Page last updated: 2024-12-11

phytochlorin

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

phytochlorin: RN given refers to (2S-trans)-isomer; structure given in the first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID5479494
CHEMBL ID1956500
CHEBI ID168630
SCHEMBL ID119595
SCHEMBL ID13806508
MeSH IDM0174055

Synonyms (44)

Synonym
CHEBI:168630
(17s,18s)-18-(2-carboxyethyl)-20-(carboxymethyl)-12-ethenyl-7-ethyl-3,8,13,17-tetramethyl-17,18,22,23-tetrahydroporphyrin-2-carboxylic acid
19660-77-6
phytochlorin
(1z,4z,9z,15z,17s,18s)-18-(2-carboxyethyl)-20-(carboxymethyl)-7-ethyl-3,8,13,17-tetramethyl-12-vinyl-17,18,21,23-tetrahydroporphyrin-2-carboxylic acid
3(s),7,12,17-tetramethyl-13-ethyl-8-ethenyl-2,3-dihydro-18-carboxy-20-(carboxymethyl)-21h,23h-porphine-2(s)-propanoic acid
chlorin e6
21h,23h-porphine-2-propanoic acid, 18-carboxy-20-(carboxymethyl)-8-ethenyl-13-ethyl-2,3-dihydro-3,7,12,17-tetramethyl-,(2s-trans)-
einecs 243-209-4
(2s-trans)-18-carboxy-20-(carboxymethyl)-13-ethyl-2,3-dihydro-3,7,12,17-tetramethyl-8-vinyl-21h,23h-porphine-2-propionic acid
chlorine a6
chlorine e6
chlorin a6
photochlorine
21h,23h-porphine-7-propanoic acid, 3-carboxy-5-(carboxymethyl)-13-ethenyl-18-ethyl-7,8-dihydro-2,8,12,17-tetramethyl-, (7s,8s)-
photolon
5s2ccf3t1z ,
unii-5s2ccf3t1z
CHEMBL1956500
phytochlorin [mi]
2-porphinepropionic acid, 18-carboxy-20-(carboxymethyl)-13-ethyl-2.beta.,3-dihydro-3.beta.,7,12,17-tetramethyl-8-vinyl-
phytochlorin [who-dd]
21h,23h-porphine-2-propanoic acid, 18-carboxy-20-(carboxymethyl)-8-ethenyl-13-ethyl-2,3-dihydro-3,7,12,17-tetramethyl-, (2s-trans)-
phytochlorin e6
phytochlorine e6
VAJLRIOJDADNAT-UWJYYQICSA-N
chlorin-e6
SCHEMBL119595
SCHEMBL13806508
Q-101877
AC-22575
AKOS025401593
AS-75137
(19s,20s)-20-(2-carboxyethyl)-2-(carboxymethyl)-14-ethenyl-9-ethyl-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1(3),?.1?,(1)(1).1(1)(3),(1)?]tetracosa-1,3,5,7,9,11(23),12,14,16,18(21)-decaene-4-carboxylic acid
HY-13594
(7s,8s)-13-vinyl-5-(carboxymethyl)-7-(2-carboxyethyl)-2,8,12,17-tetramethyl-18-ethyl-7h,8h-porphyrin-3-carboxylic acid
2-[(7s,8s)-3-carboxy-7-(2-carboxyethyl)-13-ethenyl-18-ethyl-7,8-dihydro-2,8,12,17-tetramethyl-21h,23h-porphin-5-yl]acetic acid
CS-0007379
E78640
chlorophyll impurity 11
(7s,8s)-3-carboxy-5-(carboxymethyl)-13-ethenyl-18-ethyl-7,8-dihydro-2,8,12,17-tetramethyl-21h,23h-porphine-7-propanoic acid
DTXSID70885088
21h,23h-porphine-7-propanoic acid,3-carboxy-5-(carboxymethyl)-13-ethenyl-18-ethyl-7,8-dihydro-2,8,12,17-tetramethyl-, (7s,8s)-
(7S,8S)-7-(2-CARBOXYETHYL)-5-(CARBOXYMETHYL)-18-ETHYL-2,8,12,17-TETRAMETHYL-13-VINYL-7H,8H-PORPHYRIN-3-CARBOXYLIC ACID

