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1.
E. Lukevics D. Zaruma J. Ashaks I. Shestakova I. Domracheva A. Gulbe V. Bridane 《Chemistry of Heterocyclic Compounds》2008,44(5):559-564
It has been found that the nature of the substituent, its position in the quinoline ring, and the nature of the metal significantly
affect the antitumor activity and toxicity of metal 8-quinolinethiolates. The most cytotoxic towards human fibrosarcoma HT-1080
and mouse hepatoma MG-22A tumor cells are the 6-methoxy-8-quinolinethiolates of rhodium, osmium, iridium, indium, antimony,
and bismuth, however these are highly toxic towards normal mouse embryonic NIH 3T3 fibroblasts. The iridium 5-methyl-8-quinolinethiolate
is somewhat less active to MG-22A cells but shows quite good selectivity of action because of its markedly lower toxicity.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 711–717, May, 2008. 相似文献
2.
D. Zaruma E. Lukevics L. Ignatovich I. Shestakova I. Domracheva V. Bridane E. Yashchenko J. Ashaks 《Chemistry of Heterocyclic Compounds》2012,47(12):1539-1543
A series of 8-quinolinethiolates, and 3-methyl-, 4-methyl-, 5-methyl-, 6-methyl-, 7-methyl-, and 6-methoxy-8-quinolinethiolates
of tin(II), vanadium(IV), and molybdenum(VI) has been synthesized. Their cytotoxicity on HT-1080 tumor cells (human fibrosarcoma)
and MG-22A (mouse hepatoma) cells has been studied. It was established that all of the investigated complexes of 8-quinolinethiol
and majority of the complexes of 8-quinolinethiol derivatives possessed very high cytotoxicity towards both cell lines. Their
toxicity in relation to mouse embryo fibroblasts NIH 3T3 depended on the position of the substituent in the quinoline ring.
Complexes of tin and vanadium with 4-methyl-, 5-methyl-, and 6-methoxy-8-quinolinethiol derivatives were less toxic. 4-Methyl-,
5-methyl-, and 6-methoxy-8-quinolinethiolates of vanadium demonstrated the highest selectivity of cytotoxic action. 相似文献
3.
E. Lukevics D. Zaruma J. Ashaks I. Shestakova I. Domracheva V. Bridane E. Yashchenko 《Chemistry of Heterocyclic Compounds》2009,45(2):182-187
A series of 2-methyl, 4-methyl, and 2,4-dimethyl-8-quinolineselenolates of ruthenium, rhodium, osmium, and iridium has been
synthesized and their cytotoxicity towards HT-1080 (human fibrosarcoma) and MG-22A (mouse hepatoma) tumor cells studied. It
was found that all of the osmium complexes had a high cytotoxicity towards both cell lines. Their toxicity towards the normal
mouse embryonic fibroblasts NIH-3T3 depends on the position and number of methyl groups in the quinoline ring and decreases
in the order 2-Me > 4-Me > 2,4-Me2. The greatest selectivity in cytoxic activity is noted for iridium 4-methyl-8-quinolineselenolate and ruthenium 2-methyl-8-quinolineselenolate.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 230–236, February, 2009. 相似文献
4.
E. Lukevics I. Shestakova I. Domracheva A. Nesterova J. Ashaks D. Zaruma 《Chemistry of Heterocyclic Compounds》2006,42(1):53-59
A series of 2-methyl-, 4-methyl-, and 2,4-dimethyl-8-quinolineselenolates of zinc, cadmium, mercury, nickel, palladium, platinum,
arsenic, antimony, and bismuth has been synthesized and their cytotoxicity has been studied on HT-1080 (human fibrosarcoma),
MG-22A (mouse hepatoma), B16 (mouse melanoma), and Neuro 2A (mouse neuroblastoma) tumor cells. Mercury complexes were distinguished
by high cytotoxicity on all the cell lines. Palladium complexes possessed somewhat lower activity and were significantly less
toxic in relation to normal NIH 3T3 mouse embryo fibroblasts. All the studied metal 2-methyl-8-quinolineselenolates displayed
high cytotoxicity on B16 melanoma, arsenic 4-methyl-8-quinolineselenolate acted most effectively on HT-1080 and MG-22A cells.
