Date of Award

2025

Document Type

Open Access Master's Thesis

Degree Name

Master of Science in Chemistry (MS)

Administrative Home Department

Department of Chemistry

Advisor 1

Haiying Liu

Committee Member 1

Tarun Dam

Committee Member 2

Momoko Tajiri

Abstract

A near-infrared fluorescent probe, A, was designed by substituting the carbonyl group of the coumarin dye’s lactone with a 4-cyano-1-methylpyridinium methylene group and then attaching an electron-withdrawing NADH-sensing methylquinolinium acceptor via a vinyl bond linkage to the coumarin dye at the 4-position. The probe exhibits primary absorption maxima at 603, 428, and 361 nm, and fluoresces weakly at 703 nm. The addition of NAD(P)H results in a significant blue shift in the fluorescence peak from 703 to 670 nm, accompanied an increase in fluorescence intensity. This spectral shift is attributed to the transformation of A−π–A−π–D configuration to D−π–A−π–D pyridinium platform in probe AH, owing to the addition of a hydride from NADH to the electron-accepting quinolinium acceptor producing the electron-contributing 1-methyl-1,4-dihydroquinoline donor in probe AH. This conclusion is supported by theoretical calculations. The near-infrared emissive probe offers a highly sensitive and specific method for monitoring NAD(P)H levels across cellular, tissue and whole-organism systems. The ability to detect NAD(P)H variations in reaction to varying stimuli, including nutrient availability and chemotherapeutic stress, underscores its potential as a valuable resource for biomedical research and therapeutic monitoring.

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