Effect of the organotin compound triethyltin on Ca2+ handling in human prostate cancer cells

Jan, Chung‐Ren; Jiann, Bang‐Ping; Lu, Yih-Chau; Chang, Hong‐Tai; Su, Warren; Chen, Wei‐Chung; Yu, Chia‐Cheng; Huang, Jong‐Khing

doi:10.1016/s0024-3205(01)01500-4

Cited by 27 publications

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“…The design of improved organotin(IV) antitumour agents occupies a significant place in cancer chemotherapy, as revealed from their remarkable therapeutic potential reflected in recent research reports [1][2][3][4][5][6][7][8][9][10][11][12]. Consequently, a large number of organotin(IV) carboxylates have been investigated for their antitumour potential owing to their better hydrolytic stability compared to organotin(IV) halides.…”

Section: Introductionmentioning

confidence: 99%

“…In view of the increasing interest in organotin(IV) carboxylates, a few organotin(IV) complexes of Schiff bases derived from amino acids have also been investigated extensively [24][25][26][27][28][29][30][31][32][33][34][35] and the in vitro cytotoxicity results demonstrated that triphenyltin(IV) compounds are generally more active than CDDP (cisplatin) [34,35]. On the other hand, examples of organotin(IV) carboxylate containing -N=N-skeleton are scanty except for the recent ones on the diorganotin(IV) compounds of the formulations n Bu 2 Sn(LH) 2 and {[ n Bu 2 Sn(LH) 2 ] 2 O} 2 (LH=5-[(E)-2-(aryl)-1-diazenyl]-2-hydroxybenzoate) and the in vitro cytotoxic results were quite promising at least with respect to the some of the standard drugs [36,37]. Recently, three triphenyltin(IV) compounds involving the 2-{[(2Z)-(3-hydroxy-1-methyl-2-butenylidene)]amino}-4-methyl-pentanoate and 2-{[(E)-1-(2-hydroxyphenyl)-alkylidene]amino}-4-methyl-pentanoate skeletons showed encouraging cytotoxic activity across a panel of cell lines [35] and this has prompted us to investigate related systems by modifying the ligand part of the molecule, which might improve dissolution properties and thereby influence cytotoxicity.…”

Section: Introductionmentioning

confidence: 99%

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Triphenyltin(IV) 2-[(E)-2-(aryl)-1-diazenyl]benzoates as anticancer drugs: synthesis, structural characterization, in vitro cytotoxicity and study of its influence towards the mechanistic role of some key enzymes

et al. 2009

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Triphenyltin(IV) complexes of composition [Ph(3)SnL(1)H](n) (1) and [Ph(3)SnL(2)H](n) (2) (where L(1)H = 2-[(E)-2-(3-formyl-4-hydroxyphenyl)-1-diazenyl]benzoate and L(2)H = 2-[(E)-2-(4-Hydroxy-5-methylphenyl)-1-diazenyl]benzoate) were synthesized and characterized by spectroscopic ((1)H, (13)C and (119)Sn NMR, IR, (119)Sn Mössbauer) techniques in combination with elemental analysis. The molecular structures and geometries of the complexes (1 and 2) were fully optimized using the quantum mechanical method (PM3). Complexes (1 and 2) were found to exhibit stronger cytotoxic activity in vitro across a panel of human tumour cell lines viz., A498, EVSA-T, H226, IGROV, M19 MEL, MCF-7 and WIDR. The test compounds 1 and 2 exhibit comparable results and both the compounds are found to be far superior to CCDP (cisplatin), 5-FU (5-fluorouracil) and ETO (etoposide) across a panel of cell lines and the activity is more pronounced for the A498 (22 fold) and H226 (33 fold) cell lines compared to CCDP, and A498 (13 fold), H226 (39 fold) and MCF-7 (33 fold) cell lines compared to ETO. The test compounds are even 23 fold more active in magnitude in terms of the ID(50) value at least against the H226 cell lines when compared with MTX (methotrexate). Further, the mechanistic role of cytotoxic activity of test compounds (1 and 2), are discussed in relations to the theoretical results of docking studies with some of the key enzymes such as ribonucleotide reductase, thymidylate synthase, thymidylate phosphorylase and topoisomerase II.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Triphenyltin(IV) 2-[(E)-2-(aryl)-1-diazenyl]benzoates as anticancer drugs: synthesis, structural characterization, in vitro cytotoxicity and study of its influence towards the mechanistic role of some key enzymes

et al. 2009

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“…It is well established that organotin(IV) compounds are very important in cancer chemotherapy because of their apoptotic inducing character [6,7]. The design of improved organotin(IV) antitumour agents occupies a significant place in cancer chemotherapy, as revealed from their remarkable therapeutic potential reflected in recent research reports [8][9][10][11][12][13][14][15][16][17][18][19].…”

