Page last updated: 2024-12-11

carbocyanines

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

Description

Carbocyanines: Compounds that contain three methine groups. They are frequently used as cationic dyes used for differential staining of biological materials. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID5709754
CHEMBL ID2361697
SCHEMBL ID58012
MeSH IDM0003347

Synonyms (19)

Synonym
g 1700
1-ethyl-2-(3-(1-ethyl-2(1h)-quinolylidene)propenyl)quinolinium iodide
nsc 403532
quinolinium, 1-ethyl-2-(3-(1-ethyl-2(1h)-quinolylidene)propenyl)-, iodide
1-ethyl-2-(3-(1-ethyl-2(1h)-quinolylidene)prop-1-enyl)quinolinium iodide
eastman kodak 622
einecs 210-099-4
unii-94623a1122
carbocyanines
94623a1122 ,
quinolinium, 1-ethyl-2-(3-(1-ethyl-2(1h)-quinolinylidene)-1-propen-1-yl)-, iodide (1:1)
nk-3
SCHEMBL58012
AKOS024302141
CHEMBL2361697
1-ethyl-2-((1e,3z)-3-(1-ethylquinolin-2(1h)-ylidene)prop-1-en-1-yl)quinolin-1-ium iodide
Q27123307
AS-81192
quinolinium, 1-ethyl-2-[3-(1-ethyl-2(1h)-quinolinylidene)-1-propen-1-yl]-, iodide (1:1)

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" When the neurons from these regions were placed in culture, the neurons labeled by the dye were found to die rapidly, suggesting that DiIC18(3) can be toxic to neurons of these types."( Toxicity of "DiI" for embryonic rat motoneurons and sensory neurons in vitro.
St John, PA, 1991
)
0.28
" These results demonstrate that the most toxic substance for growing fibroblasts was the solvent DMSO."( Toxicity in vital fluorescence microscopy: effect of dimethylsulfoxide, rhodamine-123, and DiI-low density lipoprotein on fibroblast growth in vitro.
Braunwald, NS; Crawford, JM, 1991
)
0.28
" The mechanism may involve electron transfer to oxygen and subsequent formation of toxic photoproducts from EDKC+."( Phototoxicity mechanism of a kryptocyanine dye in human red cell membranes and isolated murine mitochondria.
Ara, G; Kochevar, IE; Valdes-Aguilera, O, 1988
)
0.27
"Mitochondrial toxicity is a serious side-effect of antiretroviral drugs, especially nucleoside reverse transcriptase inhibitors (NRTI)."( Direct analysis of mitochondrial toxicity of antiretroviral drugs.
Bareggi, A; Benvenuto, F; Cossarizza, A; Foli, A; Lisziewicz, J; Lori, F; Piccinini, G, 2001
)
0.31
" HU alone was not toxic (MTI 7 +/- 10 at 100 microM, 2 +/- 2 at 50 microM and 2 +/- 4 at 10 microM HU); however, HU increased the toxicity of high, but not low, concentrations of ddI."( Direct analysis of mitochondrial toxicity of antiretroviral drugs.
Bareggi, A; Benvenuto, F; Cossarizza, A; Foli, A; Lisziewicz, J; Lori, F; Piccinini, G, 2001
)
0.31
" With the exception of 5-O-PN, all the other naringenins showed only weak toxic effects at concentrations below 50 micromol/l."( Toxicity and cell cycle effects of synthetic 8-prenylnaringenin and derivatives in human cells.
Gutzeit, HO; Henker, Y; Metz, P; Schwab, P; Tokalov, SV, 2004
)
0.32
" The results of in vitro erythrocyte hemolysis and the cell viability of breast cancer MCF-7 cells showed that the PBCA nanocapsules are quite safe carriers of IR-768 in the circulation, having a very low hemolytic potential and being non-toxic to the studied cells."( New approach to hydrophobic cyanine-type photosensitizer delivery using polymeric oil-cored nanocarriers: hemolytic activity, in vitro cytotoxicity and localization in cancer cells.
Kulbacka, J; Majkowski, M; Pietkiewicz, J; Saczko, J; Wilk, KA; Zielińska, K, 2010
)
0.36
"This study evaluates the toxic effects of catechol (a component from cigarette smoke) on Müller cells (MIO-M1) in vitro, and investigates the inhibitors memantine and epicatechin to determine if they can reverse the catechol toxic effects."( Protective effects of memantine and epicatechin on catechol-induced toxicity on Müller cells in vitro.
Gupta, N; Kenney, MC; Kuppermann, BD; Limb, GA; Luczy-Bachman, G; Mansoor, S, 2010
)
0.36
" The results of this long-term study suggest that HUMSCs transplantation, 1 of the most potential treatments for Parkinson's disease, is an effective and safe approach."( Long-term efficacy and safety of human umbilical cord mesenchymal stromal cells in rotenone-induced hemiparkinsonian rats.
Cao, X; Chen, C; Huang, J; Jia, M; Liang, Z; Lin, Z; Sun, S; Wang, T; Xiong, J; Xiong, N; Zhang, Z, 2010
)
0.36
"Analysis of (1)H and (13)C NMR and mass spectral data for the fluorescent nucleic acid stain SYBR Safe indicates that it contains a cyanine-based cationic core structure identical to thiazole orange."( 1H and 13C NMR assignments for the cyanine dyes SYBR Safe and thiazole orange.
Boden, LM; Evenson, WE; Muzikar, KA; O'Leary, DJ, 2012
)
0.38
"DiI is a convenient method for ASCs labeling which causes no toxic effects and does not impair the proliferation, migration or differentiation potential of ASCs after the labeling procedure."( DiI labeling of human adipose-derived stem cells: evaluation of DNA damage, toxicity and functional impairment.
Froelich, K; Hackenberg, S; Hagen, R; Kleinsasser, N; Radeloff, A; Ramos Tirado, M; Scherzed, A; Schmidt, K; Steussloff, G; Technau, A, 2013
)
0.39
"5 with MW around 100 kDa and biodegradable moiety in the main chain might be utilized as safe nanoscale carrier."( The Potential of Poly[N-(2-hydroxypropyl)methacrylamide] via Reversible Addition-Fragmentation Chain Transfer Polymerization as Safe Nanocarrier.
Gu, Z; Guo, C; Hu, J; Li, S; Luo, K; Zhang, Y, 2016
)
0.43
"A safe and efficient delivery system is critical for clinical application of siRNA."( Microfluidic-Based Holonomic Constraints of siRNA in the Kernel of Lipid/Polymer Hybrid Nanoassemblies for Improving Stable and Safe In Vivo Delivery.
Chen, X; Guo, XY; Pang, WH; Qiu, C; Sun, J; Wang, JC; Wang, R; Wei, W; Zhang, HT; Zhang, Q, 2020
)
0.56