Di(4-methyl-8-quinolyl) diselenide also possessed high cytotoxicity on these same cells.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 59–66, January, 2006. 相似文献
5.
J. Ashaks Yu. Bankovsky D. Zaruma I. Shestakova I. Domracheva A. Nesterova E. Lukevics 《Chemistry of Heterocyclic Compounds》2004,40(6):776-780
We have developed a novel method for synthesis of quinoline-8-selenol using selenourea instead of the previously used potassium selenocyanate. We have synthesized a series of metal quinoline-8-selenolates. We have studied the cytotoxic activity of the synthesized compounds against HT-1080, MG-22A, B16, Neuro 2A tumor cells. Mercury quinoline-8-selenolate is distinguished by high cytotoxicity for the three cell lines; the cadmium complex is most effective against B16 melanoma cells. 相似文献
6.
Pavel Arsenyan Irina Shestakova 《Phosphorus, sulfur, and silicon and the related elements》2013,188(9):2427-2430
The cytotoxic activity of a series of methylammonium tellurates on human fibrosarcoma HT-1080, mouse hepatoma MG-22A, and mouse fibroblasts 3T3 cell lines is described. The role of tellurates as free radical regulators is discussed. 相似文献
7.
Luba Ignatovich Olga Starkova Vitalijs Romanovs Ilze Sleiksha Irina Shestakova Jury Popelis Edmunds Lukevics 《Comptes Rendus Chimie》2013,16(6):621-627
The reaction of 1,2-phenylenediamine with a variety of silicon- or germanium-containing 2-furaldehydes or 2-thienylcarbaldehydes in DMFA gave the corresponding benzimidazole derivatives in moderate yields (36–49%) in the presence of sodium hydrogen sulfite. As a result, a new series of silyl, germyl substituted hetarylbenzimidazoles were synthesized and their in vitro cytotoxicity was studied. The quaternisation of N-substituted benzimidazoles by heating with various alkyl, allyl and propargyl chlorides and bromides leads to the formation of benzimidazolinium salts. Potential cytotoxic activity of synthesized new benzimidazoles and benzimidazolinium salts was tested in vitro on two monolayer tumour cell lines: MG-22A (mouse hepatoma), HT-1080 (human fibrosarcoma) and normal mouse fibroblasts (NIH 3T3) and compared with corresponding benzimidazoles. 相似文献
8.
A. Zablotskaya I. Segal S Germane I. Shestakova I. Domracheva A. Nesterova A. Geronikaki E. Lukevics 《Chemistry of Heterocyclic Compounds》2002,38(7):859-866
Trimethylsilyl ethers of various hydroxyl-containing thiazole derivatives have been synthesized. The psychotropic activity (in vivo) and the cytotoxicity (in vitro on tumor cell lines HT-1080 and MG-22A) of these ethers and of their unsilylated precursors have been studied. It was discovered that the obtained compounds possess a sedative action. A moderate cytotoxic effect was detected for piperidine-containing thiazoles, displayed most strongly in relation to MG-22A cells. 相似文献
9.
We have obtained various diphenylmethylsilyl- and carbonyl-substituted isoxazoles by [2+3]-dipolar cycloaddition of nitrile oxides to diphenylmethylsilyl-, hydroxymethyl-, methoxymethyl-, and ethoxycarbonylacetylenes. We have observed that the isoxazoles obtained exhibit moderate cytotoxicity relative to the HT-1080 and MG-22A cell lines. The highest activity level is displayed by 3-methyl-5-diphenylmethylsilylisoxazole. 相似文献
10.
E. Lukevics I. Shestakova I. Domracheva E. Yashchenko D. Zaruma J. Ashaks 《Chemistry of Heterocyclic Compounds》2007,43(5):634-636
It has been shown that the introduction of a methyl group at position 4 of the quinoline ring in metal 8-quinolinethiolates
brings about a significant increase in the selectivity of their cytotoxic activity. It was found that rhodium 4-methyl-8-quinolinethiolate
is 46 times less toxic than the unsubstituted 8-quinolinethiolate but with comparable toxicity towards MG-22A tumor cells
(LC50 2 μg/ml).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 755–758, May, 2007. 相似文献
11.
