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Organotin Polyethers as Biomaterials

Published on Oct 21, 2009in Materials 2.97
· DOI :10.3390/ma2041558
Charles E. Carraher24
Estimated H-index: 24
(FAU: Florida Atlantic University),
Michael R. Roner19
Estimated H-index: 19
Cite
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.
  • References (94)
  • Citations (24)
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References94
Newest
Michael R. Roner19
Estimated H-index: 19
(UTA: University of Texas at Arlington),
Kimberly Shahi10
Estimated H-index: 10
(UTA: University of Texas at Arlington)
+ 2 AuthorsCharles E. Carraher24
Estimated H-index: 24
(FAU: Florida Atlantic University)
Pancreatic cancer kills nearly all patients within 3–6 months after detection. There is no effective chemotherapy for it. We have found a number of organotin polymers that are effective at inhibiting pancreatic cancer cell lines with Chemotherapeutic Index values greater than two with some to values of 50.
24 Citations Source Cite
Published on Apr 1, 2009in Investigational New Drugs 2.66
Angela Alama20
Estimated H-index: 20
,
Maurizio Viale18
Estimated H-index: 18
+ 4 AuthorsFabio Sparatore21
Estimated H-index: 21
(UniGe: University of Genoa)
The cytotoxicity in vitro and antitumor activity in vivo of the organotin compound tri-n-butyltin(IV)lupinylsulfide hydrogen fumarate (IST-FS 35) have been investigated. The IC50 values obtained in a panel of tumor cell lines were compared to those of the parental compound IST-FS 29 in the same cells. IST-FS 35 resulted significantly more active than IST-FS 29 with IC50 values in the range 0.16–1.8 μM. Toxicity studies in vivo, after intravenous administration of escalating concentrations of IST...
15 Citations Source Cite
Girish Barot11
Estimated H-index: 11
(FAU: Florida Atlantic University),
Michael R. Roner19
Estimated H-index: 19
(UTA: University of Texas at Arlington)
+ 3 AuthorsCharles E. Carraher24
Estimated H-index: 24
(FAU: Florida Atlantic University)
A variety of dibutyltin polyethers have been synthesized employing the interfacial polymerization technique. The products are polymers with degrees of polymerization ranging from 60 to 390. Infrared spectral and mass spectral results are consistent with the proposed structure. The products show good inhibition of a variety of cancer cells including those associated with bone, breast, prostrate, and lung cancers. Some also show good viral inhibition of the HSV-1 (herpes simplex) and Vaccina (smal...
26 Citations Source Cite
Published on Jan 1, 2009in Coordination Chemistry Reviews 13.48
Sotiris K. Hadjikakou34
Estimated H-index: 34
(UoI: University of Ioannina),
Nick Hadjiliadis36
Estimated H-index: 36
(UoI: University of Ioannina)
Tin compounds and their therapeutic potentials are under consideration from many research groups, while a number of early reviews recording advances in the screening for antiproliferative potential of organotins are also available. This review focuses upon results obtained on the antiproliferative activity of tin compounds in the past 5 years.
270 Citations Source Cite
Published on May 1, 2008in Journal of Applied Toxicology 3.06
Biplob Koch17
Estimated H-index: 17
(NEHU: North Eastern Hill University),
Tushar S. Basu Baul23
Estimated H-index: 23
(NEHU: North Eastern Hill University),
Anupam Chatterjee17
Estimated H-index: 17
(NEHU: North Eastern Hill University)
Diorganotin(IV) compounds, R2SnCl2 are often tetrahedral, and structurally resemble the active platinum compounds, i.e. cisplatin, and consequently a large number of such complexes have been tested for antitumor activity. A structural correlation with biological activity for diorganotin(IV) complexes has shown that active species are associated with complexes having Sn–N bonds longer than 2.39 A which in turn determines the formation of a tin–DNA complex. In view of these, a series of diorganoti...
