pH-responsive supramolecular nanoparticles based on sulfobutylether₇-β-CD/cationic surfactant and its controllable release of doxorubicin

References

• Hou, X. Y.; Zhang, W. J.; He, M. Y.; Lu, Y. B.; Lou, K. Y.; Gao, F. Preparation and Characterization of β-Cyclodextrin Grafted N-Maleoyl Chitosan Nanoparticles for Drug Delivery. Asian J. Pharm. Sci. 2017, 12, 558–568. DOI: 10.1016/j.ajps.2017.07.007.
   PubMed Web of Science ®Google Scholar
• Qian, Y. Y.; You, D.; Lin, F.; Wei, J. W.; Wang, Y. J.; Bi, Y. M. Enzyme Triggered Disassembly of Amphiphilic Linear-Dendritic Block Copolymer Micelles Based on Poly[ N -(2-Hydroxyethyl- l -Glutamine)]. Polym. Chem. 2019, 10, 94–105. DOI: 10.1039/C8PY01231H.
   Web of Science ®Google Scholar
• Wei, J. W.; Lin, F.; You, D.; Qian, Y. Y.; Wang, Y. J.; Bi, Y. M. Self-Assembly and Enzyme Responsiveness of Amphiphilic Linear-Dendritic Block Copolymers Based on Poly(N-vinylpyrrolidone) and Dendritic Phenylalanyl-lysine Dipeptides. Polymers 2019, 11, 1625. DOI: 10.3390/polym11101625.
   PubMed Web of Science ®Google Scholar
• Liu, Y. Self-Assembly: Supramolecular Basketry. Nat. Chem. 2017, 9, 1037–1038. DOI: 10.1038/nchem.2883.
   PubMed Web of Science ®Google Scholar
• Whitton, G.; Gillies, E. R. Functional Aqueous Assemblies of Linear-Dendron Hybrids. J. Polym. Sci. Part A: Polym. Chem. 2015, 53, 148–172. DOI: 10.1002/pola.27316.
   Web of Science ®Google Scholar
• Rosenbaum, I.; Harnoy, A. J.; Tirosh, E.; Buzhor, M.; Segal, M.; Frid, L.; Shaharabani, R.; Avinery, R.; Beck, R.; Amir, R. J. Encapsulation and Covalent Binding of Molecular Payload in Enzymatically Activated Micellar Nanocarriers. J. Am. Chem. Soc. 2015, 137, 2276–2284. DOI: 10.1021/ja510085s.
   PubMed Web of Science ®Google Scholar
• Wang, W. Y.; Guo, H. C.; Zeng, L. H.; Zhou, J. T.; Zhao, L.; Zhang, G. J.; Wang, C.; Xu, B. C. Colloids and Surfaces A: Physicochem. Eng. Aspects 2018, 558, 117–122. DOI: 10.1016/j.colsurfa.2018.08.070.
   Web of Science ®Google Scholar
• Hu, Y.; Qiu, C.; Jin, Z.; Qin, Y.; Zhan, C.; Xu, X.; Wang, J. Pickering Emulsions with Enhanced Storage Stabilities by Using Hybrid β-Cyclodextrin/Short Linear Glucan Nanoparticles as Stabilizers. Carbohydr. Polym. 2020, 229, 115418. DOI: 10.1016/j.carbpol.2019.115418.
   PubMed Web of Science ®Google Scholar
• Chen, Y.; Liu, Y. Construction and Functions of Cyclodextrin-Based 1D Supramolecular Strands and Their Secondary Assemblies. Adv. Mater. 2015, 27, 5403–5409. DOI: 10.1002/adma.201501216.
   PubMed Web of Science ®Google Scholar
• Pennakalathil, J.; Jahja, E.; Ozdemir, E. S.; Konu, O.; Tuncel, D. Red Emitting, Cucurbituril-Capped, pH-Responsive Conjugated Oligomer-Based Nanoparticles for Drug Delivery and Cellular Imaging. Biomacromolecules 2014, 15, 3366–3374. DOI: 10.1021/bm500839j.