R. Abele E. Abele K. Rubina O. Dzenitis P. Arsenyan I. Shestakova A. Nesterova I. Domracheva J. Popelis S. Grinberga E. Lukevics 《Chemistry of Heterocyclic Compounds》2002,38(7):867-872
We have developed a two-step method for synthesis of 3-(hetarylthio)-1-propynyl(trimethyl)silanes from thiols in a phase-transfer catalysis system HCCCH2Br-solid K2CO3-18-crown-6-toluene followed by reaction with n-BuLi-Me3SiCl in ether or THF. We have observed that 3-[1,3-bis(trimethylsilyl)-2-propynyl]thioindole displays high cytotoxicity in HT-1080 and MG-22A tumor cell lines. 相似文献
12.
E. Abele J. Popelis I. Shestakova I. Domracheva P. Arsenyan E. Lukevics 《Chemistry of Heterocyclic Compounds》2004,40(6):742-746
A method has been developed for the synthesis of di(3-indolyl) selenides. From indole and SeO2. N-Alkyl derivatives of di(3-indolyl) selenide have been obtained in the two-phase system alkyl halide–solid K2CO3 (or KOH)–18-crown-6–toluene. It was discovered that N-unsubstituted di(3-indolyl) selenides possess high cytotoxicity on HT-1080 and MG-22A tumor cell lines. 相似文献
13.
E. Lukevics I. Shestakova I. Domracheva E. Yashchenko D. Zaruma J. Ashaks 《Chemistry of Heterocyclic Compounds》2007,43(5):629-633
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 (LC50 <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 (NH2, Cl, OMe, NO2) 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 (LC50 100 μg/ml with a corresponding LD50 of 874 mg/kg ).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 750–754, May 2007. 相似文献
14.
The cytotoxicity of 39 compounds, including eighteen flavonoids (flavanones, 1-10; flavones, 11-17; flavanol, 18), sixteen phenolic acid derivatives (aromatic acids, 19-24; aldehyde, 25; esters, 26-34) and five glycerides (35-39), isolated from Mexican propolis, were evaluated against a panel of six different cancer cell lines; murine colon 26-L5 carcinoma, murine B16-BL6 melanoma, murine Lewis lung carcinoma, human lung A549 adenocarcinoma, human cervix HeLa adenocarcinoma and human HT-1080 fibrosarcoma. A phenylpropanoid-substituted flavanol, (2R,3S)-8-[4-phenylprop-2-en-1-one]-4',7-dihydroxy-3',5-dimethoxyflavan-3-ol (18), showed the most potent cytotoxicity against A549 cells (IC50, 6.2 microM) and HT-1080 cells (IC50, 3.9 microM), stronger than those of the clinically used anticancer drug, 5-fluorouracil (IC50, 7.5 microM and 5.4 microM, respectively). Based on the observed results, the structure-activity relationships are discussed. 相似文献
15.
E. Lukevics L. Ignatovich I. Sleiksha V. Romanov S. Grinberga J. Popelis I. Shestakova 《Chemistry of Heterocyclic Compounds》2007,43(2):143-150
A new method was developed for the synthesis of silicon-and germanium-containing acetylfurans and acetylthiophene by metallation
of 2-acetylfuran or 2-acetylthiophene with n-BuLi at low temperature after protection of the carbonyl group with lithium N-methylpiperazide
and reaction of the lithium derivative with various trialkyl-, alkylphenyl-, and cycloalkylchlorosilanes or trialkylchloro(bromo)germanes.
The cytotoxic activity of the new compounds was studied, and it was established that the silicon-and germanium-containing
acetylfurans and acetylthiophenes are substances with low toxicity (LD50 312->2000 mg/kg) and have low cytotoxicity toward HT-1080 and MG-22A tumor cells.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 192–199, February, 2007. 相似文献
16.
