US 12,440,581 B2
Fluorophores for super-resolution imaging
Luke D. Lavis, Leesburg, VA (US); and Qinsi Zheng, Ashburn, VA (US)
Assigned to HOWARD HUGHES MEDICAL INSTITUTE, Chevy Chase, MD (US)
Filed by HOWARD HUGHES MEDICAL INSTITUTE, Chevy Chase, MD (US)
Filed on Sep. 21, 2020, as Appl. No. 17/027,286.
Claims priority of provisional application 62/902,708, filed on Sep. 19, 2019.
Prior Publication US 2021/0085805 A1, Mar. 25, 2021
Int. Cl. A61K 49/00 (2006.01); C07D 311/04 (2006.01); C07F 7/08 (2006.01); G01N 21/64 (2006.01)
CPC A61K 49/0021 (2013.01) [C07D 311/04 (2013.01); C07F 7/0816 (2013.01); G01N 21/64 (2013.01); G01N 2223/406 (2013.01)] 24 Claims
 
1. A compound of the formula:

OG Complex Work Unit Chemistry
or a closed form thereof, wherein
(a) X is selected from the group consisting of O, N-alkyl, S, and C(alkyl)2;
Y is —NH2 or

OG Complex Work Unit Chemistry
wherein each Y1 and Y2 is each independently selected from the group consisting of H, F, CN, OCH3, SO2CH3, CF3, CH3, and CO2H;
R1 and R2 are each independently selected from the group consisting of H, alkyl, and halogen;
R3, which can be a substitution at either the 5 position or the 6 position of the ring to which it is bound, is selected from the group consisting of H, self-labeling protein tag ligand, CO2H, CO2CH3, CO2t-Bu, N-hydroxysuccinimidyl (NHS) ester, and a targeting moiety; and
R4 is CH2OH;
(b) X is Si(alkyl)2;
Y is —NH2;
R1 and R2 are each independently selected from the group consisting of H, alkyl, and halogen;
R3, which can be a substitution at either the 5 position or the 6 position of the ring to which it is bound, is selected from the group consisting of H, self-labeling protein tag ligand, CO2H, CO2CH3, CO2t-Bu, NHS ester, and a targeting moiety; and
R4 is CH2OH;
(c) X is Si(alkyl)2;
Y is

OG Complex Work Unit Chemistry
wherein each Y1 and Y2 is each independently selected from the group consisting of F, CN, OCH3, SO2CH3, CF3, CH3, and CO2H;
R1 and R2 are each independently selected from the group consisting of H, alkyl, and halogen;
R3, which can be a substitution at either the 5 position or the 6 position of the ring to which it is bound, is selected from the group consisting of H, self-labeling protein tag ligand, CO2H, CO2CH3, CO2t-Bu, NHS ester, and a targeting moiety; and
R4 is CH2OH;
(d) X is Si(alkyl)2;
Y is

OG Complex Work Unit Chemistry
wherein Y1 and Y2 are H;
R1 and R2 are each independently selected from the group consisting of alkyl, and halogen;
R3, which can be a substitution at either the 5 position or the 6 position of the ring to which it is bound, is selected from the group consisting of H, self-labeling protein tag ligand, CO2H, CO2CH3, CO2t-Bu, NHS ester, and a targeting moiety; and
R4 is CH2OH; or
(e) X is Si(alkyl)2;
Y is

OG Complex Work Unit Chemistry
wherein Y1 and Y2 are H;
R1 and R2 are H;
R3, which can be a substitution at either the 5 position or the 6 position of the ring to which it is bound, is selected from the group consisting of H, self-labeling protein tag ligand, CO2H, CO2CH3, CO2t-Bu, and a targeting moiety; and
R4 is CH2OH.