Metallocene-containing polyesters from reaction of 3,5-pyridinedicarboxylic acid and metallocene dihalides and their preliminary ability to inhibit cancer cell growth

References

• C. Carraher. (Eds: A. Abd-El-Aziz, C. Carraher, C. Pittman, M. Zeldin), Macromolecules Containing Metal and Metal-Like Elements, Vol. 4. Group IVA Polymer. Wiley, 2005, Chapter-10, 263–310.
   Google Scholar
• C. Carraher, G. Scherubel. Synthesis of poly[alkylene(arylene)oxystannanes] using a new modified system. Makromolekular Chemie, 1972, 152, 61–69.
   Google Scholar
• C. Carraher, G. Scherubel. Synthesis of polyoxystannyloxyalkylenes. J. Polym. Sci, 1971, 9, 983–990.
   Web of Science ®Google Scholar
• C. Carraher, G. Scherubel. Synthesis of poly(tin ethers) employing alkoxides. Makromolekular Chemie, 1972, 160, 259–261.
   Google Scholar
• G. Barot, K. Shahi, M. Roner, C. Carraher. Synthesis, anomalous fiber formation, and preliminary anticancer study of the organotin polyether derived from 2-butyne-1,4-diol. J. Polym. Mater, 2006, 23, 423–436.
   Web of Science ®Google Scholar
• G. Barot, M. Roner, Y. Naoshima, K. Nagao, K. Shahi, C. Carraher. Synthesis, structural characterization, and preliminary biological characterization of organotin polyethers derived from hydroquinone and substituted hydroquinones. J. Inorg. Organomet. Polym. Mater, 2009, 19, 12–27.
   Web of Science ®Google Scholar
• M. Roner, K. R. Shahi, G. Barot, A. Battin, C. Carraher. Preliminary results for the inhibition of pancreatic cancer cells by organotin polymers. J. Inorg. Organomet. Polym. Mater, 2009, 19, 410–414.
   Web of Science ®Google Scholar
• M. Roner, C. Carraher, K. Shahi, G. Barot. Antiviral activity of metal-containing polymers-organotin and cisplatin-like polymers. Materials, 2011, 4, 991–1012.
   PubMed Web of Science ®Google Scholar
• G. Barot, K. Shahi, M. Roner, C. Carraher. Synthesis, structural characterization, and ability to inhibit cancer growth of a series of organotin poly(ethylene glycols). J. Inorg. Organomet. Polym. Mater, 2007, 17, 595–603.
   Web of Science ®Google Scholar
• C. Carraher, Y. Naoshima, K. Nagao, M. Roner, A. Zhao, G. Barot, A. Battin. Antibacterial, yeast and fungal polymeric materials derived from organotin-containing materials. J. Polym. Mater, 2011, 28, 303–336.
   Web of Science ®Google Scholar
• C. Carraher, A. Battin, K. Shahi, M. Roner. Synthesis, structural characterization, and initial evaluation as anticancer drugs of dibutyltin polyamines derived from various 4,6-diaminopyrimidines. J. Inorg. Organomet. Polym. Mater, 2007, 17, 631–639.
   Web of Science ®Google Scholar
• C. Carraher, F. Blum, M. Nair, G. Barot, A. Battin, T. Fiore, C. Pellerito, M. Scopelliti, A. Zhao, M. Roner, L. Pellerito. Solid state analysis of metal-containing polymers employing Mossbauer spectroscopy, solid state NMR and F EI TOF MALDI MS. J. Inorg. Organomet. Polym. Mater, 2010, 20, 570–585.
   Web of Science ®Google Scholar
• A. Zhao, K. Shahi, M. Roner, G. Barot, T. Fiore, C. Pellerito, M. Scopelliti, L. Pellerito, C. Carraher. Ciprofloxacin polymers derived from diallyltin and divinyltin dihalides. J. Polym. Mater, 2008, 25, 213–236.
   Web of Science ®Google Scholar
• M. Roner, C. Carraher, J. Roehr, K. Bassett. Antiviral and anticancer activity of organotin polymers and reactants derived from norfloxacin and ampicillin. J. Polym. Mater, 2006, 23, 153–159.
