Thermoresponsive Carbohydrate‑b‑Polypeptoid Polymer Vesicles with Selective Solute Permeability and Permeable Factors for Solutes

Solute-permeable polymer vesicles are structural compartments for nanoreactors/nanofactories in the context of drug delivery and artificial cells. We previously proposed design guidelines for polymers that form solute-permeable vesicles, yet we did not provide enough experimental verification. In ad...

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Published inBiomacromolecules Vol. 22; no. 7; pp. 3099 - 3106
Main Authors Okuno, Yota, Nishimura, Tomoki, Sasaki, Yoshihiro, Akiyoshi, Kazunari
Format Journal Article
LanguageEnglish
Published American Chemical Society 12.07.2021
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Abstract Solute-permeable polymer vesicles are structural compartments for nanoreactors/nanofactories in the context of drug delivery and artificial cells. We previously proposed design guidelines for polymers that form solute-permeable vesicles, yet we did not provide enough experimental verification. In addition, the fact that there is no clear factor for identifying permeable solutes necessitates extensive trial and error. Herein, we report solute-permeable polymer vesicles based on an amphiphilic copolymer, thermoresponsive oligosaccharide-block-poly­(N-n-propylglycine). The introduction of a thermoresponsive polymer as a hydrophobic segment into amphiphilic polymers is a viable approach to construct solute-permeable polymer vesicles. We also demonstrate that the polymer vesicles are preferentially permeable to cationic and neutral fluorophores and are hardly permeable to anionic fluorophores due to the electrostatic repulsion between the bilayer and anionic fluorophores. In addition, the permeability of neutral fluorophores increases with the increasing log P value of the fluorophores. Thus, the electrical charge and log P value are important factors for membrane permeability. These findings will help researchers develop advanced nanoreactors based on permeable vesicles for a broad range of fundamental and biomedical applications.
AbstractList Solute-permeable polymer vesicles are structural compartments for nanoreactors/nanofactories in the context of drug delivery and artificial cells. We previously proposed design guidelines for polymers that form solute-permeable vesicles, yet we did not provide enough experimental verification. In addition, the fact that there is no clear factor for identifying permeable solutes necessitates extensive trial and error. Herein, we report solute-permeable polymer vesicles based on an amphiphilic copolymer, thermoresponsive oligosaccharide-block-poly­(N-n-propylglycine). The introduction of a thermoresponsive polymer as a hydrophobic segment into amphiphilic polymers is a viable approach to construct solute-permeable polymer vesicles. We also demonstrate that the polymer vesicles are preferentially permeable to cationic and neutral fluorophores and are hardly permeable to anionic fluorophores due to the electrostatic repulsion between the bilayer and anionic fluorophores. In addition, the permeability of neutral fluorophores increases with the increasing log P value of the fluorophores. Thus, the electrical charge and log P value are important factors for membrane permeability. These findings will help researchers develop advanced nanoreactors based on permeable vesicles for a broad range of fundamental and biomedical applications.
