ; Mayer, RH; Moore, AL; Moore, TA; Muggenburg, B; Nikula, K; Pandey, R; Ralston, W; Reynolds, JS; Sevick-Muraca, EM; Tatman, D; Thompson, AB; Troy, TL, 2000)		0.31
" The pharmacokinetic data for each patient were fitted with a standard two-compartment (biexponential) model with continuous infusion."( Population pharmacokinetics of the photodynamic therapy agent 2-[1-hexyloxyethyl]-2-devinyl pyropheophorbide-a in cancer patients.
Bellnier, DA; Dougherty, TJ; Greco, WR; Loewen, GM; Nava, H; Oseroff, AR; Pandey, RK; Tsuchida, T, 2003)		0.32
" Pharmacokinetic (PK) data from these individual studies were pooled and analyzed."( Clinical pharmacokinetics of the PDT photosensitizers porfimer sodium (Photofrin), 2-[1-hexyloxyethyl]-2-devinyl pyropheophorbide-a (Photochlor) and 5-ALA-induced protoporphyrin IX.
Bellnier, DA; Dougherty, TJ; Greco, WR; Loewen, GM; Nava, H; Oseroff, AR, 2006)		0.33
" The method was applied for carrying out pharmacokinetic study of HPPH."( Pre-clinical compartmental pharmacokinetic modeling of 2-[1-hexyloxyethyl]-2-devinyl pyropheophorbide-a (HPPH) as a photosensitizer in rat plasma by validated HPLC method.
Dubey, SK; Krishna, KV; Puri, A; Saha, RN; Shapiro, BA; Viard, M, 2019)		0.51

Bioavailability

ExcerptReferenceRelevance
"Drug bioavailability is a key consideration for drug delivery systems."( Porphyrin-phospholipid liposomes with tunable leakiness.
Carter, KA; Geng, J; Lin, C; Lovell, JF; Luo, D; Ortega, J; Razi, A; Shao, S, 2015)		0.42

Dosage Studied

ExcerptRelevanceReference
" The routine assay for characterizing a specific photosensitizer at a standard dose consists of the sequential allocation of eight mice to a set of different light doses designed to span the dose-response range of fluorescein fluorescence exclusion (measured 8-10 min after fluorescein injection)."( The validation of a new vascular damage assay for photodynamic therapy agents.
Bellnier, DA; Greco, WR; Henderson, BW; Johnson, P; Parsons, JC; Potter, WR; Sitnik, TM; Vaughan, LA; Whitaker, J, 1995)		0.29
"A strategy combining covalent conjugation of photosensitizers to a peptide ligand directed to the melanocortin 1 (MC1) receptor with the application of sequential LED light dosage at near-IR wavelengths was developed to achieve specific cytotoxicity to melanocytes and melanoma (MEL) with minimal collateral damage to surrounding cells such as keratinocytes (KER)."( Specific Targeting of Melanotic Cells with Peptide Ligated Photosensitizers for Photodynamic Therapy.
Bigliardi, PL; Bigliardi-Qi, M; Burkett, BA; Eberle, AN; Krishnan-Kutty, V; Pant, A; Rout, B; Srinivas, R, 2017)		0.46
" The simulated HPPH human serum concentrations yield a satisfactory agreement with observations at multiple dosing levels."( Development and application of a physiologically based pharmacokinetic model for HPPH in rats and extrapolate to humans.
Cao, Q; Chen, L; Tong, H; Wang, X; Wu, Y; Yang, J; Zhang, T; Zhang, X, 2019)		0.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (42)

Assay IDTitleYearJournalArticle
AID1582038Phototoxicity in ICR mouse assessed as change in skin of the backs 0.45 mg/kg, iv in presence of 10 mW/cm2 light irradiation for 10 mins upto 7 days measured after 1 day of light irradiation by H and E staining based microscopic analysis2020European journal of medicinal chemistry, Feb-01, Volume: 187Synthesis and evaluation of novel chlorophyll a derivatives as potent photosensitizers for photodynamic therapy.
AID1582041Phototoxicity in guinea pig assessed as change in back skin weight 4.5 mg/kg, iv followed by 10 mW/cm2 light irradiation for 10 mins measured after 1day of light irradiation (Rvb = 72.4 +/- 3.1 mg)2020European journal of medicinal chemistry, Feb-01, Volume: 187Synthesis and evaluation of novel chlorophyll a derivatives as potent photosensitizers for photodynamic therapy.
AID1582006Emission property of a compound in DMSO assessed as red shift at 5 uM on excitation with light at 410 to 415 nm by 3D fluorescence spectra analysis2020European journal of medicinal chemistry, Feb-01, Volume: 187Synthesis and evaluation of novel chlorophyll a derivatives as potent photosensitizers for photodynamic therapy.
AID1730105Photodynamic antitumor activity against human FaDu cels xenografted in SCID mouse assessed as cure rate at 0.47 micromol/kg, iv pretreated with compound followed by light irradiation at a dose of 135 J/cm2 and 75 mW/cm2 and measured at 24 hrs post dose re2021Journal of medicinal chemistry, 01-14, Volume: 64, Issue:1
Synthesis, Tumor Specificity, and Photosensitizing Efficacy of Erlotinib-Conjugated Chlorins and Bacteriochlorins: Identification of a Highly Effective Candidate for Photodynamic Therapy of Cancer.
