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Synthesis and properties of two PRODAN-based fluorescent models of cholesterol

Paper ID Volume ID Publish Year Pages File Format Full-Text
28163 44062 2012 6 PDF Available
Title
Synthesis and properties of two PRODAN-based fluorescent models of cholesterol
Abstract

The syntheses and photophysical properties of 1-(5-methylhexyl)-2,3,7,8-tetrahydro-1H-naphtho[2,1-e]indol-9(6H)-one (7a) and 1-(5-methylhexyl)-2,3,8,9-tetrahydro-1H-naphtho[2,1-e]indol-6(7H)-one (7b) are reported. They are prepared in eight steps from the corresponding bromonaphthylamines. These fluorescent compounds have PRODAN-like cores, and they are structurally similar to cholesterol. Compound 7a is the first reported PRODAN derivative where both the amino and carbonyl groups are constrained to be coplanar with the naphthalene core. Comparing the photophysical behavior of these compounds with related compounds indicates that locking the amino group in a five-membered ring enhances their desirable properties as solvent polarity sensors.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Two cholesterol models bearing a PRODAN chromophore are prepared. ► The fluorescence of both is solvatochromic and similar to structurally related compounds with freely rotating dimethylamino groups. ► The photophysical properties of both are ideal for studying interactions with biological structures.

Keywords
PRODAN; Fluorescent cholesterol model; Solvatochromism
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Synthesis and properties of two PRODAN-based fluorescent models of cholesterol
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 238, 15 June 2012, Pages 35–40
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us