US 11,696,960 B2
Methods and compounds for detection and binding of aldehydes
Adam Shuhendler, Ottawa (CA); Mojmir Suchy, Ottawa (CA); and Trina Dang, Mississauga (CA)
Assigned to UNIVERSITY OF OTTAWA, Ottawa (CA)
Appl. No. 16/482,492
Filed by UNIVERSITY OF OTTAWA, Ottawa (CA)
PCT Filed Feb. 5, 2018, PCT No. PCT/CA2018/050125
§ 371(c)(1), (2) Date Jul. 31, 2019,
PCT Pub. No. WO2018/141069, PCT Pub. Date Aug. 9, 2018.
Claims priority of provisional application 62/455,132, filed on Feb. 6, 2017.
Prior Publication US 2020/0376144 A1, Dec. 3, 2020
Int. Cl. A61K 49/10 (2006.01); A61K 51/04 (2006.01); C07C 251/76 (2006.01); C07C 309/46 (2006.01)
CPC A61K 49/10 (2013.01) [A61K 51/04 (2013.01); C07C 251/76 (2013.01); C07C 309/46 (2013.01)] 11 Claims
 
1. A method of detecting a freely diffusing small molecule aldehyde in a subject comprising administering an aldehyde-binding compound of Formula I to the subject and detecting the product of the compound of Formula I and the freely diffusing small molecule aldehyde using magnetic resonance imaging (MRI), CEST-MRI or positron emission tomography (PET) imaging;

OG Complex Work Unit Chemistry
wherein:
X is C or N;
Z is H, alkyl, cycloalkyl, or aryl;
Y1 and Y3 are H;
Y2 is CHs3—O—; and
Y4 is independently:
H;
a substituent selected from the group consisting of Br, CI, I, nitro, sulfo, carboxy, hydroxyl, alkoxy, cycloalkoxy, aryloxy, C1-6 alkyl, aryl, cycloalkyl, alkyne, propargyl, and tetrazine;
wherein detection of said freely diffusing small molecule aldehyde is indicative of a brain injury or of cell death optionally wherein the aldehyde-binding compound additionally comprises a radio-label for use in positron emission tomography imaging.