1,693
Views
0
CrossRef citations to date
0
Altmetric
Full Length Article

Synthesis, characterization, thermokinetic analysis and biological application of novel allyl glucosamine based glycopolymers

, ORCID Icon, &
Pages 117-131 | Received 16 Nov 2022, Accepted 02 Apr 2023, Published online: 11 Apr 2023

References

  • Varma AJ, Kennedy JF, Galgali P. Synthetic polymers functionalized by carbohydrates: a review. Carbohydr Polym. 2004;56:429–445.
  • Telli FC. Synthesis, characterization and thermokinetic analysis of the novel sugar based styrene co-polymer. Polimeros. 2020;30:1–8.
  • Vert M. Polymeric biomaterials: strategies of the past vs. strategies of the future. Prog Polym Sci. 2007;32:755–761.
  • Pachence JM, Kohn J, In R, et al. Principles of tissue engineering. Academic Press/R G Landes Company. 1997;1:273–285.
  • Louwrier A. Industrial products—the return to carbohydrate- based industries. Biotechnol Appl Biochem. 1998;27:1–8.
  • Singh R, Bhattacharya B, Rhee HW, et al. Solid gellan gum polymer electrolyte for energy application. Int J Hydrog Energ. 2015;40:9365–9372.
  • Methven JM. Polymeric materials from renewable resources. RAPRA Rev Rep. 1991;4:1–134.
  • Borges MR, JAd S, Vieira M, et al. Polymerization of a water soluble glucose vinyl ester monomer with tensoactive properties synthesized by enzymatic catalyst. Mater Sci Eng C. 2009;29:519–523.
  • Majeti NV, Kumar R. A review of chitin and chitosan applications. React Funct Polym. 2000;46:1–27.
  • Dodane V, Vilivalam VD. Pharmaceutical applications of chitosan. Pharm Sci Technol. 1998;1:246–253.
  • Carneiro MJ, Fernandes AC, Figueiredo CM, et al. Synthesis of carbohydrate based polymers. Carbohydr Polym. 2001;45:135–138.
  • Neto CGT, Giacometti JA, Job AE, et al. Thermal analysis of chitosan based networks. Carbohydr Polym. 2005;62:97–103.
  • Rinaudo M. Chitin and chitosan: properties and application. Prog Polym Sci. 2006;31:603–632.
  • Zhang L, Liu W, Han B, et al. Synthesis and antitumor activity of arginine–glucosamine conjugate. Carbohydr Polym. 2007;69:644–650.
  • Orgueira HA, Bartolozzi A, Schell P, et al. Modular synthesis of heparin oligosaccharides. Chemistry. 2003;9:140–169.
  • Goyal N, Cheuk S, Wang G. Synthesis and characterization of d-glucosamine-derived low molecular weight gelators. Tetrahedron. 2010;66:5962–5971.
  • Jiang ZH, Budzynski WA, Qiu D, et al. Monophosphoryl lipid a analogues with varying 3-O-substitution: synthesis and potent adjuvant activity. Carbohydr Res. 2007;342:784–796.
  • Yamatani K, Kawatani R, Ajiro H. Synthesis of glucosamine derivative with double caffeic acid moieties at N- and 6-O-positions for developments of natural based materials. J Mol Struct. 2020;1206:127689–127695.
  • Zhang J, Zhao M, Peng S. Synthesis of mimetic peptides containing glucosamine. Carbohydr Res. 2011;346:1997–2003.
  • Lowe AB, Wang R. Synthesis of controlled-structure AB diblock copolymers of 3-O-methacryloyl-1,2: 3,4-di-O-isopropylidene-D-galactopyranose and 2-(dimethylamino) ethyl methacrylate. Polymer. 2007;48:2221–2230.
  • Wulff G, Schmid J, Venhoff T. The synthesis of polymerizable vinyl sugars. Macromol Chem Phys. 1996;197:259–274.