   PubMed Web of Science ®Google Scholar
• Zhao, Q.; Sun, J. Z.; Ling, Q. C.; Zhou, Q. Y. Effect of 1,4-Dioxane on Synthesis of Macroporous Poly (N -Isopropylacrylamide) Hydrogels. J. Polym. Sci. A Polym. Chem. 2008, 46, 6594–6603. DOI: 10.1002/pola.22969.
   Web of Science ®Google Scholar
• Han, X.; Chen, Y.; Sun, H. L.; Liu, Y. Enzyme-Responsive Supramolecular Nanoparticles Based on Carboxyl-Modified Cyclodextrins for Dual Substrate Loading. Asian J. Org. Chem. 2018, 7, 870–874. DOI: 10.1002/ajoc.201800076.
   Web of Science ®Google Scholar
• Popat, A.; Karmakar, S.; Jambhrunkar, S.; Xu, C.; Yu, C. Z. Curcumin-Cyclodextrin Encapsulated Chitosan Nanoconjugates with Enhanced Solubility and Cell Cytotoxicity. Colloids Surf. B Biointerfaces 2014, 117, 520–527. DOI: 10.1016/j.colsurfb.2014.03.005.
   PubMed Web of Science ®Google Scholar
• Chen, X. M.; Chen, Y.; Hou, X. F.; Wu, X.; Gu, B. H.; Liu, Y. Sulfonato-β-Cyclodextrin Mediated Supramolecular Nanoparticle for Controlled Release of Berberine. ACS Appl. Mater. Interfaces 2018, 10, 24987–24992. DOI: 10.1021/acsami.8b08651.
   PubMed Web of Science ®Google Scholar
• Hou, X. F.; Chen, Y.; Liu, Y. Enzyme-Responsive Protein/Polysaccharide Supramolecular Nanoparticles. Soft Matter. 2015, 11, 2488–2493. DOI: 10.1039/c4sm02896a.
   PubMed Web of Science ®Google Scholar
• Guan, X. R.; Chen, Y.; Wu, X.; Li, P. Y.; Liu, Y. Enzyme-Responsive Sulfatocyclodextrin/Prodrug Supramolecular Assembly for Controlled Release of Anti-Cancer Drug Chlorambucil. Chem. Commun. (Camb.) 2019, 55, 953–956. DOI: 10.1039/c8cc09047e.
   PubMed Web of Science ®Google Scholar
• Wang, Y. w.; Qin, F.; Tan, H.; Zhang, Y.; Jiang, M.; Lu, M.; Yao, X. pH-Responsive Glycol Chitosan-Cross-Linked Carboxymethyl-β-Cyclodextrin Nanoparticles for Controlled Release of Anticancer Drugs. Int. J. Nanomed. 2015, 10, 7359–7370. DOI: 10.2147/IJN.S91906.
   PubMed Web of Science ®Google Scholar
• Rastegari, B.; Karbalaei-Heidari, H. R.; Zeinali, S.; Sheardown, H. The Enzyme-Sensitive Release of Prodigiosin Grafted β-Cyclodextrin and Chitosan Magnetic Nanoparticles as an Anticancer Drug Delivery System: Synthesis, Characterization and Cytotoxicity Studies. Colloids Surf B Biointerfaces 2017, 158, 589–601. DOI: 10.1016/j.colsurfb.2017.07.044.
   PubMed Web of Science ®Google Scholar
• Sun, H. L.; Chen, Y.; Zhao, J.; Liu, Y. Photocontrolled Reversible Conversion of Nanotube and Nanoparticle Mediated by β-Cyclodextrin Dimers. Angew. Chem. Int. Ed. Engl. 2015, 54, 9376–9380. Edition, DOI: 10.1002/anie.201503614.
   PubMed Web of Science ®Google Scholar
• Fu, H. G.; Chen, Y.; Yu, Q. L.; Liu, Y. A Tumor-Targeting Ru/Polysaccharide/Protein Supramolecular Assembly with High Photodynamic Therapy Ability. Chem. Commun. (Camb.) 2019, 55, 3148–3151. DOI: 10.1039/c8cc09964b.