Author Akiyoshi, Kazunari
Okuno, Yota
Nishimura, Tomoki
Sasaki, Yoshihiro
AuthorAffiliation Shinshu University
Department of Polymer Chemistry, Graduate School of Engineering
Kyoto University, Kyoto Daigaku-Katsura
Department of Chemistry and Materials, Faculty of Textile Science and Technology
AuthorAffiliation_xml – name: Department of Chemistry and Materials, Faculty of Textile Science and Technology
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Cites_doi 10.1021/la950928i
10.1140/epje/i2011-11014-y
10.1021/acs.biomac.9b01754
10.1039/c9nr02507c
10.3390/polym5010112
10.1021/bc7001665
10.1002/anie.201706964
10.1038/nnano.2006.180
10.1002/advs.201800801
10.1002/mabi.201500023
10.1002/adma.201500275
10.1021/ar200036k
10.1021/acscentsci.8b00168
10.1016/j.colsurfb.2008.09.023
10.1126/science.1074972
10.1016/j.molliq.2014.04.001
10.1021/acs.biomac.6b01870
10.1039/c2cc33881e
10.1021/nn4015714
10.1007/s10822-013-9655-5
10.1002/cnma.201900245
10.1021/ja050742y
10.1021/acscentsci.0c01196
10.1016/j.biomaterials.2014.02.029
10.1021/acs.chemmater.5b03048
10.1039/c9mh01669d
10.1021/ma302412v
10.1016/s0021-9797(02)00082-6
10.1016/s1359-0294(00)00045-5
10.1021/acsnano.8b09082
10.1021/acsmacrolett.7b00725
10.1021/ja012091l
10.1039/c8py01502c
10.1021/nl401215n
10.1021/acs.macromol.8b00986
10.1021/acs.chemrev.5b00201
10.1021/ja01600a017
10.1039/b905635a
10.1002/chem.201801159
10.1038/nmat1081
10.1039/c1sm06518a
10.1016/j.jconrel.2019.04.032
10.1021/bm8000155
10.1021/ma201015y
10.1021/acs.nanolett.7b03531
10.1002/adma.201702406
10.1021/jacs.9b08598
10.1021/ma202319g
10.1021/acs.biomac.0c01465
10.1016/j.biomaterials.2012.04.060
10.1021/ja404175x
10.1002/bip.23070
10.1039/c6py01320a
10.1039/b818869f
10.1021/acs.macromol.0c01261
10.1002/adma.200300010
10.1039/C4CC05983B
10.1021/bm401542z
10.1246/bcsj.20170044
10.1016/0584-8539(95)01421-p
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References ref9/cit9
ref45/cit45
ref3/cit3
ref27/cit27
ref56/cit56
ref16/cit16
ref52/cit52
ref23/cit23
ref8/cit8
ref31/cit31
ref59/cit59
ref2/cit2
ref34/cit34
ref37/cit37
ref20/cit20
ref48/cit48
ref60/cit60
ref17/cit17
ref10/cit10
ref35/cit35
ref53/cit53
ref19/cit19
ref21/cit21
ref42/cit42
ref46/cit46
ref49/cit49
ref13/cit13
ref24/cit24
ref38/cit38
ref50/cit50
ref54/cit54
ref6/cit6
ref36/cit36
ref18/cit18
ref11/cit11
ref25/cit25
ref29/cit29
ref32/cit32
ref39/cit39
ref14/cit14
Gang L. (ref15/cit15) 2014; 50
ref57/cit57
ref5/cit5
ref51/cit51
ref43/cit43
ref28/cit28
ref40/cit40
ref26/cit26
ref55/cit55
ref12/cit12
ref41/cit41
ref58/cit58
ref22/cit22
ref33/cit33
ref4/cit4
ref30/cit30
ref47/cit47
ref1/cit1
ref44/cit44
ref7/cit7
References_xml – ident: ref58/cit58
  doi: 10.1021/la950928i
– ident: ref26/cit26
  doi: 10.1140/epje/i2011-11014-y
– ident: ref13/cit13
  doi: 10.1021/acs.biomac.9b01754
– ident: ref34/cit34
  doi: 10.1039/c9nr02507c
– ident: ref49/cit49
  doi: 10.3390/polym5010112
– ident: ref36/cit36
