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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. Carraher24
Estimated H-index: 24
(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 (25)
  • Citations (34)
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References25
Newest
Mala Nath22
Estimated H-index: 22
(Indian Institute of Technology Roorkee),
Ruchi Jairath5
Estimated H-index: 5
(Indian Institute of Technology Roorkee)
+ 2 AuthorsAshok Kumar37
Estimated H-index: 37
Abstract New organotin(IV) complexes of the general formula R 3 Sn(L) (where R = Me, n -Bu and HL = l -proline; R = Me, Ph and HL = trans -hydroxy- l -proline and l -glutamine) and R 2 Sn(L) 2 (where R = n -Bu, Ph and HL = l -proline; R = Ph, HL = trans -hydroxy- l -proline) have been synthesized by the reaction of R n SnCl 4− n (where n = 2 or 3) with sodium salt of the amino acid (HL). n -Bu 2 Sn(Pro) 2 was synthesized by the reaction of n -Bu 2 SnO with l -proline under azeotropic removal of ...
30 Citations Source Cite
Published on Jan 1, 2004in Drug Metabolism Reviews 4.45
Klaus E. Appel27
Estimated H-index: 27
(Federal Institute for Risk Assessment)
Organotin compounds have a broad range of applications. While dialkyltin compounds are used primarily as stabilizers for plastics, trisubstituted organotins are mainly used as biocides e.g., as an active ingredient of marine antifouling paints for boats and ships. Since a number of organotin compounds have been demonstrated to be toxic, there is increasing concern that their widespread use may cause adverse effects within environmental and biological systems. Besides carcinogenic and neurotoxic ...
148 Citations Source Cite
Published on Feb 1, 2002in Life Sciences 3.23
Chung-Ren Jan23
Estimated H-index: 23
,
Bang-Ping Jiann11
Estimated H-index: 11
+ 5 AuthorsJong-Khing Huang19
Estimated H-index: 19
Abstract The effects of triethyltin on Ca 2+ mobilization in human PC3 prostate cancer cells have been explored. Triethyltin increased [Ca 2+ ] i at concentrations larger than 3 μM with an EC 50 of 30 μM. Within 5 min, the [Ca 2+ ] i signal was composed of a gradual rise and a sustained phase. The [Ca 2+ ] i signal was reduced by half by removing extracellular Ca 2+ . The triethyltin-induced [Ca 2+ ] i increases were inhibited by 40% by 10 μM nifedipine, nimodipine and nicardipine, but were not ...
26 Citations Source Cite
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 5, 2001in Chemistry: A European Journal 5.16
Martine Kemmer7
Estimated H-index: 7
(Free University of Brussels),
Monique Biesemans34
Estimated H-index: 34
(Free University of Brussels)
+ 3 AuthorsRudolph Willem38
Estimated H-index: 38
(Free University of Brussels)
Investigations of the simultaneous complexation of tri-n-butyltin and triphenyltin derivatives of [18]crown-6- or [15]crown-5-(benzo-4-carboxylate) by the anion and cation from NaSCN or KSCN are reported. The crystal structure of [Na+ is included in [15]crown-5-C6H3-4-COOSn(C6H5)3NCS]-], 4 NaSCN, displays an unusual zwitterionic nature with one intramolecular charge separation characterized by an Na-Sn distance of 9.29(1) A, and several intermolecular charge separations, the shortest being 5.48(...
29 Citations Source Cite
Published on Jul 1, 2001in Chemical Research in Toxicology 3.43
Hélène Stridh6
Estimated H-index: 6
,
Ian A. Cotgreave47
Estimated H-index: 47
+ 2 AuthorsDulceaydee Gigliotti13
Estimated H-index: 13
In the present study, we show that the immunotoxicant, tributyltin (TBT), induces a dose-dependent activation of caspases followed by typical apoptotic morphology in resting human peripheral blood lymphocytes. TBT also caused an early loss of mitochondrial membrane potential (ΔΨm) and release of cytochrome c, suggesting that apoptosis was triggered by the mitochondrial pathway. When CD4+ T-cells were sorted from peripheral blood and exposed to TBT for 30 min, caspase activation and apoptosis wer...
