Nanoparticles stabilized with nitrophenylboronic acid compositions

1. A polymer conjugate comprising a polymer containing a polyol and a polymer containing a nitrophenylboronic acid,

wherein the polymer containing a nitrophenylboronic acid is conjugated to the polymer containing a polyol with a reversible borate ester linkage, and

wherein the polymer containing the polyol is derived from the coupling of a compound of Formula A with a compound of Formula B;

wherein

the compound of Formula A is:

in which

the spacer is independently selected from any organic group;

the amino acid is selected from any organic group bearing a free amine and a free carboxylic acid group;

n is 1-20; and

Z 1 is independently selected from —NH 2 , —OH, —SH, and —COOH; and

the compound of Formula B is:

in which

q is a number from 1 to 20;

p is a number from 20 to 200; and

L is a leaving group.

2. The polymer conjugate of claim 1 , wherein the compound of Formula A is:

wherein n is a number from 1 to 20.

3. The polymer conjugate of claim 1 , wherein compound of Formula B is:

4. The polymer conjugate of claim 3 , wherein the polymer containing the polyol comprises units of the formula:

5. The polymer conjugate of claim 3 , wherein n is 1 and q is 1.

6. The polymer conjugate of claim 1 , wherein compound of Formula B is:

7. The polymer conjugate of claim 6 , wherein the polymer containing the polyol comprises units of the formula:

8. The polymer conjugate of claim 7 , wherein n is 1 and p is 1.

9. The polymer conjugate of claim 1 , wherein the polymer containing a nitrophenylboronic acid comprises at least one terminal nitrophenylboronic acid group and has the general formula:

wherein

R 3 and R 4 are independently (CH 2 CH 2 O) t , where t is from 2 to 2000;

X 1 is —NH—C(═O)—, —S—S—, —C(═O)—NH—, —O—C(═O)— or —C(═O)—O—;

Y 1 is a nitrophenyl group; r=1; a=0; and b=1; and

wherein Functional group 1 and Functional group 2 independently comprise a —B(OH) 2 , —OCH 3 , —COOH, —NH 2 , or —OH group.

10. The polymer conjugate of claim 2 , wherein the polymer containing a nitrophenylboronic acid comprises at least one terminal nitrophenylboronic acid group and has the general formula:

wherein

R 3 and R 4 are independently (CH 2 CH 2 O) t , where t is from 2 to 2000;

X 1 is —NH—C(═O)—, —S—S—, —C(═O)—NH—, —O—C(═O)— or —C(═O)—O—;

Y 1 is a nitrophenyl group;

r=1; a=0; and b=1; and

wherein Functional group 1 and Functional group 2 independently comprise a —B(OH) 2 , —OCH 3 , —COOH, —NH 2 , or —OH group.

11. The polymer conjugate of claim 9 , wherein Functional group 2 comprises a —B(OH) 2 , —OCH 3 , —OH, or —COOH group.

12. The polymer conjugate of claim 9 , wherein the polymer containing a nitrophenylboronic acid is:

wherein t is a number from 200 to 300.

13. The polymer conjugate of claim 10 , wherein the polymer containing a nitrophenylboronic acid is:

wherein t is a number from 2 to 2000.

14. The polymer conjugate of claim 9 , in which the polymer conjugate is in the form of a nanoparticle.

15. The polymer conjugate of claim 10 , in which the polymer conjugate is in the form of a nanoparticle.

16. The nanoparticle of claim 14 , further comprising a therapeutic agent.

17. The nanoparticle of claim 15 , further comprising a therapeutic agent.

18. The nanoparticle of claim 14 , further comprising a small molecule chemotherapeutic agent or a polynucleotide.

19. The nanoparticle of claim 17 , wherein the polynucleotide is interfering RNA.

20. The nanoparticle of claim 17 , wherein the small molecule chemotherapeutic is camptothecin, an epothilone, a taxane or a combination thereof.

21. The nanoparticle of claim 14 , wherein the nitrophenylboronic acid that is coupled to the polymer containing a polyol with a reversible covalent linkage is further conjugated to any of 5, 4, 3, 2, or 1 targeting ligands.

22. The nanoparticle of claim 15 , wherein the nitrophenylboronic acid that is coupled to the polymer containing a polyol with a reversible covalent linkage is further conjugated to any of 5, 4, 3, 2, or 1 targeting ligands, each targeting ligand being conjugated to the terminal portion of the polymer containing a nitrophenylboronic acid.

23. The nanoparticle of claim 14 , where the nanoparticle is further conjugated to only a single targeting ligand.

24. The nanoparticle of claim 15 , wherein the nanoparticle is further conjugated to only a single targeting ligand.

25. The nanoparticle of claim 21 , wherein at least one of the targeting ligand is a protein, an aptamer, a small molecule, an antibody, or an antibody fragment.

26. A method to deliver a therapeutic agent to a target, the method comprising contacting the target with the nanoparticle of claim 16 .

27. The method of claim 26 , wherein the target is a cancer cell within the body of a mammal.

28. A population of nanoparticles of claim 14 dispersed in an aqueous medium.

29. A population of nanoparticles of claim 15 dispersed in an aqueous medium.

30. A population of nanoparticles of claim 16 dispersed in an aqueous medium.

31. A population of nanoparticles of claim 17 dispersed in an aqueous medium.

32. A population of nanoparticles of claim 21 dispersed in an aqueous medium.

33. A population of nanoparticles of claim 22 dispersed in an aqueous medium.

34. A population of nanoparticles of claim 23 dispersed in an aqueous medium.

35. A population of nanoparticles of claim 24 dispersed in an aqueous medium.