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High Resolution Features from Low Affinity Interactions: Photoactive Analogs of the Haloether Anesthetics

Journal Article · · ACS Chemical Biology
DOI:https://doi.org/10.1021/cb600207d· OSTI ID:930124
The difficulty in obtaining binding target and site information for low-affinity drugs, like the inhaled anesthetics, has limited identification of their molecular effectors. Because such information can be provided by photoactive analogues, we designed, synthesized, and characterized a novel diazirnyl haloether that closely mimics isoflurane, the most widely used clinical general anesthetic. This compound, H-diaziflurane, is a nontoxic, potent anesthetic that potentiates GABA-gated ion channels in primary cultures of hippocampal neurons. Calorimetric and structural characterizations show that H-diaziflurane binds a model anesthetic host protein with similar energetics as isoflurane and forms photoadducts with residues lining the isoflurane binding site. H-diaziflurane will be immediately useful for identifying targets and sites important for the molecular pharmacology of the inhaled haloether anesthetics.
Research Organization:
Brookhaven National Laboratory (BNL) National Synchrotron Light Source
Sponsoring Organization:
Doe - Office Of Science
DOE Contract Number:
AC02-98CH10886
OSTI ID:
930124
Report Number(s):
BNL--80769-2008-JA
Journal Information:
ACS Chemical Biology, Journal Name: ACS Chemical Biology Vol. 1
Country of Publication:
United States
Language:
English

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