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" In PDT, the Ce6-PVP compound was most toxic at the 1h drug-light interval at 200J/cm(2), while Ce6 alone was most toxic at a light dose of more that 50J/cm(2) at the 1 and 3h drug-light interval."( Fluorescence imaging and phototoxicity effects of new formulation of chlorin e6-polyvinylpyrrolidone.
Bhuvaneswari, R; Chin, WW; Heng, PW; Lau, WK; Olivo, M, 2006
)
0.33
"Cancer cells can be killed by photosensitizing agents that induce toxic effects when exposed to nonhazardous light, but this also causes significant damage to surrounding healthy cells."( SNAP-tag technology mediates site specific conjugation of antibody fragments with a photosensitizer and improves target specific phototoxicity in tumor cells.
Barth, S; Hussain, AF; Kampmeier, F; Merk, HF; Tur, MK; von Felbert, V, 2011
)
0.37
" It is not toxic to cells without activation by neutrons or photons."( Chlorin e6 fused with a cobalt-bis(dicarbollide) nanoparticle provides efficient boron delivery and photoinduced cytotoxicity in cancer cells.
Bregadze, VI; Efremenko, AV; Feofanov, AV; Grin, MA; Ignatova, AA; Mironov, AF; Sivaev, IB, 2014
)
0.4

Pharmacokinetics

ExcerptReferenceRelevance
"Similar pharmacokinetic trends of Ce6 in mice were observed either by fluorescence spectrophotometry or by bio-optical imaging."( Pharmacokinetic study of a novel sonosensitizer chlorin-e6 and its sonodynamic anti-cancer activity in hepatoma-22 tumor-bearing mice.
Liu, Q; Qin, X; Shi, H; Wang, P; Wang, X, 2011
)
0.37

Compound-Compound Interactions

ExcerptReferenceRelevance
" Thus, the aim of study was to evaluate the cytotoxic effect of PDT in combination with EP."( Evaluation of cytotoxic effect of photodynamic therapy in combination with electroporation in vitro.
Didziapetriene, J; Gehl, J; Labanauskiene, J, 2007
)
0.34
" PDT employed a conjugate between polyethylenimine and chlorin(e6) as the photosensitizer (PS) and 660-nm diode laser light delivered into the root canal via a 200-micro fiber, and this was compared and combined with standard endodontic treatment using mechanical debridement and antiseptic irrigation."( Antimicrobial photodynamic therapy combined with conventional endodontic treatment to eliminate root canal biofilm infection.
Garcez, AS; Hamblin, MR; Jorge, AO; Núñez, SC; Ribeiro, MS; Tegos, GP, 2007
)
0.34
" More significantly, PDT with UCNP-Ce6-R837 in combination with the cytotoxic T-lymphocyte-associated protein 4 (CTLA-4) checkpoint blockade not only shows excellent efficacy in eliminating tumors exposed to the NIR laser but also results in strong antitumor immunities to inhibit the growth of distant tumors left behind after PDT treatment."( Near-Infrared-Triggered Photodynamic Therapy with Multitasking Upconversion Nanoparticles in Combination with Checkpoint Blockade for Immunotherapy of Colorectal Cancer.
Dong, Z; Han, X; Liu, Z; Peng, R; Wang, C; Xu, J; Xu, L; Yang, R; Zhu, W; Zhuang, Q, 2017
)
0.46

Bioavailability

ExcerptReferenceRelevance
" The relative bioavailability of brain tissues for Photolon was estimated as 82%, T(max)-30 min, mean residual time (MRT)-1."( Pharmacokinetics and biodistribution of Photolon (Fotolon) in intact and tumor-bearing rats.
Isakau, HA; Istomin, YP; Shliakhtsin, SV; Trukhachova, TV, 2009
)
0.35
" In vitro studies were conducted to assess the cellular uptake and bioavailability of the photosensitizer in OSCC cells."( Novel delivery of Chlorin e6 using anti-EGFR antibody tagged virosomes for fluorescence diagnosis of oral cancer in a hamster cheek pouch model.
Bhuvaneswari, R; Bunte, RM; Low, KP; Soo, KC; Thong, PS, 2016
)
0.43
" This nanoplatform can address the major issues of these two capable photoactive agents, such as limited biocompatibility, lack of functional chemical groups, and poor bioavailability due to rapid blood clearance or self-aggregation."( Light-activatable Chlorin e6 (Ce6)-imbedded erythrocyte membrane vesicles camouflaged Prussian blue nanoparticles for synergistic photothermal and photodynamic therapies of cancer.
Gao, Y; Hou, M; Kang, Y; Li, Q; Sun, L; Xu, Z; Xue, P; Yang, R; Zhang, L, 2018
)
0.48

