Details
Stereochemistry | ACHIRAL |
Molecular Formula | C23H25N2 |
Molecular Weight | 329.458 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 1 |
SHOW SMILES / InChI
SMILES
CN(C)C1=CC=C(C=C1)C(C2=CC=CC=C2)=C3C=CC(C=C3)=[N+](C)C
InChI
InChIKey=VFCNQNZNPKRXIT-UHFFFAOYSA-N
InChI=1S/C23H25N2/c1-24(2)21-14-10-19(11-15-21)23(18-8-6-5-7-9-18)20-12-16-22(17-13-20)25(3)4/h5-17H,1-4H3/q+1
Molecular Formula | C23H25N2 |
Molecular Weight | 329.458 |
Charge | 1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Malachite green, an N-methylated diaminotriphenylmethane dye, is used primarily as a therapeutic agent in aquaculture. It controls fungal attacks, protozoan infections and some other diseases caused by helminths on a wide variety of fish and other aquatic organisms. In solution, the dye exists as a mixture of the cation (chromatic malachite green) and its carbinol base, with the ratio depending on the pH of the solution; the dye also can undergo chemical and metabolic reduction to a leuco derivative. Malachite green intercalates with DNA, with a preference for A:T-rich regions, and the leuco derivative bears a structural resemblance to carcinogenic aromatic amines that can form covalent DNA adducts. In mammalian cells, it shows marked cytotoxicity and the ability to induce cell transformation and lipid peroxidation. The toxicity of this dye increases with exposure time, temperature and concentration. It has been reported to cause carcinogenesis, mutagenesis, chromosomal fractures, teratogenecity and respiratory toxicity.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL614058 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16061355 |
15.0 µM [IC50] | ||
Target ID: CHEMBL614735 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16061355 |
2.0 µM [IC50] | ||
Target ID: CHEMBL1075358 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25085484 |
PubMed
Title | Date | PubMed |
---|---|---|
Overexpression of G1/S cyclins and PCNA and their relationship to tyrosine phosphorylation and dephosphorylation during tumor promotion by metanil yellow and malachite green. | 2000 Jul 27 |
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Malachite green induced malignant transformation of Syrian hamster embryo (SHE) cells in primary culture: transformation is associated with enhanced expression of altered p53, bcl-2 and decreased sensitivity to apoptosis. | 2000 Mar |
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Effect of metanil yellow and malachite green on DNA synthesis in N-nitrosodiethylamine induced preneoplastic rat livers. | 2001 Sep |
|
Tumor promotion by metanil yellow and malachite green during rat hepatocarcinogenesis is associated with dysregulated expression of cell cycle regulatory proteins. | 2003 |
|
Hyperphosphorylation of extracellular regulated kinase 2 (ERK2) and inhibition of JNK2 phosphorylation are associated with increased S-phase during transformation of Syrian hamster embryo cells by Malachite Green. | 2004 |
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Treatment of ichthyophthiriasis after malachite green. I. Concrete tanks at salmonid farms. | 2005 Apr 6 |
|
Inhibition of human plasma cholinesterase by malachite green and related triarylmethane dyes: mechanistic implications. | 2005 Aug 15 |
|
Treatment of ichthyophthiriasis after malachite green. II. Earth ponds at salmonid farms. | 2005 Aug 9 |
|
DNA damage and G2/M arrest in Syrian hamster embryo cells during Malachite green exposure are associated with elevated phosphorylation of ERK1 and JNK1. | 2005 Dec 18 |
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Decreased phosphoactive ERKs and JNKs in Malachite-green-transformed Syrian hamster embryo fibroblasts are associated with increased phosphoactive p38 kinase: possible therapeutic importance. | 2006 |
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Elevated phosphorylation of Chk1 and decreased phosphorylation of Chk2 are associated with abrogation of G2/M checkpoint control during transformation of Syrian hamster embryo (SHE) cells by Malachite green. | 2006 Jun 18 |
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Methemoglobinemia due to malachite green ingestion in a child. | 2008 Apr |
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Establishment of a transgenic yeast screening system for estrogenicity and identification of the anti-estrogenic activity of malachite green. | 2008 Dec 15 |
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Inhibition of electric eel acetylcholinesterase by triarylmethane dyes. | 2008 Sep 25 |
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Disrupting actions of bisphenol A and malachite green on growth hormone receptor gene expression and signal transduction in seabream. | 2010 Jun |
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Identification of quaternary ammonium compounds as potent inhibitors of hERG potassium channels. | 2011 May 1 |
|
Population-based in vitro hazard and concentration-response assessment of chemicals: the 1000 genomes high-throughput screening study. | 2015 May |
Substance Class |
Chemical
Created
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Record UNII |
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Record Status |
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