   Web of Science ®Google Scholar
• C. Carraher, L. Lanz. Synthesis and initial structural characterization of organotin polymers containing norfloxacin (TM). J. Polym. Mater, 2003, 20, 91–99.
   Web of Science ®Google Scholar
• C. Carraher, K. Morie. Synthesis of organotin polyesters containing ticarcillin, J. Polym. Mater, 2004, 21, 383–391.
   Web of Science ®Google Scholar
• C. Carraher, T. Sabir, M. Roner, K. Shahi, R. Bleicher, J. Roehr, K. Bassett. Synthesis of organotin polyamine ethers containing acyclovir and their preliminary anticancer and antiviral activity. J. Inorg. Organomet. Polym. Mater, 2006, 16, 249–257.
   PubMed Web of Science ®Google Scholar
• C. Carraher, D. Siegmann-Louda. (Eds: A. Abd-El-Aziz, C. Carraher, C. Pittman, M. Zeldin), Macromolecules Containing Metal and Metal-Like Elements, Vol 3. Biomedical Applications. Wiley, 2004, Chapter-4, 57–74.
   Google Scholar
• C. Carraher, R. Schwarz, J. Schroeder, M. Schwarz. Organotitanium polydyes derived from phenylsulfonphthalein dyes, and Congo red, Eriochrome Black-T, nigrosine and indigo carmine-synthesis and doping characteristics. J. Macromol. Sci. Chem, 1981, A15, 773–785.
   Web of Science ®Google Scholar
• C. Carraher, L. P. Torre, H. M. Molloy. Synthesis and structural characterization of titanium polyoximes. J. Macromol. Sci. Chem, 1981, A15, 757–771.
   Web of Science ®Google Scholar
• C. Carraher, M. Christensen, J. A. Schroeder. Physical characterization of titanium poly-ferrocene oximes. J. Macromol. Sci. Chem, 1977, A11, 2021–2028.
   Web of Science ®Google Scholar
• C. Carraher, G. Burrish. Synthesis and initial thermal characterization of titanium polyferrocene ethers. J. Macromol. Sci. Chem, 1976, A10, 1457–1465.
   Web of Science ®Google Scholar
• C. Carraher, S. Bajah. Synthesis of titanium polyethers by the interfacial and aqueous solution techniques. Polymer, 1973, 14, 42–44.
   Web of Science ®Google Scholar
• C. Carraher, S. Bajah. Effects of base nature, base concentration, and method of synthesis of titanium polyether. Br. Polym. J, 1975, 7, 155–159.
   Google Scholar
• C. Carraher, R. Frary. Synthesis of zirconium poly-O-amidoximes. J. Polym. Sci. Chem, 1974, 12, 799–805.
   Web of Science ®Google Scholar
• C. Carraher, L. Jambaya. Initial synthesis and thermal characterization of hafnium polyethers. Angew Makromol. Chem, 1976, 52, 111–116.
   Google Scholar
• C. Carraher, A. Battin, M. Roner. Effect of bulk doping on the electrical conductivity of selected metallocene polyamines. J. Inorg. Organomet. Polym. Mater, 2013, 23, 61–73.
   Web of Science ®Google Scholar
• M. Roner, C. Carraher, Jr., K. Shahi, Y. Ashida, G. Barot. Ability of Group IVB metallocene polyethers containing dienestrol to arrest the growth of selected cancer cell lines. BMC Cancer, 2009, 9, 358.
   PubMed Web of Science ®Google Scholar
• C. Carraher, M. Roner, K. Shahi, Y. Ashida, G. Barot. Synthesis, structural characterization, and anti-cancer evaluation of group IVB-metallocene polyethers containing the synthetic estrogen diethylstilbestrol. J. Polym. Mater, 2007, 24, 357–369.
   Web of Science ®Google Scholar
• C. Carraher. Condensation metallocene polymers. J. Inorg. Organomet. Polym. Mater, 2005, 15, 121–145.