Dosage Studied

ExcerptRelevanceReference
" Though these data argue strongly for photolysis by the cumulative dosage of singlet oxygen at the cell membrane, nonetheless, the concurrent photoinduced release of other cytotoxic agents should not be ruled out."( Antibody-targeted photolysis: in vitro immunological, photophysical, and cytotoxic properties of monoclonal antibody-dextran-Sn(IV) chlorin e6 immunoconjugates.
Ford, WE; Rakestraw, SL; Rodgers, MA; Thorpe, WP; Tompkins, RG; Yarmush, ML,
)
0.13
" dosing (2."( Combination chemotherapy and photodynamic therapy with N-(2-hydroxypropyl) methacrylamide copolymer-bound anticancer drugs inhibit human ovarian carcinoma heterotransplanted in nude mice.
Kopecek, J; Lu, JM; Peterson, CA; Peterson, CM; Shiah, JG; Straight, RC; Sun, Y, 1996
)
0.29
" Meanwhile, traditional photodynamic therapy (PDT) has been substantially restricted by the low dosage of photosensitizer and limited penetration depth of the ultraviolet (UV) or visible light used for excitation."( Degradable Calcium Phosphate-Coated Upconversion Nanoparticles for Highly Efficient Chemo-Photodynamic Therapy.
Dai, Y; Dong, S; Dong, Y; Gai, S; He, F; Li, W; Liu, S; Yang, D; Yang, P, 2019
)
0.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (22)

