Synthesis and Initial Cell Line Results of Organotin Polyethers Containing Diethylstilbestrol

Carraher, Charles E.; Roner, Michael R.; Shahi, Kimberly; Ashida, Yuki; Barot, Girish

doi:10.1007/s10904-007-9184-6

Cited by 30 publications

(19 citation statements)

References 8 publications

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“…All band locations are given cm -1 . Infrared spectral analysis is consistent with the proposed structure and with other reported analyses for KA [14][15][16] and organotin polymers [17][18][19]. Table 2 contains results for the dibutyltin and diphenyltin polymers.…”

Section: Infrared Resultssupporting

confidence: 87%

Synthesis of organotin polymers from 2-ketoglutaric acid and their ability to inhibit the growth of human cancer cell lines

Carraher¹,

Roner²,

Patel³

et al. 2018

Hematol Med Oncol

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Reaction of organotin dichlorides with the salt of 2-ketoglutaric acid is rapid forming organotin polyether polymers in low to moderate yield within 15 seconds or less employing the interfacial polycondensation process. The average chain length generally decreases as the alkyl chain length on the organotin increases. Infrared spectroscopy shows bands characteristic of both reactants and the formation of the linkage ester linkage. MALDI MS shows formation of ion fragments characteristic of 5 to 8 repeat units and good isotopic abundance matches consistent with the presence of the organotin moiety in these ion fragments. NMR is also consistent with the formation of the organotin polyester. The polymers exhibit good inhibition of all cancer cell lines tested including two breast and two pancreatic cancer cell lines.

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Section: Infrared Resultssupporting

confidence: 87%

Synthesis of organotin polymers from 2-ketoglutaric acid and their ability to inhibit the growth of human cancer cell lines

Carraher¹,

Roner²,

Patel³

et al. 2018

Hematol Med Oncol

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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%

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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“…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

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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Synthesis and Initial Cell Line Results of Organotin Polyethers Containing Diethylstilbestrol

Cited by 30 publications

References 8 publications

Synthesis of organotin polymers from 2-ketoglutaric acid and their ability to inhibit the growth of human cancer cell lines

Synthesis of organotin polymers from 2-ketoglutaric acid and their ability to inhibit the growth of human cancer cell lines

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

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