Bioengineering functional copolymers. XII. Interaction of boron-containing and PEO branched derivatives of poly(MA-alt-MVE) with HeLa cells — Oak Academic Publishing
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Bioengineering functional copolymers. XII. Interaction of boron-containing and PEO branched derivatives of poly(MA-alt-MVE) with HeLa cells
Novel boron-containing bioengineering copoly- mer and its α-hydoxy-ω-methoxy-poly(ethy- lene oxide (PEO) macrobranched derivatives were synthesized by (1) partially amidolysis of poly(maleic anhydride-alt-methyl vinyl ether) w?th ethanolamine ester of diphenylboronic acid and (2) esterification of synthesized B-con- taining copolymers with PEO. They had a com- bination of hydrophilic/hydrophobic linkages, free carboxylic groups, positive charges and an ionized organoboron linkage as antitumor sites, along with an ability to interact with HeLa cells. The structure, composition and properties (cy- totoxicity and antitumor activity) of synthe- sized copolymers were investigated. In vitro cytotoxicity results, obtained by the fluore scence microscopy measurements indicate that unlike the virgin copolymer, boron-containing and PEO macrobranched derivatives exhibit higher antitumor activity. It was found that organoboron copolymer exhibits the most apo- ptotic and necrotic effects against HeLa cells whereas a minor effect relative to cancer cells was observed on L929 Fibroblast cells.
Albertsson, P.A. (1986) Partition of Cell Particles and Macromolecules. New York, Wiley.
Herold, D.A., Keil, K., Bruns, D.E. (1989) Oxidation of polyethylene glycols by alcohol dehydrogenase.Biochem Pharmacol, 38(1), 73.
Sinha, V.R., Aggarwal, A., Trehan, A. (2004) Biode- gradable PEGylated microspheres and nanospheres. Amer J Drug Deliv, 2(3), 157.
K??eli, V., Rzaev, Z.M.O., Pi?kin, E. (2003) Bioengi- neering functional copolymers. III. Synthesis of biocom- patible poly(NIPA-co-MA)-g-PEO/PEI macrocomplexes and their thermostabilization effect on the activity of the enzyme penicillin G acylase. J Polym Sci Part A: Polym Chem, 41(11), 1580.
Mazi, H., Emregül, E., Rzaev, Z.M.O., Kibarer, G. (2006) Preparation and properties of invertase immobilized on a poly(maleic anhydride-hexen-1) membrane. J Biomater Sci, Polym Ed, 17, 821.
Rzaev, Z.M.O., Din?er, S., Pi?kin, E. (2007) Functional copolymers of N-isopropyl-acrylamide for bioengineering applications. Prog Polym Sci, 32(5), 534.
Butler, G.B. (1992) Cyclopolymerization and cyclopo- lymerization. New York, Marcel Dekker.
Veron, L., Bignicount, M.C.D., Delair, T., Pichot, C., Mandrand, B. (1996) Syntheses of poly [N-(2,2-dimetho- xyethyl)-N-methyl acrylamide] for the immobilization of oligo-nucleotides. J Appl Polym Sci, 60(2), 235.
Ladavière, C., Delair, T., Domard, A., Pichot, C., Man-drand, B. (1999) Covalent immobilization of biological molecules to maleic anhydride and methyl vinyl ether copolymers-A physico-chemical approach. J Appl Polym Sci, 71(6), 927.
Chaix, C., Minard-Basquin, C., Delair, T., Pichot, C., and Mandrand, B. (1998) Oligonucleotide synthesis maleic anhydride copolymers covalently bound to silica spherical support and characterization of the on obtained conjugates. J Appl Polym Sci 70(12), 2487.
Volkova, F., Gorshkova, M.Yu., Ivanov, P. E., Stotskaya, L. L. (2002) New scope for synthesis of divinyl ether and maleic anhydride copolymer with narrow molecular mass distribution. Polym Adv Technol, 13(10-12), 1067.
