IP Library Granted Patent US 9,593,052
Granted Patent B2
US 9,593,052 · App. 14/958,185 · Granted Mar 14, 2017

Arsenic complexes for potential diagnostic applications

Inventors: Silvia S. Jurisson (Columbia, MO); Cathy S. Cutler (Columbia, MO); Donald E. Wycoff (Columbia, MO); Anthony J. DeGraffenreid (Columbia, MO)
Assignee: The Curators of the University of Missouri
C07B59/004C07F9/743C07F9/74
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Quick Facts
Patent No.
US 9,593,052
App. No.
14/958,185
Granted
Mar 14, 2017
Kind
B2
Abstract

The present invention provides radioactive arsenic complexes useful in diagnostic and therapeutic applications and methods for forming those arsenic complexes.

Claims (22)

1. A method of producing radiolabeled phenylarsonic acid, the method comprising:

(a) contacting a radiolabeled no-carrier added arsenic acid with a monothiol to form a first solution; and

(b) contacting the first solution with a copper-based catalyst and a phenyldiazonium salt to give a second solution comprising the radiolabeled phenylarsonic acid.

2. The method of claim 1 , wherein the radiolabeled no-carrier added arsenic acid is chosen from H 3 AsO 4 or AsO 4 3− .

3. The method of claim 1 , wherein the arsenic is 77 As or 72 As.

4. The method of claim 1 , wherein the monothiol is ammonium thioglycolate.

5. The method of claim 1 , wherein the mole:mole ratio of the no-carrier added arsenic acid to monothiol ranges from about 1:10 5 to about 1:10 7 .

6. The method of claim 1 , wherein the first solution is heated to about 50° C. to about 70° C.

7. The method of claim 1 , wherein step (a) is allowed to proceed for a period of time ranging from about 30 minutes to about 1 hour.

8. The method of claim 1 , wherein the phenyldiazonium salt is tetrafluoroborate salt.

9. The method of claim 1 , wherein the phenyldiazonium salt is ethoxybenzendiazonium salt.

10. The method of claim 1 , wherein the mole:mole ratio of the reaction intermediate from step (a) to phenyldiazonium salt ranges from about 1:10 7 to about 1:10 10 .

11. The method of claim 1 , wherein the copper-based catalyst is copper(0) nanoparticles.

12. The method of claim 1 , wherein the copper-based catalyst is copper(0) nanoparticles; and the mole to mole ratio of the reaction intermediate from step (a) to copper(0) nanoparticles ranges from about 1:10 5 to about 1:10 6 .

13. The method of claim 1 , wherein step (b) is conducted at about 20° C. to about 30° C.

14. The method of claim 1 , wherein step (b) is allowed to proceed for a period of time ranging from about 30 minutes to about 1 hour.

15. The method of claim 1 , wherein the radiolabeled phenylarsonic acid is further reacted with a monothiol and a monothiol or dithiol.

16. The method of claim 15 , wherein the monothiol is ammonium thioglycolate.

17. The method of claim 15 , wherein the mole:mole ratio of the radiolabeled phenylarsonic acid to the monothiol ranges from about 1:10 5 to about 1:10 7 .

18. The method of claim 15 , wherein the dithiol is ethane-1,2-dithiol.

19. The method of claim 15 , wherein the mole:mole ratio of the radiolabeled phenylarsonic acid to the dithiol ranges from about 1:10 6 to about 1:10 8 .

20. The method of claim 1 , wherein the radiolabeled phenylarsonic acid is 2-(4-(methoxymethyl)phenyl)-1,3,2-dithiarsolane.

Assignments (2)
CONFIRMATORY LICENSE Recorded Apr 6, 2018
From: UNIVERSITY OF MISSOURI-COLUMBIA
To: UNITED STATES DEPARTMENT OF ENERGY
Reel/Frame 045545/0145 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 4, 2016
From: JURISSON, SILVIA S.; CUTLER, CATHY S.; WYCOFF, DONALD E.; DEGRAFFENREID, ANTHONY J.
To: THE CURATORS OF THE UNIVERSITY OF MISSOURI
Reel/Frame 039581/0796 →
Continuity (3)
Continuation In Part 13969196 · Aug 16, 2013
Provisional Application 61684421 · Aug 17, 2012
Related Publication 20160083408A1 · Mar 24, 2016