Design and Synthesis of a Quinocyanine for Medicinal Chemistry Applications

Authors: Ethan Hadley, Ron Bishop, Angela Migues

SUNY Campus: SUNY Oneonta

Presentation Type: Poster

Location: Old Union Hall

Presentation #: 31

Timeslot: Session A 9:00-10:00 AM

Abstract: The aims of this work were twofold: in silico investigation of solvatochromism, and the chemical synthesis, purification, and analysis of a novel merocyanine incorporating quinaldine. The goals of these and related studies are to design and produce merocyanines that act as antagonists of Transient Receptor Potential Vanilloid Type 1 (TRPV1) receptors. These ion channels, also known as vanilloid 1 receptors, are primarily responsible for triggering nociceptive pain. Meta-analysis of compounds known to activate or deactivate these receptors (to trigger or suppress pain), suggested to us that the agonist capsaicin (from hot peppers) and some receptor antagonists had molecular shapes that could be mimicked by a class of molecules called merocyanines. Merocyanines have peculiar abilities to electronically “tune” surface characteristics to their environments (i.e., surrounding solvents), behavior that can be observed visually as solvatochromism. Therefore, they might offer unique abilities to shape-shift upon migration from aqueous solution to protein interiors. We report the first in silico solvatochromism studies, as well as organic synthesis and analysis by FTIR, NMR and physical solvatochromism, of a merocyanine that incorporates a quinoline derivative (quinaldine). We call this new class of molecules quinocyanines.