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Synthesis, Characterization and Hydrolytic Degradation of p-Cresol-Substituted Polyphosphazenes

  • Research Article-Chemistry
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Abstract

Two polymers poly[bis(p-Cresol)phosphazenes] (PBPP) and poly[bis(p-cresoldiethyl amino)phosphazenes] (PBPDEAP) were synthesized, characterized and subjected to hydrolytic degradation and investigated in vitro degradation for drug delivery. The syntheses were carried out by thermal ring-opening polymerization followed by chlorine replacement via macromolecular substitution reaction. The polymeric products were characterized by FTIR, 1H NMR, thermal analysis (DSC), elemental analysis and gel permeation chromatography (GPC) analysis. Hydrolytic degradation was observed by percentage weight loss in buffer solutions of a broad pH range (4.5–10) in deionized water at body temperature (37 °C). It was found that PBPDEAP degraded more rapidly than PBPP, and hydrolytic degradation mechanism was proposed. It was found that PBPP and PBPDEAP are biodegradable, biocompatible and non-toxic and can be tailored for in vitro and later in vivo studies.

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References

  1. Amin, A.M.; Wang, L.; Wang, J.; Yu, H.; Huo, J.; Gao, J.; Xiao, A.: Recent research progress in the synthesis of polyphosphazenes and their applications. Desig. Mono. Polym. 12, 357–375 (2009)

    Article  Google Scholar 

  2. Amin, A.M.; Wang, L.; Wang, J.; Yu, H.; Gao, J.; Li, C.; Huo, J.; Amer, W.A.; Yan, G.; Ma, L.: Recent research progress in the synthesis of polyphosphazenes elastomers and their applications. J. Polym. Plast. Technol. Eng. 49, 1399–1405 (2010)

    Article  Google Scholar 

  3. Krogman, N.R.; Singh, A.; Nair, L.S.; Laurencin, C.T.; Allcock, H.R.: Miscibility of bioerodible polyphosphazene/poly(lactide-co-glycolide). Blends Biomac. 8, 1306–1312 (2007)

    Article  Google Scholar 

  4. Cho, J.-K.; Hong, K.-Y.; Park, J.W.; Yang, H.-K.; Song, S.-C.: Injectable delivery system of 2-methoxyestradiol for breast cancer therapy using biodegradable thermosensitive poly(organophosphazene) hydrogel. J. Drug Target. 19, 270–280 (2011)

    Article  Google Scholar 

  5. Chaubal, M.V.: Polymeric materials for drug delivery applications. Market Report, Techvest LLC (2003)

    Google Scholar 

  6. Eng, N.F.; Garlapati, S.; Gerdts, V.; Potter, A.; Babiuk, L.A.; Mutwiri, G.K.: The potential of polyphosphazenes for delivery of vaccine antigens and immunotherapeutic agents. Curr. Drug Deliv. 7, 13–20 (2010)

    Article  Google Scholar 

  7. Mutwiri, G.; Benjamin, P.; Soita, H.; Townsend, H.; Yost, R.; Roberts, B.; Andrianov, A.K.; Babiuk, L.A.: Poly[di(sodium carboxylatoethylphenoxy)phosphazene] (PCEP) is a potent enhancer of mixed Th1/Th2 immune responses in mice immunized with influenza virus antigens. Vaccine. 25, 1204–1213 (2007)

    Article  Google Scholar 

  8. Le Cam, N.B.; Ronco, J.; Francon, A.; Blondeau, C.; Fanget, B.: Adjuvants for influenza vaccine. Res. Immunol. 149, 19–23 (1998)

    Article  Google Scholar 

  9. Deng, M.; Nair, L.S.; Nukavarapu, S.P.; Jiang, T.; Kanner, W.A.; Li, X.; Kumbar, S.G.; Weikel, A.L.; Krogman, N.R.; Allcock, H.R.; Laurencin, C.T.: Dipeptide-based polyphosphazene and polyester blends for bone tissue engineering. Biomaterials 31, 4898–4908 (2010)

    Article  Google Scholar 

  10. Deng, M.; Nair, L.S.; Nukavarapu, S.P.; Kumbar, S.G.; Jiang, T.; Weikel, A.L.; Krogman, N.R.; Allcock, H.R.; Laurencin, C.T.: In situ porous structures: a unique polymer erosion mechanism in biodegradable dipeptide-based polyphosphazene and polyester blends producing matrices for regenerative engineering. Adv. Funct. Mater. 20, 2794–2806 (2010)