AID1582000Phototoxicity in ICR mouse assessed as ear weight at 0.45 mg/kg, iv followed by 10 mW/cm2 light irradiation for 10 mins at 1 day after drug challenge measured after 1 day of light irradiation (Rvb = 12.6 +/- 1.2 mg)2020European journal of medicinal chemistry, Feb-01, Volume: 187Synthesis and evaluation of novel chlorophyll a derivatives as potent photosensitizers for photodynamic therapy.
AID1582007Induction of ROS generation in DMF solution assessed as slope of the photodegradation rate of DPBF at 2 uM followed by irradiation measured every 10 secs by spectrophotometric analysis2020European journal of medicinal chemistry, Feb-01, Volume: 187Synthesis and evaluation of novel chlorophyll a derivatives as potent photosensitizers for photodynamic therapy.
AID1730076Drug uptake in human HNT1 cells at 3.2 uM incubated for 30 mins in DMEM media with 10% FBS followed by 24 hrs chase period in compound-free medium by inverted fluorescence microscopic analysis2021Journal of medicinal chemistry, 01-14, Volume: 64, Issue:1
Synthesis, Tumor Specificity, and Photosensitizing Efficacy of Erlotinib-Conjugated Chlorins and Bacteriochlorins: Identification of a Highly Effective Candidate for Photodynamic Therapy of Cancer.
AID1582015Phototoxicity against human A549 cells assessed as reduction in cell proliferation irradiated with 1 J/cm2 of 650 nanometer laser light preincubated for 24 hrs measured after 48 hrs by MTT assay2020European journal of medicinal chemistry, Feb-01, Volume: 187Synthesis and evaluation of novel chlorophyll a derivatives as potent photosensitizers for photodynamic therapy.
AID1582029Photodynamic antitumor activity against human A549 cells xenografted in BALB/c nude mouse assessed as survival time at 0.3 mg/kg, iv incubated for 24 hrs followed by laser light irradiation at 120 J/cm2 measured up to 70 days2020European journal of medicinal chemistry, Feb-01, Volume: 187Synthesis and evaluation of novel chlorophyll a derivatives as potent photosensitizers for photodynamic therapy.
AID397022Drug uptake in ABCG2-expressing mouse RIF cells assessed as increase in mitochondrial localization at 3 uM for 24 hrs in presence of 10% FCS by fluorescence microscopy2009Journal of medicinal chemistry, Jul-23, Volume: 52, Issue:14
Conjugation of 2-(1'-hexyloxyethyl)-2-devinylpyropheophorbide-a (HPPH) to carbohydrates changes its subcellular distribution and enhances photodynamic activity in vivo.
AID397026Photosensitizing activity in ABCG2-expressing mouse RIF cells assessed as induction STAT3 covalent cross linking pretreated for 4 hrs followed by irradiation exposure to 665 nm light at 3 J/cm2 by Western blotting2009Journal of medicinal chemistry, Jul-23, Volume: 52, Issue:14
Conjugation of 2-(1'-hexyloxyethyl)-2-devinylpyropheophorbide-a (HPPH) to carbohydrates changes its subcellular distribution and enhances photodynamic activity in vivo.
AID1730108Drug uptake in skin of SCID mouse xenografted with FaDu cells at 0.47 micromol/kg, iv pretreated with compound followed by light irradiation at a dose of 135 J/cm2 and 75 mW/cm2 and measured at 24 hrs by IVIS analysis2021Journal of medicinal chemistry, 01-14, Volume: 64, Issue:1
Synthesis, Tumor Specificity, and Photosensitizing Efficacy of Erlotinib-Conjugated Chlorins and Bacteriochlorins: Identification of a Highly Effective Candidate for Photodynamic Therapy of Cancer.
AID1730104Drug uptake in tumor of SCID mouse xenografted with FaDu cells at 0.47 micromol/kg, iv pretreated with compound followed by light irradiation at a dose of 135 J/cm2 and 75 mW/cm2 and measured at 24 hrs by IVIS analysis2021Journal of medicinal chemistry, 01-14, Volume: 64, Issue:1
Synthesis, Tumor Specificity, and Photosensitizing Efficacy of Erlotinib-Conjugated Chlorins and Bacteriochlorins: Identification of a Highly Effective Candidate for Photodynamic Therapy of Cancer.
AID1582040Phototoxicity in guinea pig assessed as change in right ear weight 4.5 mg/kg, iv followed by 10 mW/cm2 light irradiation for 10 mins measured after 1 day of light irradiation (Rvb = 40.4 +/- 2.4 mg)2020European journal of medicinal chemistry, Feb-01, Volume: 187Synthesis and evaluation of novel chlorophyll a derivatives as potent photosensitizers for photodynamic therapy.
AID1582037Phototoxicity in ICR mouse assessed as change in exposed neck skin 0.45 mg/kg, iv in presence of 10 mW/cm2 light irradiation for 10 mins upto 7 days measured after 1day of light irradiation by H and E staining based microscopic analysis2020European journal of medicinal chemistry, Feb-01, Volume: 187Synthesis and evaluation of novel chlorophyll a derivatives as potent photosensitizers for photodynamic therapy.