Pharmacokinetics

ExcerptReferenceRelevance
" Pharmacokinetic (PK) and biodistribution studies can help inform decisions determining particle size, coatings, or other features early in nanoparticle development."( Rapid pharmacokinetic and biodistribution studies using cholorotoxin-conjugated iron oxide nanoparticles: a novel non-radioactive method.
Bhattarai, N; Ditzler, S; Ellenbogen, R; Hansen, SJ; Knoblaugh, S; Lee, D; Lee, MJ; Olson, JM; Sun, C; Veiseh, O; Zhang, M, 2010
)
0.36
"To address this problem, we developed an economical, radioactivity-free method for assessing serum half-life and tissue distribution of nanoparticles in mice."( Rapid pharmacokinetic and biodistribution studies using cholorotoxin-conjugated iron oxide nanoparticles: a novel non-radioactive method.
Bhattarai, N; Ditzler, S; Ellenbogen, R; Hansen, SJ; Knoblaugh, S; Lee, D; Lee, MJ; Olson, JM; Sun, C; Veiseh, O; Zhang, M, 2010
)
0.36
"We report here a simple near-infrared fluorescence based methodology to assess PK properties of nanoparticles in order to integrate pharmacokinetic data into early nanoparticle design and synthesis."( Rapid pharmacokinetic and biodistribution studies using cholorotoxin-conjugated iron oxide nanoparticles: a novel non-radioactive method.
Bhattarai, N; Ditzler, S; Ellenbogen, R; Hansen, SJ; Knoblaugh, S; Lee, D; Lee, MJ; Olson, JM; Sun, C; Veiseh, O; Zhang, M, 2010
)
0.36
" Contrary to ICG, the pharmacokinetic properties of SIDAG are shifted toward renal elimination, caused by the high hydrophilicity of the molecule."( Cyanine dyes as contrast agents for near-infrared imaging in vivo: acute tolerance, pharmacokinetics, and fluorescence imaging.
Ebert, B; Licha, K; Riefke, B; Sukowski, U, 2011
)
0.37
"5-HSA/TIMP-2 exhibited a prolongation of blood half-life to 19."( Pharmacokinetics and biodistribution of human serum albumin-TIMP-2 fusion protein using near-infrared optical imaging.
Bang, JK; Hahm, DH; Han, D; Her, S; Kim, YH; Kim, YJ; Kwon, SH; Lee, MS; Lee, SM; Shim, I; Song, YS, 2011
)
0.37
"We evaluated the pharmacokinetic profile and biodistribution of HSA/TIMP-2 with favorable results, providing new information for more effective approaches to cancer therapeutics using HSA/TIMP-2."( Pharmacokinetics and biodistribution of human serum albumin-TIMP-2 fusion protein using near-infrared optical imaging.
Bang, JK; Hahm, DH; Han, D; Her, S; Kim, YH; Kim, YJ; Kwon, SH; Lee, MS; Lee, SM; Shim, I; Song, YS, 2011
)
0.37
" The binding potential (Bp) and the sum of the pharmacokinetic rate constants (SKRC) of Cy5."( Investigation of injection dose and camera integration time on quantifying pharmacokinetics of a Cy5.5-GX1 probe with dynamic fluorescence imaging in vivo.
Chen, X; Dai, Y; Kang, X; Liang, J; Nie, Y; Wang, G; Wu, K; Yin, J; Zhang, X, 2016
)
0.43

