Fluorescent substrates for monoamine transporters as optical false neurotransmitters

US8337941B2 · kind B2 · utility

Assignee

• The Trustees of Columbia University in the City of New York · US

Inventors

• Niko Gubernator · Del Mar, US
• Dalibor Sames · New York, US
• David Sulzer · New York, US
• Paul Vadola · New York, US

Key dates

• Filing date: Jul 27, 2007
• Grant date: Dec 25, 2012
• Expiry date: Dec 8, 2028

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D491/16
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The present invention relates to compounds of the general structure: wherein Y is O, X is O, bond α is absent and bond β is present, or Y is H, X is CH, bond α is present, and bond β is absent; atom Z is a carbon and bonds χ, δ and γ are present, or is a nitrogen and bonds χ, δ and γ are absent; R1 is —H, —OH, —O—R7, —N(H)—R8, —N(H)—(CH2)n—NH2, —N(R9)(R10), or a piperazine cation; R2 is either covalently bound to R9, or is —H, or is covalently bound to R3 so as to form a substituted or unsubstituted pyrrole or R2 is covalently bound to R9 or R8 or R7; or R1 and R2 are covalently joined to form an aromatic ring; R3 is either covalently bound to R2 so as to form a pyrrole, or is, inter alia, —H, —OH, alkyl, or when Z is nitrogen R3 is ═O; R4 is, inter alia, —H, —OH, or —R11NH2; R5 is, inter alia, —H, —OH, or —R12NH2, and R6 is either is covalently bound to R10 or is —H, or R6 is covalently bound to R10 or R8 or R7. This invention also provides processes for making the compounds as well as methods for monitoring activity of monoamine transporters or treating monoamine transporter-associated diseases by employing the compounds.