pH-responsive intermediary layer cross-linked micelles from zwitterionic triblock copolymers and investigation of their drug-release behaviors

Wibowo, Agung Ari; Butun, Vural

doi:10.55730/1300-0527.3597

pH-responsive intermediary layer cross-linked micelles from zwitterionic triblock copolymers and investigation of their drug-release behaviors

Agung Ari WIBOWO, (Osmangazi Üniversitesi, Fen Bilimleri Enstitüsü, Polimer Bilimi ve Teknolojisi Anabilim Dalı, Eskisehir, Türkiye)

Vural BÜTÜN (Osmangazi Üniversitesi, Fen Bilimleri Enstitüsü, Polimer Bilimi ve Teknolojisi Anabilim Dalı, Eskisehir, Türkiye)

Turkish Journal of Chemistry

5 0

Yıl: 2023 Cilt: 47 Sayı: 5 Sayfa Aralığı: 1103 - 1115 Metin Dili: İngilizce DOI: 10.55730/1300-0527.3597 İndeks Tarihi: 21-11-2023

pH-responsive intermediary layer cross-linked micelles from zwitterionic triblock copolymers and investigation of their drug-release behaviors

Öz:

ABC-type triblock copolymers, namely poly[(ethylene glycol)methyl ether]-block-poly(tert-butyl methacrylate)-block- poly[2-N-(diisopropylamino)ethyl methacrylate] (MPEG-b-PBuMA-b-PDPA), were first synthesized and then the middle blocks were successfully converted into poly(methacrylic acid) to obtain MPEG-b-PMAA-b-PDPA zwitterionic triblock copolymers. These block copolymers were soluble in water and formed micellar aggregates with complex cores via hydrogen bonding interactions between MPEG and PMAA blocks below pH 4.0. When the pH was between 5.0 and 7.0, due to charge compensation between partially protonated PDPA and partially ionized PMAA blocks, micelles with polyion complex cores were observed. If the solution pH was above 8.0, deprotonation of tertiary amine groups provided a hydrophobic character to the PDPA block, which resulted in the formation of PDPA- core micelles while MPEG/anionic PMAA hybrid blocks formed hydrated coronas. Intermediary layer cross-linked (ILCL) micelles from PDPA-core micelles were also prepared by cross-linking the inner PMAA shell. The hydrophobic drug dipyridamole (DIP) was used to investigate the release profile of ILCL micelles. DIP can be loaded to the PDPA cores of the micelles in basic aqueous media. An increase in the degree of cross-linking causes slower release for the model drug. It was concluded that the more complex matrix formation in the intermediary layer of the micelles via cross-linking retards the drug release from the core.

Anahtar Kelime: Atom transfer radical polymerization pH-responsive polymer zwitterionic polymer micelles cross-linked micelles drug release