Compound-Compound Interactions

ExcerptReferenceRelevance
" It appears that DiI tracing of neural connections in the teleost CNS yields very consistent results and that the combination with immunocytochemistry is very reliable."( DiI tracing in combination with immunocytochemistry for analysis of connectivities and chemoarchitectonics of specific neural systems in a teleost, the Atlantic salmon.
Ekström, P; Holmqvist, BI; Ostholm, T, 1992
)
0.28
" In conclusion, Cy dye labeling combined with three-dimensional fractionation is a feasible strategy for identifying differentially expressed serum proteins in an NPC xenograft model, and Prx-II may represent a potential NPC biomarker."( Identification of potential serum markers for nasopharyngeal carcinoma from a xenografted mouse model using Cy-dye labeling combined with three-dimensional fractionation.
Chang, KP; Chang, YS; Chang, YT; Hao, SP; Huang, YS; Peng, PH; Tsang, NM; Wu, CC; Yeh, CT; Yu, JS, 2008
)
0.35
"The aim of the present study was to investigate the efficacy of human umbilical cord‑derived mesenchymal stem cell (HUMSCs) embedded in platelet poor plasma (PPP) gel combined with amnion (PPPA) in improving wound healing on Sprague‑Dawley (SD) rats."( Platelet poor plasma gel combined with amnion improves the therapeutic effects of human umbilical cord‑derived mesenchymal stem cells on wound healing in rats.
Chu, S; Gan, S; Ma, J; Ma, L; Maldonado, M; Tang, S; Yang, L; Zhou, J, 2017
)
0.46
" This study presents response of wild and drug resistant breast cancer cells to classical photodynamic therapy with Photofrin or experimental photodynamic therapy with cyanine IR-775, combined with electroporation."( Biological effects in photodynamic treatment combined with electropermeabilization in wild and drug resistant breast cancer cells.
Chodaczek, G; Kotulska, M; Kulbacka, J; Rossowska, J; Saczko, J; Weżgowiec, J, 2018
)
0.48

