Organotin Polyethers as Biomaterials

Published on Oct 21, 2009in Materials 2.47
· DOI :10.3390/ma2041558
Charles E. Carraher23
Estimated H-index: 23
(Florida Atlantic University),
Michael R. Roner19
Estimated H-index: 19
Abstract
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 synthetic diols. Included in these materials are the first water soluble organotin polymers. The organotin polyethers exhibit a wide range of biological activities. Some selectively inhibit a number of unwanted bacteria, including Staph. MRSA, and unwanted yeasts such as Candida albicans. Some also inhibit a variety of viruses including those responsible for herpes infections and smallpox. Others show good inhibition of a wide variety of cancer cell lines including cell lines associated with ovarian, colon, lung, prostrate, pancreatic and breast cancer. The synthesis, structural characterization, and biological characterization of these materials is described in this review.
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  • Citations (24)
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References94
Published on Aug 15, 1990in Biochemical Journal 3.86
Marc Claeyssens43
Estimated H-index: 43
,
H van Tilbeurgh2
Estimated H-index: 2
+ 3 AuthorsP Biely1
Estimated H-index: 1
Endoglucanase I from the filamentous fungus Trichoderma reesei catalyses hydrolysis and glycosyl-transfer reactions of cello-oligosaccharides. Initial bond-cleaving frequencies determined with 1-3H-labelled cello-oligosaccharides proved to be substrate-concentration-dependent. Using chromophoric glycosides and analysing the reaction products by h.p.l.c., kinetic data are obtained and, as typical for an endo-type depolymerase, apparent hydrolytic parameters (kcat., kcat./Km) increase steadily as ...
51 Citations Source Cite
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 Jan 1, 1998in Nature 41.58
Hideki Sakahira17
Estimated H-index: 17
(Osaka University),
Masato Enari22
Estimated H-index: 22
(Osaka University),
Shigekazu Nagata S111
Estimated H-index: 111
Various molecules such as cytokines and anticancer drugs, as well as factor deprivation, rapidly induce apoptosis (programmed cell death) 1,2 , which is morphologically characterized by cell shrinkage and the blebbing of plasma membranes and by nuclear condensation 3,4 . Caspases, particularly caspase 3, are proteases that are activated during apoptosis and which cleave substrates such as poly(ADP-ribose) polymerase, actin, fodrin, and lamin 5,6 . Apoptosis is also accompanied by the internucleo...
1,385 Citations Source Cite
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 Feb 28, 1973in Angewandte Makromolekulare Chemie
Charles E. Carraher13
Estimated H-index: 13
(University of South Dakota),
John D. Piersma4
Estimated H-index: 4
(University of South Dakota)
The modification of poly(vinyl alcohol) was effected via condensation with tin compounds, utilizing the interfacial technique. Products obtained with R2SnCl2 are crosslinked. Thermal properties are reported. Die Modifizierung von Polyvinylalkohol wurde durch Kondensation mit ZinnVerbindungen unter Anwendung der Grenzflachentechnik erzielt. Mit R2SnCl2 entstehen vernetzte Produkte. Die thermischen Eigenschaften dieser Produkte werden angegeben.
14 Citations Source Cite
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, 1998
P. G. Harrison1
Estimated H-index: 1
Tin - the element. Compounds of tin General trends. The inorganic chemistry of tin. Formation and cleavage of the tin-carbon bond. Organometallic compounds of tetravalent tin. Organometallic compounds of bivalent tin. Tin-metal bonded compounds. Radical chemistry of tin. The uses of organotin compounds in organic synthesis. Recent studies on the mode of biological action of the di- and trialkyltin compounds. Health and safety aspects of tin chemicals. Industrial uses of tin chemicals. Solid stat...
315 Citations Source Cite
Published on May 1, 1998in Nature 41.58
Masato Enari M15
Estimated H-index: 15
,
Hideki Sakahira17
Estimated H-index: 17
+ 3 AuthorsShigekazu Nagata S111
Estimated H-index: 111
correction: A caspase-activated DNase that degrades DNA during apoptosis, and its inhibitor ICAD
18 Citations Source Cite
Cited By24
Charles E. Carraher23
Estimated H-index: 23
(Florida Atlantic University),
Michael R. Roner19
Estimated H-index: 19
(University of Texas at Arlington)
+ 2 AuthorsLindsey Miller4
Estimated H-index: 4
(University of Texas at Arlington)
Organotin polyamine ethers containing thiamine (Vitamin B1) were synthesized employing the interfacial polymerization of thiamine and organotin dichlorides. Reaction is rapid occurring in less than 15 s in moderate to poor yield with chain length ranging from 86 to 860 units. Infrared spectroscopy shows new bands characteristic of the formation of the Sn–N and Sn–O linkages. Proton NMR shows the presence of both the organotin and thiamine moieties. MALDI MS results shows ion fragment clusters to...
8 Citations Source Cite
Published on Oct 3, 2015in Journal of Macromolecular Science, Part A 1.06
Carraher E. Charles1
Estimated H-index: 1
(Florida Atlantic University),
Michael R. Roner19
Estimated H-index: 19
(University of Texas at Arlington)
+ 3 AuthorsRyan Crichton3
Estimated H-index: 3
(Florida Atlantic University)
Organotin polyesters were synthesized in good to poor yield with yield and chain length generally decreasing as the alkyl chain on the organotin increases. MALDI MS, NMR, and IR data is consistent with the proposed repeat unit. MALDI MS ion fragment clusters to four repeat units are found. The IR shows the presence of a new band assigned to the formation of the Sn-O. With the exception of the dimethyltin polymer, all of the polymers exhibit good inhibition of a variety of cancer cell lines inclu...
1 Citations Source Cite
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
Published on Mar 1, 2013in Toxicology in Vitro 3.10
Alessandra Pagliarani17
Estimated H-index: 17
(University of Bologna),
Salvatore Nesci10
Estimated H-index: 10
(University of Bologna),
Vittoria Ventrella17
Estimated H-index: 17
(University of Bologna)
Abstract Most biochemical effects of organotin compounds leading to toxicity are astonishingly similar in different animal species. In vitro tests, designed to explore organotin action modes at cell level by minimizing interfering factors, point out akin responses to these man-made environmental pollutants from prokaryotes to mammals. On the other hand, a broad susceptibility range to organotin toxicants of animal cells and variegated action mechanisms of these compounds have been reported both ...
41 Citations Source Cite
Published on Nov 1, 2014in Inorganica Chimica Acta 2.26
Charles E. Carraher7
Estimated H-index: 7
(Florida Atlantic University),
Ngoc Trang Caroline Truong2
Estimated H-index: 2
(Florida Atlantic University)
+ 3 AuthorsNancy T. Trang5
Estimated H-index: 5
(University of Texas at Arlington)
Abstract Polyether esters are rapidly formed employing the interfacial condensation of organotin dihalides with glycyrrhetinic acid in high yield and oligomeric to polymeric chain length. Infrared spectroscopy shows the formation of tin–oxygen bonds. The products are a mixture of bridging and non-bridging structures about the tin atom. Proton NMR and MALDI MS results are consistent with the formation of the poly(ether esters). The dimethyltin, dibutyltin, and diphenyltin polymers exhibit good in...
7 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. 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...
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