Design, Synthesis and Characterization of 1,2-Phenylenediamine Functionalized Poly (Maleic Anhydride-alt-Vinyl Acetate) as a Potential New Bioactive Formulation

Year 2022, , 305 - 311, 31.12.2022

Gülderen Karakuş

https://doi.org/10.17350/HJSE19030000284

Cited By: 1

Abstract

This study includes the design, synthesis and characterization of 1,2-phenylenediamine (o-PDA) functionalized maleic anhydride (MA)-vinyl acetate (VA) copolymer-based conjugate to develop a new formulation. The 1,2-phenylenediamine molecule is a fluorescent dye that allows designing new chemotherapeutic polymeric molecules. Poly(maleic anhydride-alt-vinyl acetate) [Poly(MA-alt-VA)] was obtained via charge transfer complex (CTC) radical polymerization presence of methyl ethyl ketone (MEK), utilizing benzoyl peroxide (BPO) free-radical initiator at 80 °C, as a potential functional polymeric carrier. Structural characterization of the surface functionalized poly(MA-alt-VA)/1,2-PDA conjugate was performed by Attenuated Total Reflectance-Fourier Transform Infrared (ATR-FTIR) and Nuclear Magnetic Resonance (1H-NMR). Spectroscopic methods and water solubility results confirmed that the conjugation took place successfully after the ring opening reaction by the amidation mechanism.

