Interactions of two cytotoxic organotin(IV) compounds with calf thymus DNA

Casini, Angela; Messori, Luigi; Orioli, Pierluigi; Gielen, Marcel; Kemmer, Martine; Willem, Rudolph

doi:10.1016/s0162-0134(01)00215-x

Cited by 50 publications

(31 citation statements)

References 17 publications

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“…Synthesis of dimethyl, diethyl, diphenyl, and dibenzyltin complexes of monomethyl glutarate (1)(2)(3)(4)(5). The monomethyl glutarate (10 mmol) was dissolved in a minimum amount of methanol (25 mL).…”

Section: Synthesesmentioning

confidence: 99%

“…Synthesis of dibutyltin complex of monomethyl glutarate (3). The complex was prepared under anhydrous conditions by drop wise addition of dry, hot benzenemethanolic (3:1 v/v, 100 mL) solution of dibutyltin oxide (4 mmol) to a hot methanolic solution of monomethyl glutarate (8mmol).…”

Section: Synthesesmentioning

confidence: 99%

“…[1][2][3][4][5][6][7][8][9][10] In recent years, investigations have been carried out to test their antitumor activity, and it has been observed that indeed several di and triorganotin(IV) species were found to be active against various types of cancer. 11-13. Biological activity of organotin complexes is believed to be independent on the structure of molecule and coordination number of the metal.…”

Section: Introductionmentioning

confidence: 99%

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Comparative study of structure: activity relationship of di and triorganotin (IV) complexes of monomethyl glutarate

Rehman¹,

Baloch²,

Badshah³

2005

J. Braz. Chem. Soc.

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Uma série de complexos di-e tri-organoestanho(IV) de metilglutarato foram sintetizados e caracterizados por espectroscopia de RMN de 1 H, 13 C e 119 Sn, no infravermelho e Mössbauer de 119 Sn. Baseado nestas técnicas propõe-se que o ligante se encontra ligado ao estanho através do oxigênio da carbonila. Os dados revelam também que os complexos diorganoestanho(IV) são hexacoordenados, com geometria octaedrica, enquanto que os complexos triorganoestanho(IV) são pentacoordenados e possuem geometria bipiramidal trigonal. A avaliação biológica contra vários microorganismos indica que os complexos diorganoestanho(IV) são menos ativos que os triorganoestanho(IV).A series of di and triorganotin(IV) complexes of monomethyl glutarate have been synthesized and characterized through 1 H 13 C 119 Sn NMR, FT-IR and 119 Sn Mössbauer spectroscopy. On the basis of these techniques, it is proposed that the ligand molecule is bound to the tin atom through the carbonyl oxygen. The data reveal that diorganotin(IV) complexes exhibit hexa-coordination with octahedral geometry, while triorganotin(IV) complexes have penta-coordination with trigonal bipyramidal geometry. Biological evaluation against various microorganisms indicate that diorganotin(IV) complexes are less active than the triorganotin(IV) complexes.Keywords: organotin(IV), monomethyl glutarate, biological activity IntroductionOrganotin(IV) complexes have wide applications as catalysts, stabilizers as biocides, as antifouling agents, and for wood preservers. [1][2][3][4][5][6][7][8][9][10] In recent years, investigations have been carried out to test their antitumor activity, and it has been observed that indeed several di and triorganotin(IV) species were found to be active against various types of cancer. 11-13. Biological activity of organotin complexes is believed to be independent on the structure of molecule and coordination number of the metal. [4][5][6] It has also been noted that many di and triorganotin(IV) carboxylates display interesting anti tumor activities. [13][14][15][16][17][18][19][20] However the solubility of di and tri-organotin(IV) carboxylates in water and water-ethanol is poor, therefore many organotin(IV) complexes with carboxylate ligands containing polar subsitituents (hydroxo and oxo groups) have been prepared and studied. [13][14][15][16][17][18][19][20] In a previous paper we described the synthesis of organotin(IV) complexes of maleimidoacetic acid. 21 In the present work we report the synthesis, spectroscopic characterization, antibacterial and various biological activities of a series of di and triorganotin(IV) complexes of monomethyl glutarate. ExperimentalAll the di and triorganotin(IV) compounds except for dibenzyl and tribenzyl tin chlorides were purchased from Fluka and were used as such. Di and tribenzyltin chlorides were synthesized from the literature method. 22 All the reactions were carried out under anhydrous and oxygen free nitrogen atmosphere. The solvents used were dried before use according to the literature method. 23 The...

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Section: Synthesesmentioning

confidence: 99%

Section: Synthesesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Comparative study of structure: activity relationship of di and triorganotin (IV) complexes of monomethyl glutarate

Rehman¹,

Baloch²,

Badshah³

2005

J. Braz. Chem. Soc.

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“…However, the variations in in vitro cytotoxicity of the triphenyltin(IV) complexes may be due to different kinetic and mechanistic behaviour [49]. Conversely, the possibility of organotin compounds to interact with DNA at the level of the phosphate groups can not be completely ruled out [70]. cytotoxicity In conclusion, the present study describes new structures with improved in vitro anti-tumour activity, which is of added value in determining the structure activity relationship in the area of organotin(IV) chemistry with possible future clinical application.…”

mentioning

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

Invest New Drugs

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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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“…Unfavorable drug interaction with lipid membrane can have adverse effects, such as drug resistance. Some authors proposed that DNA may be the probable target for the cytotoxic activity of organotin complex [15][16][17][18][19]. The ability of these complexes to bind with DNA depends on the coordination number and the nature of groups bonded to the central tin atom.…”

Section: Introductionmentioning

confidence: 99%

Lipid and DNA interaction with the triorganotin dimethylaminophenylazobenzoates studied by DSC and spectroscopy methods

Pruchnik

Kral

Hof

2018

J Therm Anal Calorim

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The aim of the study was to investigate and compare the interaction of tributyltin (TBTA) and triphenyltin (TPhTA) 2-[4 (dimethylamino)phenylazo]benzoates complexes with the lipid membrane and plasmid DNA. Both TBTA and TPhTA belong to the group of promising anticancer agents. Differential scanning calorimetry method was employed to examine the heat signal associated with phase transitions of liposomes formed from dipalmitoylphosphatidylcholine (DPPC) or DPPC/cholesterol and modified with TBTA and TPhTA. The investigated compounds influence the thermotropic parameters of the DPPC and DPPC/cholesterol lipid bilayer in a slightly different way: Although the temperature of the main phase transition of the DPPC remains almost unaffected, the addition of TPhTA can abolish sub-and pre-transition when added in sufficiently high concentrations. At the same time, the addition of the TBTA practically does not change the sub-transition and only slightly influences the pre-transition. The effect of organotin compounds on plasmid DNA was investigated using single-molecule florescence technique and time-correlated single-photon counting fluorescence correlation spectroscopy. Influence of TBTA and TPhTA on DNA resulted only in fractional conformation change which did not lead to the tightly packed conformation however, analysis of the diffusion times indicates that TPhTA interacts with DNA in a different mode than TBTA.

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Interactions of two cytotoxic organotin(IV) compounds with calf thymus DNA

Cited by 50 publications

References 17 publications

Comparative study of structure: activity relationship of di and triorganotin (IV) complexes of monomethyl glutarate

Comparative study of structure: activity relationship of di and triorganotin (IV) complexes of monomethyl glutarate

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

Lipid and DNA interaction with the triorganotin dimethylaminophenylazobenzoates studied by DSC and spectroscopy methods

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