Abstract
A series of new compounds—arylbis(indol-3-yl)methylium derivatives—were synthesized and their antimicrobial activity was evaluated. All the compounds turned out to be highly active, with MIC depending on their structure and the length of N-alkyl residues. The parent triarylmethane compounds possess weaker activity.
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References
Culp SJ, Beland FA. Malachite green: a toxicological review. J Am Coll Toxicol. 1996;15:219–38.
National Toxicology Program. Toxicology and carcinogenesis studies of malachite green chloride and leucomalachite green. Natl. Toxicol. Program Tech. Rep. Ser. 2005;527:1–312. https://pubmed.ncbi.nlm.nih.gov/15891780/.
Gillespie DE, Brady SF, Bettermann AD, Cianciotto NP, Liles MR, Rondon MR, et al. Isolation of antibiotics turbomycin A and B from a metagenomic library of soil microbial DNA. Appl Environ Microbiol. 2002;68:4301–6.
Lavrenov SN, Luzikov YN, Bykov EE, Reznikova MI, Stepanova EV, Glazunova VA, et al. Preobrazhenskaya MN. Synthesis and cytotoxic potency of novel tris(1-alkylindol-3-yl)methylium salts: Role of N-alkyl substituents. Bioorg Med Chem. 2010;18:6905–13.
Durandin NA, Tsvetkov VB, Bykov EE, Kaluzhny DN, Lavrenov SN, Tevyashova AN, et al. Quantitative parameters of complexes of tris(1-alkylindol-3-yl)methylium salts with serum albumin: Relevance for the design of drug candidates. J Photochem Photobiol B Biol. 2016;162:570–6.
Efimova SS, Tertychnaya TE, Lavrenov SN, Ostroumova OS. The mechanisms of action of triindolylmethane derivatives on lipid membranes. Acta Nat. 2019;3:38–45.
MP MacWilliams. Indole test protocol. American Society for Microbiology; 2009. http://www.asmscience.org/content/education/protocol/protocol.3202.
El Sayed MT, Ahmed KM, Mahmoud K, Hilgeroth A. Synthesis, cytostatic evaluation and structure activity relationships of novel bis-indolylmethanes and their corresponding tetrahydroindolocarbazoles. Eur J Med Chem. 2015;90:845–59. https://doi.org/10.1016/j.ejmech.2014.12.008.
Praveen C, DheenKumar P, Muralidharan D, Perumal PT. Synthesis, antimicrobial and antioxidant evaluation of quinolines and bis(indolyl)methanes. Bioorg Med Chem Lett. 2010;20:7292–6. https://doi.org/10.1016/j.bmcl.2010.10.075. ISSN 0960-894X.
NCCLS. Reference method for broth dilution antibacterial susceptibility testing. USA: NCCLS; 2000.
Acknowledgements
The research was supported by a grant from the Russian Science Foundation (project no. 16-15-10300P).
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Panov, A.A., Lavrenov, S.N., Mirchink, E.P. et al. Synthesis and antibacterial activity of novel arylbis(indol-3-yl)methane derivatives. J Antibiot 74, 219–224 (2021). https://doi.org/10.1038/s41429-020-00389-9
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DOI: https://doi.org/10.1038/s41429-020-00389-9
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