Amphiphilic Block Copolymer Micelles for Gene Delivery

doi:10.1007/s40242-022-2005-1

Abstract

Abstract: Gene therapy is a promising method to treat acquired and inherited diseases by introducing exogenous genes into specific recipient cells. Polymeric micelles with different nanoscopic morphologies and properties hold great promise for gene delivery system. Conventional cationic polymers, poly(ethyleneimine)(PEI), poly(L-lysine)(PLL), poly(2-dimethyla-minoethyl methacrylate)(PDMAEMA) and novel cationic polymers poly(2-oxazoline)s(POxs), have been incorporated into block copolymers and decorated with targeting moieties to enhance transfection efficiency. In order to minimize cytotoxicity, nonionic block copolymer micelles are utilized to load gene through hydrophilic and hydrophobic interactions or covalent conjugations, recently. From our perspective, properties(shape, size, and mechanical stiffness, etc.) of block copolymer micelles may significantly affect cytotoxicity, transfection efficiency, circulation time, and load capacity of gene vectors in vivo and in vitro. This review briefly sums up recent efforts in cationic and nonionic amphiphilic polymeric micelles for gene delivery.

Key words: Polymeric micelle, Block copolymer, Gene delivery

LI Qin, JIN Bixin, LUO Yunjun, LI Xiaoyu. Amphiphilic Block Copolymer Micelles for Gene Delivery[J]. Chemical Research in Chinese Universities, 2022, 38(6): 1368-1379.

References

[1] Pahle J., Walther W., Expert Opin. Biol. Th., 2016, 16, 443;
[2] Piotrowski-Daspit A. S., Kauffman A. C., Bracaglia L. G., Saltzman W. M., Adv. Drug Deliv. Rev., 2020, 156, 119;
[3] Davis M. E., Curr. Opin. Biotech., 2002, 13, 128;
[4] Han S.-O., Mahato R. I., Sung Y. K., Kim S. W., Mol. Ther., 2000, 2, 302;
[5] Huang Y., Hong J., Zheng S., Ding Y., Guo S., Zhang H., Zhang X., Du Q., Liang Z., Mol. Ther., 2011, 19, 381;
[6] Green J. J., Langer R., Anderson D. G., Acc. Chem. Res., 2008, 41, 749;
[7] Smith A. E., Annu. Rev. Microbiol., 1995, 49, 807;
[8] Park T. G., Jeong J. H., Kim S. W., Adv. Drug Deliv. Rev., 2006, 58, 467;
[9] Li C., Li Q., Kaneti Y. V., Hou D., Yamauchi Y., Mai Y., Chem. Soc. Rev., 2020, 49, 4681;
[10] Tritschler U., Pearce S., Gwyther J., Whittell G. R., Manners I., Macromo-lecules, 2017, 50, 3439;
[11] Shin J. J., Kim E. J., Ku K. H., Lee Y. J., Hawker C. J., Kim B. J., ACS Macro Lett., 2020, 9, 306;
[12] Cabral H., Miyata K., Osada K., Kataoka K., Chem. Rev., 2018, 118, 6844;
[13] Liu X., Zhao K., Cao J., Qi X., Wu L., Shen S., Int. J. Pharmaceut., 2021, 608, 121052;
[14] Maeda H., Adv. Drug Deliv. Rev., 2015, 91, 3;