Izumrudov, V.A., Gorshkova, M.Yu., Volkova, F. (2005) Controlled phase separations in solution of soluble poly-electrolyte complex of DIVEMA (copolymer of divinyl ether and maleic anhydride. Eur Polym J, 41(6), 1251.
Ladavière, C., Delair, T., Domard, A., Pichot, C., Mandrand, B. (1999) Covalent immobilization of bovine serum albumin onto (maleic anhydride-alt-methyl vinyl ether) copolymers. J Appl Polym Sci, 72(12), 1565.
Delair, T., Badey, B., Domard, A., Pichot, C., Mandrand, B. (1997) Polym Adv Technol, 8(5), 297.
Patel, H., Raval, D.A., Madamwar, D., Sinha, T.J.M. (1997) Polymeric prodrugs. Synthesis, release study and antim-icrobial properties of polymer-bound acriflavine. Angew Makromol Chem, 245(1), 1.
Patel, H., Raval, D.A., Madamwar, D., Patel, S.R. (1998) Polymeric prodrug: Synthesis, release study and anti- microbial property of poly(styrene-co-maleicanhy- dride)-bound acriflavine. Angew Makromol Chem, 263(1), 25.
Hirano, T., Todorski, T., Kato, S., Yamamoto, H., Caliceti, P. (1994) Synthesis of the conjugate of superoxide dismutase with the copolymer of divinyl ether and maleic anhydride retaining enzymatic activity. J Control Release, 28(1-3), 203.
Hirano, T., Todorski, T., Morita, R., Kato, S., Ito, Y., Kim, K., Shukla, G., Veronese, F., Maeda, H., Ohashi, S. (1997) Anti-inflammatory effect of the conjugate of superoxide dismutase with the copolymer of divinyl ether and maleic anhydride against rat re-expansion pulmonary edema. J Control Release, 48(2-3), 131.
Maeda, H.H. (1991) SMANCS and polymer-conjugated macromolecular drugs: advantages in cancer chemo- therapy. Adv Drug Delivery Rev, 6(2), 181.
Gam, G.-T., Jeong, J.-G., Lee, N.-J., Lee, W., Ha, C.-S., Cho, W.-J. (1995) Synthesis and biological activities of copolymers of N-glycinyl maleimide with methacrylic acid and vinyl acetate. J Appl Polym Sci, 57(2), 219.
James, T.D., Sandanayake, S., Shinkay, S. (1996) Sac- charide sensing with molecular receptors based on boronic acid. Angew Chem Inter Ed Eng, 35(17), 1910.
Barth, R.F., Yang, W., Rotaru, J.H., Moeschberger, M.L., Boesel, C.P., Soloway, A.H., Joel, D.D., Nawrocky, M.M., Ono, K., Goodman, J.H. (2000) Boron neutron cupture therapy of brain tumors: enchanced survival and cure following blood-brain barrier disruption and ?ntracarotid injection of sodium borocaptate and boronophenyl aniline. Int J Radiat Oncol Biol Phys, 47(1), 209.
Siebert, W. (Ed.) (1887): Advances in Boron Chemistry. Cambridge, Royal Society Chemistry.
Mishima Y. (Ed.) (1996) Cancer Neutron Capture Therapy. New York, Plenum Press.
Kettner, C.A. and Shenvi, A.B. (1984) Inhibition of the serine proteases leukocyte elastase, pancreatic elastase, cathepsin G, and chymotrypsin by peptide boronic acids. J Biol Chem, 259(24), 15106. Miyazaki, H., Kikuchi, A., Kitano, S., Koyama, Y., Okano, T., Sakurai, Y., Kataoka, K. (1993)
Boronate-containing polymer as novel mitogen for lymphocytes. Biochem Biophys Res Commun, 195(2), 829.
Aoki, T., Nagao, Y., Terada, E., Sanui, K., Ogata N., Yamada, N., Sakurai, Y., Kataoka, K., Okano, T. (1995) Endothelial cell differentiation into capillary structures by copolymer surfaces with phenylboronic acid group. J Biomater Sci Polym Ed, 7(7), 539.
