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Proceedings of the National Academy of Sciences of the United States of America logoLink to Proceedings of the National Academy of Sciences of the United States of America
. 1972 Nov;69(11):3416–3419. doi: 10.1073/pnas.69.11.3416

Conformational Relationships Between Analogs of Acetylcholine and Those of Local Anesthetics in Solution

Alexandros Makriyannis 1, Richard F Sullivan 1, Henry G Mautner 1
PMCID: PMC389783  PMID: 4508331

Abstract

Conformations of analogs of acetylcholine and of related local anesthetics, in which either of the oxygen atoms had been replaced by other heteroatoms, were studied in solution by nuclear magnetic resonance. Several correlations between structure and conformation could be made.

Keywords: NMR conformational analysis

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Bartels E., Nachmansohn D. Molecular structure determining the action of local anesthetics on the acetylcholine receptor. Biochem Z. 1965 Aug 19;342(4):359–374. [PubMed] [Google Scholar]
  2. Bartels E. Relationship between acetylcholine and local anesthetics. Biochim Biophys Acta. 1965 Sep 27;109(1):194–203. doi: 10.1016/0926-6585(65)90103-2. [DOI] [PubMed] [Google Scholar]
  3. Beall R., Herdklotz J., Sass R. L. Molecular properties of local anesthetics: the crystal structure of procaine hydrochloride. Biochem Biophys Res Commun. 1970 May 11;39(3):329–334. doi: 10.1016/0006-291x(70)90580-2. [DOI] [PubMed] [Google Scholar]
  4. Canepa F. G., Pauling P., Sörum H. Structure of acetylcholine and other substrates of cholinergic systems. Nature. 1966 May 28;210(5039):907–909. doi: 10.1038/210907a0. [DOI] [PubMed] [Google Scholar]
  5. Cannon J. G., Rege A. B., Gruen T. L., Long J. P. 1,2-Disubstituted cyclopropane and cyclobutane derivatives related to acetylcholine. J Med Chem. 1972 Jan;15(1):71–75. doi: 10.1021/jm00271a019. [DOI] [PubMed] [Google Scholar]
  6. Casy A. F., Hassan M. M., Wu E. C. Conformation of some acetylcholine analogs as solutes in deuterium oxide and other solvents. J Pharm Sci. 1971 Jan;60(1):67–73. doi: 10.1002/jps.2600600112. [DOI] [PubMed] [Google Scholar]
  7. Chu S. H., Hillman G. R., Mautner H. G. Sulfur and selenium compounds related to acetylcholine and choline. 11. Selenocarbonyl ester and selenocarboxamide analogs of local anesthetics. J Med Chem. 1972 Jul;15(7):760–762. doi: 10.1021/jm00277a016. [DOI] [PubMed] [Google Scholar]
  8. Chu S. H., Mautner H. G. Sulfur and selenium compounds related to acetylcholine and choline. VII. Isologs of benzoylthionocholine and of 2-dimethylaminoethyl thionobenzoate. J Med Chem. 1968 May;11(3):446–450. doi: 10.1021/jm00309a006. [DOI] [PubMed] [Google Scholar]
  9. Chu S. H., Mautner H. G. Sulfur and selenium compounds related to acetylcholine and choline. X. Acetylhionocholine. J Med Chem. 1970 Mar;13(2):214–215. doi: 10.1021/jm00296a011. [DOI] [PubMed] [Google Scholar]
  10. GUENTHER W. H., MAUTNER H. G. ANALOGS OF PARASYMPATHETIC NEUROEFFECTORS. I. ACETYLSELENOCHOLINE, SELENOCHOLINE, AND RELATED COMPOUNDS. J Med Chem. 1964 Mar;7:229–232. doi: 10.1021/jm00332a023. [DOI] [PubMed] [Google Scholar]
  11. Mautner H. G., Dexter D. D., Low B. W. Conformational requirements of acetylcholine analogues and local anaesthetics. Nat New Biol. 1972 Jul 19;238(81):87–88. doi: 10.1038/newbio238087a0. [DOI] [PubMed] [Google Scholar]
  12. NACHMANSOHN D. Metabolism and function of the nerve cell. Harvey Lect. 1953;49:57–99. [PubMed] [Google Scholar]
  13. Partington P., Feeney J., Burgen A. S. The conformation of acetylcholine and related compounds in aqueous solution as studied by nuclear magnetic resonance spectroscopy. Mol Pharmacol. 1972 May;8(3):269–277. [PubMed] [Google Scholar]
  14. Shefter E., Mautner H. G. Acetylcholine and its thiolester and selenolester analogs: conformation, electron distribution, and biological activity. Proc Natl Acad Sci U S A. 1969 Aug;63(4):1253–1260. doi: 10.1073/pnas.63.4.1253. [DOI] [PMC free article] [PubMed] [Google Scholar]

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