[15] Yu L., Yao L., Yang K., Fei W., Chen Q., Qin L., Liu S., Zou Z., Qin B., Polym. Sci. Ser. A, 2021, 63, 769;
[16] Dutta D., Ke W., Xi L., Yin W., Zhou M., Ge Z., WIREs Nanomed Nano-biotechnol., 2020, 12, e1585;
[17] Geng Y., Dalhaimer P., Cai S., Tsai R., Tewari M., Minko T., Discher D. E., Nat. Nanotechnol., 2007, 2, 249;
[18] Fox M. E., Szoka F. C., Fréchet J. M. J., Acc. Chem. Res., 2009, 42, 1141;
[19] Sato K., Ji W., Palmer L. C., Weber B., Barz M., Stupp S. I., J. Am. Chem. Soc., 2017, 139, 8995;
[20] Wang W., Gaus K., Tilley R. D., Gooding J. J., Mater. Horiz., 2019, 6, 1538;
[21] Elsabahy M., Wooley K. L., Chem. Soc. Rev., 2012, 41, 2545;
[22] Perrault S. D., Walkey C., Jennings T., Fischer H. C., Chan W. C. W., Nano Lett., 2009, 9, 1909;
[23] Nomoto T., Fukushima S., Kumagai M., Machitani K., Arnida M. Y., Oba M., Miyata K., Osada K., Nishiyama N., Kataoka K., Nat. Commun., 2014, 5, 3545;
[24] Yi Y., Kim H. J., Mi P., Zheng M., Takemoto H., Toh K., Kim B. S., Hayashi K., Naito M., Matsumoto Y., Miyata K., Kataoka K., J. Control. Release, 2016, 244, 247;
[25] Takeda K. M., Yamasaki Y., Dirisala A., Ikeda S., Tockary T. A., Toh K., Osada K., Kataoka K., Biomaterials, 2017, 126, 31;
[26] Dash T. K., Konkimalla V. B., J. Control. Release, 2012, 158, 15;
[27] Gupta A. P., Kumar V., Eur. Polym. J., 2007, 43, 4053;
[28] Kumari A., Yadav S. K., Yadav S. C., Colloids Surf. B, 2010, 75, 1;
[29] Zhao X., Li X., Zhao Y., Cheng Y., Yang Y., Fang Z., Xie Y., Liu Y., Chen Y., Ouyang Y., Yuan W., Front. Pharmacol., 2017, 8, 510;
[30] Männistö M., Vanderkerken S., Toncheva V., Elomaa M., Ruponen M., Schacht E., Urtti A., J. Control. Release, 2002, 83, 169;
[31] Simanek E. E., Mintzer M. A., Chem. Rev., 2009, 109, 259;
[32] Zhou Q., Xiang J., Hao L., Xu X., Zhou Z., Tang J., Ping Y., Shen Y., Nano Today, 2021, 39;
[33] Takeda K. M., Osada K., Tockary T. A., Dirisala A., Chen Q., Kataoka K., Biomacromolecules, 2017, 18, 36;
[34] He Z., Miao L., Jordan R., S-Manickam D., Luxenhofer R., Kabanov A. V., Macromol. Biosci., 2015, 15, 1004;
[35] Sedlacek O., Monnery B. D., Filippov S. K., Hoogenboom R., Hruby M., Macromol. Rapid Commun., 2012, 33, 1648;
[36] Osawa S., Osada K., Hiki S., Dirisala A., Ishii T., Kataoka K., Biomacromolecules, 2016, 17, 354;
[37] Mastrobattista E., Hennink W. E., Nat. Mater., 2011, 11, 10;
[38] Klausen L. H., Fuhs T., Dong M., Nat. Commun., 2016, 7, 12447;
[39] Hafner A. M., Corthesy B., Textor M., Merkle H. P., Int. J. Pharm., 2016, 514, 176;
[40] Danhier F., Ansorena E., Silva J. M., Coco R., Le Breton A., Preat V., J. Control. Release, 2012, 161, 505;