    Article  Google Scholar 

  11. Deng, M.; Kumbar, S.G.; Nair, L.S.; Weikel, A.L.; Allcock, H.R.; Laurencin, C.T.: Biomimetic structures: biological implications of dipeptide-substituted polyphosphazene-polyester blend nanofiber matrices for load-bearing bone regeneration. Adv. Funct. Mater. 21, 2641–2651 (2011)

    Article  Google Scholar 

  12. Akram, M.; Yu, H.; Wang, L.; Khalid, H.; Abbasi, N.M.; Zainul, A.; Chen, Y.; Ren, F.; Saleem, M.: Sustained release of hydrophilic drug from polyphosphazenes/poly (methyl methacrylate) based microspheres and their degradation study. Mater. Sci. Eng., C 58, 169–179 (2016)

    Article  Google Scholar 

  13. Wei, R.R.; Cheng, L.; Zheng, M.; Cheng, R.; Meng, F.H.; Deng, C.; Zhong, Z.Y.: Reduction-responsive disassemblable core-cross-linked micelles based on poly(ethylene glycol)-b-poly(N-2-hydroxypropyl methacrylamide)–lipoic acid conjugates for triggered intracellular anticancer drug release. Biomacromol 13, 2429–2438 (2012)

    Article  Google Scholar 

  14. Chun, C.; Lee, S.M.; Kim, C.W.; Hong, K.Y.; Kim, S.Y.; Yang, H.K.; Song, S.C.: Doxorubicin–polyphosphazene conjugate hydrogels for locally controlled delivery of cancer therapeutics. Biomaterials 30, 4752–4762 (2009)

    Article  Google Scholar 

  15. Shoichet, M.S.: Polymer scaffolds for biomaterials applications. Macromolecules 43, 581–591 (2010)

    Article  Google Scholar 

  16. Laurencin, C.T.; El-Amin, S.F.; Ibim, S.E.; Willoughby, D.A.; Attawia, M.; Allcock, H.R.; Ambrosio, A.A.: A highly porous 3-dimensional polyphosphazene polymer matrix for skeletal tissue regeneration. J. Biomed. Mater. Res. 30, 133–138 (1996)

    Article  Google Scholar 

  17. Langone, F.; Lora, S.; Veronese, F.M.; Caliceti, P.; Parnigotto, P.P.; Valenti, F.; Palma, G.: Peripheral nerve repair using a poly(organo)phosphazene tubular prosthesis. Biomaterials 16, 347–353 (1995)

    Article  Google Scholar 

  18. Veronese, F.M.; Marsilio, F.; Lora, S.; Caliceti, P.; Passi, P.; Orsolini, P.: Polyphosphazene membranes and microspheres in periodontal diseases and implant surgery. Biomaterials 20, 91–98 (1999)

    Article  Google Scholar 

  19. Andrianov, A.K.; Payne, L.G.: Polymeric carriers for oral uptake of microparticulates. Adv. Drug Delivery Rev. 34, 155–170 (1998)

    Article  Google Scholar 

  20. Wyrsta, M.D.; Cogen, A.L.; Deming, T.: A parallel synthetic approach for the analysis of membrane interactive copolypeptides. J. Am. Chem. Soc. 123, 12919–12920 (2001)

    Article  Google Scholar 

  21. Gunatillake, P.A.; Adhikari, R.: Biodegradable synthetic polymers for tissue engineering. Eur. Cells Mater. 5, 1–16 (2003)

    Article  Google Scholar 

  22. Grodzinski-Jagur, : Polymers for tissue engineering, medical devices, and regenerative medicine concise general review of recent studies. J. Polym. Adv. Technol. 17, 395–418 (2006)

    Article  Google Scholar 

  23. Andrianov, A.K.; Payne, L.G.: Protein release from polyphosphazene matrices. Adv. Drug Delivery Rev. 31, 185–196 (1998)

    Article  Google Scholar 

  24. Lakshmi, S.; Katti, D.S.; Laurencin, C.T.: Biodegradable polyphosphazenes for drug delivery applications. Adv. Drug Deliv. Rev. 55, 467–482 (2003)

    Article  Google Scholar 

  25. Akram, M.; Wang, L.; Yu, H.; Amer, W.A.; Khalid, H.; Abbasi, N.M.; Chen, Y.; Saleem, Z.; Tong, M.: Polyphophazenes as anti-cancer drug carriers: from synthesis to application. R. Prog. Polym. Sci. 39, 1987–2009 (2014)

    Article  Google Scholar 

  26. Sarfraz, M., Suleman, M., Tikoo, S.K., Wheler, C., Potter, A.A., Gerdts, V. and Dar, A. Immune responses to in ovo vaccine formulations containing inactivated fowl adenovirus 8b with poly[di(sodium carboxylatoethylphenoxy)]phosphazene (PCEP) and avian beta defensin as adjuvants in chickens Vaccine. 35, 981-986(2017).