30 Citations Source Cite
Charles E. Carraher24
Estimated H-index: 24
(FAU: Florida Atlantic University),
Michael R. Roner19
Estimated H-index: 19
(UTA: University of Texas at Arlington)
+ 2 AuthorsGirish Barot11
Estimated H-index: 11
(FAU: Florida Atlantic University)
Organotin polyethers containing the synthetic estrogen diethylstilbestrol have been made in moderate yield with chain lengths ranging from 20 to 200 repeat units employing the interfacial polycondensation procedure. Infrared spectroscopy shows the absence of the O–H group and formation of the Sn–O linkage consistent with the formation of the polyether. F-MALDI MS results are consistent with the presence of organotin-containing fragmentation clusters containing one and two tin atoms and ion fragm...
23 Citations Source Cite
Published on Feb 1, 2008in European Journal of Medicinal Chemistry 4.83
Marianna N. Xanthopoulou9
Estimated H-index: 9
(UoI: University of Ioannina),
Sotiris K. Hadjikakou34
Estimated H-index: 34
(UoI: University of Ioannina)
+ 8 AuthorsSpyros Karkabounas14
Estimated H-index: 14
(UoI: University of Ioannina)
Abstract New organotin(IV) complexes with heterocyclic thioamides 2-mercapto-benzothiazole (Hmbzt), 5-chloro-2-mercapto-benzothiazole (Hcmbzt) and 2-mercapto-benzoxazole (Hmbzo) of formulae [(C 6 H 5 ) 3 Sn(mbzt)] ( 1 ), [(C 6 H 5 ) 3 Sn(cmbzt)] ( 3 ) and [(C 6 H 5 ) 2 Sn(cmbzt) 2 ] ( 4 ), together with the already known [(C 6 H 5 ) 3 Sn(mbzo)] ( 2 ), [( n -C 4 H 9 ) 2 Sn(cmbzt) 2 ] ( 5 ) and [(CH 3 ) 2 Sn(cmbzt) 2 ] ( 6 ) were used to study their influence on the peroxidation of oleic acid. The...
91 Citations Source Cite
Published on Jan 1, 2008in Aquatic Toxicology 3.79
Francesca Cima25
Estimated H-index: 25
(UNIPD: University of Padua),
Marcantonio Bragadin18
Estimated H-index: 18
,
Loriano Ballarin15
Estimated H-index: 15
(UNIPD: University of Padua)
After the definitive ban on tin-based antifouling substances, new organic compounds have recently been introduced in antifouling paint formulations, as either principal or booster biocides. In most cases, previous risk assessment of these biocides has been inadequate so that their possible effects on aquatic ecosystems is a matter of great concern. We studied the effects of two new organic biocides often associated in paint formulations, Sea-Nine 211 TM (4,5 dichloro-2-n-octyl-4-isothiazoline3-o...
57 Citations Source Cite
Published on Jan 1, 2008
Charles E. Carraher2
Estimated H-index: 2
,
Yoshinobu Naoshima12
Estimated H-index: 12
(Okayama University of Science)
+ 4 AuthorsAmitabh Battin6
Estimated H-index: 6
(FAU: Florida Atlantic University)
2 Citations Source Cite
Published on Jan 1, 2008
Charles E. Carraher2
Estimated H-index: 2
,
Theodore S. Sabir1
Estimated H-index: 1
(Providence Christian College),
Cara Carraher3
Estimated H-index: 3
(Princeton University)
In 1981 Barber and Liu and coworkers [1,2] independently introduced the concept of employing matrix-assisted desorption/ionization where the absorption of the matrix is chosen to coincide with the wavelength of the employed laser to assist in the volatilization of materials. In 1988 Tanaka, Hillenkamp and coworkers [3,4] employed the laser as the energy source giving birth to matrix-assisted laser/ desorption mass spectroscopy (MALDI MS). MALDI MS was developed for the analysis of nonvolative sa...
16 Citations Source Cite
Cited By24
Newest
Published on Jun 26, 2018
Charles E. Carraher24
Estimated H-index: 24
,
Michael R. Roner19
Estimated H-index: 19
+ 1 AuthorsFrancesca Mosca2
Estimated H-index: 2
Group 4 metallocene polymers offer a wide variety of unique properties. Some of these are reviewed in this paper, including the ability to form fibers and to absorb laser radiation, thereby protecting materials containing them in small amounts; the possibility of becoming conductive materials through simple doping; increasing the productivity of damaged, old and mold-infested seeds through incorporation of plant growth hormones; and acting as anticancer drugs that inhibit a variety of human canc...