[41] Yang H. W., Ye L., Guo X. D., Yang C., Compans R. W., Prausnitz M. R., Adv. Healthc. Mater., 2017, 6, 1600750;
[42] Zhang X., Wang Q., Qin L., Fu H., Fang Y., Han B., Duan Y., Drug Deliv., 2016, 23, 2936;
[43] Cai C., Xie Y., Wu L., Chen X., Liu H., Zhou Y., Zou H., Liu D., Zhao Y., Kong X., Liu P., Sci. Rep., 2017, 7, 46250;
[44] Zhang J., Chen C., Fu H., Yu J., Sun Y., Huang H., Tang Y., Shen N., Duan Y., ACS Nano, 2020, 14, 4414;
[45] Chen L. Q., Pagel M. D., Adv. Radiol., 2015, 2015;
[46] Sun W., Chen X., Xie C., Wang Y., Lin L., Zhu K., Shuai X., Biomacro-molecules, 2018, 19, 2248;
[47] Mura S., Nicolas J., Couvreur P., Nat. Mater., 2013, 12, 991;
[48] Kamaly N., Yameen B., Wu J., Farokhzad O. C., Chem. Rev., 2016, 116, 2602;
[49] Sun B., Deng C., Meng F., Zhang J., Zhong Z., Acta Biomater., 2016, 45, 223;
[50] Zou Y., Meng F., Deng C., Zhong Z., J. Control. Release, 2016, 239, 149;
[51] Chen S., Rong L., Lei Q., Cao P. X., Qin S. Y., Zheng D. W., Jia H. Z., Zhu J., Cheng S. X., Zhuo R. X., Zhang X. Z., Biomaterials, 2016, 77, 149;
[52] Deng J., Gao N., Wang Y., Yi H., Fang S., Ma Y., Cai L., Biomacromolecules, 2012, 13, 3795;
[53] Luo Z., Li P., Deng J., Gao N., Zhang Y., Pan H., Liu L., Wang C., Cai L., Ma Y., J. Control. Release, 2013, 170, 259;
[54] Luo Z., Wang C., Yi H., Li P., Pan H., Liu L., Cai L., Ma Y., Biomaterials, 2015, 38, 50;
[55] Garnett M. C., Crit. Rev. Ther. Drug Carr. Syst., 1999, 16, 147;
[56] Kichler A., Leborgne C., Coeytaux E., Danos O., J. Gene Med., 2001, 3, 135;
[57] Boussif O., Lezoualc'h F., Zanta M. A., Mergny M. D., Scherman D., Demeneix B., Behr J. P., Proc. Natl. Acad. Sci. USA, 1995, 92, 7297;
[58] Li L., Wei Y., Gong C., J. Biomed. Nanotechnol., 2015, 11, 739;
[59] Jaeger M., Schubert S., Ochrimenko S., Fischer D., Schubert U. S., ChemInform., 2012, 41, 4755;
[60] Lungwitz U., Breunig M., Blunk T., Gopferich A., Eur. J. Pharm. Biopharm., 2005, 60, 247;
[61] Zhu J., Tang A., Law L. P., Feng M., Ho K. M., Lee D. K. L., Harris F. W., Li P., Bioconjugate Chem., 2005, 16, 139;
[62] Endres T. K., Beck-Broichsitter M., Samsonova O., Renette T., Kissel T. H., Biomaterials, 2011, 32, 7721;
[63] Shi S., Zhu X., Guo Q., Wang Y., Zuo T., Luo F., Qian Z., Int. J. Nano-medicine, 2012, 7, 1749;
[64] Shi S., Fan M., Wang X., Zhao C., Wang Y., Luo F., Zhao X., Qian Z., J. Phys. Chem. C, 2010, 114, 21315;
[65] Zheng M., Librizzi D., Kılıç A., Liu Y., Renz H., Merkel O. M., Kissel T., Biomaterials, 2012, 33, 6551;
[66] Cao N., Cheng D., Zou S., Ai H., Gao J., Shuai X., Biomaterials, 2011, 32, 2222;
