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Synthesis, Structural Characterization, and Water Solubility of a Novel Modified Poly maleic anhydride-co-vinyl acetate /Acriflavine Conjugate

Year 2016, Volume: 44 Issue: 4, 549 - 558, 01.11.2016

Abstract

Novel functional poly maleic anhydride-co-vinyl acetate /acriflavine conjugate, MAVA/AF, was synthesized in two different ways that copolymer:drug ratio was designed as 1:1 and 1:2, respectively. Nontoxic poly- meric drug carrier was prepared for conjugation reaction. The purified copolymer, MAVA, was modified with an antiexternal fungal and anticancer active agent acriflavine AF at 60°C for 72 hours in dimethylformami- de DMF , using triethylamine TEA as the catalyst. Structural characterizations were carried out by Fourier Transform Infrared FTIR and Nuclear Magnetic Resonance 1H-NMR . The spectroscopic results confirmed that conjugated/modification reaction was successfully carried out by amidification reaction.

References

  • 1. G. Vilara, J. Tulla-Puchea, F. Albericio, Polymers and Drug Delivery Systems, Curr. Drug. Deliv., 9 (2012) 1-28.
  • 2. W.B. Liechty1, D.R. Kryscio1, B.V. Slaughter, N.A. Peppas, Polymers for Drug Delivery Systems, Annu. Rev. Chem. Biomol. Eng., 1 (2010) 149–173.
  • 3. G.R. Saad, RE. 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.
  • 4. O.G. Atıcı, A. Akar, R. Rahimian, Modification of poly(maleic anhydride-co- styrene) with hydroxyl containing compounds, Turk. J. Chem., 25 (2001) 259-266.
  • 5. H. Patel, DA. 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.
  • 6. H.Y. Liu, K. Cao, Z. Yao, B.G. Li, GH. Hu, Variations of the glass-transition temperature in the imidization of poly(styrene-co-maleic anhydride), J. Appl. Polym. Sci., 104 (2007) 2418-2422.
  • 7. I. Popescu, D.M. Suflet, I.M. Pelin, G.C. Chitanu, Biomedical applications of maleic anhydride copolymers, Rev. Roum. Chim., 56 (2011) 173-188.
  • 8. R. Duncan, Polymer conjugates for tumour targeting and intracytoplasmic delivery. The EPR effect as a common gateway?, Research focus reviews, 2 (1999) 441-449.
  • 9. K. Hoste, K.D. Winne, E. Schacht, Polymeric prodrugs, Int. J. Pharmaceut., 277 (2004) 119-131.
  • 10. H. Ringsdorf, Structure and properties of pharmacologically active polymers, J. Polym. SCI., 51 (1975) 135-153.
  • 11. K. Greish, T. Sawa, J. Fang, T. Akaika, H. Maeda, SMA-doxorubicin, a new polymeric micellar drug for effective targeting to solid tumors, J. Control. Release., 97 (2004) 219-230.
  • 12. H. Maeda, SMANCS and polymer-conjugated macromolecular drugs: advantages in cancer chemotherapy, Adv. Drug. Deliv. Rev., 6 (1991) 181-202.
  • 13. N. Doğan, Farmasötik Kimyaya Giriş, Nobel Tıp Kitabevleri, (2007) İstanbul, 126s.
  • 14. H.H. Eldaroti, AS. Gadir, S.M. Refat, A. Adam, Charge Transfer Complexes of the Donor Acriflavine and the Acceptors Quinol, Picric acid, TCNQ and DDQ: Synthesis, Spectroscopic Characterizations and Antimicrobial Studies. Int. J. Electrochem. Sci., 8 (2013) 5774-5800.
  • 15. G. Karakus, H.B. Zengin, Z. Akin Polat, A.F. Yenidunya and S. Aydin, Cytotoxicity of three maleic anhydride copolymers and common solvents used for polymer solvation, Polym. Bull., 70 (2013) 1591-1612 .
  • 16. G. Karakus, Z. Akin Polat, A.F. Yenidunya, HB. Zengin, C.B. Karakus, Synthesis, characterization and cytotoxicity of novel modified poly[(maleic anhydride)-co-(vinyl acetate)]/noradrenaline conjugate, Polym. Int., (2013) 492-500.
  • 17. H. Kaplan Can, A.L. Doğan, Z.M.O. Rzaev, A.H. Uner, A. Güner, Synthesis and antitumor activity of poly(3,4- dihydro-2H-pyran-co-maleic anhydride-co-vinyl acetate), J. Appl. Polym. Sci., 96 (2005) 2352-2359.
  • 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. M.A. Krayukhina, S.A. Kozybakova, N.A. Samoilava, VG. Babak, SZ. Karaeva, IA. Yamskov, Synthesis and properties of amphiphilic maleic acid copolymers. Russ. J. Appl. Chem., 80 (2007) 1145–1150.
  • 22. 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.
  • 23. V. Sunel, M. Popa, AD. Stoican, AA. Popa, C. Uglea, Poly (maleic anhydride-alt-vinyl acetate) conjugate with Alkylating Agents, Materiale. Plastice., 45 (2008) 149-153.
  • 24. Z.M.O. Rzayev, Graft copolymers of maleic anhydride and its isostructurel analogues: High performance engineering materials, Int. Rev. Chem. Eng., 3 (2011) 153-215.
  • 25. J. Pal, H. Singh, A.K. Ghosh, Modification of LLDPE using esterified styrene maleic anhydride copolymer: Study of its properties and environmental degradability, J. Appl. Polym. Sci., 92 (2004) 102-108.
  • 26. 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.
  • 27. J. John, M.K. Dalal, D.R. Patel, R.N. Ram, Preparation, Properties, and Catalytic Application of PolymerBound Ru(III) Complexes, JMS-Pure. Appl. Chem., A34 (1997) 489-501.
  • 28. R.A. Tripp, R.A. Dluhy, Y. Zhao, Novel nanostructures for SERS biosensing. Nanotoday (Review)., 3 (2008) 31-37.
  • 29. Z.M.O. Rzayev, Complex-radical terpolymerization of glycidyl(methyl) methacrylates, styrene, and maleic anhydride, J. Pol. Sc. Pc., 37 (1999) 1095-1102.
  • 30. S. Gunasekaran, B. Anita, Spectral investigation and normal coordinate analysis of piperazine, Indian. J. Pure. Ap. Phy., 46 (2008) 833-838.
  • 31. S. Mallakpour, A. Zadehnazarı, Nanostructure formation in chiral poly(amide-imide)s based on dopamine moiety and n-trimellitylimido-l-amino acids in the main chain, J. Chil. Chem. Soc., 57 (2012) 1248-1252.
  • 32. 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.
  • 33. B. Marjanović, G. irić-Marjanović, A. Radulović, I. Juranić, P. Holler, Synthesis and characterization of polyacriflavine, Mater. Sci. Forum., 555 (2007) 503- 508.
  • 34. M.K.I. Senevirathne, P.K.D.D.P. Pitigala, V. Sivakumar, P.V.V. Jayaweera, A.G.U. Perera, K. Tennakone, Sensitization of TiO2 and ZnO nanocrystalline films with acriflavine, J. Photochem. Photobiol. A. Chem., 195 (2008) 364–367.
  • 35. R.S. Rajput, D.C. Rupainwar, R.K. Singh, A. Singh, Study on characterization and degree of esterification of styrene maleic anhydride by some medicines, Indian. J. Chem., B:48 (2009) 1597-1600.
  • 36. R. Dahiya, Synthesis, characterization and biological evaluation of a glycine-rich peptidecherimolacyclopeptide, J. Chil. Chem. Soc. 52 (2007) 1224-1229.
  • 37. G. Karakus, A. Ece, A.S. 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. (2016). doi:10.1007/s00289- 016-1821-1.
  • 38. C.J. Cox, K. Dutta, E.T. Petri, W.C. Hwang, Y. Lin, S.M. Pascal, R. Basavappa, The regions of securing and cyclin B proteins recognized by the ubiquitination machinery are natively unfolded, Febs. Lett., (2002) 527:303-308.