Belge Türü: Makale Makale Türü: Araştırma Makalesi Erişim Türü: Erişime Açık

1. Martinho N, Damgé C, Reis CP. Recent advances in drug delivery systems. Journal of Biomaterial Nanobiotechnology 2011; 2 (5): 510-526. https://doi:10.4236/jbnb.2011.225062
[2] Park H, Otte A, Park K. Evolution of drug delivery systems: from 1950 to 2020 and beyond. Journal of Controlled Release 2022; 342: 53-65. https://doi.org/10.1016/j.jconrel.2021.12.030
[3] Mahapatro A, Singh DK. Biodegradable nanoparticles are excellent vehicle for site directed in-vivo delivery of drugs and vaccines. Journal of Nanobiotechnology 2011; 9: 55. https://doi.org/10.1186/1477-3155-9-55
[4] Zelikin AN. Drug releasing polymer thin films: new era of surface-mediated drug delivery. ACS Nano 2010; 4 (5): 2494-2509. https://doi. org/10.1021/nn100634r
[5] O’Reilly KR, Hawker CJ, Wooley KL. Cross-linked block copolymer micelles: functional nanostructures of great potential and versatility. Chemical Society Reviews 2006; 35 (11): 1068-1083. https://doi.org/10.1039/B514858H
[6] Read ES, Armes SP. Recent advances in shell cross-linked micelles. Chemical Communications 2007; 29: 3021-3035. https://doi. org/10.1039/B701217A
[7] Li Y, Xiao K, Zhu W, Denga W, Lama KS. Stimuli-responsive cross-linked micelles for on-demand drug delivery against cancers. Advanced Drug Delivery Reviews 2014; 66: 58-73. https://doi.org/10.1016/j.addr.2013.09.008
[8] Kocak G, Tuncer C, Bütün V. pH-responsive polymers. Polymer Chemistry 2017; 8: 144-176. https://doi.org/10.1039/C6PY01872F
[9] Kocak G, Bütün V. Synthesis and stabilization of Pt nanoparticles in core cross-linked micelles prepared from an amphiphilic diblock copolymer. Colloid Polymer Science 2015; 293 (12): 3563-3572. https://doi.org/10.1007/s00396-015-3727-0
[10] Calik F, Degirmenci A, Eceoglu M, Sanyal A, Sanyal R. Dendron-polymer conjugate based cross-linked micelles: a robust and versatile nanosystem for targeted delivery. Bioconjugate Chemistry 2019; 30: 1087-1097. https://doi.org/10.1021/acs.bioconjchem.9b00027
[11] Gebrie HT, Addisu KD, Darge HF, Birhan YS, Thankachan D et al. pH/redox-responsive core cross-linked based prodrug micelle for enhancing micellar stability and controlling delivery of chemo drugs: an effective combination drug delivery platform for cancer therapy. Biomaterials Advances 2022; 139: 213015. https://doi.org/10.1016/j.bioadv.2022.213015
[12] Jimaja S, Varlas S, Foster JC. Stimuli-responsive and core cross-linked micelles developed by NiCCo-PISA of helical poly(arylisocyanide) s. Polymer Chemistry 2022; 13: 4047-4053. https://doi.org/10.1039/d2py00397j
[13] Li A, Zhang D. Synthesis and characterization of cleavable core-cross-linked micelles based on amphiphilic block copolypeptoids as smart drug carriers. Biomacromolecules 2016; 17: 852-861. https://doi.org/10.1021/acs.biomac.5b01561
[14] Deng H, Zhan Y, Wang X, Cao Y, Liu J et al. Balancing the stability and drug release of polymer micelles by the coordination of dual- sensitive cleavable bonds in cross-linked core. Acta Biomaterialia 2015; 11: 126-136. https://doi.org/10.1016/j.actbio.2014.09.047
[15] Zhang L, Liu W, Lin L, Chen D, Stenzel MH. Degradable disulfide core-cross-linked micelles as a drug delivery system prepared from vinyl functionalized nucleosides via the RAFT process. Biomacromolecules 2008; 9: 3321-3331. https://doi.org/10.1021/bm800867n
[16] Bütün V, Wang XS, de Paz Banez MV, Robinson KL, Billingham NC et al. Synthesis of shell cross-linked micelles at high solids in aqueous media. Macromolecules 2000; 33: 1-3. https://doi.org/10.1021/ma9914669
[17] Hajebi S, Rabiee N, Bagherzadeh M, Ahmadi S, Rabiee M et al. Stimulus-responsive polymeric nanogels as smart drug delivery systems. Acta Biomaterialia 2019; 92: 1-18. https://doi.org/10.1016/j.actbio.2019.05.018
[18] He X, Wu X, Gao C, Wang K, Lin S et al. Synthesis and self-assembly of a hydrophilic, thermo-responsive poly(ethylene oxide)monomethyl ether-b-poly(acrylic acid)-b-poly(N-isopropylacrylamide) copolymer to form micelles for drug delivery. Reactive and Functional Polymers 2011; 71 (5): 544-552. https://doi.org/10.1016/j.reactfunctpolym.2011.02.001
[19] Xu X, Flores JD, McCormick CL. Reversible imine shell cross-linked micelles from aqueous RAFT synthesized thermoresponsive triblock copolymers as potential nanocarriers for “pH-triggered” drug release. Macromolecules 2011; 44: 1327-1334. https://doi.org/10.1021/ ma102804h
[20] Jiang X, Ge Z, Xu J, Liu H, Liu S. Fabrication of multiresponsive shell cross-linked micelles possessing pH-controllable core swellability and thermo-tunable corona permeability. Biomacromolecules 2007; 8 (10): 3184-3192. https://doi.org/10.1021/bm700743h
[21] Aydın O. Engineering of pH-sensitive cross-linked micelles for drug delivery. Journal of Research Pharmacy 2021; 25 (4); 359-370. https:// dx.doi.org/10.29228/jrp.26
[22] Bontha S, Kabanov AV, Bronich TK. Polymer micelles with cross-linked ionic cores for delivery of anticancer drugs. Journal of Controlled Release 2006; 114: 163-174. https://doi.org/10.1016/j.jconrel.2006.06.015
[23] Lin W, Ma G, Kampf N, Yuan Z, Chen S. Development of long-circulating zwitterionic cross-linked micelles for active-targeted drug delivery. Biomacromolecules 2016; 17: 2010-2018. https://doi.org/10.1021/acs.biomac.6b00168
[24] Gurdap S, Bayram NN, Isoglu IA, Dincer Isoglu S. Sulfobetaine-based homo- and copolymers by RAFT: Cross-linked micelles and aqueous solution properties. ACS Applied Polymer Materials 2022; 4: 6303-6311. https://doi.org/10.1021/acsapm.1c01873
[25] Bütün V, Taktak FF, Tuncer C. Tertiary amine methacrylate-based ABC triblock copolymers: synthesis, characterization, and self-assembly in both aqueous and nonaqueous media. Macromolecular Chemistry and Physics 2011; 212 (11): 1115-1128. https://doi.org/10.1002/ macp.201100057
[26] Bütün V, Lowe AB, Billingham NC, Armes SP. Synthesis of zwitterionic shell cross-linked micelles. Journal of American Chemical Society 1999; 121 (17): 4288-4289. https://doi.org/10.1021/ja9840596
[27] Liu H, Li C, Liu H, Liu S. pH-responsive supramolecular self-assembly of well-defined zwitterionic ABC miktoarm star terpolymers. Langmuir 2009; 25 (8): 4724-4734. https://doi.org/10.1021/la803813r
[28] Liu S, Weaver JVM, Tang Y, Billingham C, Armes SP et al. Synthesis of shell cross-linked micelles with pH-responsive cores using ABC triblock copolymers. Macromolecules 2002; 35 (16): 6121-6131. https://doi.org/10.1021/ma020447n
[29] Bütün V, Top RB, Ufuklar S. Synthesis and characterization of novel ‘schizophrenic’ water-soluble triblock copolymers and shell cross- linked micelles. Macromolecules 2006; 39 (3): 1216-1225. https://doi.org/10.1021/ma052052k
[30] Liu S, Armes SP. The facile one-pot synthesis of shell cross-linked micelles in aqueous solution at high solids. Journal of American Chemical Society 2001; 123 (40): 9910-9911. https://doi.org/10.1021/ja011206i
[31] Tang Y, Liu SY, Armes SP, Billingham NC. Solubilisation and controlled release of a model hydrophobic drug using novel micelle-forming ABC triblock copolymers. Biomacromolecules 2003; 4 (6): 1636-1645. https://doi.org/10.1021/bm030026t

