Skip to main content
PMC home page
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
. 1969 Aug;63(4):1253–1260. doi: 10.1073/pnas.63.4.1253

ACETYLCHOLINE AND ITS THIOLESTER AND SELENOLESTER ANALOGS: CONFORMATION, ELECTRON DISTRIBUTION, AND BIOLOGICAL ACTIVITY*

Eli Shefter 1,2, Henry G Mautner 1,2
PMCID: PMC223458  PMID: 5260928

Abstract

The crystal structures of acetylthiolcholine bromide and propionylthiolcholine iodide were elucidated. Acetylthiolcholine was found to be essentially isosteric with acetylselenolcholine, while the conformation of these compounds was quite different from that of acetylcholine.

The importance of conformation and electron distribution in the biological actions of choline esters is discussed.

Full text

PDF
1253

Selected References

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

  1. Abrahamsson S., Pascher I. Crystal and molecular structure of L-alpha-glycerylphosphorylcholin. Acta Crystallogr. 1966 Jul 10;21(1):79–87. doi: 10.1107/s0365110x66002366. [DOI] [PubMed] [Google Scholar]
  2. 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]
  3. 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]
  4. Kier L. B. Molecular orbital calculation of preferred conformations of acetylcholine, muscarine, and muscarone. Mol Pharmacol. 1967 Sep;3(5):487–494. [PubMed] [Google Scholar]
  5. Krupka R. M. Chemical structure and function of the active center of acetylcholinesterase. Biochemistry. 1966 Jun;5(6):1988–1997. doi: 10.1021/bi00870a029. [DOI] [PubMed] [Google Scholar]
  6. Liquori A. M., Damiani A., De Coen J. L. Calculated minimum energy conformations of acetylcholine. J Mol Biol. 1968 Apr 28;33(2):445–450. doi: 10.1016/0022-2836(68)90201-5. [DOI] [PubMed] [Google Scholar]
  7. Mautner H. G., Bartels E., Webb G. D. Sulfur and selenium isologs related to acetycholine. and choline IV. Activity in the electroplax preparation. Biochem Pharmacol. 1966 Feb;15(2):187–193. doi: 10.1016/0006-2952(66)90059-1. [DOI] [PubMed] [Google Scholar]
  8. NACHMANSOHN D. Metabolism and function of the nerve cell. Harvey Lect. 1953;49:57–99. [PubMed] [Google Scholar]
  9. Rosenberg P., Mautner H. G. Acetylcholine receptor: similarity in axons and junctions. Science. 1967 Mar 24;155(3769):1569–1571. doi: 10.1126/science.155.3769.1569. [DOI] [PubMed] [Google Scholar]
  10. Rosenberg P., Mautner H. G., Nachmansohn D. Similarity of effects of oxygen, sulfur, and selenium isologs on the acetylcholine receptor in excitable membranes of junctions and axons. Proc Natl Acad Sci U S A. 1966 Apr;55(4):835–838. doi: 10.1073/pnas.55.4.835. [DOI] [PMC free article] [PubMed] [Google Scholar]
  11. SCOTT K. A., MAUTNER H. G. ANALOGS OF PARASYMPATHETIC NEUROEFFECTORS. II. COMPARATIVE PHARMACOLOGICAL STUDIES OF ACETYLCHOLINE, ITS THIO AND SELENO ANALOGS, AND THEIR HYDROLYSIS PRODUCTS. Biochem Pharmacol. 1964 Jun;13:907–920. doi: 10.1016/0006-2952(64)90034-6. [DOI] [PubMed] [Google Scholar]
  12. Scott K. A., Mautner H. G. Sulfur and selenium isologs related to acetylcholine and choline. IX. Further comparative studies of the pharmacological effects of acetylcholine and its thio and seleno analogs and their hydrolysis products. Biochem Pharmacol. 1967 Oct;16(10):1903–1918. doi: 10.1016/0006-2952(67)90301-2. [DOI] [PubMed] [Google Scholar]
  13. Shefter E. Crystal structure of thiolphthalide. J Pharm Sci. 1968 Jan;57(1):175–177. doi: 10.1002/jps.2600570139. [DOI] [PubMed] [Google Scholar]
  14. Shefter E., Kennard O. Crystal and molecular structure of acetylselenocholine iodide. Science. 1966 Sep 16;153(3742):1389–1390. doi: 10.1126/science.153.3742.1389. [DOI] [PubMed] [Google Scholar]
  15. Shefter E., Mautner H. G. The crystal and molecular structure of 2,4-dithiouracil. J Am Chem Soc. 1967 Mar 1;89(5):1249–1253. doi: 10.1021/ja00981a035. [DOI] [PubMed] [Google Scholar]
  16. WASER P. G. Chemistry and pharmacology of muscarine, muscarone, and some related compounds. Pharmacol Rev. 1961 Dec;13:465–515. [PubMed] [Google Scholar]
  17. Webb G. D., Mautner H. G. Sulfur and selenium compounds related to acetylcholine and choline. VI. Effects of homocholine derivatives on the electroplax preparation. Biochem Pharmacol. 1966 Dec;15(12):2105–2111. doi: 10.1016/0006-2952(66)90240-1. [DOI] [PubMed] [Google Scholar]

Articles from Proceedings of the National Academy of Sciences of the United States of America are provided here courtesy of National Academy of Sciences

RESOURCES