Assay IDTitleYearJournalArticle
AID648265Drug uptake in human Hep2 cells at 10 uM measured up to 25 hrs by fluorescence microscopic analysis2011Journal of medicinal chemistry, Nov-10, Volume: 54, Issue:21
Syntheses and cellular investigations of 17(3)-, 15(2)-, and 13(1)-amino acid derivatives of chlorin e(6).
AID1722760Phototoxicity against human MCF7 cells assessed as reduction in cell viability preincubated for 3 hrs followed by 54 J/cm2 light irradiation and measured after 24 hrs by MTT assay
AID1722761Dark toxicity in human SW480 cells assessed as reduction in cell viability after 3 hrs by MTT assay
AID648260Drug uptake in human Hep2 cell lysosomes at 10 uM after 18 hrs by fluorescence microscopic analysis2011Journal of medicinal chemistry, Nov-10, Volume: 54, Issue:21
Syntheses and cellular investigations of 17(3)-, 15(2)-, and 13(1)-amino acid derivatives of chlorin e(6).
AID648263Drug uptake in human Hep2 cell mitochondria at 10 uM after 18 hrs by fluorescence microscopic analysis2011Journal of medicinal chemistry, Nov-10, Volume: 54, Issue:21
Syntheses and cellular investigations of 17(3)-, 15(2)-, and 13(1)-amino acid derivatives of chlorin e(6).
AID1722762Phototoxicity against human SW480 cells assessed as reduction in cell viability preincubated for 3 hrs followed by 54 J/cm2 light irradiation and measured after 24 hrs by MTT assay
AID648258Cytotoxicity against human Hep2 cells after overnight incubation followed by cells irradiated with 1 J/cm'2 light for 20 mins measured after overnight incubation by celltiter blue assay2011Journal of medicinal chemistry, Nov-10, Volume: 54, Issue:21
Syntheses and cellular investigations of 17(3)-, 15(2)-, and 13(1)-amino acid derivatives of chlorin e(6).
AID1722797Toxicity in human HeLa cells xenografted Balb/c nu/nu mouse assessed as body weight loss at 2 mg/kg, iv pretreated for 15 mins followed by 54 J/cm2 light irradiation for 10 mins and measured for 24 days
AID648257Cytotoxicity against human Hep2 cells under dark condition after 18 hrs by celltiter blue assay2011Journal of medicinal chemistry, Nov-10, Volume: 54, Issue:21
Syntheses and cellular investigations of 17(3)-, 15(2)-, and 13(1)-amino acid derivatives of chlorin e(6).
AID1410381Photocytotoxicity in human SKOV3 cells assessed as cell death incubated for 6 hrs followed by PDT-1200 light irradiation at 20 J/cm2 measured after 16 hrs using liposome-encapsulated compound by MTT assay2018ACS medicinal chemistry letters, Apr-12, Volume: 9, Issue:4
Study on Liposomal Encapsulation of New Bodipy Sensitizers for Photodynamic Therapy.
AID648262Drug uptake in human Hep2 cell golgi at 10 uM after 18 hrs by fluorescence microscopic analysis2011Journal of medicinal chemistry, Nov-10, Volume: 54, Issue:21
Syntheses and cellular investigations of 17(3)-, 15(2)-, and 13(1)-amino acid derivatives of chlorin e(6).
AID1250261Ratio of IC50 for dark toxicity in human HepG2 cells to IC50 for photo cytotoxic activity against human HepG2 cells irradiated with 1.7 J/cm'2 light dose2015Bioorganic & medicinal chemistry letters, Oct-01, Volume: 25, Issue:19
Syntheses of new chlorin derivatives containing maleimide functional group and their photodynamic activity evaluation.
AID648261Drug uptake in human Hep2 cell endoplasmic reticulum at 10 uM after 18 hrs by fluorescence microscopic analysis2011Journal of medicinal chemistry, Nov-10, Volume: 54, Issue:21
Syntheses and cellular investigations of 17(3)-, 15(2)-, and 13(1)-amino acid derivatives of chlorin e(6).
AID1250260Dark toxicity in human HepG2 cells after overnight incubation by MTT assay2015Bioorganic & medicinal chemistry letters, Oct-01, Volume: 25, Issue:19
Syntheses of new chlorin derivatives containing maleimide functional group and their photodynamic activity evaluation.
AID1722758Phototoxicity against human HeLa cells assessed as reduction in cell viability preincubated for 3 hrs followed by 54 J/cm2 light irradiation and measured after 24 hrs by MTT assay
AID648259Ratio of IC50 for cytotoxicity against human Hep2 cells under dark condition to IC50 for human Hep2 cells in presence of 1 J/cm'2 light2011Journal of medicinal chemistry, Nov-10, Volume: 54, Issue:21
Syntheses and cellular investigations of 17(3)-, 15(2)-, and 13(1)-amino acid derivatives of chlorin e(6).
AID1722757Dark toxicity in human HeLa cells assessed as reduction in cell viability after 3 hrs by MTT assay
AID1819606Antitumor activity against mouse B16-F10 cells implanted in C57BL/6 mouse assessed as inhibition of tumor growth at 2 mg/kg, iv irradiated with 60 J/cm^2 laser light by IVIS imaging analysis measured upto 48 hrs2022Journal of medicinal chemistry, 02-24, Volume: 65, Issue:4
Discovery of an Amino Acid-Modified Near-Infrared Aza-BODIPY Photosensitizer as an Immune Initiator for Potent Photodynamic Therapy in Melanoma.
AID1722796Antitumor activity against human HeLa cells xenografted in Balb/c nu/nu mouse assessed as tumor growth inhibition at 2 mg/kg, iv pretreated for 15 mins followed by 54 J/cm2 light irradiation for 10 mins and measured after 24 days
AID1819608Toxicity in C57BL/6 mouse harboring mouse B16-F10 cells assessed as change in body weight at 2 mg/kg, iv irradiated with 60 J/cm^2 laser light measured upto 14 days2022Journal of medicinal chemistry, 02-24, Volume: 65, Issue:4
Discovery of an Amino Acid-Modified Near-Infrared Aza-BODIPY Photosensitizer as an Immune Initiator for Potent Photodynamic Therapy in Melanoma.
AID1722759Dark toxicity in human MCF7 cells assessed as reduction in cell viability after 3 hrs by MTT assay
AID1250259Photo cytotoxic activity against human HepG2 cells irradiated with 1.7 J/cm'2 light dose for 10 mins measured after overnight incubation by MTT assay2015Bioorganic & medicinal chemistry letters, Oct-01, Volume: 25, Issue:19
Syntheses of new chlorin derivatives containing maleimide functional group and their photodynamic activity evaluation.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (652)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (0.15)18.7374
1990's33 (5.06)18.2507
2000's86 (13.19)29.6817
2010's359 (55.06)24.3611
2020's173 (26.53)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 10.22

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 Index10.22 (24.57)
Research Supply Index6.53 (2.92)
Research Growth Index6.76 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.22)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials5 (0.73%)5.53%
Reviews6 (0.88%)6.00%
Case Studies4 (0.59%)4.05%
Observational0 (0.00%)0.25%
Other667 (97.80%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]