Synthesis, Structural Characterization, and Ability to Inhibit Cancer Growth of a Series of Organotin Poly(ethylene glycols)

Published on Oct 17, 2007in Journal of Inorganic and Organometallic Polymers and Materials 1.75
· DOI :10.1007/s10904-007-9158-8
Girish Barot11
Estimated H-index: 11
(Florida Atlantic University),
Kimberly Shahi10
Estimated H-index: 10
(University of Texas at Arlington)
+ 1 AuthorsCharles E. Carraher23
Estimated H-index: 23
(Florida Atlantic University)
Abstract
A series of organotin poly(ethylene glycols) were synthesized including the first water soluble organotin polymers. These products are all polymeric with weight average molecular weights about 105. Infrared spectroscopy shows the presence of moieties from both reactants and the formation of the Sn–O linkage. F MALDI MS shows the presence of up to over a hundred units and by isotopic abundance the presence of one, two, and three tin-containing ion fragments. The polymers inhibit the growth of cancer cell lines from bone, prostate, colon, breast, and lung cancers. In a number of instances chemotherapeutic index values of two and greater are found consistent with these polymers being more active against cancer cells than non-cancerous healthy cells. Thus, some of these polymers show good promise as a new family of anticancer drugs including the water-soluble organotin-containing polymers.
  • References (24)
  • Citations (34)
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References24
Published on Jan 1, 1995in in Vivo 1.12
Marcel Gielen32
Estimated H-index: 32
,
Rudolph Willem37
Estimated H-index: 37
+ 4 AuthorsG. Peters2
Estimated H-index: 2
The in vitro antiproliferative effects, the toxicity profiles in vivo in mice and the antitumour activity in tumour-bearing mice were screened for five recently synthesized organotin compounds: triphenyltin 5-sulfosalicylate (1), triphenyltin 5-aminosalicylate (2), triphenyltin 4-fluorobenzoate (3), tri-n-butyltin 2,6-difluorobenzoate (4) and di-n-butyltin bis (2,5-dihydroxybenzoate) (5). The in vitro chemosensitivity tests showed that compound 1 has the lowest antiproliferative effect in C26-10...
16 Citations
Published on Sep 15, 1991in Journal of Biological Chemistry 4.01
M F Powers4
Estimated H-index: 4
,
Andrew D. Beavis13
Estimated H-index: 13
Abstract The inner membrane of liver and heart mitochondria possesses an anion uniport pathway, known as the inner membrane anion channel (IMAC). IMAC is inhibited by matrix Mg2+, matrix H+, N,N'-dicyclohexycarbodiimide, mercurials and amphiphilic amines such as propranolol. Most of these agents react with a number of different mitochondrial proteins and, therefore, more selective inhibitors have been sought. In this paper, we report the discovery of a new class of inhibitors, triorganotin compo...
63 Citations
Published on Jan 1, 1980
G. Socrates1
Estimated H-index: 1
2,339 Citations
Published on Jan 1, 1992in Anticancer Research 1.86
Marcel Gielen32
Estimated H-index: 32
,
Rudolph Willem37
Estimated H-index: 37
Bis[di-n-butyl (4-aminosalicylato)tin] oxide [NSC: 628561] (compound 1), bis [diphenyl(4-aminosalicylato)tin] oxide [NSC: 628562] (compound 2), and six other analogous compounds of the type [n-Bu2 (XYZ-C6H2COO)Sn]2O (compounds 3 to 8), were tested in vitro at the National Cancer Institute, Bethesda, Maryland, USA, for cytotoxic activity against a series of human cell lines. Compounds 1, 6 and 8 score globally satisfactorily since four of the five relevant sensitivity or selectivity parameters, D...