E. Lukevics D. Jansone L. Leite J. Popelis G. Andreeva I. Shestakova I. Domracheva V. Bridane I. Kanepe 《Chemistry of Heterocyclic Compounds》2009,45(10):1226-1234
A series of phenylvinyl derivatives of 4,6,6-trimethyl-2-oxo-1,2,5,6-tetrahydropyridine-3-carbonitriles has been synthesized
and their cytotoxic activity towards HT-1080 (human fibrosarcoma) and MG 22A (mouse hepatoma) tumor cells studied. It was
found that the 2-nitro-, 2- and 3-chloro, 2-fluoro, and 2-bromophenyl derivatives showed high cytotoxic activity towards both
cell lines. The toxicity towards NIH 3T3 normal mouse embryonic fibroblasts depends on the nature and position of the substituent
in the phenyl ring. The greatest selectivity of cytotoxic effect was seen in the 2-bromophenyl derivative. 相似文献
17.
Zhai X Zhao YF Liu YJ Zhang Y Xun FQ Liu J Gong P 《Chemical & pharmaceutical bulletin》2008,56(7):941-945
A series of novel N-anilino-5-methyl-2-(3-(5-(alkylaminomethyl)furan-2-yl-methylthio)propyl)-[1,2,4]triazolo-[1,5-a]pyrimidine-7-amine derivatives were synthesized and evaluated for their in vitro cytotoxicity against two cancer cell lines, Bel-7402 and HT-1080. Compounds 9, 14, 19 and 23 possessed marked cytotoxicity, especially 23 (with IC(50) values of 15.0 microM and 7.8 microM against Bel-7402 and HT-1080 cell lines, respectively), which had emerged as lead compound. The activity was found to depend strongly on substitution pattern of the side chains at C-2 position, and 4-triflouromethylanilino substituent at C-7 position was an option for anticancer potency. 相似文献
18.
A series of novel [1,2,4]triazolo[1,5-a]pyrimidine derivatives has been designed and synthesized in order to find novel anti-tumor compounds. The structures of all the compounds were confirmed by IR, 1H-NMR, MS and elemental analysis. Their anti-tumor activities against cancer cell lines (HT-1080 and Bel-7402) were tested by the MTT method in vitro. Among them, compound 19 displayed the best anti-tumor activity with IC50 values of 12.3 microM and 6.1 microM against Bel-7402 and HT-1080 cell lines respectively. 相似文献
19.
Xinyang Zhao Jingyi Zhang Wei Zhang Zijian Guo Wei Wei Xiuxiu Wang Jing Zhao 《Chemical science》2023,14(5):1114
Ferroptosis has recently emerged as a non-apoptotic form of programmed cell death and promising target for anticancer treatment. However, it is challenging to discover ferroptosis inducers with both highly selective tumour targeting and low cytotoxicity to normal cells. Here, we report an Ir(iii) complex, Ir1, that contains a novel chiral pyridine RAS-selective lethal ligand (Py-RSL). This complex effectively inhibits glutathione peroxidase 4 (GPX4) and ferroptosis suppressor protein 1 (FSP1) to induce ferroptosis in human fibrosarcoma (HT-1080) cells. Notably, metal coordination not only endows Ir1 with fluorescent properties for convenient cellular real-time tracking but also efficiently reduces the off-target toxicity of the Py-RSL ligand. Furthermore, label-free quantitative proteomic profiling revealed that Ir1 simultaneously inhibits the ErbB signalling pathway to enhance tumour suppression. Our work is the first to report a ferroptosis-inducing iridium complex with dual mechanisms of inhibition and provides a highly selective and efficient route to develop new ferroptosis-inducing metallodrugs.Here, we report an Ir(iii) complex that contains a novel chiral pyridine RAS-selective lethal ligand and effectively inhibits GPX4 and FSP1 to induce ferroptosis in human fibrosarcoma (HT-1080) cells. 相似文献
20.
E. Silina S. Belyakov J. Ashaks A. Tokmakov L. Pech D. Zaruma 《Chemistry of Heterocyclic Compounds》2009,45(7):860-865
Bismuth 2-methyl-8-quinolineselenolate, Bi[C9H5(CH3)NSe]3, was synthesized. X-ray analysis was used to determine the structure of this complex. The crystal chemistry of bismuth(III),
antimony(III), and arsenic(III) 2-methyl-8-quinolineselenolates and 2-methyl-8-quinolinethiolates was discussed relative to
the effect of going from Se to S as the ligand atoms and presence of a methyl group at C-2 of the quinoline system and unshared
electron pair of the central atom in the complex. 相似文献