[67] Zhou Z., Shen Y., Tang J., Jin E., Ma X., Sun Q., Zhang B., Van Kirk E. A., Murdoch W. J., J. Mater. Chem., 2011, 21, 19114;
[68] Wang Q., Jiang H., Li Y., Chen W., Li H., Peng K., Zhang Z., Sun X., Biomaterials, 2017, 122, 10;
[69] Jin M., Jin G., Kang L., Chen L., Gao Z., Huang W., Int. J. Nanomedicine, 2018, 13, 2405;
[70] Abebe D. G., Kandil R., Kraus T., Elsayed M., Merkel O. M., Fujiwara T., Macromol. Biosci., 2015, 15, 698;
[71] Hoogenboom R., Thijs H. M., Jochems M. J., van Lankvelt B. M., Fijten M. W., Schubert U. S., Chem. Commun., 2008, 5758;
[72] Kataoka K., Park J., Macromolecules, 2007, 40, 3599;
[73] Lin P., Clash C., Pearce E. M., Kwei T. K., Aponte M. A., J. Polym. Sci. Pt. B:Polym. Phys., 1988, 26, 603;
[74] Mees M., Haladjova E., Momekova D., Momekov G., Shestakova P. S., Tsvetanov C. B., Hoogenboom R., Rangelov S., Biomacromolecules, 2016, 17, 3580;
[75] Kara A., Ozturk N., Esendagli G., Ozkose U. U., Gulyuz S., Yilmaz O., Telci D., Bozkir A., Vural I., Artif. Cell. Nanomed. Biotechnol., 2018, 46, S264;
[76] Du X. J., Wang Z. Y., Wang Y. C., Biomater. Sci., 2018, 6, 2122;
[77] Gaspar V. M., Baril P., Costa E. C., de Melo-Diogo D., Foucher F., Queiroz J. A., Sousa F., Pichon C., Correia I. J., J. Control. Release, 2015, 213, 175;
[78] Wu P., Yin S., Liu T., Ding D., Wang K., Sci. China Mater., 2020, 64, 241;
[79] Salazar M. D., Ratnam M., Cancer Metastasis Rev., 2007, 26, 141;
[80] Kim S. H., Mok H., Jeong J. H., Kim S. W., Park T. G., Bioconjugate Chem., 2005, 17, 241;
[81] Kim S. H., Jeong J. H., Cho K. C., Kim S. W., Park T. G., J. Control. Release, 2005, 104, 223;
[82] Liu L., Zheng M., Renette T., Kissel T., Bioconjugate Chem., 2012, 23, 1211;
[83] Liu L., Zheng M., Librizzi D., Renette T., Merkel O. M., Kissel T., Mol. Pharm., 2016, 13, 134;
[84] Jones S. K., Lizzio V., Merkel O. M., Biomacromolecules, 2016, 17, 76;
[85] Wu Y., Zhang Y., Zhang W., Sun C., Wu J., Tang J., Colloid Surf. B- Biointerfaces, 2016, 138, 60;
[86] Wang H., Feng, Y., Yang J., Guo J., Zhang W., J. Mater. Chem. B, 2015, 3, 3379;
[87] Liu C., Xie Y., Li X., Yao X., Wang X., Wang M., Li Z., Cao F., Mol. Biotechnol., 2021, 63, 63;
[88] Jiang B., Yang J., Rahoui N., Taloub N., Huang Y. D., Adv. Colloid Interface Sci., 2017, 250, 185;
[89] Stanley E. D., Mark H. G., Edward F. P., Trends Biochem. Sci., 1991, 16, 246;
[90] Hennink W. E., Cherng J., Wetering P., Talsma H., Crommelin D. J. A., Pharm. Res., 1996, 13, 1038;
[91] Long T. E., Layman J. M., Ramirez S. M., Green M. D., Biomacromolecules, 2009, 10, 1244;
[92] Agarwal S., Zhang Y., Maji S., Greiner A., Materials Today, 2012, 15, 388;