  • Black WAP, Dewar ET, Rutherford D. Polymerisation of unsaturated derivatives of 1,2: 5,6-di-O-isoprop ylidene-d-glucofuranose. J Chem Soc. 1963;1:4433–4439.
  • Z-K X, Kou R-Q, Liu Z-M, et al. Incorporating α-allyl glucoside into polyacrylonitrile by water-phase precipitation copolymerization to reduce protein adsorption and cell adhesion. Macromolecules. 2003;36:2441–2447.
  • Krasteva N, Harms U, Albrecht W, et al. Membranes for biohybrid liver support systems—investigations on hepatocyte attachment, morphology and growth. Biomaterials. 2002;23:2467–2478.
  • Lin WC, Liu TY, Yang MC. Hemocompatibility of polyacrylonitrile dialysis membrane immobilized with chitosan and heparin conjugate. Biomaterials. 2004;25:1947–1957.
  • Park CH, Nam SY, Lee YM, et al. Pervaporation of pyridine–water mixture through poly(acrylonitrile-co-monoacryloxyethyl phosphate) membrane. J Membr Sci. 2000;164:121–128.
  • Kimura S, Hirai K. Vinyl polymerization LIX. On the syntheses of polymethacrylates of D-glucose and L-sorbose. Makromol Chem. 1962;58:232–236.
  • Muthukrishnan S, Mori H, Müller AHE. Synthesis and characterization of methacrylate-type hyperbranched glycopolymers via self-condensing atom transfer radical copolymerization. Macromolecules. 2005;38: 3108:3119.
  • Kimura S, Imoto M. Synthesis of polymethacryloyl-D-glucose and its copolymers with acrylonitrile. Vinyl polymerization LIV. Makromol Chem. 1961;50:155–160.
  • Patil DR, Dordick JS, Rethwisch DG. Chemoenzymatic synthesis of novel sucrose-containing polymers. Macromolecules. 1991;24:3462–3463.
  • Ohno K, Tsujii Y, Fukuda T. Synthesis of a well‐defined glycopolymer by atom transfer radical polymerization. J Polym Sci A Polym Chem. 1998;36:2473–2481.
  • Stubbs KA, Macauley MS, Vocadlo DJ. A highly concise preparation of O-deacetylated arylthioglycosides of N-acetyl-D-glucosamine from 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl chloride and aryl thiols or disulfides. Carbohydr Res. 2006;341:1764–1769.
  • Saltan F. Preparation of poly(eugenol-co-methyl methacrylate)/polypropylene blend by creative route approach: structural and thermal characterization. Iran Polym J. 2021;30:1227–1236.
  • Arcos-Hernandez M, Naidjonoka P, Butler SJ, et al. Thermoresponsive glycopolymers based on enzymatically synthesized oligo-β-mannosyl ethyl methacrylates and N-Isopropylacrylamide. Biomacromolecules. 2021;22:2338–2351.
  • Godjevargova T. Behavior of glucose oxidase immobilized on ultrafiltration membranes obtained by copolymerizing acrylonitrile and N-vinylimidazol. J Membr Sci. 2000;172(1–2):279–285.
  • Miura Y. Design and synthesis of well-defined glycopolymers for the control of biological functionalities. Polym J. 2012;44:679–689.
  • Narain R, Jhurry D, Wulff G. Synthesis and characterization of polymers containing linear sugar moieties as side groups. Eur Polym J. 2002;38:273–280.
  • Slavin S, Burns J, Haddleton DM, et al. Synthesis of glycopolymers via click reactions. Eur Polym J. 2011;47:435–446.
  • Yadav P, Yadav H, Shah VG, et al. Biomedical biopolymers, their origin and evolution in biomedical sciences: a systematic review. J Clin Diagn Res. 2015;9:21–25.
  • Song R, Murphy M, Li C, et al. Current development of biodegradable polymeric materials for biomedical applications. Drug Des Devel Ther. 2018;12:3117–3145.
