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. 2021 Feb 8;15(2):2068–2098. doi: 10.1021/acsnano.0c09115

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© 2021 The Authors. Published by American Chemical Society

Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).

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Summary of the functional groups and linkers used in the development of pH-sensitive materials. (A) pH-responsive cationic polymers: (i) poly(2-dimethylaminoethyl methacrylate) (PDMAEMA), (ii) poly(2-diethylaminoethyl methacrylate) (PDEAEMA), (iii) poly(2-diisopropylaminoethyl methacrylate) (PDPAEMA), (iv) poly(4-vinylpyridine) (PVP), (v) poly(4-(1H-imidazol-1-yl)butyl methacrylate (PImBuMA), (vi) poly(lysine) (PLys), (vii) poly(histidine) (PHis), (viii) poly(ethylenimine) (PEI), (ix) chitosan, and (x) poly(β-amino ester) (PbAE). (B) pH-responsive anionic polymers: (i) poly(acrylic acid) (PAA), (ii) poly(2-carboxyethyl acrylate) (PCEA), (iii) poly(2-propylacrylic acid) (PPAA), (iv) poly(4-vinylbenzoic acid) (PVBA), (v) poly(aspartic acid) (PAsA), (vi) poly(glutamic acid) (PGA), (vii) poly(vinylsulfonic acid) (PVSA), (viii) poly(vinylphenylboronic acid) (PVPBA), and (ix) hyaluronic acid. (C) pH-cleavable linkers: (i) ortho-esters, (ii) ketals/acetals, (iii) hydrazones, (iv) imines, (v) maleic acid amide derivatives (including cis-aconityl shown), (vi) silyl ethers, and (vii) trityl derivatives.