APA	Wibowo A, Butun V (2023). pH-responsive intermediary layer cross-linked micelles from zwitterionic triblock copolymers and investigation of their drug-release behaviors. , 1103 - 1115. 10.55730/1300-0527.3597
Chicago	Wibowo Agung Ari,Butun Vural pH-responsive intermediary layer cross-linked micelles from zwitterionic triblock copolymers and investigation of their drug-release behaviors. (2023): 1103 - 1115. 10.55730/1300-0527.3597
MLA	Wibowo Agung Ari,Butun Vural pH-responsive intermediary layer cross-linked micelles from zwitterionic triblock copolymers and investigation of their drug-release behaviors. , 2023, ss.1103 - 1115. 10.55730/1300-0527.3597
AMA	Wibowo A,Butun V pH-responsive intermediary layer cross-linked micelles from zwitterionic triblock copolymers and investigation of their drug-release behaviors. . 2023; 1103 - 1115. 10.55730/1300-0527.3597
Vancouver	Wibowo A,Butun V pH-responsive intermediary layer cross-linked micelles from zwitterionic triblock copolymers and investigation of their drug-release behaviors. . 2023; 1103 - 1115. 10.55730/1300-0527.3597
IEEE	Wibowo A,Butun V "pH-responsive intermediary layer cross-linked micelles from zwitterionic triblock copolymers and investigation of their drug-release behaviors." , ss.1103 - 1115, 2023. 10.55730/1300-0527.3597
ISNAD	Wibowo, Agung Ari - Butun, Vural. "pH-responsive intermediary layer cross-linked micelles from zwitterionic triblock copolymers and investigation of their drug-release behaviors". (2023), 1103-1115. https://doi.org/10.55730/1300-0527.3597

APA	Wibowo A, Butun V (2023). pH-responsive intermediary layer cross-linked micelles from zwitterionic triblock copolymers and investigation of their drug-release behaviors. Turkish Journal of Chemistry, 47(5), 1103 - 1115. 10.55730/1300-0527.3597
Chicago	Wibowo Agung Ari,Butun Vural pH-responsive intermediary layer cross-linked micelles from zwitterionic triblock copolymers and investigation of their drug-release behaviors. Turkish Journal of Chemistry 47, no.5 (2023): 1103 - 1115. 10.55730/1300-0527.3597
MLA	Wibowo Agung Ari,Butun Vural pH-responsive intermediary layer cross-linked micelles from zwitterionic triblock copolymers and investigation of their drug-release behaviors. Turkish Journal of Chemistry, vol.47, no.5, 2023, ss.1103 - 1115. 10.55730/1300-0527.3597
AMA	Wibowo A,Butun V pH-responsive intermediary layer cross-linked micelles from zwitterionic triblock copolymers and investigation of their drug-release behaviors. Turkish Journal of Chemistry. 2023; 47(5): 1103 - 1115. 10.55730/1300-0527.3597
Vancouver	Wibowo A,Butun V pH-responsive intermediary layer cross-linked micelles from zwitterionic triblock copolymers and investigation of their drug-release behaviors. Turkish Journal of Chemistry. 2023; 47(5): 1103 - 1115. 10.55730/1300-0527.3597
IEEE	Wibowo A,Butun V "pH-responsive intermediary layer cross-linked micelles from zwitterionic triblock copolymers and investigation of their drug-release behaviors." Turkish Journal of Chemistry, 47, ss.1103 - 1115, 2023. 10.55730/1300-0527.3597
ISNAD	Wibowo, Agung Ari - Butun, Vural. "pH-responsive intermediary layer cross-linked micelles from zwitterionic triblock copolymers and investigation of their drug-release behaviors". Turkish Journal of Chemistry 47/5 (2023), 1103-1115. https://doi.org/10.55730/1300-0527.3597