   Web of Science ®Google Scholar
• C. Carraher, W. J. Scott, J. Schroeder, D. J. Giron. Poly(cis-dihalodiamine platinum(Ii)) compounds – synthesis and biological-activity. J. Macromol. Sci. Chem, 1981, A15, 625–631.
   Web of Science ®Google Scholar
• D. Siegmann-Louda, C. Carraher. Effect of poly(dichloro-2-chloro-p-phenylenediamineplatinum(II) on normal and transformed cells. J. Polym. Mater, 1987, 4, 29–34.
   Google Scholar
• C. Carraher. Organoantimony-containing polymers. J. Polym. Mater, 2008, 25, 35–50.
   Web of Science ®Google Scholar
• T. Sabir, C. Carraher. Synthesis of triphenylantimony and triphenylbismuth-containing polyether amines containing acyclovir. J. Polym. Mater, 2006, 4, 403–413.
   Google Scholar
• D. Siegmann-Louda, C. Carraher, Q. Quinones, G. McBride. Preliminary evaluation of organoarsenic and organoantimony polymers derived from cephalexin as potential anticancer drugs. Polym. Mater. Sci. Eng, 2003, 88, 390–392.
   Google Scholar
• C. Carraher, M. Nass, D. Giron. Antimony polyamines as antibacterial additives. Org. Coat. Appl. Polym. Sci. Proc, 1983, 48, 523–527.
   Google Scholar
• C. Carraher, L. Hedlund. Synthesis and characterization of antimony (V) polyoximes. J. Macromol. Sci. Chem, 1980, A14, 713–728.
   Web of Science ®Google Scholar
• C. Carraher, W. Venable, H. S. Blaxall, J. E. Sheats. Synthesis and characterization of antimony (V)-polycobalticinium exters. J. Macromol. Sci. Chem, 1980, A14, 571–579.
   Web of Science ®Google Scholar
• C. Carraher, H. S. Blaxall. Synthesis and solution characterization of antimony polyesters. Angew. Makromol. Chemie, 1979, 83, 37–45.
   Web of Science ®Google Scholar
• C. Carraher, M. Naas, D. J. Giron, D. R. Cerutis. Structural and biological characterization of antimony V polyamines. J. Macromol. Sci. Chem, 1983, A19, 1101–1120.
   Web of Science ®Google Scholar
• M. Roner, C. Carraher, A. Moric, N. Trang, N. Truong, Z. Islam, A. Morrison. Inhibition of pancreatic cancer cell lines by group IVB and group VA polymers derived from glycyrrhetinic acid, 3,5-pyridinedicarboxylic acid, and histamine. Polym. Mater. Sci. Eng, 2012, 107, 325–328.
   Google Scholar
• W. Lee, J. Elliott, R. Brownsey. Inhibition of acetyl-CoA carboxylase isoforms by pyridoxal phosphate. J. Biol. Chem, 2005, 280, 41835–41843.
   PubMed Web of Science ®Google Scholar
• K. McCann, J. Laane. Ramon and infrared spectra and theoretical calculations of dipicolinic acid, dinicotinic acid, and their dianions. J. Mol. Struct, 2008, 890, 346–358.
   Web of Science ®Google Scholar
• N. Ogata. Synthesis of polyamides and polyesters having various functional groups. J. Macromol. Sci. Chem, 1979, A13, 477–501.
   Web of Science ®Google Scholar
• C. Marvel, H. Vogel. Polybenzimidazoles. US Patent 3174947, 1965.
   Google Scholar
• H. Hoff, A. Krieger. Polyamides from heterocyclic dicarboxylic acids. Makromolecular Chemie, 1961, 47, 93–113.
   Google Scholar
• H. Shizunobu, N. Yasuhiko. Synthesis of polyesters containing pyridine rings in the main chains. Kobunshi Kagaku, 1967, 24, 215–223.
   Google Scholar
• G. I. Braz, I. E. Kardash, V. S. Yakubovick, G. V. Myasnikova, A. Ardashnikov, A. Oleinik, A. Pravednikov, A. Yakubovick. Polybenzosazoles, their synthesis and thermal degradation. Vysokomoleculyarnye Soedineniya, 1966, 8, 272–277.
