160290-93-7Relevant academic research and scientific papers
Synthesis and Preliminary Chemi- and Bio-luminescence Studies of a Novel Photolabile Coelenterazine Analogue with a Trifluoromethyl Diazirine Group
Chen, Feng-Qi,Hirano, Takashi,Hashizume, Yoshinobu,Ohmiya, Yoshihiro,Ohashi, Mamoru
, p. 2405 - 2406 (1994)
A novel photolabile analogue of coelenterazine with a trifluoromethyl diazirine group is successfully synthesized for photoaffinity labelling of the active site of aequorin; preliminary studies on its chemi- and bio-luminescence demonstrate that the photo
Insecticidal quinazoline derivatives with (trifluoromethyl)diazirinyl and azido substituents as NADH:ubiquinone oxidoreductase inhibitors and candidate photoaffinity probes
Latli, Bachir,Wood, Edgardo,Casida, John E.
, p. 445 - 450 (2007/10/03)
Two candidate photoaffinity probes are designed from 4-substituted quinazolines known to be potent insecticides/acaricides and NADH:ubiquinone oxidoreductase inhibitors acting at or near the rotenone site. 4-(11- Azidoundecyl-2-amino)quinazoline, based on the undecylamino analog SAN 548A as a prototype, was synthesized in 18% overall yield from ethyl 10- undecenoate by oxidation of the terminal double bond, reductive amination, coupling to 4-chloroquinazoline, and functional group manipulation of the terminal ethyl ester to an alcohol, a mesylate and finally nucleophilic displacement with azide ions. 4-(4-(3-(Trifluoromethyl)-3H-diazirin-3- yl)phenethoxy)quinazoline [the (trifluoromethyl)diazirinyl analog of fenazaquin insecticide/acaricide] was prepared from 4-bromophenethyl alcohol in 31% overall yield by first introducing the trifluoromethylketone moiety followed by its conversion to the (trifluoromethyl)-diazirine and finally coupling to 4-chloroquinazoline as above. Both candidate photoaffinity probes have the inhibitory potency of rotenone (IC50 of 3-4 nM in each case). The azidoundecylamino compound has inadequate photoreactivity whereas that of the (trifluoromethyl)diazirinyl analog is ideal at 350 nm. Radiosynthesis of the latter photoaffinity ligand included introduction of the diazirinyl moiety as the carbene precursor, oxidation of (trifluoromethyl)diazirinylphenethyl alcohol to the corresponding acid with Jones' reagent, and reduction of the phenacetyl chloride intermediate with sodium borotritide to incorporate tritium.
A potential photoaffinity probe for labelling the active site of aequorin: a photolabiile coelenterazine analogue with a trifluoromethyldiazirine group
Chen, Feng Qi,Zheng, Jing Ling,Hirano, Takashi,Niwa, Haruki,Ohmiya, Yoshihiro,Ohashi, Mamoru
, p. 2129 - 2134 (2007/10/02)
In order to clarify the active site of aequorin, we have succesfully synthesized a photolabile analogue of coelenterazine with a trifluoromethyl diazirine group as a photoaffinity probe.Our studies of the chemi- and bioluminescence of this novel analogue indicate that its behaviour is almost identical with that of natural coelenterazine in terms of luminescence characteristics.Therefore, the analogue with the photolabile diazirine should be a useful photoaffinity label for probing the detailed structure of aequorin.
