Cationic polymer and use for biomolecule delivery

A polymer comprising a structure of Formula 4:

• wherein,
• each of m1 and n1 is an integer from 0 to 1000;
• provided that the sum of m1+n1 is greater than 2;
• the symbol “/” indicates that the units separated thereby are linked randomly or in any order;
• A1 and A2 are each independently a group of formula
• wherein p1 to p4, q1 to q6, and r1 and r2 are each independently an integer of 1 to 5;
• each instance of R2 is independently hydrogen or a C1-C12 alkyl group, alkenyl group, cycloalkyl group, or cycloalkenyl group, provided that A1 and A2 each comprise at least one tertiary amine;
• R3a and R3b are each independently a methylene or ethylene group;
• and
• each instance of R13 is independently hydrogen or a C1-C12 alkyl group, alkenyl group, cycloalkyl group, or cycloalkenyl group.

A method of preparing a polymer, the method comprising modifying at least a portion of groups A1 and/or A2 of a polymer comprising a structure of Formula 3:

• wherein:
• each of m1 and n1 is an integer from 0 to 1000, provided that m1+n1 is greater than 5;
• the symbol “/” indicates that the units separated thereby are linked randomly or in any order;
• R3a and R3b are each independently a methylene or ethylene group;
• each instance of R13 is independently hydrogen or a C1-C12 alkyl group, alkenyl group, cycloalkyl group, or cycloalkenyl group;
• A1 and A2 are each independently a group of formula
• wherein p1 to p4, q1 to q6, and r1 and r2 are each independently an integer of 1 to 5;
• and each instance of R2 is independently hydrogen or a C1-C12 alkyl group, alkenyl group, cycloalkyl group, or cycloalkenyl group,
• to produce a polymer comprising a structure of Formula 1:
• wherein:
• each of m1 and n1 is an integer from 0 to 1000;
• each of m2 and n2 is an integer from 0 to 1000, provided that the sum of m2+n2 is greater than 5;
• the symbol “/” indicates that the units separated thereby are linked randomly or in any order;
• R3a and R3b are each independently a methylene or ethylene group;
• each instance of R13 is independently hydrogen or a C1-C12 alkyl group, alkenyl group, cycloalkyl group, or cycloalkenyl group;
• A1 and A2 are each independently a group of formula
• B1 and B2 are each independently
• wherein p1 to p4, q1 to q6, r1 and r2, and s1 to s4 are each independently an integer of 1 to 5;
• each instance of R2 is independently hydrogen or a C1-C12 alkyl group, alkenyl group, cycloalkyl group, or cycloalkenyl group;
• each instance of R4 is independently —C(O)O—, —C(O)NH—, or —S(O)(O)—;
• and each instance of R5 is independently an alkyl group, cycloalkyl group, alkenyl group, cycloalkenyl group, aryl group, heteroalkyl group, heterocyclic group, or combination thereof optionally comprising from 1 to 8 secondary or tertiary amines or a substituent comprising a tissue-specific or cell-specific targeting moiety;
• or
• the method comprising a ring-opening polymerization of a compound Formula A by contacting an amine containing compound with a compound of Formula A, wherein the compound of Formula 5 has the structure:
• wherein,
• m1 is an integer from 1 to 2000;
• R3b is a methylene or ethylene group;
• R17 is hydrogen or a C1-C12 alkyl group, alkenyl group, cycloalkyl group, or cycloalkenyl group;
• A1 is a group of formula
• wherein p1 to p4, q1 to q6, and r1 and r2 are each independently an integer of 1 to 5;
• and each instance of R2 is independently hydrogen or a C1-C12 alkyl group, alkenyl group, cycloalkyl group, or cycloalkenyl group,
• and the compound of Formula A has the structure:
• wherein,
• R3b is a methylene or ethylene group;
• W is —NR14— or —O—, wherein R14 is hydrogen or a C1-C12 alkyl group, alkenyl group, cycloalkyl group, or cycloalkenyl group;
• Z is A1, or an alkyl group, cycloalkyl group, alkenyl group, cycloalkenyl group, aryl group, arylalkyl group, heteroalkyl group, heterocyclic group, or combination thereof optionally comprising from 1 to 8 secondary or tertiary amines or a substituent comprising a tissue-specific or cell-specific targeting moiety;
• A1 is a group of formula
• wherein p1 to p4, q1 to q6, and r1 and r2 are each independently an integer of 1 to 5;
• and
• each instance of R2 is independently hydrogen or a C1-C12 alkyl group, alkenyl group, cycloalkyl group, or cycloalkenyl group.