43 Citations Source Cite
Published on Mar 1, 2001in Toxicology and Applied Pharmacology 3.62
Margaret M. Whalen20
Estimated H-index: 20
(Tennessee State University),
Bommanna G. Loganathan25
Estimated H-index: 25
(Murray State University)
Natural killer (NK) cells are a subset of lymphocytes that are capable of killing tumor cells, virally infected cells, and antibody-coated cells. Butyltins (BTs) are used in a variety of consumer products and industrial applications. Tributyltin (TBT) is found in dairy products, meat, and fish. Dibutyltin (DBT) is found in plastic products, beverages stored in PVC pipes during manufacturing, and poultry products. BTs appear to increase the risk of cancer and viral infections in exposed individua...
44 Citations Source Cite
Published on Mar 1, 2001in Chemico-Biological Interactions 3.30
Federica Barbieri32
Estimated H-index: 32
,
Fabio Sparatore21
Estimated H-index: 21
+ 3 AuthorsAngela Alama20
Estimated H-index: 20
Abstract Organotin compounds, particularly tri-organotin, have demonstrated cytotoxic properties against a number of tumor cell lines. On this basis, triethyltin(IV)lupinylsulfide hydrochloride (IST-FS 29), a quinolizidine derivative, was synthesized and developed as a potential antitumor agent. This tin-derived compound exhibited potent antiproliferative effects on three different human cancer cell lines: teratocarcinoma of the ovary (PA-1), colon carcinoma (HCT-8) and glioblastoma (A-172). Cyt...
26 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
Cited By34
Newest
Published on Jul 1, 2018in Applied Organometallic Chemistry 3.58
T.A. Antonenko3
Estimated H-index: 3
(Moscow State University),
D.B. Shpakovsky8
Estimated H-index: 8
(Moscow State University)
+ 9 AuthorsA.G. Iksanova (Kazan Federal University)
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Published on Feb 1, 2018in Applied Organometallic Chemistry 3.58
Safaa El-din H. Etaiw16
Estimated H-index: 16
(Tanta University),
Safaa N. Abdou8
Estimated H-index: 8
(Tanta University)
The new synthesized supramolecular complexes (SC); [Cu2(CN)4(Et3Sn)2(tbpe)], 1 and [Cu2(CN)3(Et3Sn)(bpe)], 2 (tbpe = trans-1,2-bis(4-pyridyl)ethene and bpe = 1,2-bis(4-pyridyl)ethane), were characterized by elemental analyses, electrical conductance, spectroscopic studies and thermal analyses. UV–Vis spectra and magnetic moment data suggested the tetrahedral geometry around Cu(I) atoms. The structures of the SC 1 and 2 were also theoretically studied using molecular mechanics (MM+). The structur...
Source Cite
Charles E. Carraher24
Estimated H-index: 24
(Florida Atlantic University),
Michael R. Roner19
Estimated H-index: 19
(University of Texas at Arlington)
+ 4 AuthorsFloyd Russell3
Estimated H-index: 3
(Florida Atlantic University)
ABSTRACTThe initial synthesis of DMSO and water-soluble hafnocene polyethers is described. The polyethers are formed through reaction of the hafnocene dichloride with various poly(ethylene glycols) employing commercially available reactants. Infrared, proton NMR, and MALDI MS results are consistent with the hafnocene-containing polyether structure. The materials are polymeric with chain lengths ranging from 1200 to 8 with moderate product yield. They exhibit good inhibition of a variety of cance...
