Document Detail

Naphthyl- and quinolylluciferin: green and red light emitting firefly luciferin analogues.
MedLine Citation:
PMID:  2756004     Owner:  NLM     Status:  MEDLINE    
In the course of investigations on the possible involvement of the CIEEL (chemically initiated electron-exchange luminescence) mechanism in firefly bioluminescence, we have synthesized two novel firefly luciferin substrate analogues. D-Naphthylluciferin and D-quinolylluciferin were prepared by condensing D-cysteine with 2-cyano-6-hydroxynaphthalene and 2-cyano-6-hydroxyquinoline, respectively. These analogues are the first examples of bioluminescent substrates for firefly luciferase that do not contain a benzothiazole moiety. Firefly luciferase-catalyzed bioluminescence emission spectra revealed that compared to the normal yellow-green light of luciferin (lambda max = 559 nm), the emission from naphthylluciferin is significantly blue-shifted (lambda max = 524 nm); whereas quinolylluciferin emits orange-red light (lambda max = 608 nm). The fluorescence emission spectra, reaction pH optima, relative light yields, light emission kinetics and KM values of the analogues also were measured and compared to those of luciferin. Neither of the analogues produced the characteristic flash kinetics observed for the natural substrate. Instead, slower rise times to peak emission intensity were recorded. It appears that the formation of an intermediate from the analogue adenylates prior to the addition of oxygen is responsible for the slow rise times. The synthetic substrate analogues described here should be useful for future mechanistic studies.
B R Branchini; M M Hayward; S Bamford; P M Brennan; E J Lajiness
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, Non-P.H.S.    
Journal Detail:
Title:  Photochemistry and photobiology     Volume:  49     ISSN:  0031-8655     ISO Abbreviation:  Photochem. Photobiol.     Publication Date:  1989 May 
Date Detail:
Created Date:  1989-09-07     Completed Date:  1989-09-07     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0376425     Medline TA:  Photochem Photobiol     Country:  ENGLAND    
Other Details:
Languages:  eng     Pagination:  689-95     Citation Subset:  IM    
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MeSH Terms
Beetles / metabolism*
Firefly Luciferin / analogs & derivatives*
Spectrum Analysis
Reg. No./Substance:
0/Hydroxyquinolines; 0/Naphthols; 0/Thiazoles; 122364-82-3/3-(7-hydroxynaphthyl)-2-thiazole-4-carboxylic acid; 122364-83-4/2-(6-hydroxyquinolyl)-2-thiazole-4-carboxylic acid; 2591-17-5/Firefly Luciferin

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