[93] van de Wetering P., Cherng J. Y., Talsma H., Hennink W. E., J. Control. Release, 1997, 49, 59;
[94] Rungsardthong U., Deshpande M., Bailey L., Vamvakaki M., Armes S. P., Garnett M. C., Stolnik S., J. Control. Release, 2001, 73, 359;
[95] Song M., Zeng L., Hong X., Meng Z., Yin J., Wang H., Liang Y., Jiang G., Environ. Sci. Technol., 2013, 47, 2886;
[96] Song Y., Zhang T., Song X., Zhang L., Zhang C., Xing J., Liang X. J., J. Mater. Chem. B, 2015, 3, 911;
[97] Chrysostomou V., Pispas S., J. Polym. Sci. Pol. Chem., 2018, 56, 598;
[98] Cordeiro R. A., Santo D., Farinha D., Serra A., Faneca H., Coelho J. F. J., Acta Biomater., 2017, 47, 113;
[99] Zhu C., Jung S., Luo S., Meng F., Zhu X., Park T. G., Zhong Z., Biomaterials, 2010, 31, 2408;
[100] Yue X., Qiao Y., Qiao N., Guo S., Xing J., Deng L., Xu J., Dong A., Biomacromolecules, 2010, 11, 2306;
[101] Diaz I. L., Sierra C. A., Jérôme V., Freitag R., Perez L. D., J. Polym. Sci., 2020, 58, 2168;
[102] Cheng Q., Du L., Meng L., Han S., Wei T., Wang X., Wu Y., Song X., Zhou J., Zheng S., Huang Y., Liang X. J., Cao H., Dong A., Liang Z., ACS Appl. Mater. Interfaces, 2016, 8, 4347;
[103] Li H., Miteva M., Kirkbride K. C., Cheng M. J., Nelson C. E., Simpson E. M., Gupta M. K., Duvall C. L., Giorgio T. D., Biomacromolecules, 2015, 16, 192;
[104] Cheng Y., Sellers D. L., Tan J. Y., Peeler D. J., Horner P. J., Pun S. H., Biomaterials, 2017, 127, 89;
[105] Tan Z., Jiang Y., Zhang W., Karls L., Lodge T. P., Reineke T. M., J. Am. Chem. Soc., 2019, 141, 15804;
[106] Tan Z., Jiang Y., Ganewatta M. S., Kumar R., Keith A., Twaroski K., Pengo T., Tolar J., Lodge T. P., Reineke T. M., Macromolecules, 2019, 52, 8197;
[107] Zhang Z., Shen W., Ling J., Yan Y., Hu J., Cheng Y., Nat. Commun., 2018, 9, 1377;
[108] Wang M., Cheng Y., Biomaterials, 2014, 35, 6603;
[109] Tan E., Lv J., Hu J., Shen W., Wang H., Cheng Y., J. Mater. Chem. B, 2018, 6, 7230;
[110] Alabi C. A., Love K. T., Sahay G., Yin H., Luly K. M., Langer R., Anderson D. G., Proc. Natl. Acad. Sci. USA, 2013, 110, 12881;
[111] Jayaraman M., Ansell S. M., Mui B. L., Tam Y. K., Chen J., Du X., Butler D., Eltepu L., Matsuda S., Narayanannair J. K., Rajeev K. G., Hafez I. M., Akinc A., Maier M. A., Tracy M. A., Cullis P. R., Madden T. D., Manoharan M., Hope M. J., Angew. Chem. Int. Ed., 2012, 51, 8529;
[112] Du L., Wang C., Meng L., Cheng Q., Zhou J., Wang X., Zhao D., Zhang J., Deng L., Liang Z., Dong A., Cao H., Biomaterials, 2018, 176, 84;
[113] Zhou J., Wu Y., Wang C., Cheng, Q., Han S., Wang X., Zhang J., Deng L., Zhao D., Du L., Cao H., Liang Z., Huang Y., Dong A., Nano Lett., 2016, 16, 6916;
