US 12,358,923 B2
Seminaphthofluorophore-selenium probes for thioredoxin reductase
Robert M. Strongin, Portland, OR (US); Jorge O. Escobedo Cordova, Portland, OR (US); and Tendai Mafireyi, Portland, OR (US)
Assigned to Portland State University, Portland, OR (US)
Appl. No. 17/762,348
Filed by Portland State University, Portland, OR (US)
PCT Filed Sep. 24, 2020, PCT No. PCT/US2020/052511
§ 371(c)(1), (2) Date Mar. 21, 2022,
PCT Pub. No. WO2021/062000, PCT Pub. Date Apr. 1, 2021.
Claims priority of provisional application 62/907,177, filed on Sep. 27, 2019.
Prior Publication US 2023/0002803 A1, Jan. 5, 2023
Int. Cl. C07D 493/10 (2006.01); C12Q 1/26 (2006.01); G01N 21/29 (2006.01); G01N 21/64 (2006.01); G01N 21/78 (2006.01)
CPC C07D 493/10 (2013.01) [C12Q 1/26 (2013.01); C12Y 108/01009 (2013.01); G01N 21/29 (2013.01); G01N 21/6428 (2013.01); G01N 21/78 (2013.01)] 20 Claims
 
1. A compound according to Formula I, or an ionized form or salt thereof:

OG Complex Work Unit Chemistry
where each bond depicted as “custom character” is a single or double bond as needed to satisfy valence requirements;
Z1 and Z2 independently are hydrogen, hydroxyl, or thiol, or Z1 and Z2 together with the atoms to which they are attached form a substituted or unsubstituted 6-membered ring;
X1 is O, S, Se, Si(Ra)(Rb), Ge(Ra)(Rb), Sn(Ra)(Rb)2, C(Ra)(Rb)2, or NRb where Ra is H or C1-C10 alkyl and Rb is H, C1-C10 alkyl, —COOH, or —COORc where Rc is C1-C10 alkyl or a conjugatable moiety;
R1 is hydrogen, hydroxyl, halogen, thiol, amino, alkyl amino, oxygen, sulfur, imino, iminium, alkyl imino, alkyl iminium, cycloalkyl imino, or a diselenide moiety, and R2 and R3 independently are hydrogen, hydroxy, thiol, C1-C10 alkyl, carboxyalkyl, amino, alkoxy, or halogen, or R1-R3 together with Ring A form a tricyclic ring system with a nitrogen at R1 and a single bond between R1 and ring A;
R4-R6 independently are hydrogen, hydroxy, thiol, C1-C10 alkyl, carboxyalkyl, amino, alkoxy, or halogen;
R7, R8, and R10 independently are hydrogen, alkyl, acyl, carboxyl, nitro, amino, alkyl amino, —SO3H, —COOH, or —COORd where Rd is C1-C10 alkyl or a conjugatable moiety;
R9 is hydrogen, alkyl, acyl, carboxyl, nitro, amino, alkyl amino, —SO3H, a diselenide moiety, —COOH, or —COORd where Rd is C1-C10 alkyl or a conjugatable moiety; and
R11 is one or more atoms forming a ring system with rings C and B and the bond depicted as “custom character” in ring C is a single bond, or R11 is —COOH, —COO− or —COORe where Re is C1-C10 alkyl or a counter ion with a net single positive charge and the bond depicted as “custom character” in ring C is a double bond,
wherein the compound comprises at least one diselenide moiety, and each diselenide moiety independently has a formula —Y—C(Q)O—(CH2)m—Se—Se—(CH2)n—ORf, where Rf is hydrogen or C1-C3alkyl, Q is O or S, Y is O or N(Rg) where Rg is H or alkyl, and m and n independently are integers from 1-5.