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The pH-Triggered Amphiphilic Polycarbodiimides as Nanovesicles

Received: 24 February 2021     Accepted: 22 March 2021     Published: 30 March 2021
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Abstract

The pH-triggered polymers are a sub-class of stimuli-responsive macromolecules. These smart polymers can experience physical or chemical transition due to small pH responses. pH-dependent materials gain great demand within a short period, by considering their potential applications. pH-triggered macromolecules typically possess weak basic or weak acidic functional groups. The functional groups often used include tertiary amines, pyridines, phosphate, and carboxylic acids. These stimuli-dependent materials are ideal candidates for the biomedical field. Herein, report pH-dependent chiral amphiphilic carbodiimide polymers. Helical polycarbodiimides consist of alternating imine and amine backbone, attached to different pendant groups. Substituting the pendant groups, enable to change of the properties of polycarbodiimides. Thus, we invented polar functional groups such as dimethylamine and piperazine to the side chains to enhance the solubility in an aqueous medium. Moreover, each unit of these polymers consists of hydrophobic methyl functionality and hydrophilic dimethyl and piperazine side groups. Thus, these carbodiimide polymers were self-assembled in aqueous solutions as well as buffer solutions due to the hydrophilic and hydrophobic moieties of the polymer. The micelles can be used as nanocarriers. Furthermore, the pH-dependent swelling properties were observed in these polymeric nanoparticles in different time intervals. Thus, the pH-triggered volume change of the micelles can be used as a controlled release, targeted site drug delivery applications.

Published in American Journal of Polymer Science and Technology (Volume 7, Issue 1)
DOI 10.11648/j.ajpst.20210701.13
Page(s) 16-22
Creative Commons

This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.

