Document Detail

Absorption and fluorescence spectra of ring-substituted indole-3-acetic acids.
MedLine Citation:
PMID:  15501568     Owner:  NLM     Status:  MEDLINE    
The absorption and fluorescence spectra of indole-3-acetic acid (1), a plant growth regulator (auxin) and experimental cancer therapeutic, 29 ring-substituted derivatives and the 7-aza analogue (1H-pyrrolo[2,3b]pyridine-3-acetic acid) are compared. Two to four absorbance maxima in the 260-310-nm range are interpreted as overlapping vibronic lines of the 1La<--1A and 1Lb<--1A transitions. Two further maxima in the 200-230-nm region are assigned to the 1Ba<--1A and 1Bb<--1A transitions. 4- and 7-Fluoroindole-3-acetic acid exhibit blue shifts with respect to 1, most other derivatives show red shifts. All indole-3-acetic acids studied, with the exception of chloro-, bromo- and 4- or 7-fluoro-derivatives, fluoresce at 345-370 nm when excited at 275-280 nm. 7-Azaindole-3-acetic acid emits at 411 nm. The fluorescence quantum yield of 6-fluoroindole-3-acetic acid significantly exceeds that of 1 (0.3); the other derivatives have lower quantum yields. The plant-growth promoting activity of the ring-substituted indole-3-acetic acids studied correlates with the position of the 1Bb<--1A transition band.
Dejana Carić; Vladislav Tomisić; Marina Kveder; Nives Galić; Greta Pifat; Volker Magnus; Milan Soskić
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Biophysical chemistry     Volume:  111     ISSN:  0301-4622     ISO Abbreviation:  Biophys. Chem.     Publication Date:  2004 Nov 
Date Detail:
Created Date:  2004-10-25     Completed Date:  2005-06-03     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0403171     Medline TA:  Biophys Chem     Country:  Netherlands    
Other Details:
Languages:  eng     Pagination:  247-57     Citation Subset:  IM    
Faculty of Agronomy, Svetosimunska cesta 25, 10000 Zagreb, Croatia.
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MeSH Terms
Hydrogen-Ion Concentration
Indoleacetic Acids / chemistry*
Molecular Structure
Spectrometry, Fluorescence / methods
Spectrophotometry, Ultraviolet / methods
Reg. No./Substance:
0/Indoleacetic Acids

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