Yeni Modifiye Poli maleik anhidrid-ko-vinil asetat /Akriflavin Konjugatının Sentezi, Yapısal Karakterizasyonu ve Suda Çözünürlüğü

Year 2016, Volume: 44 Issue: 4, 549 - 558, 01.11.2016

Abstract

Y eni fonksiyonel poli maleik anhidrit-ko-vinil asetat /Akriflavin konjugatı, MAVA/AF, iki farklı yolla kopolimer:ilaç oranı sırasıyla 1:1 ve 1:2 olacak şekilde sentezlendi. Konjugasyon tepkimesi için toksik olmayan polimerik ilaç taşıyıcı hazırlandı. Saflaştırılan kopolimer, MAVA, antikanser aktif akriflavin AF ajanı ile 60°C’da 72 saat dimetilformamid DMF içinde, trietilamin TEA katalizörlüğünde modifiye edildi. Yapısal karakterizasyon Fourier Transform Infrared FTIR ve Nükleer Magnetik Rezonans 1H-NMR ile yapıldı. Spektroskopik analiz sonuçları konjugasyon/modifikasyon tepkimesinin başarılı bir şekilde amidleşme reaksiyonu ile olduğunu doğrulamaktadır

References

  • 1. G. Vilara, J. Tulla-Puchea, F. Albericio, Polymers and Drug Delivery Systems, Curr. Drug. Deliv., 9 (2012) 1-28.
  • 2. W.B. Liechty1, D.R. Kryscio1, B.V. Slaughter, N.A. Peppas, Polymers for Drug Delivery Systems, Annu. Rev. Chem. Biomol. Eng., 1 (2010) 149–173.
  • 3. G.R. Saad, RE. 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.
  • 4. O.G. Atıcı, A. Akar, R. Rahimian, Modification of poly(maleic anhydride-co- styrene) with hydroxyl containing compounds, Turk. J. Chem., 25 (2001) 259-266.
  • 5. H. Patel, DA. 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.
  • 6. H.Y. Liu, K. Cao, Z. Yao, B.G. Li, GH. Hu, Variations of the glass-transition temperature in the imidization of poly(styrene-co-maleic anhydride), J. Appl. Polym. Sci., 104 (2007) 2418-2422.
  • 7. I. Popescu, D.M. Suflet, I.M. Pelin, G.C. Chitanu, Biomedical applications of maleic anhydride copolymers, Rev. Roum. Chim., 56 (2011) 173-188.
  • 8. R. Duncan, Polymer conjugates for tumour targeting and intracytoplasmic delivery. The EPR effect as a common gateway?, Research focus reviews, 2 (1999) 441-449.
  • 9. K. Hoste, K.D. Winne, E. Schacht, Polymeric prodrugs, Int. J. Pharmaceut., 277 (2004) 119-131.
  • 10. H. Ringsdorf, Structure and properties of pharmacologically active polymers, J. Polym. SCI., 51 (1975) 135-153.
  • 11. K. Greish, T. Sawa, J. Fang, T. Akaika, H. Maeda, SMA-doxorubicin, a new polymeric micellar drug for effective targeting to solid tumors, J. Control. Release., 97 (2004) 219-230.
  • 12. H. Maeda, SMANCS and polymer-conjugated macromolecular drugs: advantages in cancer chemotherapy, Adv. Drug. Deliv. Rev., 6 (1991) 181-202.
  • 13. N. Doğan, Farmasötik Kimyaya Giriş, Nobel Tıp Kitabevleri, (2007) İstanbul, 126s.
  • 14. H.H. Eldaroti, AS. Gadir, S.M. Refat, A. Adam, Charge Transfer Complexes of the Donor Acriflavine and the Acceptors Quinol, Picric acid, TCNQ and DDQ: Synthesis, Spectroscopic Characterizations and Antimicrobial Studies. Int. J. Electrochem. Sci., 8 (2013) 5774-5800.
  • 15. G. Karakus, H.B. Zengin, Z. Akin Polat, A.F. Yenidunya and S. Aydin, Cytotoxicity of three maleic anhydride copolymers and common solvents used for polymer solvation, Polym. Bull., 70 (2013) 1591-1612 .
  • 16. G. Karakus, Z. Akin Polat, A.F. Yenidunya, HB. Zengin, C.B. Karakus, Synthesis, characterization and cytotoxicity of novel modified poly[(maleic anhydride)-co-(vinyl acetate)]/noradrenaline conjugate, Polym. Int., (2013) 492-500.