AID1581998Phototoxicity in ICR mouse assessed as ear weight at 0.45 mg/kg, iv followed by 10 mW/cm2 light irradiation for 10 mins at 5 days after drug challenge measured after 1 day of light irradiation (Rvb = 12.9 +/- 1.4 mg)2020European journal of medicinal chemistry, Feb-01, Volume: 187Synthesis and evaluation of novel chlorophyll a derivatives as potent photosensitizers for photodynamic therapy.
AID1581995Therapeutic index, ratio of TC50 for human A549 cells under dark to IC50 for human A549 cells irradiated with 1 J/cm2 of 650 nanometer laser light2020European journal of medicinal chemistry, Feb-01, Volume: 187Synthesis and evaluation of novel chlorophyll a derivatives as potent photosensitizers for photodynamic therapy.
AID1582026Photodynamic antitumor activity against human A549 cells xenografted in BALB/c nude mouse assessed as decrease in tumor weight at 0.3 mg/kg, iv followed by laser light irradiation at 120 J/cm2 measured after 14 days2020European journal of medicinal chemistry, Feb-01, Volume: 187Synthesis and evaluation of novel chlorophyll a derivatives as potent photosensitizers for photodynamic therapy.
AID1581997Phototoxicity in ICR mouse assessed as ear weight at 0.45 mg/kg, iv followed by 10 mW/cm2 light irradiation for 10 mins at 7 days after drug challenge measured after 1 day of light irradiation (13.2 +/- 1.6 mg)2020European journal of medicinal chemistry, Feb-01, Volume: 187Synthesis and evaluation of novel chlorophyll a derivatives as potent photosensitizers for photodynamic therapy.
AID1730083Photosensitizing activity in human UMUC3 cells assessed as reduction in cell viability pretreated with compound for 24 hrs followed by light irradiation at 1 J/cm2 and measured after 48 hrs by MTT assay2021Journal of medicinal chemistry, 01-14, Volume: 64, Issue:1
Synthesis, Tumor Specificity, and Photosensitizing Efficacy of Erlotinib-Conjugated Chlorins and Bacteriochlorins: Identification of a Highly Effective Candidate for Photodynamic Therapy of Cancer.
AID397030Photocytotoxicity against ABCG2-expressing mouse RIF cells xenografted in C3H mouse assessed as tumor control at 0.47 umol/kg, iv followed by exposure to irradiation at 135 J/cm2 relative to control2009Journal of medicinal chemistry, Jul-23, Volume: 52, Issue:14
Conjugation of 2-(1'-hexyloxyethyl)-2-devinylpyropheophorbide-a (HPPH) to carbohydrates changes its subcellular distribution and enhances photodynamic activity in vivo.
AID1730074Drug uptake in tumor of SCID mouse xenografted with human UMUC3 cells at 0.47 micromol/kg, iv pretreated with compound followed by light irradiation at a dose of 135 J/cm2 and 75 mW/cm2 measured after 24 hrs by IVIS analysis2021Journal of medicinal chemistry, 01-14, Volume: 64, Issue:1
Synthesis, Tumor Specificity, and Photosensitizing Efficacy of Erlotinib-Conjugated Chlorins and Bacteriochlorins: Identification of a Highly Effective Candidate for Photodynamic Therapy of Cancer.
AID1581996Phototoxicity in ICR mouse assessed as change in auricles 0.45 mg/kg, iv in presence of 10 mW/cm2 light irradiation for 10 mins upto 7 days measured after 1day of light irradiation by H and E staining based microscopic analysis2020European journal of medicinal chemistry, Feb-01, Volume: 187Synthesis and evaluation of novel chlorophyll a derivatives as potent photosensitizers for photodynamic therapy.
AID1730099Photodynamic antitumor activity against human UMUC3 cells xenografted in SCID mouse assessed as tumor retention at 0.47 micromol/kg, iv pretreated with compound followed by light irradiation at a dose of 135 J/cm2 and 75 mW/cm2 measured at day 30 post dos2021Journal of medicinal chemistry, 01-14, Volume: 64, Issue:1
Synthesis, Tumor Specificity, and Photosensitizing Efficacy of Erlotinib-Conjugated Chlorins and Bacteriochlorins: Identification of a Highly Effective Candidate for Photodynamic Therapy of Cancer.
AID397031Skin toxicity in ABCG2-expressing mouse RIF cells xenografted in irradiation exposed C3H mouse assessed as foot response after 24 to 96 hrs2009Journal of medicinal chemistry, Jul-23, Volume: 52, Issue:14
Conjugation of 2-(1'-hexyloxyethyl)-2-devinylpyropheophorbide-a (HPPH) to carbohydrates changes its subcellular distribution and enhances photodynamic activity in vivo.
AID397028Photocytotoxicity against ABCG2-expressing mouse RIF cells xenografted in C3H mouse assessed as tumor control at 0.47 umol/kg, iv followed by exposure to irradiation at 48 J/cm2 relative to control2009Journal of medicinal chemistry, Jul-23, Volume: 52, Issue:14
Conjugation of 2-(1'-hexyloxyethyl)-2-devinylpyropheophorbide-a (HPPH) to carbohydrates changes its subcellular distribution and enhances photodynamic activity in vivo.
AID1582027Photodynamic antitumor activity against human A549 cells xenografted in BALB/c nude mouse assessed as increase in tumor tissue damage at 0.3 mg/kg, iv incubated for 24 hrs followed by laser light irradiation at 120 J/cm2 measured up to 14 days2020European journal of medicinal chemistry, Feb-01, Volume: 187Synthesis and evaluation of novel chlorophyll a derivatives as potent photosensitizers for photodynamic therapy.