   Google Scholar
• P. Hergenrother, W. Wrasidlo, H. Levine. Polybenzothiazoles. I. Synthesis and preliminary stability evaluation. J. Polym. Sci, 1965, 3, 1665–1674.
   Web of Science ®Google Scholar
• A. Szorcsik, L. Nagy, M. Scopelliti, A. Deak, L. Pellerito, G. Galbacs, M. Hered. Preparation and structural characterization of [Ph3Sn(IV)]+ complexes with pyridine-carboxylic acids or hydroxypyridine, -pyrimidine and –quinolone. J. Organomet. Chem, 2006, 691, 1622–1630.
   Web of Science ®Google Scholar
• C. Ma, J. Li, R. Zhang. Synthesis and crystal structures of polymeric ionic triorganotin esters of 3,5-pyridinedicarboxylic acid and 5-nitroisophthalic acid. J. Coord. Chem, 2006, 59, 1891–1904.
   Web of Science ®Google Scholar
• H. Qisong, H. Benfeng, L. Qiuyan, L. Taiqi. Synthesis, crystal structure and fluorescence property of terbium coordination polymers with pyridine-3,5-dicarboxylic acid. Mater. Sci. Forum, 2010, 663, 72–75.
   Google Scholar
• Q. Shi, F. Liang. Synthesis, crystal structure and characterization of a novel terbium fluorescent coordination polymer. Xiyou Jinshu Cailiao Yu Gongcheng, 2010, 39, 1202–1205.
   Web of Science ®Google Scholar
• V. Chandrasekhar, R. Thirumoorthi. Self-assembly of triorganotin (V) moieties with 1,2,4,5,-benzenetetracarboxylic acid: synthesis, characterizations and influence of solvent on the molecular structure. J. Organomet. Chem, 2009, 28, 2096–2106.
   Web of Science ®Google Scholar
• H. Fei, X. Liu, Z. Li, W. Feng. Metal dicarboxylates: new anode materials for lithium-ion batteries with good cycling performance. Dalton Trans, 2015, 44, 9909–9914.
   PubMed Web of Science ®Google Scholar
• S. Alisir, S. Demir, B. Sariboga, O. Buyukgungor. A disparate 3-D silver(I) coordination polymer of pyridine-3,5-dicarboxylate and pyrimidine with strong intermetallic interactins: X-ray crystaliography, photoluminescane and antimicrobial activity. J. Coord. Chem, 2015, 68, 155–168.
   Web of Science ®Google Scholar
• M. Wang, F. Wang, J. Ma, J. Xu. Organic linker geometry controlled synthesis of coordination polymer spheres and their thermal transformation to yolk-shell metal oxides. J. Mater. Chem. A, 2014, 2, 15480–15487.
   Web of Science ®Google Scholar
• J. Chen, H. Zhao, H. Li, S. Huang, N. Ding, W. Chen, D. Houng, W. Zhang, T. Andy Hor. Cryst. Eng. Comm, 2014, 16, 7722–7730.
   Web of Science ®Google Scholar
• Y. Liu, Y. Du, X. Wu, Z. Zheng, X. Lin, L. Zhu, Y. Cai. A series of lanthanide complexes based on pyridine-3,5-dicarboxylate and succinate ligands: syntheses, structures, and properties. Cryst. Eng. Comm, 2014, 16, 6797–6802.
   Web of Science ®Google Scholar
• J. Chen, M. Chen, N. Ding, W. Chen, H. wen-Hua, T. S. Andy, D. J. Young. Transmetalation of a dodecahedral Na9 aggregate-based polymer: a facile route to water stable Cu(II) coordination networks. Inorg. Chem, 2014, 53, 7446–7454.
   PubMed Web of Science ®Google Scholar
• K. Liu, H. Liu, L. Yang, F. Zho, Y. Li, W. Ruan. One-pot synthesis of monodisperse Zn coordination polymer micro/nanostructures and their transformation to mesoporours ZnO photocatalysts. RSC Adv, 2014, 4, 25160–25164.
