Details
Stereochemistry | ACHIRAL |
Molecular Formula | C23H25N2.HO |
Molecular Weight | 346.4653 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[OH-].CN(C)C1=CC=C(C=C1)C(C2=CC=CC=C2)=C3C=CC(C=C3)=[N+](C)C
InChI
InChIKey=WETHTEMZJSDITG-UHFFFAOYSA-M
InChI=1S/C23H25N2.H2O/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;1H2/q+1;/p-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 |
Molecular Formula | HO |
Molecular Weight | 17.0073 |
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 |
|
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 |
|
Tumor promotion by metanil yellow and malachite green during rat hepatocarcinogenesis is associated with dysregulated expression of cell cycle regulatory proteins. | 2003 |
|
Establishment of a transgenic yeast screening system for estrogenicity and identification of the anti-estrogenic activity of malachite green. | 2008 Dec 15 |
|
Inhibition of electric eel acetylcholinesterase by triarylmethane dyes. | 2008 Sep 25 |
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 18:37:10 GMT 2023
by
admin
on
Sat Dec 16 18:37:10 GMT 2023
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Record UNII |
ZB3Z3WF9UT
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Record Status |
Validated (UNII)
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Record Version |
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