  • 17. H. Kaplan Can, A.L. Doğan, Z.M.O. Rzaev, A.H. Uner, A. Güner, Synthesis and antitumor activity of poly(3,4- dihydro-2H-pyran-co-maleic anhydride-co-vinyl acetate), J. Appl. Polym. Sci., 96 (2005) 2352-2359.
  • 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. M.A. Krayukhina, S.A. Kozybakova, N.A. Samoilava, VG. Babak, SZ. Karaeva, IA. Yamskov, Synthesis and properties of amphiphilic maleic acid copolymers. Russ. J. Appl. Chem., 80 (2007) 1145–1150.
  • 22. 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.
  • 23. V. Sunel, M. Popa, AD. Stoican, AA. Popa, C. Uglea, Poly (maleic anhydride-alt-vinyl acetate) conjugate with Alkylating Agents, Materiale. Plastice., 45 (2008) 149-153.
  • 24. Z.M.O. Rzayev, Graft copolymers of maleic anhydride and its isostructurel analogues: High performance engineering materials, Int. Rev. Chem. Eng., 3 (2011) 153-215.
  • 25. J. Pal, H. Singh, A.K. Ghosh, Modification of LLDPE using esterified styrene maleic anhydride copolymer: Study of its properties and environmental degradability, J. Appl. Polym. Sci., 92 (2004) 102-108.
  • 26. 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.
  • 27. J. John, M.K. Dalal, D.R. Patel, R.N. Ram, Preparation, Properties, and Catalytic Application of PolymerBound Ru(III) Complexes, JMS-Pure. Appl. Chem., A34 (1997) 489-501.
  • 28. R.A. Tripp, R.A. Dluhy, Y. Zhao, Novel nanostructures for SERS biosensing. Nanotoday (Review)., 3 (2008) 31-37.
  • 29. Z.M.O. Rzayev, Complex-radical terpolymerization of glycidyl(methyl) methacrylates, styrene, and maleic anhydride, J. Pol. Sc. Pc., 37 (1999) 1095-1102.
  • 30. S. Gunasekaran, B. Anita, Spectral investigation and normal coordinate analysis of piperazine, Indian. J. Pure. Ap. Phy., 46 (2008) 833-838.
  • 31. S. Mallakpour, A. Zadehnazarı, Nanostructure formation in chiral poly(amide-imide)s based on dopamine moiety and n-trimellitylimido-l-amino acids in the main chain, J. Chil. Chem. Soc., 57 (2012) 1248-1252.
  • 32. 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.
  • 33. B. Marjanović, G. irić-Marjanović, A. Radulović, I. Juranić, P. Holler, Synthesis and characterization of polyacriflavine, Mater. Sci. Forum., 555 (2007) 503- 508.
  • 34. M.K.I. Senevirathne, P.K.D.D.P. Pitigala, V. Sivakumar, P.V.V. Jayaweera, A.G.U. Perera, K. Tennakone, Sensitization of TiO2 and ZnO nanocrystalline films with acriflavine, J. Photochem. Photobiol. A. Chem., 195 (2008) 364–367.
  • 35. R.S. Rajput, D.C. Rupainwar, R.K. Singh, A. Singh, Study on characterization and degree of esterification of styrene maleic anhydride by some medicines, Indian. J. Chem., B:48 (2009) 1597-1600.
  • 36. R. Dahiya, Synthesis, characterization and biological evaluation of a glycine-rich peptidecherimolacyclopeptide, J. Chil. Chem. Soc. 52 (2007) 1224-1229.
  • 37. G. Karakus, A. Ece, A.S. 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. (2016). doi:10.1007/s00289- 016-1821-1.
  • 38. C.J. Cox, K. Dutta, E.T. Petri, W.C. Hwang, Y. Lin, S.M. Pascal, R. Basavappa, The regions of securing and cyclin B proteins recognized by the ubiquitination machinery are natively unfolded, Febs. Lett., (2002) 527:303-308.
There are 38 citations in total.