AID1582014Dark toxicity in human A549 cells assessed as reduction in cell viability incubated under dark for 24 hrs measured after 48 hrs by MTT assay2020European journal of medicinal chemistry, Feb-01, Volume: 187Synthesis and evaluation of novel chlorophyll a derivatives as potent photosensitizers for photodynamic therapy.
AID1582044Induction of ROS generation in DMF solution assessed as ROS quantum yield at 2 uM followed by irradiation measured every 10 secs by spectrophotometric analysis2020European journal of medicinal chemistry, Feb-01, Volume: 187Synthesis and evaluation of novel chlorophyll a derivatives as potent photosensitizers for photodynamic therapy.
AID1730075Drug uptake in human HNT1 cells at 3.2 uM incubated for 30 mins in serum free medium followed by 24 hrs chase period in compound-free medium by inverted fluorescence microscopic analysis2021Journal of medicinal chemistry, 01-14, Volume: 64, Issue:1
Synthesis, Tumor Specificity, and Photosensitizing Efficacy of Erlotinib-Conjugated Chlorins and Bacteriochlorins: Identification of a Highly Effective Candidate for Photodynamic Therapy of Cancer.
AID397029Photocytotoxicity against ABCG2-deficient mouse Colon 26 cells xenografted in BALB/c mouse assessed as tumor control at 0.47 umol/kg, iv followed by exposure to irradiation at 48 J/cm2 relative to control2009Journal of medicinal chemistry, Jul-23, Volume: 52, Issue:14
Conjugation of 2-(1'-hexyloxyethyl)-2-devinylpyropheophorbide-a (HPPH) to carbohydrates changes its subcellular distribution and enhances photodynamic activity in vivo.
AID1582043Phototoxicity in guinea pig assessed as change in back skin at 4.5 mg/kg, iv in presence of 10 mW/cm2 light irradiation for 10 mins measured after 1day of light irradiation by H and E staining based microscopic analysis2020European journal of medicinal chemistry, Feb-01, Volume: 187Synthesis and evaluation of novel chlorophyll a derivatives as potent photosensitizers for photodynamic therapy.
AID397021Partition coefficient, log P of the compound2009Journal of medicinal chemistry, Jul-23, Volume: 52, Issue:14
Conjugation of 2-(1'-hexyloxyethyl)-2-devinylpyropheophorbide-a (HPPH) to carbohydrates changes its subcellular distribution and enhances photodynamic activity in vivo.
AID1582042Phototoxicity in guinea pig assessed as change in auricles of left ear at 4.5 mg/kg, iv in presence of 10 mW/cm2 light irradiation for 10 mins measured after 1day of light irradiation by H and E staining based microscopic analysis2020European journal of medicinal chemistry, Feb-01, Volume: 187Synthesis and evaluation of novel chlorophyll a derivatives as potent photosensitizers for photodynamic therapy.
AID1730109Drug uptake in liver of SCID mouse xenografted with FaDu cells at 0.47 micromol/kg, iv pretreated with compound followed by light irradiation at a dose of 135 J/cm2 and 75 mW/cm2 and measured at 24 hrs by IVIS analysis2021Journal of medicinal chemistry, 01-14, Volume: 64, Issue:1
Synthesis, Tumor Specificity, and Photosensitizing Efficacy of Erlotinib-Conjugated Chlorins and Bacteriochlorins: Identification of a Highly Effective Candidate for Photodynamic Therapy of Cancer.
AID1730084Photosensitizing activity in human FaDu cells assessed as reduction in cell viability pretreated with compound for 24 hrs followed by light irradiation at 1 J/cm2 and measured after 48 hrs by MTT assay2021Journal of medicinal chemistry, 01-14, Volume: 64, Issue:1
Synthesis, Tumor Specificity, and Photosensitizing Efficacy of Erlotinib-Conjugated Chlorins and Bacteriochlorins: Identification of a Highly Effective Candidate for Photodynamic Therapy of Cancer.
AID1581999Phototoxicity in ICR mouse assessed as ear weight at 0.45 mg/kg, iv followed by 10 mW/cm2 light irradiation for 10 mins at 3 days after drug challenge measured after 1 day of light irradiation (Rvb = 12.8 +/- 1.5 mg)2020European journal of medicinal chemistry, Feb-01, Volume: 187Synthesis and evaluation of novel chlorophyll a derivatives as potent photosensitizers for photodynamic therapy.
AID1582028Photodynamic antitumor activity against human A549 cells xenografted in BALB/c nude mouse assessed as reduction in tumor volume at 0.3 mg/kg, iv incubated for 24 hrs followed by laser light irradiation at 120 J/cm2 measured up to 14 days2020European journal of medicinal chemistry, Feb-01, Volume: 187Synthesis and evaluation of novel chlorophyll a derivatives as potent photosensitizers for photodynamic therapy.
AID1582039Phototoxicity in guinea pig assessed as change in left ear weight 4.5 mg/kg, iv followed by 10 mW/cm2 light irradiation for 10 mins measured after 1 day of light irradiation (Rvb = 39.2 +/- 1.8 mg)2020European journal of medicinal chemistry, Feb-01, Volume: 187Synthesis and evaluation of novel chlorophyll a derivatives as potent photosensitizers for photodynamic therapy.