28 Citations
Published on Feb 18, 1972in Macromolecular Chemistry and Physics 2.49
Charles E. Carraher13
Estimated H-index: 13
(University of South Dakota),
Gary A. Scherubel3
Estimated H-index: 3
(University of South Dakota)
Poly[alkylene(arylene)oxystannanes] of the form below have been synthesized from dichlorostannanes and diols using a modified nonaqueous interfacial system consisting of acetonitrile and hydrocarbons. The products are preferentially capped with alcohol end-groups. Poly[alkylen(arylen)oxystannane] der folgenden Struktur wurden durch Grenzflachenpolykondensation von Dichlorstannen mit Diolen hergestellt. Dabei wurden modifizierte wasserfreie Losungsmittelsysteme aus Acetonitril und Kohlenwassersto...
25 Citations Source Cite
Published on Oct 18, 1972in Macromolecular Chemistry and Physics 2.49
Charles E. Carraher13
Estimated H-index: 13
(University of South Dakota),
Gary A. Scherubel3
Estimated H-index: 3
(University of South Dakota)
The synthesis of some poly(tin ethers) according to the following route is described The number average polymerization degrees range from 78 to 1400. Die Synthese einiger Poly-(zinnather) wird beschrieben, und zwar durch die in der Summary wiedergegebene Reaktion. Die mittleren Polymerisationsgrade liegen im Bereich von 78 bis 1400.
27 Citations Source Cite
Published on Jan 1, 1992in Anticancer Research 1.86
Marcel Gielen32
Estimated H-index: 32
,
Rudolph Willem37
Estimated H-index: 37
The di-n-butyltin(IV) derivatives of N-(2-hydroxyethyl)- and N-(carbamoylmethyl)- iminodiacetic acid, compounds 1 and 2, the di-n-butyltin-, di-n-octyltin and dimethyltin-(IV) derivatives of 1,2-ethylene diamine N,N'-diacetic acid, compounds 3, 4 and 5, and di-n-butyltin bis-o-aminobenzoate, compound 6, were tested in vitro at the National Cancer Institute, Bethesda, Maryland, USA, for cytotoxic activity against a series of human tumor cell lines. Compounds 1 and 2 score globally satisfactorily ...
16 Citations
Published on Jan 1, 2002in Bioorganic & Medicinal Chemistry Letters 2.44
Purnima M. Samuel3
Estimated H-index: 3
(Indian Institute of Chemical Technology),
Dick de Vos1
Estimated H-index: 1
+ 2 AuthorsSujit Roy29
Estimated H-index: 29
(Indian Institute of Technology Kharagpur)
Abstract Dibenzyltin(IV)dichloride and dibenzyltin(IV)diisothiocyanate derivatives with N,S-donor ligands show significant cytotoxic activities against human cancer cell lines, and are well compared to analogous dialkyltin(IV) derivatives. CoMFA models were generated for the first time for these organotin derivatives using the cytotoxic activities (against two human tumor cell lines, MCF-7, a mammary carcinoma and WiDr, a colon carcinoma) of 21 complexes. High r 2 and r 2 cv values for both CoMF...
37 Citations Source Cite
Published on Nov 1, 1996in Journal of Inorganic Biochemistry 3.06
Qingshan Li1
Estimated H-index: 1
(Nanjing University),
Pin Yang9
Estimated H-index: 9
(Shanxi University)
+ 1 AuthorsMaolin Guo3
Estimated H-index: 3
Abstract This contribution reports a solution and solid-state study of the aqueous nucleotide coordination chemistry of the dieihyltin(IV) antitumor agent, (C 2 H 5 )2SnC1 2 (phen). [trans-en 2 OS(η-H 2 ] (CF 3 SO 3 ) 2 , a versatile 1 H NMR probe for biomolecules, is first used to investigate the interaction of (C 2 H 5 ) 2 SnC1 2 (phen) with DGMP in neutral aqueous solution, and then the synthesis of mixed-ligands complexes formulated as (C 2 Hn5) S nC1(phenXNu) (Nu is nucleotide) by reactions...