Copyright

Copyright © The Author(s), 2021. Published by Science Publishing Group

Keywords

pH-Triggered, Micelles, Controlled Release

References
[1] Kocak, G.; Tuncer, C.; Butun, V. pH-Responsive polymers. Polym. Chem. 2017, 8, 144-176.
[2] James, H. P.; John, R.; Alex, A.; Anoop, K. R. Smart polymers for the controlled delivery of drugs – a concise overview. Acta Pharmaceutica Sinica B 2014, 4, 120-127.
[3] Schmaljohann, D. Thermo and pH-responsive polymers in drug delivery. Advanced drug delivery reviews 2006, 58, 1655-1670.
[4] Zhang, J.; Liu, K.; Mullen, K.; Yin, M. Self-assemblies of amphiphilic homopolymer: synthesis, morphology studies and biomedical applications. Chem. Commun. 2015, 51, 11541-11555.
[5] Zhou, Y.; Liu, B.; Wang, X. Self-assembly of homopolymers through strong dipole-dipole interaction in their aqueous solutions. Polymer 2016, 97, 1-10.
[6] Sun, T.; Yang, X.; Zhu, C.; Zhao, N.; Dong, H.; Xu, J. Self-assembly of homopolymer of PAA-NH4. Chin. Chem. Lett. 2018, 1-4.
[7] Zhu, Y.; Yang, Q.; Tong, C.; Li, M.; Yu, X. The vesicle formation in a binary amphiphilic diblock copolymer/homopolymer solution. Polymer 2010, 51, 702–708.
[8] Hua, D.; Tang, J.; Jiang, J.; Zhu, X. Synthesis of phenylphosphinic acid-containing amphiphilic homopolymers by reversible addition-fragmentation transfer (RAFT) polymerization and its aggregation in water. Polymer 2009, 50, 5701–5707.
[9] Sedlak, M.; A novel approach to controlled self-assembly of pH-responsive thermosensitive homopolymer polyelectrolytes into stable nanoparticles. Advances in Colloid and Interface Science 2016, 232, 57–69.
[10] Yia, Y.; Lin, G.; Chen, S.; Liu, J.; Zhang, H.; Mi, P. Polyester micelles for drug delivery and cancer theranostics: Current achievements, progresses and future perspectives. Materials Science & Engineering C 2018, 83, 218–232.
[11] Liu, X.; Thomas, K. J. Study of surface properties of clay laponite using pyrene as a photophysical probe molecule. Langmuir 1991, 7, 2808-2816.
[12] Chin, Y.; Aiken, G. R.; Danielsen, K. M. Binding of pyrene to aquatic and commercial humic substances: the role of molecular weight and aromaticity. Environ. Sci. echnol. 1997, 31, 1630-1635.
[13] Dominguez, A.; Fernandez, A.; Gonzalez, N.; Iglesias, E.; Montenegro, L. Determination of critical micelle concentration of some surfactants by three techniques. Journal of Chemical Education 1997, 74, 1227-1231.
[14] Cheng, Y.; Hao, J.; Lee, L. A.; Biewer, M. C.; Wang, Q.; Stefan, M. C. Thermally controlled release of anticancer drug from self-assembled γ-substituted amphiphilic poly(ε-caprolactone) Micellar nanoparticles. Biomacromolecules 2012, 13, 2163-2173.
[15] Qiu, L.; Zhu, M.; Gong, K.; Peng, H.; Ge. L.; Zhao, L.; Chen, J. pH-triggered degradable polymeric micelles for targeted anti-tumor drug delivery. Material Science and Engineering C 2017, 78, 912-922.
[16] Jafarzadeh-Holagh, Samira.; Hashemi-Najafabadi, S.; Shaki, H.; Vasheghani-Farahani, E. Self-Assembled and pH sensitive mixed micelles as an intracellular doxorubicin delivery system. Journal of Colloid and Interface Science 2018, 523, 179-190.
[17] Xiao, L.; Huang, L.; Moingeon, F.; Gauthier, M.; Yang, G. pH-Responsive poly (ethylene glycol)-block-polylactide micelles for tumor-targeted drug delivery. Biomacromolecules 2017, 18, 2711−2722.
[18] Huang, Y.; Tang, Z.; Zhang, X.; Yu, H.; Sun, H.; Pang, X.; Chen, X. pH-Triggered charge-reversal polypeptide nanoparticles for cisplatin delivery: preparation and in vitro evaluation. Biomacromolecules 2013, 14, 2023−2032.
[19] Wang, Y.; Nie, J.; Chang, B.; Sun, Y.; Yang, W. Poly(vinylcaprolactam)-based biodegradable multiresponsive microgels for drug delivery. Biomacromolecules 2013, 14, 3034−3046.
[20] Li, Y.; Bui, Q. N.; Duy, T. M.; Yang, H. Y.; Lee, D. S. One-step preparation of pH-responsive polymeric nanogels as intelligent drug delivery systems fort tumor therapy. Biomacromolecules 2018, 19, 2062−2070.
[21] Huang, F.; Cheng, R.; Meng, F.; Deng, C.; Zhong, Z. Micelles based on acid degradable poly (acetal urethane): preparation, pH-sensitivity, and triggered intracellular drug release. Biomacromolecules 2015, 16, 2228−2236.
[22] Yu, Y.; Chen, C.; Law, W.; Weinheimer, E.; Sengupta, S.; Prasad, P. N.; Cheng, C. Polylactide-graft-doxorubicin nanoparticles with precisely controlled drug loading for pH-triggered drug delivery. Biomacromolecules 2014, 15, 524−532.
[23] Tang, H. Z.; Boyle, P. D.; Novak, B. M. Chiroptical Switching Polyguanidine Synthesized by Helix-Sense-Selective Polymerization Using [(R)-3,3’-Dibromo-2,2’-binaphthoxy] (di-tert-butoxy) titanium (IV) Catalyst. J. Am. Chem. Soc. 2005, 127, 2136-2142.
[24] Reuther, J. F.; Novak, B. M. Evidence of Entropy-Driven Bistability through 15N NMR Analysis of a Temperature and Solvent Induced, Chiroptical Switching Polycarbodiimide. J. Am. Chem. Soc. 2013, 135, 19292-19303.
[25] Kennemur, J. G.; Novak, B. M. Advances in polycarbodiimide chemistry. Polymer 2011, 52, 1693-1710.
[26] Sideratous, Z.; Agathokleous, M.; Theodossious, T. A.; Tsiourvas, D. functionalized hyperbranched polyethylenimines as thermosensitive drug delivery nanocarriers with controlled transition temperature. Biomacromolecules 2018, 19, 315-328.
[27] Jin, Y.; Song, L.; Su, Y.; Zhu, L.; Pang, Y.; Qiu, F.; Tong, G.; Yan, D.; Zhu, B.; Zhu, X. oxime linkage: a robust tool for the design of pH-sensitive polymeric drug carriers. Biomacromolecules 2011, 12, 3460-3468.
[28] Chen, W.; Zhou, S.; Ge, L.; Wu, W.; Jiang, X. translatable high drug loading drug delivery systems based on biocompatible polymer nanocarriers. Biomacromolecules 2018, 19, 1732-1745.
Cite This Article
  • APA Style

    Enosha Harshani De Silva, Bruce Novak. (2021). The pH-Triggered Amphiphilic Polycarbodiimides as Nanovesicles. American Journal of Polymer Science and Technology, 7(1), 16-22. https://doi.org/10.11648/j.ajpst.20210701.13