  • Udenni Gunathilake TMS, Ching YC, Ching KY, et al. Biomedical and microbiological applications of bio-based porous materials: a review. Polymers. 2017;9:160–176.
  • Jun S-K, Cha J-R, Knowles JC, et al. Development of Bis-GMA-free biopolymer to avoid estrogenicity. Dent Mater. 2020;36:157–166.
  • Walker L, Perkins E, Kratz F, et al. Cell penetrating peptides fused to a thermally targeted biopolymer drug carrier improve the delivery and antitumor efficacy of an acid-sensitive doxorubicin derivative Int. J Pharm. 2012;436:825–832.
  • Gayathri S, Ghosh OSN, Viswanath AK, et al. Synthesis of YF3: yb, Er upconverting nanofluorophores using chitosan and their cytotoxicity in MCF-7 cells. Int j biol macromol. 2015;72:1308–1312.
  • Ali U, Kjba K, Na B. A review of the properties and applications of poly (methyl methacrylate) (PMMA). Polym Rev. 2015;55:678–705.
  • Bettencourt A, Almeida AJ. Poly(methyl methacrylate) particulate carriers in drug delivery. J Microencapsul. 2012;29:353–367.
  • Kejlová K, Labský J, Jírová D, et al. Hydrophilic polymers-biocompatibility testing in vitro. Toxicol Vitro. 2005;19:957–962.
  • Pramudya I, Chung H. Recent progress of glycopolymer synthesis for biomedical applications. Biomater Sci. 2019;7:4848–4872.
  • Boullanger P, Banoub J, Descotes G. N-Allyloxycarbonyl derivatives of D-glucosamine as promotors of 1,2-trans-glucosylation in Koenigs–Knorr reactions and in Lewis acid catalyzed condensations. Can J Chem. 1987;65:1343–1348.
  • Wang D, Das A, Leuteritz A, et al. Thermal degradation behaviors of a novel nanocomposite based on polypropylene and Co–Al layered double hydroxide. Polym Degrad Stab. 2011;96:285–290.
  • Wang H, Yang J, Long S, et al. Studies on the thermal degradation of poly(phenylene sulfide sulfone). Polym Degrad Stab. 2004;83:229–235.
  • Yildirim Y, Balcan M. Comparative copolymerization of allyl glycidyl ether with styrene using radiation and chemical initiation methods. Iran Polym J. 2013;22:1–7.
  • Kissinger HE. Reaction kinetics in differential thermal analysis. Anal Chem. 1957;29:1702–1706.
  • Flynn JH, Wall LA. A quick direct method for the determination of activation energy from thermogravimetric data. J Polym Sci, Part B: Polym Phys. 1966;4:323–328.
  • Ozawa T. A new method of analyzing thermogravimetric data. Bull Chem Soc Jpn. 1965;38:1881–1886.
  • Akter R, Hossain MZ, Kleve MG, et al. Wortmannin induces MCF-7 breast cancer cell death via the apoptotic pathway, involving chromatin condensation, generation of reactive oxygen species, and membrane blebbing. Breast Cancer. 2012;4:103–113.
  • Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol L Methods. 1983;165:55–63.
  • Erol I, Guldiken A. Synthesis of novel functionalized methacrylate copolymers and their copolymerization kinetics, thermal stability, and biocidal properties. J Appl Polym Sci. 2021;138:51334–51348.
  • Szanka A, Szarka G, Ivan B. Poly(methyl methacrylate-co-2-hydroxyethyl methacrylate) four-arm star functional copolymers by Quasiliving ATRP: equivalent synthetic routes by protected and nonprotected HEMA comonomers. J Macromol Sci A. 2014;51:125–133.
  • Toms RV, Balashov MS, Shaova AA, et al. Copolymers of acrylonitrile and acrylic acid: effect of composition and distribution of chain units on the thermal behavior of copolymers. J Polym Sci B Polym Phys. 2020;62:102–115.
  • Matsumoto A. Polymerization of multiallyl monomers. Prog Polym Sci. 2001;26:189–257.