   Google Scholar
• G. Nanai, R. Thankuria, H. Titi, R. Patra, I. Goldberg. Synthesis, structure, topology and magnetic properties for new coordination polymers based on 5(-Br/-COOH substituted nicotinic acid. Cryst. Eng. Comm, 2014, 16, 5244–5256.
   Web of Science ®Google Scholar
• E. Chekmeneva, C. Hunter, M. Packer, S. Turega. Evidence for partially bound states in cooperative molecular recognition interfaces. J. Am. Chem. Soc, 2008, 130, 17718–17725.
   PubMed Web of Science ®Google Scholar
• C. Carraher. Polymer Chemistry. Taylor & Francis, 2014.
   Google Scholar
• C. Carraher. Introduction to Polymer Chemistry. CRC Press, 2013.
   Google Scholar
• F. A. Cotton, G. Wilkinson. Advanced Inorganic Chemistry, 6th ed. Interscience, 1999.
   Google Scholar
• C. E. Carraher. Synthesis of zirconium polyesters. Eur. Polym. J, 1972, 8, 215–220.
   Web of Science ®Google Scholar
• A. Battin, C. E. Carraher. Effect of doping by exposure to iodine vapor on the electrical conductivity of the polyamine from titanocene dichloride and 2-nitro-p-phenylenediamine. J. Polym. Mater, 2008, 23, 23–33.
   Web of Science ®Google Scholar
• C. E. Carraher, A. Battin, M. R. Roner. Effect of electrical conductivity through the bulk doping of the product of titanocene dichloride and 2-nitro-1,4-phenhylenediamine. J. Funct. Biomater, 2011, 2, 18–30.
   PubMedGoogle Scholar
• A. Gross, H. Alborzinia, S. Piantavigna, L. L. Martin, S. Wölfl, N. Metzler-Nolte. Vesicular disruption of lysosomal targeting organometallic polyarginine bioconjugates. Metallomics, 2015, 7(2), 371–384.
   PubMed Web of Science ®Google Scholar
• A. Gross, H. Alborzinia, S. Piantavigna, L. L. Martin, S. Wölfl, N. Metzler-Nolte. Structure-activity relationship of trifluoromethyl-containing metallocenes: electrochemistry, lipophilicity, cytotoxicity, and ROS production. Chem. Med. Chem, 2014, 9(6), 1188–1194.
   Web of Science ®Google Scholar
• R. Havelek, P. Siman, J. Cmielova, A. Stoklasova, J. Vavrova, J. Vinklarek, J. Knizek, M. Rezacova. Differences in vanadocene dichloride and cisplatin effect on MOLT-4 leukemia and human peripheral blood mononuclear cells. Med. Chem, 2012, 8(4), 615–621.
   PubMed Web of Science ®Google Scholar
• S. Gómez-Ruiz, D. Maksimović-Ivanić, S. Mijatović, G. N. Kaluđerović. On the discovery, biological effects, and use of cisplatin and metallocenes in anticancer chemotherapy. Bioinorg. Chem. Appl, 2012, 140284. doi:10.1155/2012/140284. Epub 2012 Jul 12.
   PubMed Web of Science ®Google Scholar
• D. Senthilnathan, S. Vaideeswaran, P. Venuvanalingam, G. Frenking. Antitumor activity of bent metallocenes: electronic structure analysis using DFT computations. J. Mol. Model, 2011, 17(3), 465–475.
   PubMed Web of Science ®Google Scholar
• U. Olszewski, J. Claffey, M. Hogan, M. Tacke, R. Zeillinger, P. J. Bednarski, G. Hamilton. Anticancer activity and mode of action of titanocene C. Invest. New Drugs, 2011, 29(4), 607–614.
   PubMed Web of Science ®Google Scholar
• C. E. Carraher, A. Morrison, M. R. Roner, A. Moric, N. Trang. Synthesis and characterization of organotin polyesters derived from 3,5-pyridinedicarboxylic acid. J. Inorg. Organomet. Polym. Mater, 2014, 24, 182–189.