   PubMed Web of Science ®Google Scholar
• Chen, S. L.; Li, Z. W.; Chi, S. M.; Yang, H. W.; Zhang, Y. Y.; Wang, Y. F.; Zhu, H. Y.; Zhao, Y. Preparation, Characterization and Solubilization Evaluation of Two Novel Host-Guest Complexes Based on Two Different Functional Groups of Modified β-Cyclodextrins and 20(S)-Protopanaxatriol. J. Mol. Struct. 2020, 1204, 127494. DOI: 10.1016/j.molstruc.2019.127494.
   Web of Science ®Google Scholar
• Yan, C. X.; Liang, N.; Li, Q.; Yan, P. F.; Sun, S. P. Biotin and Arginine Modified Hydroxypropyl-β-Cyclodextrin Nanoparticles as Novel Drug Delivery Systems for Paclitaxel. Carbohydr. Polym. 2019, 216, 129–139. DOI: 10.1016/j.carbpol.2019.04.024.
   PubMed Web of Science ®Google Scholar
• Yang, S. L.; Zhao, L. J.; Chi, S. M.; Du, J. J.; Ruan, Q.; Xiao, P. L.; Zhao, Y. Inclusion Complexes of Flavonoids with Propylenediamine Modified β-Cyclodextrin:Preparation, Characterization and Antioxidant. J. Mol. Struct. 2019, 1183, 118–125. DOI: 10.1016/j.molstruc.2019.01.046.
   Web of Science ®Google Scholar
• Wu, H.; Chen, Y.; Dai, X. Y.; Li, P. Y.; Stoddart, J. F.; Liu, Y. In Situ Photoconversion of Multicolor Luminescence and Pure White Light Emission Based on Carbon Dot-Supported Supramolecular Assembly. J. Am. Chem. Soc. 2019, 141, 6583–6591. − DOI: 10.1021/jacs.8b13675.
   PubMed Web of Science ®Google Scholar
• Liu, T. T.; Wang, S. D.; Li, Y. R.; Yan, H. R.; Tian, W. Triple Noncovalent-Interaction-Containing Supramolecular Polymer Vesicle Chemosensors with Dynamically Tunable Detection Ranges. Chemistry 2018, 24, 4239–4244. DOI: 10.1002/chem.201705162.
   PubMed Web of Science ®Google Scholar
• Zhang, Y. M.; Liu, J. H.; Yu, Q. L.; Wen, X.; Liu, Y. Targeted Polypeptide-Microtubule Aggregation with Cucurbit[8]Uril for Enhanced Cell Apoptosis. Angew. Chem. Int. Ed. Engl. 2019, 58, 10553–10557. Edition, DOI: 10.1002/anie.201903243.
   PubMed Web of Science ®Google Scholar
• Monteiro, A. P. F.; Caminhas, L. D.; Ardisson, J. D.; Paniago, R.; Cortés, M. E.; Sinisterra, R. D. Magnetic Nanoparticles Coated with Cyclodextrins and Citrate for Irinotecan Delivery. Carbohydr. Polym. 2017, 163, 1–9. DOI: 10.1016/j.carbpol.2016.11.091.
   PubMed Web of Science ®Google Scholar
• Da, Z.; Cao, H.; He, X.; Zhang, Z.; Zou, L.; Zeng, L.; Xu, Y.; Yin, Q.; Xu, M.; Zhong, D.; et al. A pH-Responsive Host-guest Nanosystem Loading Succinobucol Suppresses Lung Metastasis of Breast Cancer. Theranostics 2016, 6(3), 435–445. DOI: 10.7150/thno.13896.
   Web of Science ®Google Scholar
• Cheng, J. G.; Zhang, Y. M.; Liu, Y. Supramolecular Assembly of Thiolated Cyclodextrin and Ferrocene Derivative for Controlled Drug Delivery. ChemNanoMat. 2018, 4, 758–763. DOI: 10.1002/cnma.201800098.
   Web of Science ®Google Scholar
• Ghosh, R.; Ekka, D.; Rajbanshi, B.; Yasmin, A.; Roy, M. N. Colloids and Surfaces A: Physicochem. Eng. Aspects 2018, 548, 206–217. DOI: 10.1016/j.colsurfa.2018.01.003.