  doi: 10.1021/bc7001665
– ident: ref18/cit18
  doi: 10.1002/anie.201706964
– ident: ref24/cit24
  doi: 10.1038/nnano.2006.180
– ident: ref25/cit25
  doi: 10.1002/advs.201800801
– ident: ref43/cit43
  doi: 10.1002/mabi.201500023
– ident: ref44/cit44
  doi: 10.1002/adma.201500275
– ident: ref9/cit9
  doi: 10.1021/ar200036k
– ident: ref33/cit33
  doi: 10.1021/acscentsci.8b00168
– ident: ref60/cit60
  doi: 10.1016/j.colsurfb.2008.09.023
– ident: ref3/cit3
  doi: 10.1126/science.1074972
– ident: ref55/cit55
  doi: 10.1016/j.molliq.2014.04.001
– ident: ref20/cit20
  doi: 10.1021/acs.biomac.6b01870
– ident: ref39/cit39
  doi: 10.1039/c2cc33881e
– ident: ref40/cit40
  doi: 10.1021/nn4015714
– ident: ref59/cit59
  doi: 10.1007/s10822-013-9655-5
– ident: ref12/cit12
  doi: 10.1002/cnma.201900245
– ident: ref5/cit5
  doi: 10.1021/ja050742y
– ident: ref28/cit28
  doi: 10.1021/acscentsci.0c01196
– ident: ref42/cit42
  doi: 10.1016/j.biomaterials.2014.02.029
– ident: ref11/cit11
  doi: 10.1021/acs.chemmater.5b03048
– ident: ref14/cit14
  doi: 10.1039/c9mh01669d
– ident: ref48/cit48
  doi: 10.1021/ma302412v
– ident: ref52/cit52
  doi: 10.1016/s0021-9797(02)00082-6
– ident: ref1/cit1
  doi: 10.1016/s1359-0294(00)00045-5
– ident: ref22/cit22
  doi: 10.1021/acsnano.8b09082
– ident: ref32/cit32
  doi: 10.1021/acsmacrolett.7b00725
– ident: ref2/cit2
  doi: 10.1021/ja012091l
– ident: ref31/cit31
  doi: 10.1039/c8py01502c
– ident: ref17/cit17
  doi: 10.1021/nl401215n
– ident: ref51/cit51
  doi: 10.1021/acs.macromol.8b00986
– ident: ref45/cit45
  doi: 10.1021/acs.chemrev.5b00201
– ident: ref53/cit53
  doi: 10.1021/ja01600a017
– ident: ref7/cit7
  doi: 10.1039/b905635a
– ident: ref21/cit21
  doi: 10.1002/chem.201801159
– ident: ref8/cit8
  doi: 10.1038/nmat1081
– ident: ref56/cit56
  doi: 10.1039/c1sm06518a
– ident: ref23/cit23
  doi: 10.1016/j.jconrel.2019.04.032
– ident: ref57/cit57
  doi: 10.1021/bm8000155
– ident: ref37/cit37
  doi: 10.1021/ma201015y
– ident: ref19/cit19
  doi: 10.1021/acs.nanolett.7b03531
– ident: ref29/cit29
  doi: 10.1002/adma.201702406
– ident: ref30/cit30
  doi: 10.1021/jacs.9b08598
– ident: ref38/cit38
  doi: 10.1021/ma202319g
– ident: ref16/cit16
  doi: 10.1021/acs.biomac.0c01465
– ident: ref10/cit10
  doi: 10.1016/j.biomaterials.2012.04.060
– ident: ref27/cit27
  doi: 10.1021/ja404175x
– ident: ref47/cit47
  doi: 10.1002/bip.23070
– ident: ref50/cit50
  doi: 10.1039/c6py01320a
– ident: ref6/cit6
  doi: 10.1039/b818869f
– ident: ref35/cit35
  doi: 10.1021/acs.macromol.0c01261
– ident: ref4/cit4
  doi: 10.1002/adma.200300010
– volume: 50
  start-page: 12538
  year: 2014
  ident: ref15/cit15
  publication-title: Chem. Commun.
  doi: 10.1039/C4CC05983B
  contributor:
    fullname: Gang L.
– ident: ref41/cit41
  doi: 10.1021/bm401542z
– ident: ref46/cit46
  doi: 10.1246/bcsj.20170044
– ident: ref54/cit54
  doi: 10.1016/0584-8539(95)01421-p
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