AID397027Photosensitizing activity in ABCG2-deficient mouse Colon 26 cells assessed as induction STAT3 covalent cross linking pretreated for 4 hrs followed by irradiation exposure to 665 nm light at 3 J/cm2 by Western blotting2009Journal of medicinal chemistry, Jul-23, Volume: 52, Issue:14
Conjugation of 2-(1'-hexyloxyethyl)-2-devinylpyropheophorbide-a (HPPH) to carbohydrates changes its subcellular distribution and enhances photodynamic activity in vivo.
AID1882394Photodynamic cytotoxicity against human FaDu cells assessed as cell growth inhibition upon light irradiation2022Journal of medicinal chemistry, 02-10, Volume: 65, Issue:3
Conjugates of Porphyrinoid-Based Photosensitizers with Cytotoxic Drugs: Current Progress and Future Directions toward Selective Photodynamic Therapy.
AID1882393Photodynamic cytotoxicity against human UMUC3 cells assessed as cell growth inhibition upon light irradiation2022Journal of medicinal chemistry, 02-10, Volume: 65, Issue:3
Conjugates of Porphyrinoid-Based Photosensitizers with Cytotoxic Drugs: Current Progress and Future Directions toward Selective Photodynamic Therapy.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (64)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's7 (10.94)18.2507
2000's16 (25.00)29.6817
2010's30 (46.88)24.3611
2020's11 (17.19)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 10.59

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index10.59 (24.57)
Research Supply Index4.32 (2.92)
Research Growth Index4.91 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.59)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials5 (7.25%)5.53%
Reviews3 (4.35%)6.00%
Case Studies1 (1.45%)4.05%
Observational0 (0.00%)0.25%
Other60 (86.96%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
aminolevulinic acid
Aminolevulinic Acid: A compound produced from succinyl-CoA and GLYCINE as an intermediate in heme synthesis. It is used as a PHOTOCHEMOTHERAPY for actinic KERATOSIS.. 5-aminolevulinic acid : The simplest delta-amino acid in which the hydrogens at the gamma position are replaced by an oxo group. It is metabolised to protoporphyrin IX, a photoactive compound which accumulates in the skin. Used (in the form of the hydrochloride salt)in combination with blue light illumination for the treatment of minimally to moderately thick actinic keratosis of the face or scalp.		2.43204-oxo monocarboxylic acid;
amino acid zwitterion;
delta-amino acid		antineoplastic agent;
dermatologic drug;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
photosensitizing agent;
plant metabolite;
prodrug;
Saccharomyces cerevisiae metabolite
phenytoin
[no description available]		2.6930imidazolidine-2,4-dioneanticonvulsant;
drug allergen;
sodium channel blocker;
teratogenic agent
carbamazepine
Carbamazepine: A dibenzazepine that acts as a sodium channel blocker. It is used as an anticonvulsant for the treatment of grand mal and psychomotor or focal SEIZURES. It may also be used in the management of BIPOLAR DISORDER, and has analgesic properties.. carbamazepine : A dibenzoazepine that is 5H-dibenzo[b,f]azepine carrying a carbamoyl substituent at the azepine nitrogen, used as an anticonvulsant.		2.0110dibenzoazepine;
ureas		analgesic;
anticonvulsant;
antimanic drug;
drug allergen;
EC 3.5.1.98 (histone deacetylase) inhibitor;
environmental contaminant;
glutamate transporter activator;
mitogen;
non-narcotic analgesic;
sodium channel blocker;
xenobiotic
erythrosine
Fluoresceins: A family of spiro(isobenzofuran-1(3H),9'-(9H)xanthen)-3-one derivatives. These are used as dyes, as indicators for various metals, and as fluorescent labels in immunoassays.		2.4320
mephenytoin
Mephenytoin: An anticonvulsant effective in tonic-clonic epilepsy (EPILEPSY, TONIC-CLONIC). It may cause blood dyscrasias.. mephenytoin : An imidazolidine-2,4-dione (hydantoin) in which the imidazolidine nucleus carries a methyl group at N-3 and has ethyl and phenyl substituents at C-5. An anticonvulsant, it is no longer available in the USA or the UK but is still studied largely because of its interesting hydroxylation polymorphism.		2.0110imidazolidine-2,4-dioneanticonvulsant
sulfaphenazole
Sulfaphenazole: A sulfonilamide anti-infective agent.. sulfaphenazole : A sulfonamide that is sulfanilamide in which the sulfonamide nitrogen is substituted by a 1-phenyl-1H-pyrazol-5-yl group. It is a selective inhibitor of cytochrome P450 (CYP) 2C9 isozyme, and antibacterial agent.		210primary amino compound;
pyrazoles;
substituted aniline;
sulfonamide antibiotic;
sulfonamide		antibacterial drug;
EC 1.14.13.181 (13-deoxydaunorubicin hydroxylase) inhibitor;
EC 1.14.13.67 (quinine 3-monooxygenase) inhibitor;
P450 inhibitor
tolbutamide
Tolbutamide: A sulphonylurea hypoglycemic agent with actions and uses similar to those of CHLORPROPAMIDE. (From Martindale, The Extra Pharmacopoeia, 30th ed, p290). tolbutamide : An N-sulfonylurea that consists of 1-butylurea having a tosyl group attached at the 3-position.		210N-sulfonylureahuman metabolite;
hypoglycemic agent;
insulin secretagogue;
potassium channel blocker
9,10-dimethyl-1,2-benzanthracene