   Web of Science ®Google Scholar
• Li, B. J.; Feng, Z. Z.; He, L. L.; Li, W. S.; Wang, Q.; Liu, J. B.; Huang, J.; Zheng, Y.; Ma, Y. Y.; Yang, X. H.; Wang, K. M. Self-Assembled Supramolecular Nanoparticles for Targeted Delivery and Combination Chemotherapy. ChemMedChem. 2018, 13, 2037–2044. DOI: 10.1002/cmdc.201800291.
   PubMed Web of Science ®Google Scholar
• Zhang, Y. M.; Xu, X.; Yu, Q. L.; Yu, H. J.; Liu, Y. Drug Displacement Strategy for Treatment of Acute Liver Injury with Cyclodextrin-Liposome Nanoassembly. IScience 2019, 15, 223–233. DOI: 10.1016/j.isci.2019.04.029.
   PubMed Web of Science ®Google Scholar
• Wang, W. X.; Feng, S. S.; Zheng, C. H. A Comparison between Conventional Liposome and Drug-Cyclodextrin Complex in Liposome System. Int. J. Pharm. 2016, 513, 387–392. DOI: 10.1016/j.ijpharm.2016.09.043.
   PubMed Web of Science ®Google Scholar
• Liang, L.; Chen, Y.; Chen, X. M.; Zhang, Y.; Liu, Y. Cyclodextrin/Polyethylenimine-BasedSupramolecular Nanoparticles for Loading and Sustained Release of ATP. Chin. Chem. Lett. 2018, 29, 989–991. DOI: 10.1016/j.cclet.2017.12.022.
   Web of Science ®Google Scholar
• Ma, M. F.; Guan, Y.; Zhang, C.; Hao, J. C.; Xing, P. Y.; Su, J.; Li, S. Y.; Chu, X. X.; Hao, A. Y. Colloids and Surfaces A: Physicochem. Eng. Aspects 2014, 454, 38–45. DOI: 10.1016/j.colsurfa.2014.04.005.
   Web of Science ®Google Scholar
• Vaidya, B.; Parvathaneni, V.; Kulkarni, N. S.; Shukla, S. K.; Damon, J. K.; Sarode, A.; Kanabar, D.; Garcia, J. V.; Mitragotri, S.; Muth, A.; Gupta, V. Cyclodextrin Modified Erlotinib Loaded PLGA Nanoparticles for Improved Therapeutic Efficacy against Non-Small Cell Lung Cancer. Int. J. Biol. Macromol. 2019, 122, 338–347. DOI: 10.1016/j.ijbiomac.2018.10.181.
   PubMed Web of Science ®Google Scholar
• Yang, Y.; Jia, X.; Zhang, Y. M.; Li, N.; Liu, Y. Supramolecular Nanoparticles Based on β-CD Modified Hyaluronic Acid for DNA Encapsulation and Controlled Release. Chem. Commun. (Camb.) 2018, 54, 8713–8716. DOI: 10.1039/c8cc04783a.
   PubMed Web of Science ®Google Scholar
• Shao, W.; Liu, X.; Sun, G. P.; Hu, X. Y.; Zhu, J. J.; Wang, L. Y. Construction of Drug-Drug Conjugate Supramolecular Nanocarriers Based on Water-Soluble Pillar[6]Arene for Combination Chemotherapy. Chem. Commun. (Camb.) 2018, 54, 9462–9465. DOI: 10.1039/c8cc05180a.
   PubMed Web of Science ®Google Scholar
• Tardy, B. L.; Tan, S.; Dam, H. H.; Ejima, H.; Blencowe, A.; Qiao, G. G.; Caruso, F. Nanoparticles Assembled via pH-Responsive Reversible Segregation of Cyclodextrins in Polyrotaxanes. Nanoscale 2016, 8, 15589–15596. DOI: 10.1039/c6nr04841b.
   PubMed Web of Science ®Google Scholar
• Zhang, Y. H.; Zhang, Y. M.; Yu, J.; Wang, J.; Liu, Y. Boronate-Crosslinked Polysaccharide Conjugates for pH-Responsive and Targeted Drug Delivery. Chem. Commun. (Camb.) 2019, 55, 1164–1167. DOI: 10.1039/c8cc09956a.
