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Date of Award

2025

Document Type

Campus Access Master's Thesis

Degree Name

Master of Science in Chemistry (MS)

Administrative Home Department

Department of Chemistry

Advisor 1

Marina Tanasova

Committee Member 1

Tarun Dam

Committee Member 2

Ashutosh Tiwari

Abstract

Coumarins have been widely utilized in designing fluorescent reporters that possess target-specific outputs. However, the coumarin core as a supporter of color-changing properties without extensive derivatization has not yet been achieved. Here, we report a small library of coumarin esters capable of red-to-blue fluorescence upon hydrolysis by cellular esterase. By stabilizing the red-transition through C4 coumarin substitution and the blue-shifted transition through C7 coumarin substitution this generates a color-changing scaffold of ~150 nm difference between the two transitions.

Varying alkyl and aryl C4-carboxylate substitution allowed for tuning of fluorescence and hydrolytic efficiency. These probes display fast cellular uptake and esterase dependent color change in live cells allowing for detection under both the red and blue channel. However, in dead cells the probes are only detectable in the red channel. This identifies alkyl and aryl 7-hydroxy-4-carboxy coumarins as small color-changing tools for live-dead cell analysis and markers for cellular esterase activity.

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