Synthesis, structural characterization, and ability to inhibit the growth of pancreatic cancer by organotin polymers containing chelidonic acid

Published on Mar 1, 2013in Journal of the Chinese Advanced Materials Society
· DOI :10.1080/22243682.2013.774522
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)
Abstract
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 bridging. The organotin polyesters exhibit reasonable inhibition of two pancreatic cancer cell lines.
  • References (29)
  • Citations (8)
Cite
References29
Published on Jan 1, 2004in Journal of Polymer Materials 0.35
Ce Carraher1
Estimated H-index: 1
,
K Morie1
Estimated H-index: 1
8 Citations
Published on Sep 5, 2003
Alaa S. Abd-El-Aziz22
Estimated H-index: 22
,
Charles E. Carraher23
Estimated H-index: 23
+ 2 AuthorsMartel Zeldin6
Estimated H-index: 6
128 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. Carraher23
Estimated H-index: 23
(Florida Atlantic University),
Kenzo Morie1
Estimated H-index: 1
Organotin polyesters have been synthesized employing the classical interfacial polycondensation of organotin dihalides and the salt of 1,1′-ferrocenedicarboxylic acid. The products are oligomeric (DP = 5) to polymeric (DP = 220). The presence of new IR bands characteristic of formation of the Sn–O band are present. Ion fragments characteristic of the repeat unit and greater are found employing F MALDI MS.
11 Citations Source Cite
Published on Jan 1, 2010in CrystEngComm 3.30
Marina Fainerman-Melnikova7
Estimated H-index: 7
(University of Sydney),
Jack K. Clegg31
Estimated H-index: 31
(University of Sydney)
+ 2 AuthorsRachel Codd22
Estimated H-index: 22
(University of Sydney)
Complexes between Cu(II) or Ni(II) and O- or N-containing ligands, pyridine-2,6-dicarboxylic acid (H2L1), 4-pyranone-2,6-dicarboxylic acid (H2L2), 4H-pyran-2,6-dicarboxylic acid (H2L3), (S)-tetrahydro-2-furoic acid (S-HL4), 2,2′-bipyridine (L5), 1,10-phenanthroline (L6) or bis(2-pyridylmethyl)amine (L7), have been synthesised and characterised by X-ray crystallography. In the ionic complex [Cu(H2L1)(L5)(OH2)]·[Cu(L1)2]·3H2O (1), one L1 group and L5 are close to parallel, which is not the case fo...
4 Citations Source Cite
Published on Jan 1, 2005in Journal of Materials Chemistry 9.93
Beverley Twaites4
Estimated H-index: 4
(University of Portsmouth),
Carolina de las Heras Alarcón10
Estimated H-index: 10
(University of Portsmouth),
Cameron Alexander40
Estimated H-index: 40
(University of Portsmouth)
Synthetic polymers are of increasing interest as therapeutic agents owing to their enhanced pharmacokinetic profiles relative to small molecule drugs. Multifunctional polymers are now being prepared that can ‘hide’ biologically active compounds, such as cytotoxic agents, therapeutic proteins or nucleic acids, until they reach target sites in the body, but which can then release the agent in situ to effect the therapy. In this feature article we consider the sophisticated macromolecular construct...
62 Citations Source Cite
Published on Dec 1, 2011in Journal of Chemical Crystallography 0.70
Vaduganathan Yasodha3
Estimated H-index: 3
(Bharathiar University),
Subbaiah Govindarajan12
Estimated H-index: 12
(Bharathiar University)
+ 1 AuthorsJanusz Leciejewicz8
Estimated H-index: 8
5 Citations Source Cite
Vaduganathan Yasodha3
Estimated H-index: 3
(Bharathiar University),
Subbaiah Govindarajan12
Estimated H-index: 12
(Bharathiar University)
+ 1 AuthorsChristopher Glidewell24
Estimated H-index: 24
(University of St Andrews)
The structures of five metal complexes containing the 4-oxo-4H-pyran-2,6-dicarboxyl­ate dianion illustrate the remarkable coordinating versatility of this ligand and the great structural diversity of its complexes. In tetra­aqua­beryllium 4-oxo-4H-pyran-2,6-dicarboxyl­ate, [Be(H2O)4](C7H2O6), (I), the ions are linked by eight independent O—H⋯O hydrogen bonds to form a three-dimensional hydrogen-bonded framework structure. Each of the ions in hydrazinium(2+) diaqua­(4-oxo-4H-­pyran-2,6-dicarboxyl...
12 Citations 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 AuthorsGirish Barot11
Estimated H-index: 11
(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
Cited By8
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 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),
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
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
Charles E. Carraher23
Estimated H-index: 23
(Florida Atlantic University),
Alicia Morrison2
Estimated H-index: 2
(Florida Atlantic University)
+ 2 AuthorsNancy T. Trang5
Estimated H-index: 5
(University of Texas at Arlington)
Organotin polyesters were synthesized from the interfacial condensation of organotin dihalides and salts of 3,5-pyridinedicarboxylic acid. The polymers are synthesized in moderate to high yields and are moderate to high polymers. MALDI MS, IR spectral, and NMR spectral results are consistent with the proposed structure. The Sn–O stretching band is found at about 1,028 cm−1. Infrared spectra are consistent with majority of the products having a non-bridged structure about the tin. All of the poly...
7 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
Charles E. Carraher23
Estimated H-index: 23
(Florida Atlantic University),
Paul Slawek2
Estimated H-index: 2
(Florida Atlantic University)
+ 4 AuthorsFloyd Russell2
Estimated H-index: 2
(Florida Atlantic University)
The interfacial polymerization is employed to produce high polymer poly(ester ethers) from the reaction of the salt of dipicolinic acid and various organotin dihalides. They are rapidly synthesized with yield increasing as the length of the organotin alkyl chain increases. Infrared spectroscopy shows the formation of new bands derived from the Sn–O and Sn–O(CO) linkages. IR also shows that the products exist as a combination of molecular geometries about the tin atom. MALDI MS shows formation of...
3 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