1 Citations Source Cite
Published on Sep 1, 2017
Charles E. Carraher24
Estimated H-index: 24
,
Michael R. Roner19
Estimated H-index: 19
+ 7 AuthorsFloyd Russell3
Estimated H-index: 3
Water-soluble metallocene and organotin-containing polyethers were synthesized employing interfacial polycondensation. The reaction involved various chain lengths of poly(ethylene glycol), and produced water-soluble polymers in decent yield. Commercially available reactants were used to allow for easy scale up. The polymers exhibited a decent ability to inhibit a range of cancer cell lines, including two pancreatic cancer cell lines. This approach should allow the synthesis of a wide variety of ...
1 Citations Source Cite
Published on Jul 2, 2016in Journal of Macromolecular Science, Part A 1.06
Charles E. Carraher7
Estimated H-index: 7
(Florida Atlantic University),
Michael R. Roner19
Estimated H-index: 19
(University of Texas at Arlington)
+ 6 AuthorsLindsey Miller4
Estimated H-index: 4
(University of Texas at Arlington)
ABSTRACTWe describe the initial synthesis of DMSO and water-soluble titanocene polyethers through reaction of the titanocene dichloride and various poly(ethylene glycols) employing commercially available reactants. Infrared, proton NMR, and MALDI MS results are consistent with the titanocene-containing polyether structure. The materials are polymeric with chain lengths ranging from 1500 to 4. They exhibit good inhibition of a variety of cancer cell lines including two pancreatic cancer cell line...
4 Citations Source Cite
Published on Feb 1, 2016in Journal of Macromolecular Science, Part A 1.06
Charles E. Carraher7
Estimated H-index: 7
(Florida Atlantic University),
Michael R. Roner19
Estimated H-index: 19
(University of Texas at Arlington)
+ 3 AuthorsNandalall Sookdeo3
Estimated H-index: 3
(Florida Atlantic University)
ABSTRACTA wide variety of organotin polyethers derived from the interfacial polymerization of dibutyltin dichloride and non-cancer inhibitory diols show decent to good inhibition of two human pancreatic cancer cell lines. In view of the general lack of ability of tested compounds to inhibit pancreatic cancer cell lines, this is significant. These cell lines are the AsPC-1 pancreatic cancer cell line which is an adenocarcinoma pancreatic cell line and the PANC-1 pancreatic cancer cell line which ...
3 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. Carraher7
Estimated H-index: 7
(Florida Atlantic University),
Alicia Morrison2
Estimated H-index: 2
(Florida Atlantic University)
+ 3 AuthorsLindsey Miller4
Estimated H-index: 4
(University of Texas at Arlington)
4 Citations Source Cite
Published on Sep 1, 2015in Heteroatom Chemistry 1.14
Aboubacar Sidiki Sougoule2
Estimated H-index: 2
(Northeast Normal University),
Cheick Abdoul Balde2
Estimated H-index: 2
+ 4 AuthorsDongsheng Zhu5
Estimated H-index: 5
(Northeast Normal University)
A new tetranuclear organotin carboxylate {[(n-Bu2SnO)2L]2}n (complex 1) was synthesized by the reaction of di-n-butyltin oxide with (p-carboxymethoxy-phenoxy) acetic acid (LH2) and characterized by elemental analyses: IR, UV–visible, 1H, 13C, 119Sn NMR spectroscopy and single crystal X-ray study. X-ray crystallography diffraction data revealed that the complex 1 was polymeric fashion with a chain structure containing a ladder-like tetranuclear organo-oxotin cluster. In the complex 1, the ligand ...
3 Citations Source Cite
B. A. Aderibigbe8
Estimated H-index: 8
(University of Fort Hare)
Prodrugs optimize the absorption, distribution, metabolism, excretion and reduce unwanted toxicity of the parent drugs. The medicinal application of polymeric prodrugs for delivery of metal-based anticancer drugs is a field of increasing prominence because metal-based drugs offer possibilities for the design of therapeutic agents that are not readily available to organic compounds. This review is focused on the progress of polymeric prodrugs of metal based anticancer agents. A better understandi...
1 Citations Source Cite