Bioavailability

ExcerptReferenceRelevance
" This drug, therefore affects the bioavailability of two major respiratory complex I substrates which would normally contribute substantially to supplying the reducing equivalents for mitochondrial electron transport for generation of ATP in the renal cell."( Action of diclofenac on kidney mitochondria and cells.
Halliwell, B; Ng, LE; Vincent, AS; Wong, KP, 2006
)
0.33
" In particular, tricarbocyanines have the advantage that light at their emission and absorption maxima in the near-infrared (NIR) region around 650-900 nm is relatively poorly absorbed by biomolecules, and so can penetrate deeply into tissues."( [Development of near-infrared fluorescent probes for in-vivo imaging].
Kojima, H, 2008
)
0.67
" This approach can significantly advance the therapeutic potential of RNA interference by providing a way not only to effectively shuttle siRNA to target sites but also to noninvasively assess the bioavailability of the siRNA molecule."( Development and application of a dual-purpose nanoparticle platform for delivery and imaging of siRNA in tumors.
Kumar, M; Medarova, Z; Moore, A; Ng, SW, 2009
)
0.35
"4 kDa) moiety in order to increase its solubility and bioavailability to circulating neutrophils."( Synthesis of the Cyanine 7 labeled neutrophil-specific agents for noninvasive near infrared fluorescence imaging.
Liu, Z; Pan, D; Pu, L; Xiao, L; Yang, M; Zhang, Y, 2010
)
0.36
" Furthermore, MRI could be used to quantitatively monitor nanodrug bioavailability in the tumor tissue throughout the course of treatment."( Image-guided breast tumor therapy using a small interfering RNA nanodrug.
Dai, G; Kumar, M; Medarova, Z; Moore, A; Yigit, M, 2010
)
0.36
" To optimize the bioavailability of existing fluorescent probes, a hydrophobic affinity tag is installed, which enhances albumin binding."( Optimizing the bioavailability of small molecular optical imaging probes by conjugation to an albumin affinity tag.
Alsibai, W; Bremer, C; Hahnenkamp, A; Höltke, C, 2014
)
0.4
" One of the ways to improve its therapeutic potential would be to enhance its bioavailability to cancer tissue by developing a method for targeted delivery."( Improving Therapeutic Potential of Farnesylthiosalicylic Acid: Tumor Specific Delivery via Conjugation with Heptamethine Cyanine Dye.
Chordia, MD; Chung, LW; Guan, Y; Li, J; Liu, ZQ; Pan, D; Wang, JP; Xiao, L; Yue, W; Zhang, Y, 2017
)
0.46
" Attempts to improve oral bioavailability have traditionally focused on enhancing drug solubility and membrane permeability, and the use of synthetic nanoparticles has also been investigated."( The Potential of Exosomes From Cow Milk for Oral Delivery.
Anchordoquy, TJ; Angle, BM; Betker, JL; Graner, MW, 2019
)
0.51
" However, the biomedical applications of them were limited by the large size, low dispersivity, poor bioavailability within cells and metabolic problems."( Renal-clearable ultrasmall covalent organic framework nanodots as photodynamic agents for effective cancer therapy.
Cao, F; Dong, K; Kang, L; Qu, X; Ren, J; Wang, F; Wang, Z; Zhang, L; Zhang, Y, 2019
)
0.51