Otsuka, H., Uchimura, E., Koshino, H., Okano, T., Kataoka, K. (2003) Anomalous binding profile of pheny-lboronic acid with N-acetylneuraminic acid (Neu5Ac) in aqueous solution with varying pH. J Am Chem Soc, 125(12), 3493.
Uchimura, E., Otsuka, H., Okano, T., Sakurai, S., Kataoka, K. (2001) Totally synthetic polymer with lectin-like function: Induction of killer cells by the copolymer of 3-acryl-amidophenylboronic acid with N,N-dimethyla- crylamide. Biotech Bioeng, 72(3), 307.
Otsuka,H., Ikeya, T., Okano, T., Kataoka, K. (2006) Activation of lymphocyte proliferation by boronate- containing polymer immobilised on substrate: The effect of boron content on lymphocyte proliferation. Eur Cells Mater, 12(1), 36.
Kataoka, K., Miyazaki, N., Okano, T., Sakurai, Y. (1994) Sensitive glucose-induced change of the lower critical solution temperature of poly [N,N-dimethylacrylamide- co-3-(acrylamido) phenylboronic acid] in physiological saline. Macromolecules, 27(4), 1061.
Uguzdo?an, E., Denkta?, E.B., Tuncel, A. (2002) RNA- sensitive N-isopropylacrylamide/vinylphenyl boronic acid random copolymer. Macromol Biosci, 2(5), 214.
Uguzdo?an, E., Kayi, H., Denkta?, E.B., Patir, S., Tuncel, A. (2003) Stimuli-responsive properties of aminophen- ylboronic acid carrying thermosensitive copolymers. Po- lym Int, 52(5), 649.
Shiomori, K., Ivanov, A.E., Galaev, I.Yu., Kawano, Y., Mattiasson, B. (2004) Thermo-responsive properties of sugar sensitive copolymer of N-isopropylacrylamide and 3-(acrylamido)phenylboronic acid Macromol Chem Phys, 205(1), 27.
Rzayev, Z.M.O., Be?karde?, O. (2007) Boron-containing functional copolymers for bioengineering applications. Collect Czech Chem Commun, 72(12), 1591.
Kahraman, G., Be?karde?, O., Rzayev, Z.M.O., Pi?kin, E. (2004) Bioengineering functional copolymers. VII. Synth- esis and characterization of boron-containing self-assem- bled supramolecular architectures. Polymer, 45(17), 5813.
?imen, E.K., Rzayev, Z.M.O., Pi?kin, E. (2005) Bioengi-neering functional copolymers. V. Synthesis LCST, and thermal behavior of poly(N-isopropylacry- lamide-co-p-vinyl-phenylboronic acid). J Appl Polym Sci, 95(3), 573.
Rzayev, Z.M.O., Erdo?an, D., Türk, M., Pi?kin, E. (2008) Bioengineering functional copolymers. VIII. Stimuli-res- ponsive boron-containing graft copolymers and their poly(ethylene imine) macrocomplexes and DNA conju- gates. J Biol Chem, 36(2), 83.
Türk, M., Dincer, S., Yulug, I.G., Piskin, E. (2004) In vitro transfection of HeLa cells with temperature sensitive polycationic copolymers. J Control Release, 96(2), 325.
Choi, S.-J., Oh, J.-M., Choy, J.-H. (2009) Toxicological effects of inorganic nanoparticle nanoparticles on human lung cancer A549 cells. J Inorg Biochem, 103(3), 463.
Ulukaya, E., Kurt, A., Wood, E.J. (2001) 4-(N-hydrox- yphenyl)retinamide can selectively induce apoptosis in human epidermoid carcinoma cells but not in normal dermal fibroblasts.Cancer Invest, 19(2), 145.
McPartland, J.L., Guzail, M.A., Kendall, C.H., Pringle, J.H. (2005) Apoptosis in chronic viral hepatitis parallels histological activity: an immunohistochemical investi- gation using antiactivated caspase-3 and M30 cytodeath antibody. Int J Exp Pathol, 86(1), 19.