Synthesis of Quinoline-8-selenol, Its Complex Compounds with Metals and Their Cytotoxic Activity

Ashaks, J.; Bankovsky, Yu.; Zaruma, D.; Шестакова, И.; Домрачева, Илона; Нестерова, А. В.; Lukevics, É.

doi:10.1023/b:cohc.0000040774.96325.d1

Cited by 15 publications

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“…Cytotoxicity of compounds 1-28. in vitro relative to monolayers of HT-1080 tumor cells (human fibrosarcoma), MG-22A (mouse hepatoma), and NIH-3T3 normal cells (embryonic mouse fibroblasts) were measured in 96 well plastic plates using the dyes CV, MTT, and NR according to methods [28,29] certified by us earlier [1, [30][31][32]. The concentrations of compounds causing the death of 50% of the cells (LC 50 , µg/ml) are given in Tables 1-3.…”

Section: Methodsmentioning

confidence: 99%

Cytotoxic di(8-quinolyl) disulfides

Lukevics

Шестакова

Домрачева

et al. 2007

Chem Heterocycl Compd

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It has been shown that the nature of the substituent and its position in the quinoline ring markedly affects the antitumor activity and toxicity of di (8-quinolyl) disulfides. The greatest cytotoxicity in the series of methyl derivatives was shown by the 7-, 6-, and 3-isomers towards HT-1080 (human fibrosarcoma) and MG-22A (mouse hepatoma) tumor cells while the 2-methyl derivatives generally have no effect on these cells. High cytotoxicity was also shown (LC 50 <1 µg/ml) by other 7-substituted compounds (Cl, PhO, PhS) but they also appear to be highly toxic towards normal NIH 3Y3 mouse embryonic fibroblasts. A similar trend was observed in the series of 5-substituted compounds (NH 2 , Cl, OMe, NO 2 ) which were highly active towards tumor cells but were toxic to normal cells. The best selectivity was found for the 6-substituted quinolines, the 6-methoxy derivative at low concentration brought about the death of tumor cells but appeared much less toxic towards normal fibroblasts (LC 50 100 µg/ml with a corresponding LD 50 of 874 mg/kg ).We have previously shown that di(8-quinolyl) disulfide 1 has high cytotoxicity (LC 50 0.3-0.4 µg/ml) towards HT-1080 tumor cells (human fibrosarcoma) and MG-22A (mouse hepatoma) [1]. However, while this disulfide is highly active towards tumor cells it is toxic towards normal NIH 3T3 mouse embryonic fibroblasts (LC 50 0.7 µg/ml) [1].With the aim of decreasing the toxicity and increasing the selectivity we have prepared a series of disulfides containing one (2-25) or two (26-28) electron donor or electron acceptor substituents both in the pyridine and in the benzene part of the quinoline ring and we have studied the effect of the nature and position of the substituent on their cytotoxicity (LC 50 ) in two lines of tumor cells (HT-1080 and MG-22A) as well as to normal NIH 3T3 fibroblasts which served as a measure of the toxicity of the compound (alternative method of determining LD 50 see [2]). N S S N R R 1-28 1 R = H, 2 R = 2-Me, 3 R = 3-Me, 4 R = 4-Me, 5 R = 5-Me, 6 R = 6-Me, 7 R = 7-Me, 8 R = 2-Ph, 9 R = 4-Ph, 10 R = 5-Ph, 11 R = 6-Ph, 12 R = 4-Cl, 13 R = 5-Cl, 14 R = 7-Cl, 15 R = 2-MeO, 16 R = 5-MeO, 17 R = 6-MeO, 18 R = 4-PhO, 19 R = 5-PhO, 20 R = 7-PhO, 21 R = 5-PhS, 22 R = 7-PhS, 23 R = 5-SO 3 H, 24 R = 5-NO 2 , 25 R = 5-NH 2 , 26 R = 2,4-Me 2 , 27 R = 2,7-Me 2 , 28 R = 5,7-Cl 2

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Section: Methodsmentioning

confidence: 99%

Cytotoxic di(8-quinolyl) disulfides

Lukevics

Шестакова

Домрачева

et al. 2007

Chem Heterocycl Compd

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“…Bismuth 8-quinolineselenolate (1) was synthesized according to our previous procedure [6]. X-ray Diffraction Structural Analysis.…”

Section: Methodsmentioning

confidence: 99%

“…Complex 1 was synthesized in 83.5% yield by the general scheme described in our previous work [6]. The molecular and crystal structure of 1 was established by X-ray diffraction structural analysis.…”

Section: ____________________________________________________________mentioning

confidence: 99%

“…Professor E. Lukevics and his coworkers have studied the cytotoxicity of a series of complexes of 8-quinolineselenol and 8-quinolinethiol synthesized in our laboratory [6,24] to evaluate the effect of the ligand on the cytotoxicity of complexes containing M-S and M-Se bonds. Complex 2 was found to have high cytotoxicity in all the tumor cell lines studied but, unfortunately, are also highly toxic relative to normal cells.…”

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confidence: 99%

“…Bankovsky [1]. At the initiative of Academician Bankovsky, studies were undertaken of chelate compounds of 8-quinolineselenol (SeQu), which is a structural analog of 8-quinolinethiol and 8-quinolinol [2][3][4][5][6][7]. 8-Quinolineselenol, its derivatives, and their complexes hold interest in regard to their possible biological activity.…”

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Synthesis and structure of bismuth 8-quinoline-selenolate Bi(C9H6NSe)3

Silina

Ashaks

Belyakov

et al. 2007

Chem Heterocycl Comp

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Bismuth 8-quinolineselenolate Bi(C 9 H 6 NSe) 3 was synthesized. The molecular and crystal structure of this compound was determined by X-ray diffraction structural analysis. The effect of replacing the ligand atoms Se→S and the role of the unshared electron pair on the formation of the coordination polyhedron of the central bismuth atom in bismuth(III) 8-quinolineselenolate and bismuth(III) 8-quinolinethiolate, which are complexes of a Group V p-element in an incomplete valence state was discussed.Keywords: bismuth chelate compounds, bismuth 8-quinolineselenolate, bismuth 8-quinolinethiolate, unshared electron pair (UEP), X-ray diffraction structural analysis.Multifaceted systematic studies of chelate compounds of transition and nontransition metals with 8-quinolinethiol (SQu), 8-quinolinol (OQu), and its derivatives have been carried out at the Chelate Compounds Laboratory in the Institute of Inorganic Chemistry at the Riga Technical University headed by Academician Yu. Bankovsky [1]. At the initiative of Academician Bankovsky, studies were undertaken of chelate compounds of 8-quinolineselenol (SeQu), which is a structural analog of 8-quinolinethiol and 8-quinolinol [2-7]. 8-Quinolineselenol, its derivatives, and their complexes hold interest in regard to their possible biological activity.In systematic studies, the differences in the physicochemical properties of chelate compounds of transition and nontransition elements and the possible use of these compounds have been repeatedly interpreted using X-ray diffraction structural analysis data, leading to an understanding of the role of the chelate-forming M-O, M-S, M-Se, and M-N chemical bonds. Physicochemical and X-ray diffraction data on the M-O, M-S, and M-Se chemical bond nature in chelate compounds of transition metals and conclusions regarding additional M←S π-bonding (direct donor-acceptor π-bond) have been examined in our previous work [8,9]. _______ * Dedicated to the memory of Academician Yurii Bankovsky, the founder of the chemistry of 8-mercaptoquinoline (December 22, 1927 -January 28, 2003 on the occasion of the eightieth anniversary of his birth. __________________________________________________________________________________________

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