Sulfonic esters of metal oxides and methods of their use

Patent metadata

Field	Value
Publication number	US-9636428-B2
Application number	US-201414492324-A
Country	US
Kind code	B2
Filing date	Sep 22, 2014
Priority date	Jan 17, 2014
Publication date	May 2, 2017
Grant date	May 2, 2017

Abstract

The present disclosure is directed to sulfonic esters of metal oxides including those of formulas I and II:

First claim

What is claimed:

1. A material according to formula I:

wherein A is a corrolyl or metallated corrolyl;
M is a surface comprising TiO 2 , BaTiO 3 , SnO 2 , Al 2 O 3 , Fe 2 O 3 , Fe 3 O 4 , ZrO 2 , CeO 2 , CdO, Cr 2 O 3 , CuO, MnO, Mn 2 O 3 , MnO 2 , NiO, SnO, SnO 2 , SiO 2 , or ZnO;
each R is independently C 1-6 alkyl;
L is a linker;
each R 1 is a non-antibody moiety or an antibody moiety, wherein the non-antibody moiety or the antibody moiety is optionally complexed to a target;
m is 1, 2, 3, or 4; and
n is 0 or 1.

2. The material according to claim 1 , wherein the surface is a nanoparticle surface.

3. The material according to claim 1 , wherein the corrolyl is:

wherein
Ar is phenyl or naphthyl, wherein the phenyl or naphthyl is optionally substituted with one or more substituents independently selected from the group consisting of halogen and —NR 3 R 4 , wherein R 3 and R 4 are each independently H, C 1-10 alkyl, C 1-10 alkenyl, or -alkaryl; or R 3 and R 4 , together with the nitrogen atom to which they are attached, form a heterocycloalkyl ring that is optionally substituted with C 1-6 alkyl; and
each R 2 is independently H, C 1-6 alkyl, halogen, or M-O—SO 2 —.

4. The material according to claim 1 , wherein the corrolyl is:

5. The material according to claim 4 , wherein each Ar is pentafluorophenyl.

6. The material according to claim 1 , wherein the metallated corrolyl is:

wherein
D is Al, Ga, Fe, Mn, Sb, Co, Cr, Rh, Ru, Ro, Ir, V, Re, Cu, Sn, Ge, Ti, or Mo, each of which is optionally coordinated to one or more ligands.

7. The material according to claim 6 , wherein D is Al or Ga.

8. The material according to claim 6 , wherein the metallated corrolyl is

9. The material according to claim 8 , wherein each Ar is pentafluorophenyl.

10. The material according to claim 9 wherein D is Al(ligand) 2 or Ga(ligand).

11. The material according to claim 10 , wherein the ligand is pyridine.

12. The material according to claim 1 , wherein n is 0.

13. The material according to claim 1 , wherein n is 1.

14. The material according to claim 1 , wherein m is 1.

15. The material according to claim 1 , wherein m is 2.

16. The material according to claim 1 , wherein m is 3.

17. The material according to claim 1 , wherein m is 4.

18. The material according to claim 1 , wherein each R is methyl.

19. The material according to claim 1 , wherein L is

20. The material according to claim 1 , wherein R 1 is a non-antibody moiety selected from the group consisting of a biotin moiety, an Arg-Gly-Asp moiety, an Asn-Gly-Arg moiety, a folate moiety, a transferrin moiety, a granulocyte-macrophage colony-stimulating gactor moiety, a galactosamine moiety, a hyaluronic acid moiety, a HERPBK10 moiety, and an F3 moiety.

21. The material according to claim 1 , wherein R 1 is an antibody moiety selected from the group consisting of an anti-VEGFR antibody, an anti-ERBB2 moiety, an anti-CD19 moiety, an anti-CD20 moiety, an anti-CD22 moiety, an anti-CD25 moiety, an anti-CD33 moiety, an anti-HLA-CD10b moiety, an anti-tenascin moiety, an anti-CEA moiety, an anti-MUC1 moiety, and an anti-TAG72 moiety.

22. The material according to claim 1 , wherein the non-antibody moiety or antibody moiety is complexed to a target.

23. The material according to claim 1 that is:

24. The material according to claim 23 , wherein each Ar is pentafluorophenyl.

25. The material according to claim 23 , wherein M is TiO 2 .

26. A material according to formula II

wherein A is a corrolyl or metallated corrolyl;
M is a surface comprising TiO 2 , BaTiO 3 , SnO 2 , Al 2 O 3 , Fe 2 O 3 , Fe 3 O 4 , ZrO 2 , CeO 2 , CdO, Cr 2 O 3 , CuO, MnO, Mn 2 O 3 , MnO 2 , NiO, SnO, SnO 2 , SiO 2 , or ZnO;
L is a linker;
R 1 is a non-antibody moiety or an antibody moiety, wherein the non-antibody moiety or the antibody moiety is optionally complexed to a target;
y is 1, 2, or 3; and
x is 0 or 1.

27. The material according to claim 26 , wherein the surface is a nanoparticle surface.

28. The material according to claim 26 , wherein the corrolyl is:

wherein
Ar is phenyl or naphthyl, wherein the phenyl or naphthyl is optionally substituted with one or more substituents independently selected from the group consisting of halogen and —NR 3 R 4 , wherein R 3 and R 4 are each independently H, C 1-10 alkyl, C 1-10 alkenyl, or -alkaryl; or R 3 and R 4 , together with the nitrogen atom to which they are attached, form a heterocycloalkyl ring that is optionally substituted with C 1-6 alkyl; and
each R 2 is independently H, C 1-6 alkyl, halogen, or M-O—SO 2 —.

29. The material according to claim 26 , wherein the corrolyl is:

30. The material according to claim 26 , wherein the metallated corrolyl is:

wherein
D is Al, Ga, Fe, Mn, Sb, Co, Cr, Rh, Ru, Ro, Ir, V, Re, Cu, Sn, Ge, Ti, or Mo, each of which is optionally coordinated to one or more ligands.

31. The material according to claim 30 , wherein D is Al or Ga.

32. The material according to claim 31 wherein D is Al(ligand) 2 or Ga(ligand).

33. The material according to claim 32 , wherein the ligand is pyridine.

34. The material according to claim 26 , wherein x is 0.

35. The material according to claim 26 , wherein x is 1.

36. The material according to claim 26 , wherein y is 1.

37. The material according to claim 26 , wherein y is 2.

38. The material according to claim 26 , wherein y is 3.

39. The material according to claim 26 , wherein L is

40. The material according to claim 26 , wherein R 1 is a non-antibody moiety selected from the group consisting of a biotin moiety, an Arg-Gly-Asp moiety, an Asn-Gly-Arg moiety, a folate mo

Assignees

• California Inst Of Techn
• Children'S Hospital Los Angeles
• Children'S Hospital Of Los Angeles

Inventors

• Blumenfeld Carl M
• Sorasaenee Karn
• Gray Harry B
• Grubbs Robert H

Classifications

• A61K49/0058

  Antibodies · CPC title

• A61K49/0052 Primary

  Small organic molecules (oligomers, polymers, dendrimers A61K49/0054) · CPC title

• A61P35/00

  Antineoplastic agents · CPC title

• A61K49/00

  Preparations for testing in vivo · CPC title

• A61K49/16 Primary

  Antibodies; Immunoglobulins; Fragments thereof · CPC title