[114] Wang C., Du L., Zhou J., Meng L., Cheng Q., Wang C., Wang X., Zhao D., Huang Y., Zheng S., Cao H., Zhang J., Deng L., Liang Z., Dong A., ACS Appl. Mater. Interfaces, 2017, 9, 32463;
[115] Li C., Zhou J., Wu, Y., Dong Y., Du L., Yang T., Wang Y., Guo S., Zhang M., Hussain A., Xiao H., Weng Y., Huang Y., Wang X., Liang Z., Cao H., Zhao Y., Liang X. J., Dong A., Huang Y., Nano Lett., 2021, 21, 3680;
[116] Zhu C., Zheng M., Meng F., Mickler F. M., Ruthardt N., Zhu X., Zhong Z., Biomacromolecules, 2012, 13, 769;
[117] Ritt N., Berger S., Wagner E., Zentel R., ACS Appl. Polym. Mater.,2020, 2, 5469;
[118] Liu J., Jiang Z., Zhou J., Zhang S., Saltzman W. M., J. Biomed. Mater. Res. A, 2011, 96, 456;
[119] Zhou J., Liu J., Cheng C. J., Patel T. R., Weller C. E., Piepmeier J. M., Jiang Z., Saltzman W. M., Nat. Mater., 2011, 11, 82;
[120] Voevodina, I., Scandola M., Zhang J., Jiang Z., RSC Adv., 2014, 4, 8953;
[121] Yang Z., Jiang Z., Cao Z., Zhang C., Gao D., Luo X., Zhang X., Luo H., Jiang Q., Liu J., Nanoscale, 2014, 6, 10193;
[122] Chen Y., Li Y., Gao J., Cao Z., Jiang Q., Liu J., Jiang Z., ACS Appl. Mater. Interfaces, 2016, 8, 490;
[123] Nazemi A., Boott C. E., Lunn D. J., Gwyther J., Hayward D. W., Richardson R. M., Winnik M. A., Manners I., J. Am. Chem. Soc., 2016, 138, 4484;
[124] Chen J., Jiang W., Han H., Yang J., Chen W., Wang Y., Tang J., Li Q., ACS Macro Lett., 2017, 6, 523;
[125] Shi C., Zhang Z., Shi J., Wang F., Luan Y., Int. J. Pharm., 2015, 495, 932;
[126] Fuentes I., Blanco-Fernandez B., Alvarado N., Leiva A., Radic D., Alvarez-Lorenzo C., Concheiro A., Langmuir, 2016, 32, 3331;
[127] Chiappetta D. A., Sosnik A., Eur. J. Pharm. Biopharm., 2007, 66, 303;
[128] Alvarez-Lorenzo C., Sosnik A., Concheiro A., Curr. Drug Targets, 2011, 12, 1112;
[129] Daima H. K., Shankar S., Anderson A., Periasamy S., Bhargava S., Bansal V., Environ. Chem. Lett., 2018, 16, 1457;
[130] Estabrook D. A., Ennis A. F., Day R. A., Sletten E. M., Chem. Sci., 2019, 10, 3994;
[131] Day R. A., Estabrook D. A., Wu C., Chapman J. O., Togle A. J., Sletten E. M., ACS Appl. Mater. Interfaces, 2020, 12, 38887;
[132] Estabrook D. A., Day R. A., Sletten E. M., Angew. Chem. Int. Ed., 2021, 60, 17362;
[133] Chen S., Qin J., Du J., Macromolecules, 2020, 53, 3978;
[134] Leonetti J. P., Degols G., Milhaud P., Gagnor C., Lemaitre M., Lebleu B., Nucleosides, Nucleotides and Nucleic Acids, 1989, 8, 825;
[135] Herrmann T. S. A., Acc. Chem. Res., 2012, 45, 1419;
[136] Zhang C., Hao L., Calabrese C. M., Zhou Y., Choi C. H., Xing H., Mirkin C. A., Small, 2015, 11, 5360;