Keywords

poli(MA-alt-VA), Surface modification, 1, 2-phenylenediamine, ATR-FTIR, 1H-NMR

References

• 1. I.D. Ibrahim, T. Jamiru, E.R. Sadiku, W.K. Kupolati, S.C. Agwuncha, Mechanical properties of sisal fibre-reinforced polymer composites: a review, Compos. Interface., 23(1) (2016) 15-36.
• 2. E.R. Fuchs, F.R. Field, R. Roth, R.E. Kirchain, Strategic materials selection in the automobile body: Economic opportunities for polymer composite design, Compos. Sci. Technol., 68 (2008) 1989-2002.
• 3. S.P. Victor, J. Muthu, Bioactive mechanically favorable, and biodegradable copolymer nanocomposites for orthopedic applications, Mater. Sci. Eng. C. Mater. Biol. Appl., 39 (2014) 150-160.
• 4. Z. Ma, Z. Mao, C. Gao, Surface modification and property analysis of biomedical polymers used for tissue engineering, Colloids. Surf. B. Biointerfaces., 60 (2007) 137-157. 5. F. Scognamiglio, A. Travan, I. Rustighi, P. Tarchi, S. Palmisano, Adhesive and sealant interfaces for general surgery applications, J. Biomed. Mater. Res. B. Appl. Biomater., 104(3) (2016) 626-639.
• 6. H. Ringsdorf, Structure and properties of pharmacologically active polymers, J. Polym. Sci., 51 (1975) 135–153.
• 7. R. Duncan, Polymer conjugates for tumour targeting and intracytoplasmic delivery. The EPR effect as a common gateway?, Res. Focus. Rev., 2 (1999) 441–449.
• 8. D. Spridon, L. Panaitescu, D. Ursu, C.V. Uglea, Synthesis and biocompatibility of maleic anhydride copolymers: 1. Maleic anhydride–vinyl acetate, maleic anhydride methyl methacrylate and maleic anhydride-styrene, Polym. Int., 43 (1997) 175–181.
• 9. G.R. Saad, R.E. Morsi, S.Z. Mohammady, M.Z. Elsabee, Dielectric relaxation of monoesters based poly(styrene-co-maleic anhydride) copolymer, J. Polym. Res., 15 (2008) 115–123.
• 10. H.Y. Liu, K. Cao, Z. Yao, B.G. Li, G.H. Hu, Variations of the glass-transition temperature in the imidization of poly(styrene-co-maleic anhydride), J. Appl. Polym. Sci., 104 (2007) 2418–2422.
• 11. R-J. Yu, J-J. Sun, H. Song, J-Z. Tian, D-W. Li, Y-T. Long, Real-Time Sensing of O-Phenylenediamine Oxidation on Gold Nanoparticles, Sensors., 17 (2017) 530.
• 12. https://www.sigmaaldrich.com.
• 13. G. Karakus, H.B. Zengin, Z. Akin-Polat, A.F. Yenidunya, S. Aydin, Cytotoxicity of three maleic anhydride copolymers and common solvents used for polymer solvation, Polym. Bull., 70 (2013) 1591–1612.
• 14. G. Karakus, Z. Akin-Polat, A.F. Yenidunya, H.B. Zengin, C.B. Karakus, Synthesis, characterization and cytotoxicity of novel modified poly[(maleic anhydride)-co-(vinyl acetate)]/noradrenaline conjugate, Polym. Int., 62 (2013) 492–500.
• 15. H. Kaplan-Can, G. Karakus, N. Tuzcu, Synthesis, characterization and in vitro antibacterial assessments of a novel modified poly [maleic anhydride-alt-acrylic acid]/acriflavine conjugate, Polym. Bull., 71 (2014) 2903–292.
• 16. H. Kaplan-Can, A.L. Doğan, Z.M.O. Rzaev, A. Hasegeli Üner, A. Güner, Synthesis, characterization, and antitumor activity of poly (maleic anhydride-co-vinyl acetate-co-acrylic acid), J. Appl. Polym. Sci., 100 (2006) 3425-3432.
• 17. G. Karakus, Synthesis, Structural Characterization, and Water Solubility of a Novel Modified Poly(maleic anhydride-co-vinyl acetate)/Acriflavine Conjugate, Hacettepe J. Biol. & Chem., 44(4) 2016 549–558.
• 18. K.J. Yoon, J.H. Woo, Y.S. Seo, Formaldehyde free cross-linking agents based on maleic anhydride copolymers, Fiber. Polym., 4 (2003) 182–187.
• 19. C.M. Xiao, J. Tan, G.N. Xue, Synthesis and properties of starch-g-poly(maleic anhydride-co-vinyl acetate), Express. Polym. Lett., 4 (2010) 9–16.
• 20. G.C. Chitanu, I. Popescu, A. Carpov, Synthesis and characterization of maleic anhydride copolymers and their derivatives. 2. New data on the copolymerization of maleic anhydride with vinyl acetate, Rev. Roum. Chim., 51 (2006) 923–929.
• 21. Z. Qiao, Y. Xie, M. Chen, J. Xu, Y. Zhu, Y. Qian, Synthesis of lead sulfide/(polyvinyl acetate) nanocomposites with controllable morphology, Chem. Phys. Lett., 321 (2000) 504–507.
• 22. V. Sunel, M. Popa, A.D. Stoican, A.A. Popa, C. Uglea, Poly (maleic anhydride-alt-vinyl acetate) conjugate with alkylating agents, Mater. Plast., 45 (2008) 149–153.