Details

Primary Language English
Journal Section Research Article
Authors

Gülderen Karakuş This is me

Publication Date November 1, 2016
Published in Issue Year 2016 Volume: 44 Issue: 4

Cite

APA Karakuş, G. (2016). Synthesis, Structural Characterization, and Water Solubility of a Novel Modified Poly maleic anhydride-co-vinyl acetate /Acriflavine Conjugate. Hacettepe Journal of Biology and Chemistry, 44(4), 549-558.
AMA Karakuş G. Synthesis, Structural Characterization, and Water Solubility of a Novel Modified Poly maleic anhydride-co-vinyl acetate /Acriflavine Conjugate. HJBC. November 2016;44(4):549-558.
Chicago Karakuş, Gülderen. “Synthesis, Structural Characterization, and Water Solubility of a Novel Modified Poly Maleic Anhydride-Co-Vinyl Acetate /Acriflavine Conjugate”. Hacettepe Journal of Biology and Chemistry 44, no. 4 (November 2016): 549-58.
EndNote Karakuş G (November 1, 2016) Synthesis, Structural Characterization, and Water Solubility of a Novel Modified Poly maleic anhydride-co-vinyl acetate /Acriflavine Conjugate. Hacettepe Journal of Biology and Chemistry 44 4 549–558.
IEEE G. Karakuş, “Synthesis, Structural Characterization, and Water Solubility of a Novel Modified Poly maleic anhydride-co-vinyl acetate /Acriflavine Conjugate”, HJBC, vol. 44, no. 4, pp. 549–558, 2016.
ISNAD Karakuş, Gülderen. “Synthesis, Structural Characterization, and Water Solubility of a Novel Modified Poly Maleic Anhydride-Co-Vinyl Acetate /Acriflavine Conjugate”. Hacettepe Journal of Biology and Chemistry 44/4 (November 2016), 549-558.
JAMA Karakuş G. Synthesis, Structural Characterization, and Water Solubility of a Novel Modified Poly maleic anhydride-co-vinyl acetate /Acriflavine Conjugate. HJBC. 2016;44:549–558.
MLA Karakuş, Gülderen. “Synthesis, Structural Characterization, and Water Solubility of a Novel Modified Poly Maleic Anhydride-Co-Vinyl Acetate /Acriflavine Conjugate”. Hacettepe Journal of Biology and Chemistry, vol. 44, no. 4, 2016, pp. 549-58.
Vancouver Karakuş G. Synthesis, Structural Characterization, and Water Solubility of a Novel Modified Poly maleic anhydride-co-vinyl acetate /Acriflavine Conjugate. HJBC. 2016;44(4):549-58.

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