[137] Wang D., Lin J., Jia F., Tan X., Wang Y., Sun X., Cao X., Che F., Lu H., Gao X., Shimkonis J. C., Nyoni Z., Lu X., Zhang K., Sci. Adv., 2019, 5, eaav9322;
[138] Naito M., Ishii T., Matsumoto A., Miyata K., Miyahara Y., Kataoka K., Angew. Chem. Int. Ed., 2012, 51, 10751;
[139] Zhou Q., Wang Y., Xiang J., Piao Y., Zhou Z., Tang J., Liu X., Shen Y., Biomater. Sci., 2018, 6, 3178;
[140] Jiang T., Qiao Y., Ruan W., Zhang D., Yang Q., Wang G., Chen Q., Zhu F., Yin J., Zou Y., Qian R., Zheng M., Shi B., Adv. Mater., 2021, 33, 2104779;
[141] Hinde E., Thammasiraphop K., Duong H. T., Yeow J., Karagoz B., Boyer C., Gooding J. J., Gaus K., Nat. Nanotechnol., 2017, 12, 81;
[142] Kretzmann J. A., Luther D. C., Evans C. W., Jeon T., Jerome W., Gopalakrishnan S., Lee Y. W., Norret M., Iyer K. S., Rotello V. M., J. Am. Chem. Soc., 2021, 143, 4758;
[143] Cheng D. B., Wang D., Gao Y. J., Wang L., Qiao Z. Y., Wang H., J. Am. Chem. Soc., 2019, 141, 4406;
[144] Kinnear C., Moore T. L., Rodriguez-Lorenzo L., Rothen-Rutishauser B., Petri-Fink A., Chem. Rev., 2017, 117, 11476;
[145] Anselmo A. C., Zhang M., Kumar S., Vogus D. R., Menegatti S., Helgeson M. E., Mitragotri S., ACS Nano, 2015, 9, 3169;
[146] Li X., Gao Y., Boott C. E., Winnik M. A., Manners I., Nat. Commun., 2015, 6, 8127;
[147] Li X., Gao Y., Boott C. E., Hayward D. W., Harniman R. L., Whittell G. R., Richardson R. M., Winnik M. A., Manners I., J. Am. Chem. Soc., 2016, 138, 4087;
[148] Li X., Gao Y., Harniman R., Winnik M. A., Manners I., J. Am. Chem. Soc., 2016, 138, 12902;
[149] Boott C. E., Gwyther J., Harniman R. L., Hayward D. W., Manners I., Nat. Chem., 2017, 9, 785;
[150] He X., Hsiao M-S., Boott C. E., Harniman R. L., Nazemi A., Li X., Winnik M. A., Manners I., Nat. Mater., 2017, 16, 481;
[151] Chen G., Zhang G., Jin B., Luo M., Luo Y., Aya S., Li X., J. Am. Chem. Soc., 2019, 141, 15498;
[152] Li X., Jin B., Gao Y., Hayward D. W., Winnik M. A., Luo Y., Manners I., Angew. Chem. Int. Ed., 2016, 55, 11392;
[153] Jin B., Sano K., Aya S., Ishida Y., Gianneschi N., Luo Y., Li X., Nat. Commun., 2019, 10, 2397;
[154] Jin B., Liu G., Li X., Chinese J. Chem., 2020, 38, 1709;
[155] Wang S., Jin B., Chen G., Luo Y., Li X., Polym. Chem., 2020, 11, 4706;
[156] Luo M., Jin B., Luo Y., Li X., Macromolecules, 2021, 54, 6845;
[157] Street S. T. G., He Y., Jin X. H., Hodgson L., Verkade P., Manners I., Chem. Sci., 2020, 11, 8394;
[158] Nowak M., Brown T. D., Graham A., Helgeson M. E., Mitragotri S., Bioeng. Transl. Med., 2020, 5, e10153;
[159] Yu Q., Roberts M. G., Houdaihed L., Liu Y., Ho K., Walker G., Allen C., Reilly R. M., Manners I., Winnik M. A., Nanoscale, 2021, 13, 280