9,10-Dimethyl-1,2-benzanthracene: Polycyclic aromatic hydrocarbon found in tobacco smoke that is a potent carcinogen.. 7,12-dimethyltetraphene : A tetraphene having methyl substituents at the 7- and 12-positions. It is a potent carcinogen and is present in tobacco smoke.		1.9910ortho-fused polycyclic arene;
tetraphenes		carcinogenic agent
galactose
galactopyranose : The pyranose form of galactose.		2.0510D-galactose;
galactopyranose		Escherichia coli metabolite;
mouse metabolite
methylene blue
Methylene Blue: A compound consisting of dark green crystals or crystalline powder, having a bronze-like luster. Solutions in water or alcohol have a deep blue color. Methylene blue is used as a bacteriologic stain and as an indicator. It inhibits GUANYLATE CYCLASE, and has been used to treat cyanide poisoning and to lower levels of METHEMOGLOBIN.. methylene blue : An organic chloride salt having 3,7-bis(dimethylamino)phenothiazin-5-ium as the counterion. A commonly used dye that also exhibits antioxidant, antimalarial, antidepressant and cardioprotective properties.		2.1510organic chloride saltacid-base indicator;
antidepressant;
antimalarial;
antimicrobial agent;
antioxidant;
cardioprotective agent;
EC 1.4.3.4 (monoamine oxidase) inhibitor;
EC 3.1.1.8 (cholinesterase) inhibitor;
EC 4.6.1.2 (guanylate cyclase) inhibitor;
fluorochrome;
histological dye;
neuroprotective agent;
physical tracer
azomycin
azomycin: RN given refers to parent cpd with specified locant; structure		2.0210C-nitro compound;
imidazoles		antitubercular agent
deoxycytidine
[no description available]		2.0710pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
fluorescein
Fluorescein: A phthalic indicator dye that appears yellow-green in normal tear film and bright green in a more alkaline medium such as the aqueous humor.. fluorescein (lactone form) : A xanthene dye that is highly fluorescent, detectable even when present in minute quantities. Used forensically to detect traces of blood, in analytical chemistry as an indicator in silver nitrate titrations and in microscopy.		1.98102-benzofurans;
gamma-lactone;
organic heteropentacyclic compound;
oxaspiro compound;
polyphenol;
xanthene dye		fluorescent dye;
radioopaque medium
1-phenyl-3,3-dimethyltriazene
[no description available]		2.4110
gadolinium
Gadolinium: An element of the rare earth family of metals. It has the atomic symbol Gd, atomic number 64, and atomic weight 157.25. Its oxide is used in the control rods of some nuclear reactors.		2.5220f-block element atom;
lanthanoid atom
gold
Gold: A yellow metallic element with the atomic symbol Au, atomic number 79, and atomic weight 197. It is used in jewelry, goldplating of other metals, as currency, and in dental restoration. Many of its clinical applications, such as ANTIRHEUMATIC AGENTS, are in the form of its salts.		2.1310copper group element atom;
elemental gold
oxcarbazepine
Oxcarbazepine: A carbamazepine derivative that acts as a voltage-gated sodium channel blocker. It is used for the treatment of PARTIAL SEIZURES with or without secondary generalization. It is also an inducer of CYTOCHROME P-450 CYP3A4.. oxcarbazepine : A dibenzoazepine derivative, having a carbamoyl group at the ring nitrogen, substituted with an oxo group at C-4 of the azepeine ring which is also hydrogenated at C-4 and C-5. It is a anticholinergic anticonvulsant and mood stabilizing drug, used primarily in the treatment of epilepsy.		2.0110cyclic ketone;
dibenzoazepine		anticonvulsant;
drug allergen
gemcitabine
gemcitabine : A 2'-deoxycytidine having geminal fluoro substituents in the 2'-position. An inhibitor of ribonucleotide reductase, gemcitabine is used in the treatment of various carcinomas, particularly non-small cell lung cancer, pancreatic cancer, bladder cancer and breast cancer.		2.0710organofluorine compound;
pyrimidine 2'-deoxyribonucleoside		antimetabolite;
antineoplastic agent;
antiviral drug;
DNA synthesis inhibitor;
EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor;
environmental contaminant;
immunosuppressive agent;
photosensitizing agent;
prodrug;
radiosensitizing agent;
xenobiotic
fluorexon
fluorexon: structure		2.1110xanthene dyefluorochrome
arginyl-glycyl-aspartic acid
arginyl-glycyl-aspartic acid: amino acid sequence of basic unit of widespread cellular recognition system		2.0610oligopeptide
4-hydroxymephenytoin
4-hydroxymephenytoin: metabolite of mephenytoin; RN given refers to cpd without isomeric designation		2.0110imidazolidine-2,4-dione
vadimezan
vadimezan : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is replaced by a 5,6-dimethyl-9-oxoxanthen-4-yl group.		2.0210monocarboxylic acid;
xanthones		antineoplastic agent
singlet oxygen
Singlet Oxygen: An excited state of molecular oxygen generated photochemically or chemically. Singlet oxygen reacts with a variety of biological molecules such as NUCLEIC ACIDS; PROTEINS; and LIPIDS; causing oxidative damages.		8.3260chalcogen;
monoatomic oxygen;
nonmetal atom		macronutrient
pyropheophorbide a
pyropheophorbide a: RN given refers to (3S-trans)-isomer		2.2510
carbocyanines
