Antimicrobial polymers
The invention generally relates to novel polymers (SMAMPs) and their syntheses and use. The polymers exhibit promising properties of AMPs. In particularly, for example, a ring-opening metathesis polymerization (ROMP) platform was developed that allows syntheses of SMAMPs that employ a minimum number of norbornene-based building blocks and/or enable easy and independent variation of hydrophobic and hydrophilic groups in the monomer units and/or along the polymeric backbone to finetune and select desirable properties of the polymers.
1. A monomer unit having the structure of:
wherein one of R 1 and R 2 comprises a hydrophobic group and the other one of R 1 and R 2 comprises a hydrophilic group; and X is C═R 3 , O or S, wherein R 3 is a C 1 -C 12 alkyl or alkoxy group.
2. The monomer of claim 1 , wherein the hydrophobic group comprises a substituted or unsubstituted alkyl group.
3. The monomer of claim 1 , wherein the hydrophilic group comprises a group selected from ammonium ions, sulfonium ions, guanidinium ions, phosphonium ions, and mono- and di-alkyl substituted amino groups.
4. The monomer of claim 1 , wherein X is O; R 1 is a linear or branched C 1 -C 12 alkyl group; and R 2 is
or a guanidinium ion wherein p is an integer from 1-10.
5. The monomer of claim 1 , wherein both —C(═O)O— groups in (I) occupy the exo-stereo position.
6. The monomer of claim 4 , wherein R 1 is a linear or branched C 1 -C 6 alkyl group; and
p is an integer from 1-5.
7. The monomer of claim 1 , wherein X is C═R 3 ; R 1 is a linear or branched C 1 -C 12 alkyl group; and R 2 is
or a guanidinium ion, wherein p is an integer from 1-10.
8. The monomer of claim 7 , wherein R 3 is a C 1 -C 12 alkyl.
9. A polymer comprising a monomer unit having the structure of:
wherein one of R 1 and R 2 comprises a hydrophobic group and the other one of R 1 and R 2 comprises a hydrophilic group; and X is C═R 3 , O or S, wherein R 3 is a C 1 -C 12 alkyl or alkoxy group.
10. The polymer of claim 9 , wherein the hydrophobic group comprises a substituted or unsubstituted alkyl group.
11. The polymer of claim 9 , wherein the hydrophilic group comprises a group selected from ammonium ions, sulfonium ions, guanidinium ions, phosphonium ions, and mono- and di-alkyl substituted amino groups.
12. The polymer of claim 9 , wherein X is O; R 1 is a linear or branched C 1 -C 12 alkyl group; and R 2 is
or a guanidinium ion, wherein p is an integer from 1-10.
13. The polymer of claim 9 , wherein both —C(═O)O— groups in (II) occupy the exo-stereo position.
14. The polymer of claim 12 , wherein R 1 is a linear or branched C 1 -C 6 alkyl group; and
p is an integer from 1-5.
15. The polymer of claim 9 , wherein X is C═R 3 ; R 1 is a linear or branched C 1 -C 12 alkyl group; R 2 is
or a guanidinium ion, wherein p is an integer from 1-10.
16. The polymer of claim 15 , wherein R 3 is a C 1 -C 12 alkyl.
17. The polymer of claim 9 , wherein n is an integer from about 1 to about 1,000.
18. The polymer of claim 9 , wherein the polymer is a co-polymer.
19. The co-polymer of claim 18 , wherein the co-polymer comprises the structural monomer units of:
wherein
each of X′ and X″ is C═R 3 , O or S, wherein R 3 is a C 1 -C 12 alkyl or alkoxy group;
each of R 1 ′ and R 1 ″ is a hydrophobic group and each of R 2 ′ and R 2 ″ is a hydrophilic group, provided that R 1 ′ and R 1 ″ are not the same, R 2 ′ and R 2 ″ are the same, or X′ and X″ are not the same; and
each of m and n is an integer from about 1 to about 1,000.
20. The polymer of claim 19 , wherein the hydrophilic group comprises a group selected from ammonium ions, sulfonium ions, guanidinium ions, phosphonium ions, and mono- and di-alkyl substituted amino groups.
21. The polymer of claim 19 , wherein all —C(═O)O— groups in (III) and (IV) occupy the exo-stereo position.
22. The co-polymer of claim 19 , wherein
each of R 1 ′ and R 1 ″ is independently a linear or branched C 1 -C 12 alkyl group; and
each of R 2 ′ and R 2 ″ is independently
or a guanidinium ion, wherein p is an integer from 1-10.
23. A polymer prepared by ring-opening metathesis polymerization, the polymer comprising hydrophobic and hydrophilic groups attached to the polymeric backbone such that, within a monomeric structural unit, the hydrophobic and hydrophilic groups are attached to the polymeric backbond at adjacent atoms.
24. The polymer of claim 23 , wherein the hydrophobic and hydrophilic groups are attached to the polymeric backbond via ester linkages.
25. The polymer of claim 23 , wherein the
hydrophobic group comprises a linear or branched C 1 -C 12 alkyl group; and
the hydrophilic group comprises a —NH 3 + group.
26. The polymer of claim 25 , wherein the hydrophilic group comprises
or a guanidinium ion, wherein p is an integer from 1-10.
27. The polymer of claim 23 , wherein the polymer is a co-polymer.