Synthesis and cytotoxic potency of novel tris(1-alkylindol-3-yl)methylium salts: Role of N-alkyl substituents

Лавренов, С. Н.; Luzikov, Yuriy N.; Bykov, Evgeniy E.; Reznikova, M. I.; Степанова, Е В; Glazunova, Valeria A.; Volodina, Yulia L.; Tatarsky, V. V.; Shtil, Alexander A.; Preobrazhenskaya, M. N.

doi:10.1016/j.bmc.2010.07.025

Cited by 20 publications

(16 citation statements)

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“…6 The hetaryl rings in the propeller compounds under study are not symmetrical: they can exist as a mixture of isomeric propeller confor mations because addition of three aromatic (indole) rings to the central atom (a hub) in triindolylmethylium salts makes up a three blade propeller. 11 Rotation of the indole 31G(d)) revealed not only a local minimum on the poten tial energy surface that corresponds to the degenerate, de localized form of triindolyl cation B but also a local mini mum corresponding to cation A with the indolenine ring.…”

Section: Synthesis and Physicochemical Properties Of Tris(1 Alkylindomentioning

confidence: 99%

“…According to data from HPLC, NMR spectroscopy, and mass spectrometry, the resulting N alkylindolylmethanes 2b-m are identical with the compounds described earlier. 6 Tris(1 alkylindol 3 yl)methylium salts 1 are prepared by oxidation of tris(1 alkylindol 3 yl)methanes 2 (e.g., with dichlorodicyanoquinone (DDQ), chloranil, 1,2 trityl ium perchlorate, 9 or FeCl 3 . 10 Earlier, 6 we have oxidized tris(1 alkylindol 3 yl) methanes into tris(1 alkylindol 3 yl)methylium salts in butanol in the presence of the corresponding acid using activated charcoal saturated with atmospheric oxygen.…”

Section: Synthesis and Physicochemical Properties Of Tris(1 Alkylindomentioning

confidence: 99%

“…Tris(1 alkylindol 3 yl)methylium salts have been found 6 to be cytotoxic. The cytotoxicity of these compounds de pends on the length of the alkyl chain, passing through a maximum at C alk = 4-5.…”

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confidence: 99%

“…Since the investigation of TPMAs has revealed the biological activity of compounds with electron donat ing substituents in the phenyl rings, it was reasonable to study first indole containing compounds. Earlier, 6 we have developed a method for the synthesis of symmetrical tris (1 alkylindol 3 yl)methanes and the corresponding tris (1 alkylindol 3 yl)methylium salts.…”

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confidence: 99%

“…The most active compounds of this series induce the apoptosis of tumor cells. 6 In the present work, we developed convenient methods for the preparation of tris(1 alkylindol 3 yl)methylium salts, studied their physicochemical properties, structure-ac tivity correlations (cytotoxicity and antitumor activity), and antibacterial and antifungal properties, and examined some parameters of the mechanism of action of these compounds.…”

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Tris(1-alkylindol-3-yl)methylium salts as a novel class of antitumor agents

et al. 2010

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Tris(1 alkylindol 3 yl)methanes were obtained and oxidized into tris(1 alkylindol 3 yl)methylium salts. The resulting salts are more toxic to cultured tumor cells than to non tumor ones. The cytotoxicity of tris(1 alkylindol 3 yl)methylium salts depends on the length of the substituent at the N atom of the heterocycle, increasing from an N unsubstituted derivative toward N butyl and N pentyl derivatives. A further increase in the length of the N alkyl substituent lowers the cytotoxicity. The cytotoxicity of tris(1 alkylindol 3 yl)methylium salts for tumor cells correlates with their antibacterial and antifungal activity. Tris(1 alkylindol 3 yl)methylium salts produced a cytocide effect on Gram positive microorganisms and the most active compounds, on Gram negative microorganisms as well. Similar patterns of the struc ture-activity relationship of N alkylated tris(indol 3 yl)methylium derivatives, which was ob served for various lines of tumor cells, bacteria, and fungi, suggest the general character of the mechanisms of the death of prokaryotic and eukaryotic cells induced by these compounds.

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Section: Synthesis and Physicochemical Properties Of Tris(1 Alkylindomentioning

confidence: 99%

Section: Synthesis and Physicochemical Properties Of Tris(1 Alkylindomentioning

confidence: 99%

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confidence: 99%

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Tris(1-alkylindol-3-yl)methylium salts as a novel class of antitumor agents

et al. 2010

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Carbocations

McClelland¹

2012

Organic Reaction Mechanisms Series

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Morpho‐functional analyses reveal that changes in the chemical structure of a marine bisindole alkaloid alter the cytotoxic effect of its derivatives

Burattini

Battistelli

Verboni

et al. 2022

Microscopy Res & Technique

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2,2-bis(6-bromo-1H-indol-3-yl) ethanamine, a marine bisindole alkaloid, showed anticancer property in several tumor cell lines thanks to the presence of a 3,3 0diindolylmethane scaffold. Here, the modifications in its chemical structure into alkaloid-like derivatives, have been evaluated, to investigate changes in its biological activities. Three derivatives have been considered and their potential apoptotic action has been evaluated through morpho-functional analyses in a human cancer cell line. Apoptosis appears strongly decreased in the derivatives without the bromine atoms (1) and in those where the bromine atoms have been substituted with fluorine atoms (2). On the contrary, the methylation of indole NH (3) does not alter the alkaloid apoptotic activity that occurs through mitochondria involvement supported by cardiolipin peroxidation and dysfunctional mitochondria presence. This manuscript highlights the alkaloid derivative cytotoxic effect, which is strictly correlated to the presence of N-methylated bisindole alkaloid and bromine atoms, conditions which assure to maintain the pro-apoptotic activity. Since molecular therapies, by targeting mitochondria pathways, have shown positive outcomes against several cancer cells, the alkaloid with bisindole methylated scaffold and the two bromine atoms can be considered a promising candidate to develop new derivatives with strong anticancer property.anticancer activity, apoptotic cell death, marine alkaloids, mitochondria damage, U937 cell line Research Highlights• 2,2-bis(6-bromo-1H-indol-3-yl) ethanamine is an alkaloid known for its anticancer properties.• Morpho-functional analyses evaluated cytotoxicity of its synthetic derivatives in tumor cells.• Anticancer properties depend on the presence of bisindole scaffold and the two bromine units.Marine bisindole alkaloids showed significant cytotoxicity, antineoplastic and antimicrobial properties (Kamel et al., 2020; Veale & Davies-Coleman, 2014). In particular, 2,2-bis(6-bromo-3-indolyl) ethanamine (BrDIMEA), extracted from the Californian tunicate Didemnum candidum and the New Caledonian sponge Orina (Salucci et al., 2018), is a strong cytotoxic agent and its anticancer

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Synthesis and cytotoxic potency of novel tris(1-alkylindol-3-yl)methylium salts: Role of N-alkyl substituents

Cited by 20 publications

References 13 publications

Tris(1-alkylindol-3-yl)methylium salts as a novel class of antitumor agents

Tris(1-alkylindol-3-yl)methylium salts as a novel class of antitumor agents

Carbocations

Morpho‐functional analyses reveal that changes in the chemical structure of a marine bisindole alkaloid alter the cytotoxic effect of its derivatives

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