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    ACS Style

    Enosha Harshani De Silva; Bruce Novak. The pH-Triggered Amphiphilic Polycarbodiimides as Nanovesicles. Am. J. Polym. Sci. Technol. 2021, 7(1), 16-22. doi: 10.11648/j.ajpst.20210701.13

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    AMA Style

    Enosha Harshani De Silva, Bruce Novak. The pH-Triggered Amphiphilic Polycarbodiimides as Nanovesicles. Am J Polym Sci Technol. 2021;7(1):16-22. doi: 10.11648/j.ajpst.20210701.13

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  • @article{10.11648/j.ajpst.20210701.13,
      author = {Enosha Harshani De Silva and Bruce Novak},
      title = {The pH-Triggered Amphiphilic Polycarbodiimides as Nanovesicles},
      journal = {American Journal of Polymer Science and Technology},
      volume = {7},
      number = {1},
      pages = {16-22},
      doi = {10.11648/j.ajpst.20210701.13},
      url = {https://doi.org/10.11648/j.ajpst.20210701.13},
      eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajpst.20210701.13},
      abstract = {The pH-triggered polymers are a sub-class of stimuli-responsive macromolecules. These smart polymers can experience physical or chemical transition due to small pH responses. pH-dependent materials gain great demand within a short period, by considering their potential applications. pH-triggered macromolecules typically possess weak basic or weak acidic functional groups. The functional groups often used include tertiary amines, pyridines, phosphate, and carboxylic acids. These stimuli-dependent materials are ideal candidates for the biomedical field. Herein, report pH-dependent chiral amphiphilic carbodiimide polymers. Helical polycarbodiimides consist of alternating imine and amine backbone, attached to different pendant groups. Substituting the pendant groups, enable to change of the properties of polycarbodiimides. Thus, we invented polar functional groups such as dimethylamine and piperazine to the side chains to enhance the solubility in an aqueous medium. Moreover, each unit of these polymers consists of hydrophobic methyl functionality and hydrophilic dimethyl and piperazine side groups. Thus, these carbodiimide polymers were self-assembled in aqueous solutions as well as buffer solutions due to the hydrophilic and hydrophobic moieties of the polymer. The micelles can be used as nanocarriers. Furthermore, the pH-dependent swelling properties were observed in these polymeric nanoparticles in different time intervals. Thus, the pH-triggered volume change of the micelles can be used as a controlled release, targeted site drug delivery applications.},
     year = {2021}
    }
    

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  • TY  - JOUR
    T1  - The pH-Triggered Amphiphilic Polycarbodiimides as Nanovesicles
    AU  - Enosha Harshani De Silva
    AU  - Bruce Novak
    Y1  - 2021/03/30
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    N1  - https://doi.org/10.11648/j.ajpst.20210701.13
    DO  - 10.11648/j.ajpst.20210701.13
    T2  - American Journal of Polymer Science and Technology
    JF  - American Journal of Polymer Science and Technology
    JO  - American Journal of Polymer Science and Technology
    SP  - 16
    EP  - 22
    PB  - Science Publishing Group
    SN  - 2575-5986
    UR  - https://doi.org/10.11648/j.ajpst.20210701.13
    AB  - The pH-triggered polymers are a sub-class of stimuli-responsive macromolecules. These smart polymers can experience physical or chemical transition due to small pH responses. pH-dependent materials gain great demand within a short period, by considering their potential applications. pH-triggered macromolecules typically possess weak basic or weak acidic functional groups. The functional groups often used include tertiary amines, pyridines, phosphate, and carboxylic acids. These stimuli-dependent materials are ideal candidates for the biomedical field. Herein, report pH-dependent chiral amphiphilic carbodiimide polymers. Helical polycarbodiimides consist of alternating imine and amine backbone, attached to different pendant groups. Substituting the pendant groups, enable to change of the properties of polycarbodiimides. Thus, we invented polar functional groups such as dimethylamine and piperazine to the side chains to enhance the solubility in an aqueous medium. Moreover, each unit of these polymers consists of hydrophobic methyl functionality and hydrophilic dimethyl and piperazine side groups. Thus, these carbodiimide polymers were self-assembled in aqueous solutions as well as buffer solutions due to the hydrophilic and hydrophobic moieties of the polymer. The micelles can be used as nanocarriers. Furthermore, the pH-dependent swelling properties were observed in these polymeric nanoparticles in different time intervals. Thus, the pH-triggered volume change of the micelles can be used as a controlled release, targeted site drug delivery applications.
    VL  - 7
    IS  - 1
    ER  - 

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Author Information
  • Department of Chemistry and Biochemistry, The University of Texas at Dallas, Richardson, USA

  • Department of Chemistry and Biochemistry, The University of Texas at Dallas, Richardson, USA

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