Megastokes Amino-Triazolyl-Bodipy Compounds And Applications To Live Neuron Staining And Human Serum Albumin FA1 Drug Site Probing
AssigneesNational University of Singapore, Agency for Science, Technology and Research
InventorsYoung-Tae Chang, Jun Cheng Er, Cheryl Kit Mun Leong, Seong Wook Yun, Marc Vendrell Escobar, Mui Kee Tang
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Abstract
A library of novel amino-triazolyl-BODIPY compounds is described. Particular compounds of the library serve as selective fluorescent probes Human Serum Albumin (HSA) and for live primary neurons. The fluorescent probe for HSA binds uniquely and specifically to the fatty acid site 1 of HSA, and thus proves a valuable and unique probe for drugs that bind to such a site on HSA. Methods of synthesis for the library compounds are also described.
Claims22
A compound having the structure of Formula (I) or a pharmaceutically acceptable salt thereof:
- wherein:
- R1 is H or CO(C1-C6)alkyl, wherein CO(C1-C6)alkyl is optionally substituted at any position with 1-3 substituents selected from halogen, hydroxyl, O-acetyl, NH-acetyl, or —NH2;
- R2 and R3 are each, independently, H, (C1-C10)alkyl, (C6-C10)aryl(C0-C6)alkyl, (C3-C10)heteroaryl, (C3-C8)cycloalkyl, (C2-C10)alkynyl or (C2-C10)alkenyl;
- wherein (C1-C10)alkyl, (C6-C10)aryl(C0-C6)alkyl, (C3-C10)heteroaryl, (C3-C8)cycloalkyl, (C2-C10)alkynyl and (C2-C10)alkenyl are optionally substituted at any position with 1-5 substituents selected from (C1-C6)alkyl, (C1-C6)alkoxy, NH2, —NH(C1-C6 alkyl), —NH(CO)(C1-C6 alkyl), —NH(CO)(C1-C6 haloalkyl), —NH(CO)(C1-C6 alkoxy), —NH(CO)(C1-C6 haloalkoxy), —NH(CO)(C2-C6 alkenyl), —Si(C1-C6 alkyl), —SO2(C1-C6 alkyl), —SH, —B(OH)2, —OTosyl, —CO(C1-C6 alkoxyl), —COH, —COOH, —CO(C1-C6 alkyl) or halogen;
- or R2 and R3 are taken together to form a ring, wherein the ring is optionally substituted with 1-5 additional substituents selected from halogen or (C1-C6)alkyl;
- and
- R4 is (C1-C10)alkyl, (C3-C8)cycloalkyl, (C6-C10)aryl, (C2-C10)alkenyl, (C2-C10)alkynyl, or (C3-C10)heteroaryl, further wherein R4 is optionally substituted at any position with 1-5 substituents selected from (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, (C3-C8)cycloalkyl, (C1-C6)alkoxy, (C6-C10)aryloxy, (C6-C10)aryl, amino, —NH(CO)(C1-C6 alkyl), —NH(CO)(C2-C6 alkenyl), —NH(CO)(C2-C6 alkynyl), —NH(CO)(C1-C6 haloalkyl), halo, OCF3, CF3, hydroxyl, or a halogen radioisotope.
A fluorescent probe for human serum albumin (HSA), comprising a compound of Formula (II):
- wherein the probe is selective for the FA1 binding site of HSA.
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A fluorescent dye for the specific staining of live neurons, comprising a compound of Formula (XV):
- wherein:
- R2 and R3 are each, independently, H, (C1-C10)alkyl, (C6-C10)aryl(C0-C6)alkyl, (C3-C10)heteroaryl, (C3-C8)cycloalkyl, (C2-C10)alkynyl or (C2-C10)alkenyl;
- wherein (C1-C10)alkyl, (C6-C10)aryl(C0-C6)alkyl, (C3-C10)heteroaryl, (C3-C8)cycloalkyl, (C2-C10)alkynyl and (C2-C10)alkenyl are optionally substituted at any position with 1-5 substituents selected from (C1-C6)alkyl, (C1-C6)alkoxy, NH2, —NH(C1-C6 alkyl), —NH(CO)(C1-C6 alkyl), —NH(CO)(C1-C6 haloalkyl), —NH(CO)(C1-C6 alkoxy), —NH(CO)(C1-C6 haloalkoxy), —NH(CO)(C2-C6 alkenyl), —Si(C1-C6 alkyl), —SO2(C1-C6 alkyl), —SH, —B(OH)2, —OTosyl, —CO(C1-C6 alkoxyl), —COH, —COOH, —CO(C1-C6 alkyl) or halogen;
- or R2 and R3 are taken together to form a ring, wherein the ring is optionally substituted with 1-5 additional substituents selected from halogen or (C1-C6)alkyl;
- R6 is H or CO(CH3);
- and
- R7 is (C1-C10)alkyl, (C3-C8)cycloalkyl, (C6-C10)aryl, (C2-C10)alkenyl, (C2-C10)alkynyl, or (C3-C10)heteroaryl, further wherein R4 is optionally substituted at any position with 1-5 substituents selected from (C1-C10)alkyl, (C2-C10)alkenyl, (C2-C10)alkynyl, (C3-C8)cycloalkyl, (C1-C6)alkoxy, (C6-C10)aryloxy, (C6-C10)aryl, amino, —NH(CO)(C1-C6 alkyl), —NH(CO)(C2-C6 alkenyl), —NH(CO)(C2-C6 alkynyl), —NH(CO)(C1-C6 haloalkyl), halo, OCF3, CF3, hydroxyl, or a halogen radioisotope.
Dependencies are inferred from the claim text.