• 23. S. Ghosh, A.K. Banthia, An approach to novel polyamidoamine (PAMAM) side chain dendritic polyesterurethane (SCDPEU) block copolymer architectures, Eur. Polym. J., 39 (2003) 2141–2146.
• 24. F. Zafar, E. Sharmin, S.M. Ashraf, S. Ahmad, Studies on poly(styrene-co-maleic anhydride)-modified polyesteramide-based anticorrosive coatings synthesized from a sustainable resource, J. Appl. Polym. Sci., 92 (2004) 2538–2544.
• 25. B.C. Smith, Spectroscopy., 30(1)(2015) 16–23.
• 26. B.C. Smith, Spectroscopy., 31(3)(2016) 34–37.
• 27. B.C. Smith, Electromagnetic Radiation, Spectral Units, and Alkanes, Spectroscopy., 30(4) (2015) 18–23.
• 28. J.H. Jeong, Y.S. Byoun, S.B. Ko, Y.S. Lee, Chemical modification of poly(styrene-alt-maleic anhydride) with antimicrobial 4-aminobenzoic acid and 4-hydroxybenzoic acid, J. Ind. Eng. Chem., 7 (2001) 310–315.
• 29. M. Ak, A. Durmus, L. Toppare, Synthesis and characterization of poly(N-(2-(thiophen-3-yl)methylcarbonyloxyethyl) maleimide) and its spectroelectrochemical properties, J. Appl. Electrochem., 37 (2007) 729–735.
• 30. S. Wang, M. Wang, Y. Lei, L. Zhang, Anchor effect in poly(styrene maleic anhydride)/TiO2 nanocomposites, J. Mater. Sci. Lett., 18 (1999) 2009–2012.
• 31. H.G.M. Edwards, E. Hickmott, M.A. Hughes, Vibrational spectroscopic studies of potential amidic extractants for lanthanides and actinides in nuclear waste treatment, Spectrochim. Acta. A., 53 (1997) 43–53.
• 32. M. Coskun, P. Seven, Synthesis, characterization and investigation of dielectric properties of two-armed graft copolymers prepared with methyl methacrylate and styrene onto PVC using atom transfer radical polymerization, React. Funct. Polym., 71 (2011) 395–401.
• 33. G. Karakus, A. Ece, A. Sahin-Yaglioglu, H.B. Zengin, M. Karahan, Synthesis, structural characterization, and antiproliferative/cytotoxic effects of a novel modified poly(maleic anhydride-co-vinyl acetate)/doxorubicin conjugate, Polym. Bull., 74 (2017) 2159–2184.
• 34. S. Hwang, C.H. Lee, I.S. Ahn, Product identification of guaiacol oxidation catalyzed by manganese peroxidase, J. Ind. Eng. Chem., 14 (2008) 487–492.
• 35. E. Lee, B.H. Moon, Y. Park, S. Hong, S. Lee, Y. Lee, Y. Lim, Effects of hydroxy and methoxy substituents on NMR data in flavonols, Bull. Korean. Chem. Soc., 29 (2008) 507–510.
• 36. D. Jacquemin, E.A. Perpete, I. Ciofini, On the performances of the M06 family of density functionals for electronic excitation energies, J. Chem. Theory. Comput., 6(2010) 2071–2085.
• 37. G. Nemtoi, C. Beldie, C. Tircolea, I. Popa, I. Cretescu, I. Humelnicu, D. Humelnicu, Behaviour of the poly(maleic anhydride-co-vinyl acetate) copolymer in aqueous solutions, Eur. Polym. J., 37 (2001) 729–735.
• 38. F. Zafar, E. Sharmin, S.M. Ashraf, S. Ahmad, Studies on poly(styrene-co-maleic anhydride)-modified polyesteramide-based anticorrosive coatings synthesized from a sustainable resource, J. Appl. Polym. Sci., 92 (2004) 2538-2544.
• 39. F. Mustata, I. Bicu, P-aminobenzoic acid/cyclohexanon/formaldehyde resins as hardner for epoxy resins. Synthesis and characterization, J. Optoelectron. Adv. M., 8 (2006) 871–875.
• 40. M. Coskun, P. Seven, Synthesis, characterization and investigation of dielectric properties of two-armed graft copolymers prepared with methyl methacrylate and styrene onto PVC using atom transfer radical polymerization, React. Funct. Polym,. 71 (2011) 395–401.
• 41. R. Ranjbar-Karimi, H. Loghmani-Khouzani, Synthesis of new azines in various reaction conditions and investigation of their cycloaddition reaction, J. Iran. Chem. Soc., 8 (2011) 223–230.
• 42. H. Maeda, M. Ueda, T. Morinaga, T. Matsumoto, Conjugation of poly(styrene-co-maleic acid) derivatives to the antitumor protein neocarzinostatin: pronounced improvements in pharmacological properties, J. Med. Chem., 28 (1985) 455-461.
• 43. H. Patel, D.A. Raval, D. Madamwar, S.R. Patel, Polymeric prodrug: synthesis, release study and antimicrobial property of poly(styrene-co-maleic anhydride)-bound acriflavine, Angew. Makromol. Chem., 263 (1998) 25-30.
• 44. C.J. Cox, K. Dutta, E.T. Petri, W.C. Hwang, Y. Lin, S.M. Pascal, R. Basavappa, The regions of securin and cyclin B proteins recognized by the ubiquitination machinery are relatively unfolded, FEBS Lett., 527 (2002) 303-308.