Publication Date:
1990-05-04
Description:
Anesthesia "cutoff" refers to the phenomenon of loss of anesthetic potency in a homologous series of alkanes and their derivatives when their sizes become too large. In this study, hydrogen bonding of 1-alkanol series (ethanol to eicosanol) to dipalmitoyl-L-alpha-phosphatidylcholine (DPPC) was studied by Fourier transform infrared spectroscopy (FTIR) in DPPC-D2O-in-CCl4 reversed micelles. The alkanols formed hydrogen bonds with the phosphate moiety of DPPC and released the DPPC-bound deuterated water, evidenced by increases in the bound O-H stretching signal of the alkanol-DPPC complex and also in the free O-D stretching band of unbound D2O. These effects increased according to the elongation of the carbon chain of 1-alkanols from ethanol (C2) to 1-decanol (C10), but suddenly almost disappeared at 1-tetradecanol (C14). Anesthetic potencies of these alkanols, estimated by the activity of brine shrimps, were linearly related to hydrogen bond-breaking activities below C10 and agreed with the FTIR data in the cutoff at C10.〈br /〉〈span class="detail_caption"〉Notes: 〈/span〉Chiou, J S -- Ma, S M -- Kamaya, H -- Ueda, I -- GM25716/GM/NIGMS NIH HHS/ -- GM27670/GM/NIGMS NIH HHS/ -- New York, N.Y. -- Science. 1990 May 4;248(4955):583-5.〈br /〉〈span class="detail_caption"〉Author address: 〈/span〉Department of Anesthesia, University of Utah School of Medicine, Salt Lake City.〈br /〉〈span class="detail_caption"〉Record origin:〈/span〉 〈a href="http://www.ncbi.nlm.nih.gov/pubmed/2159183" target="_blank"〉PubMed〈/a〉
Keywords:
*1,2-Dipalmitoylphosphatidylcholine
;
*Alcohols
;
*Anesthesia
;
*Carbon Tetrachloride
;
Deuterium
;
Deuterium Oxide
;
Fourier Analysis
;
Hydrogen Bonding
;
Liposomes
;
Models, Biological
;
Structure-Activity Relationship
;
Thermodynamics
;
Water
Print ISSN:
0036-8075
Electronic ISSN:
1095-9203
Topics:
Biology
,
Chemistry and Pharmacology
,
Computer Science
,
Medicine
,
Natural Sciences in General
,
Physics
Permalink