Carbocyanines: Compounds that contain three methine groups. They are frequently used as cationic dyes used for differential staining of biological materials.		2.4820cyanine dye;
organic iodide salt		fluorochrome
cypate
Cypate: a fluorescent dye; structure in first source		2.1710
indocyanine green
Indocyanine Green: A tricarbocyanine dye that is used diagnostically in liver function tests and to determine blood volume and cardiac output.		2101,1-diunsubstituted alkanesulfonate;
benzoindole;
cyanine dye
vpm chloride
VPM chloride: structure given in first source		2.0810
chlorophyll a
Chlorophyll: Porphyrin derivatives containing magnesium that act to convert light energy in photosynthetic organisms.. chlorophyll : A family of magnesium porphyrins, defined by the presence of a fifth ring beyond the four pyrrole-like rings. The rings can have various side chains which usually include a long phytol chain.		10.74585chlorophyll;
methyl ester		cofactor
pheophytin a
pheophytin a: structure given in first source; RN given refers to (3S-(3alpha(2E,7S*,11S*),4beta,21beta))-isomer		2.0610
5,10,15,20-tetra(4-pyridyl)porphyrin
5,10,15,20-tetra(4-pyridyl)porphyrin: structure in first source		3.5110
ConditionIndicatedRelationship StrengthStudiesTrials
Experimental Neoplasms
[description not available]		03.2960
Cancer of Head
[description not available]		05.5451
Head and Neck Neoplasms
Soft tissue tumors or cancer arising from the mucosal surfaces of the LIP; oral cavity; PHARYNX; LARYNX; and cervical esophagus. Other sites included are the NOSE and PARANASAL SINUSES; SALIVARY GLANDS; THYROID GLAND and PARATHYROID GLANDS; and MELANOMA and non-melanoma skin cancers of the head and neck. (from Holland et al., Cancer Medicine, 4th ed, p1651)		05.5451
Benign Neoplasms
[description not available]		05.36120
Neoplasms
New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.		05.36120
Neoplasms, Pleural
[description not available]		02.7220
HPV Infection
[description not available]		02.610
Papillomavirus Infections
Neoplasms of the skin and mucous membranes caused by papillomaviruses. They are usually benign but some have a high risk for malignant progression.		02.610
Cancer of Colon
[description not available]		03.6790
Colonic Neoplasms
Tumors or cancer of the COLON.		03.6790
Benign Neoplasms, Brain
[description not available]		02.4620
Brain Neoplasms
Neoplasms of the intracranial components of the central nervous system, including the cerebral hemispheres, basal ganglia, hypothalamus, thalamus, brain stem, and cerebellum. Brain neoplasms are subdivided into primary (originating from brain tissue) and secondary (i.e., metastatic) forms. Primary neoplasms are subdivided into benign and malignant forms. In general, brain tumors may also be classified by age of onset, histologic type, or presenting location in the brain.		02.4620
Malignant Melanoma
[description not available]		02.1510
Melanoma
A malignant neoplasm derived from cells that are capable of forming melanin, which may occur in the skin of any part of the body, in the eye, or, rarely, in the mucous membranes of the genitalia, anus, oral cavity, or other sites. It occurs mostly in adults and may originate de novo or from a pigmented nevus or malignant lentigo. Melanomas frequently metastasize widely, and the regional lymph nodes, liver, lungs, and brain are likely to be involved. The incidence of malignant skin melanomas is rising rapidly in all parts of the world. (Stedman, 25th ed; from Rook et al., Textbook of Dermatology, 4th ed, p2445)		02.1510
Carcinoma, Non-Small Cell Lung
[description not available]		04.4241
Cancer of Lung
[description not available]		04.7361
Carcinoma, Non-Small-Cell Lung
A heterogeneous aggregate of at least three distinct histological types of lung cancer, including SQUAMOUS CELL CARCINOMA; ADENOCARCINOMA; and LARGE CELL CARCINOMA. They are dealt with collectively because of their shared treatment strategy.		04.4241
Lung Neoplasms
Tumors or cancer of the LUNG.		04.7361
Cancer of Skin
[description not available]		05.2641
Skin Neoplasms
Tumors or cancer of the SKIN.		05.2641
Carcinoma, Epidermoid
[description not available]		05.5932
Carcinoma, Squamous Cell
A carcinoma derived from stratified SQUAMOUS EPITHELIAL CELLS. It may also occur in sites where glandular or columnar epithelium is normally present. (From Stedman, 25th ed)		05.5932
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.7830
Cancer of Mouth
[description not available]		03.4711
Mouth Neoplasms
Tumors or cancer of the MOUTH.		03.4711
Carcinoma, Basal Cell, Pigmented
[description not available]		03.3620
Carcinoma, Basal Cell
A malignant skin neoplasm that seldom metastasizes but has potentialities for local invasion and destruction. Clinically it is divided into types: nodular, cicatricial, morphaic, and erythematoid (pagetoid). They develop on hair-bearing skin, most commonly on sun-exposed areas. Approximately 85% are found on the head and neck area and the remaining 15% on the trunk and limbs. (From DeVita Jr et al., Cancer: Principles & Practice of Oncology, 3d ed, p1471)		03.3620
