TY - JOUR
T1 - Synthesis of Poly(N-vinylpyrrolidone)-based polymer bottlebrushes by ATRPA and RAFT polymerization
T2 - Toward drug delivery application
AU - Huang, Yi Shen
AU - Chen, Jem Kun
AU - Kuo, Shiao Wei
AU - Hsieh, Ya An
AU - Yamamoto, Shota
AU - Nakanishi, Jun
AU - Huang, Chih Feng
N1 - Funding Information:
Funding: The authors thank the financial support from Ministry of Science and Technology (MOST105-2221-E-005-084-MY2, MOST105-2628-E-005-003-MY3, and MOST106-2923-E-194-001). C.-F.H. thanks the financial support from TCUS exchange project.
PY - 2019
Y1 - 2019
N2 - Atom transfer radical polyaddition (ATRPA) was utilized herein to synthesize a specific functional polyester. We conductedATRPAof 4-vinylbenzyl 2-bromo-2-phenylacetate (VBBPA) inimer and successfully obtained a linear type poly(VBBPA) (PVBBPA) polyester with benzylic bromides along the backbone. To obtain a novel amphiphilic polymer bottlebrush, however, the lateral ATRP chain extension of PVBBPA with N-vinyl pyrrolidone (NVP) met the problem of quantitative dimerization. By replacing the bromides to xanthate moieties efficiently, we thus observed a pseudo linear first order reversible addition-fragmentation chain transfer (RAFT) polymerization to obtain novel poly(4-vinylbenzyl-2-phenylacetate)-g-poly(NVP) (PVBPA-g-PNVP) amphiphilic polymer bottlebrushes. The critical micelle concentration (CMC) and particle size of the amphiphilic polymer bottlebrushes were characterized by fluorescence spectroscopy, dynamic light scattering (DLS), and scanning electron microscopy (SEM) (CMCs < 0.5 mg/mL; particle sizes = ca. 100 nm). Toward drug delivery application, we examined release profiles using a model drug of Nile red at different pH environments (3, 5, and 7). Eventually, low cytotoxicity and well cell uptake of the Madin-Darby Canine Kidney Epithelial (MDCK) for the polymer bottlebrush micelles were demonstrated.
AB - Atom transfer radical polyaddition (ATRPA) was utilized herein to synthesize a specific functional polyester. We conductedATRPAof 4-vinylbenzyl 2-bromo-2-phenylacetate (VBBPA) inimer and successfully obtained a linear type poly(VBBPA) (PVBBPA) polyester with benzylic bromides along the backbone. To obtain a novel amphiphilic polymer bottlebrush, however, the lateral ATRP chain extension of PVBBPA with N-vinyl pyrrolidone (NVP) met the problem of quantitative dimerization. By replacing the bromides to xanthate moieties efficiently, we thus observed a pseudo linear first order reversible addition-fragmentation chain transfer (RAFT) polymerization to obtain novel poly(4-vinylbenzyl-2-phenylacetate)-g-poly(NVP) (PVBPA-g-PNVP) amphiphilic polymer bottlebrushes. The critical micelle concentration (CMC) and particle size of the amphiphilic polymer bottlebrushes were characterized by fluorescence spectroscopy, dynamic light scattering (DLS), and scanning electron microscopy (SEM) (CMCs < 0.5 mg/mL; particle sizes = ca. 100 nm). Toward drug delivery application, we examined release profiles using a model drug of Nile red at different pH environments (3, 5, and 7). Eventually, low cytotoxicity and well cell uptake of the Madin-Darby Canine Kidney Epithelial (MDCK) for the polymer bottlebrush micelles were demonstrated.
KW - Amphiphilic polymer bottlebrush
KW - Atom transfer radical polyaddition (ATRPA)
KW - Functional polyesters
KW - Poly(N-vinylpyrrolidone)
KW - Reversible addition-fragmentation chain transfer (RAFT) polymerization
UR - http://www.scopus.com/inward/record.url?scp=85069828005&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85069828005&partnerID=8YFLogxK
U2 - 10.3390/POLYM11061079
DO - 10.3390/POLYM11061079
M3 - Article
AN - SCOPUS:85069828005
VL - 11
JO - Polymers
JF - Polymers
SN - 2073-4360
IS - 6
M1 - 1079
ER -