Excited-state proton transfer reactions of 10-hydroxycamptothecin

Time-resolved and steady-state emission characterization of 10-hydroxycamptothecin reveals a rich but less complex proton-transfer behavior than its parent hydroxyquinoline. The electronic effect of the additional electron-withdrawing ring makes the excited-state both less basic and more acidic than...

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Veröffentlicht in:	Journal of the American Chemical Society 2004-10, Vol.126 (39), p.12701-12708
Hauptverfasser:	SOLNTSEV, Kyril M, SULLIVAN, Erica N, TOLBERT, Laren M, ASHKENAZI, Shay, LEIDERMAN, Pavel, HUPPERT, Dan
Format:	Artikel
Sprache:	eng
Schlagworte:	Antineoplastic Agents, Phytogenic - chemistry Biological and medical sciences Camptothecin - analogs & derivatives Camptothecin - chemistry Chemistry Exact sciences and technology General and physical chemistry General pharmacology Hydrogen-Ion Concentration Kinetics Medical sciences Pharmacology. Drug treatments Photochemistry Physical chemistry of induced reactions (with radiations, particles and ultrasonics) Physicochemical properties. Structure-activity relationships Protons Spectrometry, Fluorescence Structure-Activity Relationship Titrimetry
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Beschreibung
Zusammenfassung:	Time-resolved and steady-state emission characterization of 10-hydroxycamptothecin reveals a rich but less complex proton-transfer behavior than its parent hydroxyquinoline. The electronic effect of the additional electron-withdrawing ring makes the excited-state both less basic and more acidic than the parent and adds to the class of high-acidity excited-state proton donors in photochemistry and photobiology.
ISSN:	0002-7863 1520-5126
DOI:	10.1021/ja047821e