172 Citations Source Cite
Published on Dec 1, 2000in Toxicology and Applied Pharmacology 3.62
Yukako Yamabe4
Estimated H-index: 4
(Kitasato University),
Azusa Hoshino1
Estimated H-index: 1
(Kitasato University)
+ 2 AuthorsSeiichiro Himeno16
Estimated H-index: 16
(Kitasato University)
Tributyltin (TBT) and triphenyltin (TPT) are known to cause imposex, the superimposing of male genitals on female ones, in some species of gastropods. However, the molecular mechanism of the trialkyltin-induced endocrine dysfunction remains to be elucidated. To clarify the effects of organotin compounds on the activation of androgen receptor (AR)-mediated responses in mammals, a LA16 clone that stably expresses androgen-responsive luciferase reporter gene and proliferates in response to androgen...
70 Citations Source Cite
  • References (24)
  • Citations (34)
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Cited By34
Published on Nov 22, 2015in International Journal of Polymeric Materials 2.13
Charles E. Carraher7
Estimated H-index: 7
(Florida Atlantic University),
Michael R. Roner19
Estimated H-index: 19
(University of Texas at Arlington)
+ 7 AuthorsZamil Islam1
Estimated H-index: 1
(Florida Atlantic University)
The efforts described in this article are aimed at designing organotin polymers that control the growth of breast cancer and to identify structure/property relationships that assist in this goal. The growth of MCF-7 and MDA-MB-231 breast cancer cell lines is inhibited employing a wide range of organotin condensation polymers. The EC50 values are primarily dependent on the nature of the Lewis base but the CI50 is dependent on both the nature of the Lewis base and Lewis acid. A number of products ...
4 Citations Source Cite
Charles E. Carraher23
Estimated H-index: 23
(Florida Atlantic University),
Frank D. Blum25
Estimated H-index: 25
(Missouri University of Science and Technology)
+ 8 AuthorsMichael R. Roner19
Estimated H-index: 19
(University of Texas at Arlington)
Polymers in general and metal-containing polymers in particular are often sparingly soluble or insoluble, in contrast to small molecules. Thus, special significance is attached to characterization techniques that can be applied to the materials as solids. Here, three techniques are discussed that give structural information gained from the solid material. Mossbauer spectroscopy is a powerful technique that may give information on the structure about the metal-containing moiety for about 44 diffe...
11 Citations Source Cite
Charles E. Carraher7
Estimated H-index: 7
(Florida Atlantic University),
Girish Barot11
Estimated H-index: 11
(Florida Atlantic University)
+ 1 AuthorsMichael R. Roner19
Estimated H-index: 19
(University of Texas at Arlington)
The effect of solvent on the ability to inhibit a group of cell lines was studied employing a series of water-soluble dibutyltin polyethers derived from various hydroxyl-terminated poly(ethylene glycols). Molecular weight as a function of time was essentially unchanged for a period of 30 weeks for the polyethers. Variations in test media can affect biological activities on the cell level as well as at the molecular level. The current study involves the evaluation of the cellular effects when dim...
10 Citations Source Cite
Charles E. Carraher23
Estimated H-index: 23
(Florida Atlantic University),
Ngoc Trang Caroline Truong2
Estimated H-index: 2
(Florida Atlantic University)
+ 2 AuthorsNancy T. Trang5
Estimated H-index: 5
(University of Texas at Arlington)
Polyether esters were rapidly formed employing the interfacial condensation of Group VA triphenylmetal dihalides with glycyrrhetinic acid in moderate yield and chain length. Infrared spectroscopy shows the formation of metal–oxygen bonds. The products are a mixture of bridging and non-bridging structures about the metal atom. Proton NMR and MALDI MS results are consistent with the formation of the polyether esters. Some of the polymers exhibit inhibition of the growth of pancreatic cancer cell l...
