DEGRADABLE POLYCATIONS DERIVED FROM AMINO ACID VINYL ESTERS

摘要

Described herein are the synthesis and polymerization of a series of N-Boc-protected amino acid vinyl ester (BAAVE) monomers. Homopolymers and heteropolymers containing the monomers are described, particularly heteropolymers with vinyl ester monomers such as vinyl acetate. Deprotection can be used to produce hydrophilic and hydrophobic polymers that are particular useful in biological applications such as cellular delivery of biological materials.

主权项

1. A polymer consisting of units of the formulaand salts thereof, wherein
n is an integer greater than one, R is H, a substituted or unsubstituted C1-C18 alkyl, a substituted or unsubstituted C2-C18 alkenyl, a substituted or unsubstituted C2-C18 alkynyl, a substituted or unsubstituted C3-C18 cycloalkyl, a substituted or unsubstituted C1-C18 haloalkyl, a substituted or unsubstituted C2-C18 heterocycloalkyl, a substituted or unsubstituted C6-C18 aryl, a substituted or unsubstituted C7-C18 arylalkylene, or a substituted or unsubstituted C3-C18 heteroaryl, R′ is H, a substituted or unsubstituted C1-C18 alkyl, a substituted or unsubstituted C2-C18 alkenyl, a substituted or unsubstituted C2-C18 alkynyl, a substituted or unsubstituted C3-C18 cycloalkyl, a substituted or unsubstituted C1-C18 haloalkyl, a substituted or unsubstituted C2-C18 heterocycloalkyl, a substituted or unsubstituted C6-C18 aryl, a substituted or unsubstituted C7-C18 arylalkylene, or a substituted or unsubstituted C3-C18 heteroaryl, wherein substituted for R′ includes replacement of one or more hydrogen atoms of a group with a substituent selected from a C1 to C6 alkyl group, a C1 to C6 hydroxyalkyl group, a C2 to C6 alkenyl group, a C2 to C30 alkynyl group, a C6 to C30 aryl group, a C1 to C6 heteroalkyl group, a C3 to C30 cycloalkyl group, a C3 to C15 cycloalkenyl group, a C6 to C30 cycloalkynyl group, a C2 to C30 heterocycloalkyl group, halogen (Br, F or Cl,), a haloalkyl group, an alkoxy group, a nitro group (—NO2), a cyano group (—CN), an amino group (—NR′2 wherein each R′ is independently a hydrogen or a C1 to C6 alkyl group, a C2 to C6 alkynyl group, or a C6 to C30 aryl group), a carbamyl group, an ester group (—C(═O)OR″ wherein R″ is a C1 to C6 alkyl group or a C6 to C10 aryl group), or a carboxyl group (—C(═O)OH), and G is a group of the formulawherein
one of *′ and *″ indicates a point of attachment to G and the other indicates a point of attachment to N, and *′″ indicates a point of attachment to R, z is 0, 1, or 2, and Rw, Rx and Ry are each independently H, a substituted or unsubstituted C1-C18 alkyl, a substituted or unsubstituted C2-C18 alkenyl, a substituted or unsubstituted C2-C18 alkynyl, a substituted or unsubstituted C3 to C18 cycloalkyl, a substituted or unsubstituted C1-C18 haloalkyl, a substituted or unsubstituted C2-C18 heterocycloalkyl, a substituted or unsubstituted C6 to C18 aryl, a substituted or unsubstituted C7 to C18 arylalkylene, or a substituted or unsubstituted C4-C18 heteroaryl, or any two of R, R′, Rw, Rx, and Ry together form a substituted or unsubstituted C5-C18 cycloalkyl, substituted or unsubstituted C2-C18 heterocycloalkyl, or substituted or unsubstituted C2-C18 heteroaryl group, each having 5 to 8 ring members.