Biofouling resistant coatings and methods of making and using the same

1. A compound that has the structure of formula (II):

wherein

each R 1a and R 1b is independently selected from hydrogen and halogen;

each R 2a and R 2b is independently selected from halogen, —CN, and optionally substituted C 1 -C 6 fluoroalkyl;

A 1 is —S(═O) 2 —; A 2 is —C(═O)—; and A 3 is —C(═O)—;

each B 1 , B 2 , and B 3 is independently selected from —O— and —NR 3c —;

D is —S(═O) 2 O − , —S(═O) 2 OR 9a , —C(═O)O − , or —C(═O)OR 9a ;

Z 1 is —(CR 6c R 6d ) s —;

Z 2 is —(CR 6c R 6d ) t —;

Z 3 is —(CR 6c R 6d ) p —;

each R 3a and R 3b is independently selected from hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted benzyl;

each R 3c and R 3d is independently selected from hydrogen, optionally substituted C 1 -C 4 alkyl, —X— optionally substituted C 1 -C 4 alkyl, optionally substituted C 2 -C 6 alkenyl, and optionally substituted aryl;

X is —C(═O)—, —S(═O)—, or —S(═O) 2 —;

each R 4c , R 4d , R 5d , R 5e , R 6c , and R 6d is independently selected from hydrogen, halogen, —CN, —OH, optionally substituted C 1 -C 4 alkyl, optionally substituted C 1 -C 4 fluoroalkyl, optionally substituted C 2 -C 6 alkenyl, —NR 3c R 3d , —S(═O) 2 O − , —S(═O) 2 OR 9a , —C(═O)O − , and —C(═O)OR 9a ;

each R 9a , R 11a , R 11b , R 11c , R 12a , R 12b , and R 12c is independently selected from hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted aryl;

n is an integer selected from 0, 1, 2, 3, 4, 5, and 6;

s is an integer selected from 1, 2, 3, 4, or 5;

t is an integer selected from 1, 2, 3, 4, or 5;

p is an integer selected from 1, 2, 3, 4, or 5;

q is an integer greater than or equal to 3 and less than or equal to 60;

r is an integer greater than or equal to 1 and less than or equal to 50; and

wherein the compound of formula (II) is charged or zwitterionic.

2. The compound of claim 1 , wherein each R 1a and R 1b is independently halogen.

3. The compound of claim 1 , wherein each R 2a and R 2b is independently selected from halogen, —CN, and —CF 3 .

4. The compound of claim 1 , wherein B 1 and B 2 are each —NR 3c — and wherein B 3 is —O—.

5. The compound of claim 4 , wherein each R 3c is hydrogen or —CH 3 .

6. The compound of claim 1 , wherein D is —S(═O) 2 O − .

7. The compound of claim 1 , wherein each R 6c and R 6d is hydrogen and wherein each R 3a and R 3b is —CH 3 .

8. The compound of claim 1 , wherein each R 1a , R 1b , R 2a , and R 2b is F.

9. The compound of claim 1 , wherein R 11a is hydrogen or —CH 3 .

10. The compound of claim 1 , wherein q is an integer greater than or equal to 3 and less than 40.

11. The compound of claim 1 , wherein q is an integer greater than or equal to 3 and less than or equal to 50.

12. The compound of claim 1 , wherein r is an integer more than 10 and less than or equal to 50.

13. A medical device coated with a compound that has the structure of formula (II):

wherein

each R 1a and R 1b is independently selected from hydrogen and halogen;

each R 2a and R 2b is independently selected from halogen, —CN, and optionally substituted C 1 -C 6 fluoroalkyl;

each A 1 , A 2 , and A 3 is independently selected from —C(═O)—, —S(═O)—, —S(═O) 2 —, and —S(═O)(═NR 3c )—;

each B 1 , B 2 , and B 3 is independently selected from —O— and —NR 3c —;

D is —S(═O) 2 O − , —S(═O) 2 OR 9a , —C(═O)O − , or —C(═O)OR 9a ;

Z 1 is —(CR 6c R 6d ) s —;

Z 2 is —(CR 6c R 6d ) t —;

Z 3 is —(CR 6c R 6d ) p —;

each R 3a and R 3b is independently selected from hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted benzyl;

each R 3c and R 3d is independently selected from hydrogen, optionally substituted C 1 -C 4 alkyl, —X— optionally substituted C 1 -C 4 alkyl, optionally substituted C 2 -C 6 alkenyl, and optionally substituted aryl;