   Web of Science ®Google Scholar
• A. Szorcsik, L. Nagy, A. Deak, M. Scopelliti, Z. Fekete, A. Csaszar, C. Pellerito, L. Pellerito. Preparation and structural studies on the Bu2Sn(IV) complexes with aromatic mono- and dicarboxylic acids containing hetero {N} donor atmo. J. Organomet. Chem, 2004, 689, 2762–2769.
   Web of Science ®Google Scholar
• C.E. Carraher. Synthesis of titanium polyesters. J. Polym. Sci, 1971, 9, 3661–3670.
   Web of Science ®Google Scholar
• C. Carraher, T. S. Sabir, C. L. Carraher. (Eds: A. Abd-El-Aziz, C. Carraher, C. Pittman, M. Zeldin), Inorganic and Organometallic Macromolecules. Springer, 2008, Chapter-13, 329–350.
   Google Scholar
• C. Carraher, T. Sabir, C. L. Carraher. Fragmentation matrix assisted laser desorption/ionization mass spectrometry-basics. J. Polym. Mater, 2006, 23, 143–151.
   Web of Science ®Google Scholar
• C. Carraher, G. Barot, A. Battin. Reactions between the matrix and ion fragments created from the MALDI MS or organotin-containing polymers. J. Polym. Mater, 2009, 26, 17–31.
   Web of Science ®Google Scholar
• C. E. Carraher, M. R. Roner. Organotin polymers as anticancer and antiviral agents. J. Organomet. Chem, 2014, 751, 67–82.
   Web of Science ®Google Scholar
• C. E. Carraher, G. Barot, S. W. Vetter, G. Nayak, M. R. Roner. Degradation of the organotin polyether derived from dibutyltin dichloride and hydroxyl-capped poly(ethylene glycol) in trypsin and evaluation of trypsin activity employing light scattering photometry and gel electrophosphoresis. JCAMS, 2013, 1, 1–6.
   Google Scholar
• C. E. Carraher, G. Barot, K. Shahi, M. R. Roner. Influence of DMSO on the inhibition of various cancer cells by water-soluble organotin polyethers. JCAMS, 2013, 1, 294–304.
   Google Scholar
• D. Siegmann-Louda, C. E. Carraher, F. Pflueger, J. R. Ross. (Eds: C. Carraher, G. Swift), Functional Condensation Polymers. Plenum, 2002, Chapter-14, 199–206.
   Google Scholar
• R. Doucette, D. Siegmann-Louda, C. E. Carraher, A. Cardoso. Inhibition of Balb 3T3 cell as a function of metal for kinetin containing polymers. Polym. Mater. Sci. Eng, 2004, 91, 564–566.
   Google Scholar
• R. M. Roat-Malone. Bioinorganic Chemistry, 2nd ed. Wiley, 2007.
   Google Scholar
• J. B. Waern, H. H. Harris, B. Lai, Z. Cai, M. M. Harding, C. T. Dillon. Intracellular mapping of the distribution of metals derived from the antitumor metallocenes. J. Biol. Inorg. Chem, 2005, 10(5), 443–452.
   PubMed Web of Science ®Google Scholar
• M. R. Roner, K. Shahi, G. Barot, A. Battin, C. E. Carraher. Preliminary results for the inhibition of pancreatic cancer cells by organotin polymers. J. Inorg. Organomet. Polym. Mater, 2009, 19, 410–414.
   Web of Science ®Google Scholar
• C. E. Carraher, M. Ayoub, M. R. Roner, A. Moric, N. Trang. Synthesis, structural characterization, and ability to inhibit the growth of pancreatic cancer by organotin polymers containing chelidonic acid. JCAMS, 2013, 1, 65–73.
   Google Scholar
• C. E. Carraher, N. T. Truong, M. R. Roner. Synthesis of organoarsenic, organoantimony, and organobismuth poly(ether esters) from reaction with glycyrrhetinic acid and their preliminary activity against pancreatic cancer cell lines. JCAMS, 2013, 1, 134–150.
   Google Scholar
• B. Ekwall, V. Silano, A. Paganuzzi-stammati, F. Zucco. Toxicity Tests with Mammalian Cell Cultures in Short-Term Toxicity Tests for Non-genotoxic Effects. Wiley, 1990.
   Google Scholar