Dosage Studied

ExcerptRelevanceReference
" The mean dose-response curves for apoptosis of six healthy volunteers obtained with both methods were steep below 1 Gy and flatter at higher doses."( Flow cytometry as a quantitative and sensitive method to evaluate low dose radiation induced apoptosis in vitro in human peripheral blood lymphocytes.
Cornelissen, M; De Ridder, L; Hertveldt, K; Philippé, J; Thierens, H; Vral, A, 1997
)
0.3
" Moreover, the assessment of cellular functions in parasites treated with increasing concentrations of drugs certified the capacity of these techniques to establish dose-response curves and to permit the detection of side effects."( Leishmania infantum promastigotes: flow cytometry as a possible tool for assessing the effects of drugs on cellular functions.
Azas, N; Delmas, F; Di Giorgio, C; Gasquet, M; Timon-David, P, 1997
)
0.3
"5-MORF25/BHQ3-cDNA18 duplex or equal molar dosage of single-chain Cy5."( Optical pretargeting of tumor with fluorescent MORF oligomers.
Dou, S; He, J; Hnatowich, DJ; Liu, G; Liu, X; Rusckowski, M; Wang, Y; Zhang, S,
)
0.13
" Using multiparameter flow cytometry and the low-volume, high-sample format of 96-well plates, it is possible to rapidly evaluate a dose-response curve for metabolites based on variables including initial compound concentrations, hepatocyte cell line metabolic activities, and time."( A high-throughput cell-based toxicity analysis of drug metabolites using flow cytometry.
Buenz, EJ, 2007
)
0.34
"Array comparative genomic hybridization (array CGH) is a method for detecting gains and losses of DNA segments or gene dosage in the genome."( Technical demonstration of whole genome array comparative genomic hybridization.
Heryet, C; Kennett, JY; Lam, WL; Saprunoff, H; Watson, SK, 2008
)
0.35
" In the organotypic slice cultures, modulation of Tau aggregation was independent of changes in phosphorylation at disease and microtubule binding relevant epitopes for both dosing regimes."( Inhibition of tau polymerization with a cyanine dye in two distinct model systems.
Chang, E; Congdon, EE; Conrad, C; Duff, KE; Figueroa, YH; Kuret, J; Toneva, G; Wang, L, 2009
)
0.35
" In vivo, a SAV dosing of 1 mg/kg once in 48 hours (i."( The antiproliferative cytostatic effects of a self-activating viridin prodrug.
Aikawa, E; Blois, J; Cantley, LC; Ellson, C; Figueiredo, JL; Josephson, L; Kohler, R; Smith, A; Weissleder, R; Yaffe, MB; Yuan, H, 2009
)
0.35
" Compared to conventional transfection methods, the effective therapeutic dosage of microRNA-29b is reduced from the microgram level to the nanogram level by lipoplexes prepared in the microwell array."( Surface-mediated nucleic acid delivery by lipoplexes prepared in microwell arrays.
Gallego-Perez, D; Kwak, KJ; Lee, LJ; Nana-Sinkam, SP; Terp, MC; Wu, Y, 2013
)
0.39
" Here, we present a faster alternative based on flow cytometry, by determining the dose-response curve of cellular response to a cytokine."( Rapid determination of IL-6 specific activity by flow cytometry.
Cloutier, M; Néron, S; Simard, C, 2014
)
0.4
" When the dosing of oligomers was stopped the intracellular calcium returned to basal levels or below."( Individual aggregates of amyloid beta induce temporary calcium influx through the cell membrane of neuronal cells.
De Genst, E; Dobson, C; Drews, A; Flint, J; Jönsson, P; Klenerman, D; Muyldermans, S; Shivji, N; Vincke, C; Wirthensohn, D, 2016
)
0.43
" Moreover, the system's dosage control and multi-molecular delivery capabilities facilitate intracellular delivery of various molecules as a single agent or in combination and its utility in biological research has been demonstrated by conducting RNA interference assays."( Microscale Symmetrical Electroporator Array as a Versatile Molecular Delivery System.
Hill, W; Hur, SC; Lee, JH; Ouyang, M, 2017
)
0.46
" These results confirmed the ability of the controller to modulate the drug delivery dosage within a therapeutically effective range, while improving safety control."( Closed-loop control of targeted ultrasound drug delivery across the blood-brain/tumor barriers in a rat glioma model.
Alexander, PM; Aryal, M; McDannold, NJ; Miller, EL; Power, C; Sun, T; Sutton, JT; Vykhodtseva, N; Zhang, Y, 2017
)
0.46
" 94 % of the injection dosage at 24 h post-injection) and its cancer biomarker (APN=aminopeptidase N) specificity, CyP1 can be efficiently transported to the bladder and specially turn on its NIRF signal to report the detection of BC in living mice."( A Renal-Clearable Macromolecular Reporter for Near-Infrared Fluorescence Imaging of Bladder Cancer.
He, S; Huang, J; Jiang, Y; Li, J; Pu, K, 2020
)
0.56
" Sustained-release drug implants often involve burst release of the drugs and the dosage from the implants cannot be controlled after implantation, which may lead to local side effects."( Laser-Activated Drug Implant for Controlled Release to the Posterior Segment of the Eye.
Gaeke, S; He, X; Kao, WW; Li, SK; Miller, D; Park, YC; Williams, B; Yuan, Z, 2021
)
0.62
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
fluorochromeA fluorescent dye used to stain biological specimens.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (2)

ClassDescription
cyanine dyeCyanine dyes are synthetic dyes with the general formula R2N[CH=CH]nCH=N(+)R2 <-> R2N(+)=CH[CH=CH]nNR2 (n is a small number) in which the nitrogen and part of the conjugated chain usually form part of a heterocyclic system, such as imidazole, pyridine, pyrrole, quinoline and thiazole.
organic iodide salt
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Research

Studies (5,093)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990265 (5.20)18.7374
1990's909 (17.85)18.2507
2000's1600 (31.42)29.6817
2010's1970 (38.68)24.3611
2020's349 (6.85)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 6.45

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 Index6.45 (24.57)
Research Supply Index8.57 (2.92)
Research Growth Index5.02 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (6.45)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials4 (0.08%)5.53%
Reviews72 (1.36%)6.00%
Case Studies4 (0.08%)4.05%
Observational0 (0.00%)0.25%
Other5,207 (98.49%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]