Source Cite
Charles E. Carraher24
Estimated H-index: 24
(FAU: Florida Atlantic University),
Michael R. Roner19
Estimated H-index: 19
(UTA: University of Texas at Arlington)
+ 5 AuthorsPaul Slawek2
Estimated H-index: 2
(FAU: Florida Atlantic University)
Polyesters were rapidly synthesized employing interfacial polymerization from reaction of the salt of camphoric acid with Group VA (Group 15) triphenylmetallic dihalides. Yields range from 25 to 46 percent with chain lengths about 250. Infrared spectroscopy shows the formation of two new bands one assigned to the symmetrical M–O stretching and the second assigned to the asymmetrical M–O stretching. The bridging structure about the metal atom increases as the metal atom size increases. MALDI MS a...
2 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 Sep 1, 2016in Journal of Organometallic Chemistry 2.07
Khodayar Gholivand19
Estimated H-index: 19
(TMU: Tarbiat Modares University),
Rasoul Salami2
Estimated H-index: 2
(TMU: Tarbiat Modares University)
+ 1 AuthorsElham Torabi2
Estimated H-index: 2
(TMU: Tarbiat Modares University)
Abstract Two new diorganotin complexes with formula {SnCl 2 (CH 3 ) 2 L1} 2 (C1), L1 = N-nicotinyl, N′,N″-bis(diethylamine) phosphoric triamide and {SnCl 2 (CH 3 ) 2 L2} n (C2), L2 = N-nicotinyl, N′,N″-bis(cyclopentylamine) phosphoric triamide were synthesized and characterized by IR and NMR spectroscopy, and elemental analysis. Single crystal X-ray diffraction structural analyses confirmed all-trans and cis–trans configurations for distorted octahedral geometry in C1 and C2, respectively. Also,...
9 Citations Source Cite
Published on Feb 1, 2016in Journal of Macromolecular Science, Part A 1.16
Charles E. Carraher7
Estimated H-index: 7
(FAU: Florida Atlantic University),
Michael R. Roner19
Estimated H-index: 19
(UTA: University of Texas at Arlington)
+ 3 AuthorsNandalall Sookdeo3
Estimated H-index: 3
(FAU: 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 2.26
Charles E. Carraher7
Estimated H-index: 7
(FAU: Florida Atlantic University),
Michael R. Roner19
Estimated H-index: 19
(UTA: University of Texas at Arlington)
+ 7 AuthorsZamil Islam1
Estimated H-index: 1
(FAU: 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. Carraher24
Estimated H-index: 24
(FAU: Florida Atlantic University),
Michael R. Roner19
Estimated H-index: 19
(UTA: University of Texas at Arlington)
+ 2 AuthorsLindsey Miller4
Estimated H-index: 4
(UTA: 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 1.16
Carraher E. Charles1
Estimated H-index: 1
(FAU: Florida Atlantic University),
Michael R. Roner19
Estimated H-index: 19
(UTA: University of Texas at Arlington)
+ 3 AuthorsRyan Crichton3
Estimated H-index: 3
(FAU: 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 Aug 23, 2015in International Journal of Polymeric Materials 2.26
Charles E. Carraher7
Estimated H-index: 7
(FAU: Florida Atlantic University),
Michael R. Roner19
Estimated H-index: 19
(UTA: University of Texas at Arlington)
+ 2 AuthorsAlisa Moric-Johnson4
Estimated H-index: 4
(UTA: University of Texas at Arlington)
Polyesters derived from the interfacial reaction of the salt of chelidonic acid and triphenylarsenic dibromide, triphenylantimony dichloride, and triphenylbismuth dichloride are formed in moderate yield using commercially available reactants. IR data shows new bands characteristic of the formation of the M-O bond. MALDI MS shows formation of ion fragment clusters to two units. The polymers were tested for their ability to inhibit prostate, colon, breast (two cell lines), and pancreatic (two cell...
6 Citations Source Cite