Sensitivity and Specificity
Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)		03.420
Metastase
[description not available]		02.1110
Experimental Mammary Neoplasms
[description not available]		02.7430
Neoplasm Metastasis
The transfer of a neoplasm from one organ or part of the body to another remote from the primary site.		02.1110
Breast Cancer
[description not available]		02.1110
Breast Neoplasms
Tumors or cancer of the human BREAST.		02.1110
Carcinoma, Intraepithelial
[description not available]		03.5111
Carcinoma, Bronchial
[description not available]		03.5111
Carcinoma in Situ
A lesion with cytological characteristics associated with invasive carcinoma but the tumor cells are confined to the epithelium of origin, without invasion of the basement membrane.		03.5111
Carcinoma, Bronchogenic
Malignant neoplasm arising from the epithelium of the BRONCHI. It represents a large group of epithelial lung malignancies which can be divided into two clinical groups: SMALL CELL LUNG CANCER and NON-SMALL-CELL LUNG CARCINOMA.		03.5111
Fibrosarcoma
A sarcoma derived from deep fibrous tissue, characterized by bundles of immature proliferating fibroblasts with variable collagen formation, which tends to invade locally and metastasize by the bloodstream. (Stedman, 25th ed)		02.1110
Necrosis
The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.		02.1110
Cancer of Esophagus
[description not available]		05.0431
Esophageal Neoplasms
Tumors or cancer of the ESOPHAGUS.		05.0431
Adenocarcinoma, Basal Cell
[description not available]		03.8221
Barrett Epithelium
[description not available]		03.8221
Condition, Preneoplastic
[description not available]		03.4511
Adenocarcinoma
A malignant epithelial tumor with a glandular organization.		03.8221
Barrett Esophagus
A condition with damage to the lining of the lower ESOPHAGUS resulting from chronic acid reflux (ESOPHAGITIS, REFLUX). Through the process of metaplasia, the squamous cells are replaced by a columnar epithelium with cells resembling those of the INTESTINE or the salmon-pink mucosa of the STOMACH. Barrett's columnar epithelium is a marker for severe reflux and precursor to ADENOCARCINOMA of the esophagus.		03.8221
Precancerous Conditions
Pathological conditions that tend eventually to become malignant.		03.4511
Cancer of Pancreas
[description not available]		02.0710
Pancreatic Neoplasms
Tumors or cancer of the PANCREAS. Depending on the types of ISLET CELLS present in the tumors, various hormones can be secreted: GLUCAGON from PANCREATIC ALPHA CELLS; INSULIN from PANCREATIC BETA CELLS; and SOMATOSTATIN from the SOMATOSTATIN-SECRETING CELLS. Most are malignant except the insulin-producing tumors (INSULINOMA).		02.0710
Innate Inflammatory Response
[description not available]		02.4120
Inflammation
A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.		02.4120
Angiogenesis, Pathologic
[description not available]		02.0210
Glial Cell Tumors
[description not available]		02.4220
Glioma
Benign and malignant central nervous system neoplasms derived from glial cells (i.e., astrocytes, oligodendrocytes, and ependymocytes). Astrocytes may give rise to astrocytomas (ASTROCYTOMA) or glioblastoma multiforme (see GLIOBLASTOMA). Oligodendrocytes give rise to oligodendrogliomas (OLIGODENDROGLIOMA) and ependymocytes may undergo transformation to become EPENDYMOMA; CHOROID PLEXUS NEOPLASMS; or colloid cysts of the third ventricle. (From Escourolle et al., Manual of Basic Neuropathology, 2nd ed, p21)		02.4220
Cell Transformation, Neoplastic
Cell changes manifested by escape from control mechanisms, increased growth potential, alterations in the cell surface, karyotypic abnormalities, morphological and biochemical deviations from the norm, and other attributes conferring the ability to invade, metastasize, and kill.		01.9910
Anasarca
[description not available]		01.9910
Opportunistic Infections
An infection caused by an organism which becomes pathogenic under certain conditions, e.g., during immunosuppression.		01.9910
Edema
Abnormal fluid accumulation in TISSUES or body cavities. Most cases of edema are present under the SKIN in SUBCUTANEOUS TISSUE.		01.9910
Aura
[description not available]		0210
Epilepsy
A disorder characterized by recurrent episodes of paroxysmal brain dysfunction due to a sudden, disorderly, and excessive neuronal discharge. Epilepsy classification systems are generally based upon: (1) clinical features of the seizure episodes (e.g., motor seizure), (2) etiology (e.g., post-traumatic), (3) anatomic site of seizure origin (e.g., frontal lobe seizure), (4) tendency to spread to other structures in the brain, and (5) temporal patterns (e.g., nocturnal epilepsy). (From Adams et al., Principles of Neurology, 6th ed, p313)		0210
Gingival Overgrowth
Excessive growth of the gingiva either by an increase in the size of the constituent cells (GINGIVAL HYPERTROPHY) or by an increase in their number (GINGIVAL HYPERPLASIA). (From Jablonski's Dictionary of Dentistry, 1992, p574)		0210
Canine Diseases
[description not available]		0210
Animal Mammary Carcinoma
[description not available]		0210