   PubMed Web of Science ®Google Scholar
• Li, X. S.; Han, J. Y.; Qin, J. C.; Sun, M.; Wu, J. R.; Lei, L. C.; Li, J.; Fang, L.; Yang, Y. W. Mesoporous Silica Nanobeans Dual-Functionalized with AIEgens and Leaning Pillar[6]Arene-Based Supramolecular Switches for Imaging and Stimuli-Responsive Drug Release. Chem. Commun. (Camb.) 2019, 55, 14099–14102. DOI: 10.1039/C9CC07115F.
   PubMed Web of Science ®Google Scholar
• Awad, M. A.; Eisa, N. E.; Virk, P.; Hendi, A. A.; Ortashi, K. M. O. O.; Mahgoub, A. S. A.; Elobeid, M. A.; Eissa, F. Z. Green Synthesis of Gold Nanoparticles: Preparation, Characterization, Cytotoxicity, and anti-Bacterial Activities. Mater. Lett. 2019, 256, 126608–126609. DOI: 10.1016/j.matlet.2019.126608.
   Web of Science ®Google Scholar
• Matshetshe, K. I.; Parani, S.; Manki, S. M.; Oluwafemi, O. S. Preparation, Characterization and in Vitro Release Study of β-Cyclodextrin/Chitosan Nanoparticles Loaded Cinnamomum Zeylanicum Essential Oil. Int. J. Biol. Macromol. 2018, 118, 676–682. DOI: 10.1016/j.ijbiomac.2018.06.125.
   PubMed Web of Science ®Google Scholar
• Zheng, X. X.; Bian, Q.; Ye, C. X.; Wang, G. J. Visible Light-, pH-, and Cyclodextrin-Responsive Azobenzene Functionalized Polymeric Nanoparticles. Dyes Pigm. 2019, 162, 599–605. DOI: 10.1016/j.dyepig.2018.10.063.
   Web of Science ®Google Scholar
• Zhang, Y. M.; Liu, Y. H.; Liu, Y. Cyclodextrin-Based Multistimuli-Responsive Supramolecular Assemblies and Their Biological Functions. Adv. Mater. 2019, 32, 1806158(1-19). DOI: 10.1002/adma.201806158.
   Web of Science ®Google Scholar
• Leong, N. J.; Prankerd, R. J.; Shackleford, D. M.; Mcintosh, M. P. The Effect of Intravenous sulfobutylether7 -β-Cyclodextrin on the Pharmacokinetics of a Series of Adamantane-Containing Compounds. J. Pharm. Sci. 2015, 104, 1492–1498. DOI: 10.1002/jps.24331.
   PubMed Web of Science ®Google Scholar
• Migahed, M. A.; Zaki, E. G.; Shaban, M. M. Corrosion Control in the Tubing Steel of Oil Wells during Matrix Acidizing Operations. RSC Adv. 2016, 6, 71384–71396. DOI: 10.1039/C6RA12835A.
   Web of Science ®Google Scholar
• Khatoon, S.; Han, H. S.; Jeon, J.; Rao, N. V.; Jeong, D. W.; Ikram, M.; Yasin, T.; Yi, G. R.; Park, J. H. Hypoxia-Responsive Mesoporous Nanoparticles for Doxorubicin Delivery. Polymers 2018, 10, 390–4360. DOI: 10.3390/polym10040390.
   PubMed Web of Science ®Google Scholar
• Bognanni, N.; Viale, M.; Distefano, A.; Tosto, R.; Bertola, N.; Loiacono, F.; Ponassi, M.; Spinelli, D.; Pappalardo, G.; Vecchio, G. Cyclodextrin Polymers as Delivery Systems for Targeted anti-Cancer Chemotherapy. Molecules 2021, 26, 3049–6046. DOI: 10.3390/molecules26196046.
   PubMed Web of Science ®Google Scholar
• Borandeh, S.; Abdolmaleki, A.; Abolmaali, S. S.; Tamaddon, A. M. Synthesis, Structural and in-Vitro Characterization of β-Cyclodextrin Grafted L-Phenylalanine Functionalized Graphene Oxide Nanocomposite: A Versatile Nanocarrier for pH-Sensitive Doxorubicin Delivery. Carbohydr. Polym. 2018, 201, 151–161. DOI: 10.1016/j.carbpol.2018.08.064.
   PubMed Web of Science ®Google Scholar