8 Citations Source Cite
Charles E. Carraher7
Estimated H-index: 7
(Florida Atlantic University),
Girish Barot11
Estimated H-index: 11
(Boston University)
+ 2 AuthorsMichael R. Roner19
Estimated H-index: 19
(University of Texas at Arlington)
The degradation of water soluble organotin polyether in the presence of trypsin was studied. The polymer was found to be stable to 4 days, the typical cancer cell line testing time. This is consistent with polymer activity against cancer cell lines being a result of the non-degraded chain and not controlled release of the organotin moiety. As a control trypsin activity was studied employing light scattering photometry and gel electrophoresis. The trypsin was active degrading bovine serine albumi...
12 Citations Source Cite
Charles E. Carraher7
Estimated H-index: 7
(Florida Atlantic University),
Marian Ayoub3
Estimated H-index: 3
(Florida Atlantic University)
+ 2 AuthorsNancy T. Trang5
Estimated H-index: 5
(University of Texas at Arlington)
In this study, organotin polyesters have been formed from the interfacial reaction between the disodium salt of chelidonic acid and a variety of organotin dihalides. Reactions occur rapidly within less than 15 seconds. Yields vary from moderate to high, and chain length varies from 30 to 800 repeat units. Infrared spectral analysis shows the presence of the Sn–O linkage and is consistent with the geometry about the tin being generally a mixture of tetrahedral or nonbridging and octahedral or bri...
8 Citations Source Cite
Charles E. Carraher7
Estimated H-index: 7
(Florida Atlantic University),
Michael R. Roner19
Estimated H-index: 19
(University of Texas at Arlington)
+ 6 AuthorsMohammed H. Al-huniti4
Estimated H-index: 4
(Florida Atlantic University)
The efforts described in this paper are aimed at designing organotin polymers that control the growth of various cancers; here colorectal cancer and to identify structure/property relationships that will assist in this goal. The growth of colorectal cancer is affected employing a wide range of organotin condensation polymers. The EC50 values are primarily dependent on the nature of the Lewis base but the CI50 value is dependent on both the nature of the Lewis base and Lewis acid. EC50 values dow...
Source Cite
Published on Oct 21, 2009in Materials 2.47
Charles E. Carraher23
Estimated H-index: 23
(Florida Atlantic University),
Michael R. Roner19
Estimated H-index: 19
Organotin polyethers are easily synthesized employing interfacial polymerization systems involving the reaction of hydroxyl-containing Lewis bases and organotin halides. A wide variety of organotin-containing polymeric products have been synthesized including those derived from natural and synthetic polymers such as lignin, xylan, cellulose, dextran, and poly(vinyl alcohol). Others have been synthesized employing known drug diols such as dicumarol, DES, and dienestrol and a wide variety of synth...
24 Citations Source Cite
Charles E. Carraher23
Estimated H-index: 23
(Florida Atlantic University),
Michael R. Roner19
Estimated H-index: 19
(University of Texas at Arlington)
+ 2 AuthorsMohammed H. Al-huniti4
Estimated H-index: 4
(Florida Atlantic University)
Polyester amines were formed from the reaction of the salt of ampicillin with triphenyarsenic, triphenylantimony, and triphenylbismuth dihalides employing the interfacial polycondensation reaction. IR shows the formation of M–OC=O and M–N bands consistent with the proposed polymer formation. Further, IR results are consistent with the repeat units connecting in a somewhat random manner about the metal atom. MALDI MS results give ion fragments to one and two units in length that are consistent wi...
2 Citations Source Cite
Charles E. Carraher23
Estimated H-index: 23
(Florida Atlantic University),
Michael R. Roner19
Estimated H-index: 19
(University of Texas at Arlington)
+ 6 AuthorsMohammed H. Al-huniti4
Estimated H-index: 4
(Florida Atlantic University)
The current efforts described in this paper are aimed at developing compounds that inhibit the growth of prostate cancer and to identify structure/property relationships that will further assist us towards this goal. The growth of prostate cancer is affected employing a wide range of organotin condensation polymers. The EC50 values are primarily dependant on the nature of the Lewis base but the CI50 is dependent on both the nature of the Lewis base and Lewis acid. EC50 values down to the picogra...
9 Citations Source Cite
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