Section: Introductionmentioning

confidence: 99%

Amino acetate functionalized Schiff base organotin(IV) complexes as anticancer drugs: synthesis, structural characterization, and in vitro cytotoxicity studies

Baul

Basu

Vos³

et al. 2008

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Potassium 2-{[(2Z)-(3-hydroxy-1-methyl 2-butenylidene)]amino}-4-methyl-pentanoate (L1HK) and potassium 2-{[(E)-1-(2-hydroxyphenyl)alkylidene]amino}-4-methyl-pentanoates (L2HK-L3HK) underwent reactions with PhnSnCl4-n (n = 2 and 3) to give the amino acetate functionalized Schiff base organotin(IV) complexes [Ph3SnLH]n (1-3) and [Ph2SnL] (4), respectively. These complexes have been characterized by 1H, 13C, 119Sn NMR, IR spectroscopic techniques in combination with elemental analyses. The crystal structures of 1 and 3 were determined. The crystal structures reveal that the complexes exist as polymeric chains in which the L-bridged Sn-atoms adopt a trans-R3SnO2 trigonal bipyramidal configuration with the Ph groups in the equatorial positions and the axial locations occupied by a carboxylate oxygen atom from one carboxylate ligand and the alcoholic or phenolic oxygen atom of the next carboxylate ligand in the chain. The carboxylate ligands coordinate in the zwitterionic form with the alcoholic/phenolic proton moved to the nearby nitrogen atom. The solution structures were predicted by 119Sn NMR spectroscopy. When these organotin(IV) complexes were tested against A498, EVSA-T, H226, IGROV, M19 MEL, MCF7 and WIDR human tumor cell lines, the average ID50 values obtained were 55, 80 and 35 ng/ml for triphenyltin(IV) compounds 1-3, respectively. The most cytotoxic triphenyltin(IV) compound in the present report (3) with an average ID50 value of around 35 ng/ml is found to be morer cytotoxic for all the cell lines studied than doxorubicin, cisplatin, 5-fluorouracil and etoposide. (3) with an average ID 50 value of around 35 ng/ml is found to be morer cytotoxic for all the cell lines studied than doxorubicin, cisplatin, 5-fluorouracil and etoposide.

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“…Additionally, more organotin(IV) compounds have undergone testing as potential anticancer agents than any other single group of compounds [29,30]. The design of improved organotin(IV) antitumour agents occupies a significant place in cancer chemotherapy, as revealed from their remarkable therapeutic potential reflected in recent research reports [31][32][33][34][35][36][37][38][39][40][41].…”

Section: Introductionmentioning

confidence: 99%

In vitro cytotoxic evaluation of novel dichlorodiorgano[N-(2-pyridylmethylene)arylamine]tin(IV) derivatives in human tumor cell lines

Baul

Vos²

2009

Invest New Drugs

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The present report overviews the studies on diorganotin(IV) complexes of N-(2-pyridylmethylene)arylamine, R(2)SnCl(2).L (R = Me (1), Et (2), Bu (3) or Ph (4)) as cytotoxic agents. This family of complexes was designed to include highly electron-donating N;Nchelating ligand to afford octahedral R(2)SnCl(2).L complexes of relatively high hydrolytic stability, with the aim to retain ligand binding throughout the biological activity for achieving controlled processes and allowing mechanistic evaluation. It is observed that the high cytotoxic activity is dependent on the Sn-R groups and Sn-N bond lengths, and which is related to the cytotoxic potential. Complex (2) was found to exhibit stronger cytotoxic activity in vitro particularly for A498 (renal cancer), IGROV (ovarian cancer), MCF-7 (breast cancer), and WIDR (colon cancer) of human tumour cell lines and the results are far superior to standard reference drugs e.g., doxorubicin, cisplatin, 5-fluorouracil, methotrexate, etoposide including paclitaxel. The important insights gained with the diorganotin(IV) compounds in regards to their cytotoxic activity are discussed.

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Effect of the organotin compound triethyltin on Ca2+ handling in human prostate cancer cells

Cited by 27 publications

References 0 publications

Triphenyltin(IV) 2-[(E)-2-(aryl)-1-diazenyl]benzoates as anticancer drugs: synthesis, structural characterization, in vitro cytotoxicity and study of its influence towards the mechanistic role of some key enzymes

Triphenyltin(IV) 2-[(E)-2-(aryl)-1-diazenyl]benzoates as anticancer drugs: synthesis, structural characterization, in vitro cytotoxicity and study of its influence towards the mechanistic role of some key enzymes

Amino acetate functionalized Schiff base organotin(IV) complexes as anticancer drugs: synthesis, structural characterization, and in vitro cytotoxicity studies

In vitro cytotoxic evaluation of novel dichlorodiorgano[N-(2-pyridylmethylene)arylamine]tin(IV) derivatives in human tumor cell lines

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