  27. Allcock, H.R.: Chemistry and applications of polyphosphazenes. Wiley, Hoboken (2003)

    Google Scholar 

  28. De Jaeger, R.; Gleria, M.: Poly(organophosphazene)s and related compounds: synthesis, properties and applications. Prog. Polym. Sci. 23, 179–276 (1998)

    Article  Google Scholar 

  29. Yildiz, M.; Dulger, B.; Yilmaz, S.: Synthesis, spectral properties, and antimicrobial activity of phosphazene derivatives. Asian J. Chem. 20, 2719–2732 (2008)

    Google Scholar 

  30. Amin, A. M.; Wang, L.; Wang, J.; Yu, H.; Amer, W.A.; Gao, J.; Lei, Z.; Zhao, Y.; Huo, J.; Tai, Y.: Synthesis and characterization of poly[bis (p-oxybenzaldehyde diethylamino) phosphazenes], poly[bis(p-oxybenz aldehyde) phosphazene], poly[bis(di ethylamino)phosphazenes], and their self assembly behaviors. J. Macromol. Sci., Part A: Pure App. Chem. 48, 937–946 (2011).

  31. Amin, A.M.; Wang, L.; Wang, J.; Amer, W.A.; Huo, J.; Yu, H.; Gao, J.: Synthesis and characterization of poly[bis(resorcinol monobenzoate)phospha zenes], poly[bis(resorcinol monobenzoate diethylamino) phosphazene] and their self assembly behaviors. J. Inorg. Organomet. Polym Mater. 21, 283–290 (2011)

    Article  Google Scholar 

  32. Amin, A.M.; Wang, L.; Yu, H.; Amer, W.A.; Gao, J.; Huo, J.; Tai, Y.; Zhang, L.: Synthesis and characterization of poly[bis(ethyl salicylate)phosphazenes], poly[bis(ethyl salicylate diethylamino)phosphazenes] and their hydrolytic degradation. J. Inorg. Organomet. Polym Mater. 22, 196–204 (2012)

    Article  Google Scholar 

  33. Jing, X.; Xiumei, Z.; Liyan, Q.: Polyphosphazene vesicles for co-delivery of doxorubicin and chloroquine with enhanced anticancer efficacy by drug resistance reversal. Int. J. Pharm. 498, 70–81 (2016)

    Article  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, Government College University Lahore, Lahore, Pakistan

    Tanzeela Gulab Shahzady & Shazia Khurshid

  2. Department of Basic Sciences and Humanities, University of Engineering and Technology Lahore, Narowal Campus, Lahore, Pakistan

    Amin Abid

  3. Department of Basic Sciences and Humanities, University of Engineering and Technology Lahore, KSK Campus, Lahore, Pakistan

    Zulfiqar Ali

  4. School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, Wuhan, China

    Amin Abid & Shumaila Razzaque

  5. Institute of Chemistry, University of the Punjab Lahore, Lahore, Pakistan

    Hajira Rehman & Asmat Zahra

  6. Department of Chemistry, Lahore Garrison University, DHA Phase VI, Lahore, Pakistan

    Shabbir Hussain & Muhammad Waqas

Authors
  1. Tanzeela Gulab Shahzady
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  2. Shazia Khurshid
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  3. Amin Abid
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  4. Zulfiqar Ali
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  5. Shumaila Razzaque
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  8. Shabbir Hussain
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  9. Muhammad Waqas
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Correspondence to Amin Abid.

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Shahzady, T.G., Khurshid, S., Abid, A. et al. Synthesis, Characterization and Hydrolytic Degradation of p-Cresol-Substituted Polyphosphazenes. Arab J Sci Eng 44, 6445–6451 (2019). https://doi.org/10.1007/s13369-019-03952-1

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  • DOI: https://doi.org/10.1007/s13369-019-03952-1

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