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Title: Anesthesia cutoff phenomenon: Interfacial hydrogen bonding

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.
Authors:
; ; ;  [1]
  1. (Univ. of Utah School of Medicine, Salt Lake City (USA))
Publication Date:
OSTI Identifier:
6871594
Resource Type:
Journal Article
Resource Relation:
Journal Name: Science (Washington, D.C.); (USA); Journal Volume: 248:4955
Country of Publication:
United States
Language:
English
Subject:
59 BASIC BIOLOGICAL SCIENCES; ANESTHESIA; STRUCTURE-ACTIVITY RELATIONSHIPS; HYDROGEN; CHEMICAL BONDS; BIOLOGICAL MODELS; DEUTERIUM; HEAVY WATER; LIPOSOMES; SHRIMP; THERMODYNAMICS; TRACER TECHNIQUES; ANIMALS; AQUATIC ORGANISMS; ARTHROPODS; CELL CONSTITUENTS; CRUSTACEANS; DECAPODS; ELEMENTS; HYDROGEN COMPOUNDS; HYDROGEN ISOTOPES; INVERTEBRATES; ISOTOPE APPLICATIONS; ISOTOPES; LIGHT NUCLEI; NONMETALS; NUCLEI; ODD-ODD NUCLEI; ORGANOIDS; OXYGEN COMPOUNDS; STABLE ISOTOPES; WATER 550201* -- Biochemistry-- Tracer Techniques