X is —C(═O)—, —S(═O)—, or —S(═O) 2 —;

each R 4c , R 4d , R 5d , R 5e , R 6c , and R 6d is independently selected from hydrogen, halogen, —CN, —OH, optionally substituted C 1 -C 4 alkyl, optionally substituted C 1 -C 4 fluoroalkyl, optionally substituted C 2 -C 6 alkenyl, —NR 3c R 3d , —S(═O) 2 O − , —S(═O) 2 OR 9a , —C(═O)O − , and —C(═O)OR 9a ;

each R 9a , R 11a , R 11b , R 11c , R 12a , R 12b , and R 12c is independently selected from hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted aryl;

n is an integer selected from 0, 1, 2, 3, 4, 5, and 6;

s is an integer selected from 1, 2, 3, 4, or 5;

t is an integer selected from 1, 2, 3, 4, or 5;

p is an integer selected from 1, 2, 3, 4, or 5;

q is an integer greater than or equal to 3 and less than or equal to 60;

r is an integer greater than or equal to 1 and less than or equal to 50; and

wherein the compound of formula (II) is charged or zwitterionic; and

wherein the medical device is an implantable medical device.

14. The medical device of claim 13 , wherein each R 1a and R 1b is independently halogen.

15. The medical device of claim 13 , wherein each R 2a and R 2b is independently selected from halogen, —CN, and —CF 3 .

16. The medical device of claim 13 , wherein A 1 is —S(═O) 2 —; A 2 is —C(═O)—; and A 3 is —C(═O)—.

17. The medical device of claim 13 , wherein B 1 and B 2 are each —NR 3c — and wherein B 3 is —O—.

18. The medical device of claim 17 , wherein each R 3c is hydrogen or —CH 3 .

19. The medical device of claim 13 , wherein D is —S(═O) 2 O − .

20. The medical device of claim 13 , wherein each R 6c and R 6d is hydrogen and wherein each R 3a and R 3b is —CH 3 .

21. The medical device of claim 13 , wherein each R 1a , R 1b , R 2a , and R 2b is F.

22. The medical device of claim 13 , wherein R 11a is hydrogen or —CH 3 .

23. The medical device of claim 13 , wherein q is an integer greater than or equal to 3 and less than 40.

24. The medical device of claim 13 , wherein q is an integer greater than or equal to 3 and less than or equal to 50.

25. The medical device of claim 13 , wherein r is an integer more than 10 and less than or equal to 50.

26. The medical device of claim 13 , wherein the medical device comprises a tubing.

27. A medical device coated with a compound that has the structure of formula (II):

wherein

each R 1a and R 1b is independently selected from hydrogen and halogen;

each R 2a and R 2b is independently selected from halogen, —CN, and optionally substituted C 1 -C 6 fluoroalkyl;

A 1 is —S(═O) 2 —; A 2 is —C(═O)—; and A 3 is —C(═O)—;

each B 1 , B 2 , and B 3 is independently selected from —O— and —NR 3c —;

D is —S(═O) 2 O − , —S(═O) 2 OR 9a , —C(═O)O − , or —C(═O)OR 9a ;

Z 1 is —(CR 6c R 6d ) s —;

Z 2 is —(CR 6c R 6d ) t —;

Z 3 is —(CR 6c R 6d ) p —;

each R 3a and R 3b is independently selected from hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted benzyl;

each R 3c and R 3d is independently selected from hydrogen, optionally substituted C 1 -C 4 alkyl, —X— optionally substituted C 1 -C 4 alkyl, optionally substituted C 2 -C 6 alkenyl, and optionally substituted aryl;

X is —C(═O)—, —S(═O)—, or —S(═O) 2 —;

each R 4c , R 4d , R 5d , R 5e , R 6c , and R 6d is independently selected from hydrogen, halogen, —CN, —OH, optionally substituted C 1 -C 4 alkyl, optionally substituted C 1 -C 4 fluoroalkyl, optionally substituted C 2 -C 6 alkenyl, —NR 3c R 3d , —S(═O) 2 O − , —S(═O) 2 OR 9a , —C(═O)O − , and —C(═O)OR 9a ;

each R 9a , R 11a , R 11b , R 11c , R 12a , R 12b , and R 12c is independently selected from hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted aryl;

n is an integer selected from 0, 1, 2, 3, 4, 5, and 6;

s is an integer selected from 1, 2, 3, 4, or 5;

t is an integer selected from 1, 2, 3, 4, or 5;

p is an integer selected from 1, 2, 3, 4, or 5;

q is an integer greater than or equal to 3 and less than or equal to 60;

r is an integer greater than or equal to 1 and less than or equal to 50; and

wherein the compound of formula (II) is charged or zwitterionic; and

wherein the medical device comprises an implant, an IV, a prosthesis, a suturing material, a valve, a stent, a catheter, a rod, a shunt, a scope, a contact lens, a tubing, a wiring, an electrode, a clip, a fastener, a syringe, a container, a bandage, a patch, or a combination thereof.

28. The medical device of claim 27 , wherein each R 1a , R 1b , R 2a , and R 2b is F.