IP Library Granted Patent US 10,350,308
Granted Patent B2
US 10,350,308 · App. 13/806,795 · Granted Jul 16, 2019

Molecular probes for imaging myelin

Inventors: Yanming Wang (Cleveland, OH); Changning Wang (Melrose, MA)
Assignee: CASE WESTERN RESERVE UNIVERSITY
A61K49/0021A61K49/0032A61K51/0453C07D277/66A61K49/0017
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Quick Facts
Patent No.
US 10,350,308
App. No.
13/806,795
Granted
Jul 16, 2019
Kind
B2
Abstract

A molecular probe for use in the detection of myelin in a subject includes a compound having the general formula selected from the group consisting of: formula (I), and pharmaceutically acceptable salts thereof.

Claims (37)

1. A method of detecting myelin in vivo in a subject's tissue, the method comprising:

(i) administering to the subject a molecular probe including a compound having the general formula selected from the group consisting of:

wherein n is an integer from 1 to 10; A, B each independently represent CR′ 2 , O, S, NH, CH 2 CH 2 , CH═CH; R 1 , R 2 , R′, and Z each independently represent H, alkyl, alkenyl, alkynyl and/or an aryl group; X and Y each independently represent

wherein R″=H, alkyl, alkenyl, alkynyl or an aryl group; and pharmaceutically acceptable salts thereof; and

(ii) detecting the location, distribution, and/or amount of the compound that is bound to the myelin to detect the myelin in the tissue.

2. The method of claim 1 , wherein R 1 ═R 2 .

3. The method of claim 1 , wherein A=B.

4. The method of claim 1 , wherein X═Y.

5. The method of claim 1 , the molecular probe further comprising a radiolabel.

6. The method of claim 1 , the molecular probe further comprising a magnetic resonance contrast agent that is bound to the molecular probe to facilitate or enhance magnetic resonance imaging of the molecular probe.

7. The method of claim 1 , the molecular probe including a compound having the general formula:

wherein n is an integer from 1 to 10; A, B each independently represent CR′ 2 , O, S, NH, CH 2 CH 2 , CH═CH; R 1 , R 2 , R′, and Z each independently represent H, alkyl, alkenyl, alkynyl and/or an aryl group; X and Y each independently represent

wherein R″=H, alkyl, alkenyl, alkynyl or an aryl group; and pharmaceutically acceptable salts thereof.

8. The method of claim 7 comprising the formula:

and pharmaceutically acceptable salts thereof.

9. The method of claim 7 , the molecular probe including a compound having the formula:

and pharmaceutically acceptable salts thereof.

10. The method of claim 1 , the molecular probe including a compound having the general formula:

wherein n is an integer from 1 to 10; R 1 , R 2 , R′, and Z each independently represent H, alkyl, alkenyl, alkynyl and/or an aryl group; X and Y each independently represent

wherein R″=H, alkyl, alkenyl, alkynyl or an aryl group; and pharmaceutically acceptable salts thereof.

11. The method of claim 1 , wherein the location, distribution, and/or amount of the compound is detected using in vivo imaging modality comprising a near-infrared fluorescence imaging modality.

12. The method of claim 1 , the in vivo imaging modality comprising a fluorescence molecular tomography imaging modality.

13. The method of claim 1 , further comprising the step of administering the molecular probe to the subject parenterally.

14. A method of detecting myelin in vivo in a subject's tissue, the method comprising:

(i) administering to the subject a molecular probe including a compound having the general formula of:

wherein n is an integer from 3 to 10; A, B each independently represent CR′ 2 , O, S, NH, CH 2 CH 2 , CH═CH; R 1 , R 2 , R′, and Z each independently represent H, alkyl, alkenyl, alkynyl and/or an aryl group; X and Y each independently represent

wherein R″=H, alkyl, alkenyl, alkynyl or an aryl group; and pharmaceutically acceptable salts thereof; and

(ii) detecting the location, distribution, and/or amount of the compound that is bound to the myelin to detect the myelin in the tissue.

15. The method of claim 14 , wherein R 1 ═R 2 .

16. The method of claim 14 , wherein A=B.

17. The method of claim 14 , wherein X═Y.

18. The method of claim 14 , the molecular probe further comprising a radiolabel.

19. The method of claim 14 , the molecular probe further comprising a magnetic resonance contrast agent that is bound to the molecular probe to facilitate or enhance magnetic resonance imaging of the molecular probe.

20. The method of claim 14 , the molecular probe including a compound having the formula:

and pharmaceutically acceptable salts thereof.

21. The method of claim 14 , wherein the location, distribution, and/or amount of the compound is detected using an in vivo imaging modality comprising a near-infrared fluorescence imaging modality.

22. The method of claim 14 , further comprising the step of administering the molecular probe to the subject parenterally.

Assignments (3)
CONFIRMATORY LICENSE Recorded Jun 7, 2016
From: CASE WESTERN RESERVE UNIVERSITY
To: NATIONAL INSTITUTES OF HEALTH (NIH), U.S. DEPT. OF HEALTH AND HUMAN SERVICES (DHHS), U.S. GOVERNMENT
Reel/Frame 038903/0462 →
CONFIRMATORY LICENSE Recorded Feb 24, 2014
From: CASE WESTERN RESERVE UNIVERSITY
To: NATIONAL INSTITUTES OF HEALTH (NIH), U.S. DEPT. OF HEALTH AND HUMAN SERVICES (DHHS), U.S. GOVERNMENT
Reel/Frame 032329/0822 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 3, 2013
From: WANG, YANMING; WANG, CHANGNING
To: CASE WESTERN RESERVE UNIVERSITY
Reel/Frame 030143/0307 →
Continuity (2)
Provisional Application 61359865 · Jun 30, 2010
Related Publication 20130209357A1 · Aug 15, 2013