Synthesis and antitumor activity of poly(3,4‐dihydro‐2H‐pyran‐co‐maleic anhydride‐co‐vinyl acetate)

Abstract

ABSTRACT:The radical-initiated terpolymerization of 3,4-dihydro-2H-pyran (DHP), maleic anhydride (MA), and vinyl acetate (VA), which were used as a donor-acceptor-donor system, was carried out in methyl ethyl ketone in the presence of 2,2Ј-azobisisobutyronitrile as an initiator at 65°C in a nitrogen atmosphere. The synthesis and characterization of binary and ternary copolymers, some kinetic parameters of terpolymerization, the terpolymer-composition/thermal-behavior relationship, and the antitumor activity of the synthesized polymers were examined. The polymerization of the DHP-MA-VA monomer system predominantly proceeded by the alternating terpolymerization mechanism. The in vitro cytotoxicities of poly(3,4-dihydro-2H-pyran-alt-maleic anhydride) [poly(DHPalt-MA)] and poly(3,4-dihydro-2H-pyran-co-maleic anhydrideco-vinyl acetate) [poly(DHP-co-MA-co-VA)] were evaluated with Raji cells (human Burkitt lymphoma cell line). The antitumor activity of the prepared anion-active poly(DHP-alt-MA) and poly(DHP-co-MA-co-VA) polymers were studied with methyl-thiazol-tetrazolium testing, and the 50% cytotoxic dose was calculated.

Bioengineering functional copolymers. XIV. Synthesis and interaction of poly(N-isopropylacrylamide-co-3,4-dihydro-2H-pyran-alt-maleic anhydride)s with SCLC cancer cells

“…5 using calorimetric measurements of chemotherapic effect and quantitative evaluation of LD 50 dose for the total of tumor cells (Raji cells-human Burkitt lymphoma cell line). 6 It was shown that hydrolyzed terpolymer has sufficiently high antitumor activity, which depends on the amount of hydrogen bonding carboxylic groups and their regular distribution in the side chain of functional macromolecules. [6][7][8] Han et al 9,10 reported the synthesis, characterization and bioactivity of poly(DHP-alt-MA) and its derivatives, with different substituents (e.g., acetoxy, methoxy, ethoxy, methoxycarbonyl, formyl, acetoxymethyl, and tosyloxymethyl groups, as well as guanine derivatives) in the 2-position of pyran ring of the copolymer backbone.…”

“…6 It was shown that hydrolyzed terpolymer has sufficiently high antitumor activity, which depends on the amount of hydrogen bonding carboxylic groups and their regular distribution in the side chain of functional macromolecules. [6][7][8] Han et al 9,10 reported the synthesis, characterization and bioactivity of poly(DHP-alt-MA) and its derivatives, with different substituents (e.g., acetoxy, methoxy, ethoxy, methoxycarbonyl, formyl, acetoxymethyl, and tosyloxymethyl groups, as well as guanine derivatives) in the 2-position of pyran ring of the copolymer backbone. Authors found that these pyrancontaining copolymers with a high density of carboxylic acid functionality as the polynucleotide analogues exhibit antitumor activities in vitro and in vivo, 9 which were found to have higher activities against the tumor cells (B16 and 3LL) than those of their acyclic analogues, especially alternating cyclocopolymer of divinyl ether with MA.…”

Charge‐Transfer Complex of p‐Aminodiphenylamine with Maleic Anhydride: Spectroscopic, Electrochemical, and Physical Properties

“…In the spectrum of MA, the protons of the CH=CH group appear at 7.47 ppm (signal a) . The peak at 6.26 ppm (signal b) is assigned to maleic acid (CH=CH) formed from the partial hydrolysis of maleic anhydride . In the 1 H NMR spectrum of PADPA, the protons of the benzenoid rings are assigned as 6.54 (doublet, protons e), 6.59 (triplet, d), 6.76 (doublet, c), 6.82 (doublet, b) and 7.09 ppm (triplet, a), with the ratio of integrated intensity of peaks of 2:1:2:2:2, respectively (Figure ).…”

“…[17] The peak at 6.26 ppm (signal b) is assigned to maleic acid( CH=CH) formed from the partial hydrolysis of maleic anhydride. [18] In the 1 HNMR spectrum of PADPA, the protons of the benzenoid rings are assigned as 6.54 (doublet, protons e), 6.59 (triplet, d), 6.76 (doublet, c), 6.82 (doublet, b) and 7.09 ppm (triplet, a), with the ratio of integrated intensity of peaks of 2:1:2:2:2, respectively ( Figure 1). Primary and secondary amine protons appear at 4.77 (g) and 7.45 ppm (f), with an integral ratio of 2:1, respectively.I nt he 1 HNMR spectrum of PADPA, the signals corresponding to secondary amine protons were abolished due to proton exchange with D 2 Ow hen [D 6 ]DMSO/D 2 Ow as added to the sample ( Figure S1 in the Supporting Information).…”

Functional copolymer/organo‐montmorillonite nanoarchitectures. IX. Synthesis and nanostructure–morphology–thermal behaviour relationships of poly[(maleic anhydride)‐alt‐(acrylic acid)]/organo‐ montmorillonite nanocomposites

“…This observed difference can be explained by proposing the additional amidolysis of the free carboxylic groups with the primary amine groups of ODA‐MMT under isothermal conditions. It is known that other alternating copolymers of MA may undergo reversible hydrolysis–anhydridization reactions in aqueous solution and in solid‐state thermal treatment 29…”