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  Structural Studies of Nicotinoids: Cotinine versus Nicotine

Uriarte, I., Pérez, C., Caballero‐Mancebo, E., Basterretxea, F. J., Lesarri, A., Fernández, J. A., et al. (2017). Structural Studies of Nicotinoids: Cotinine versus Nicotine. Chemistry – A European Journal, 23(30), 7238-7244. doi:10.1002/chem.201700023.

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Item Permalink: http://hdl.handle.net/21.11116/0000-0001-9E80-C Version Permalink: http://hdl.handle.net/21.11116/0000-0001-B4B6-6
Genre: Journal Article

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Uriarte_et_al-2017-Chemistry_-_A_European_Journal.pdf (Publisher version), 2MB
 
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https://dx.doi.org/10.1002/chem.201700023 (Publisher version)
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 Creators:
Uriarte, I.1, Author
Pérez, C.2, Author              
Caballero‐Mancebo, E.3, Author
Basterretxea, F. J.1, Author
Lesarri, A.3, Author
Fernández, J. A.1, Author
Cocinero, E. J.1, Author
Affiliations:
1Univ Basque Country, Dept Quim Fis, UPV EHU, ou_persistent22              
2Structure and Dynamics of Cold and Controlled Molecules, Independent Research Groups, Max Planck Institute for the Structure and Dynamics of Matter, Max Planck Society, ou_1938292              
3Univ Valladolid, Dept Quim Fis & Quim Inorgan, ou_persistent22              

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Free keywords: conformation analysis; intramolecular interactions; nicotinoids; rotational spectroscopy; supersonic expansion
 Abstract: Nicotinoids are agonists of the acetylcholine receptor (nAChR) and play important biochemical and pharmacological roles. Herein, we report on the structure and conformation of cotinine, and compare its molecular properties with the nicotine prototype, from which it only differs in the addition of a carbonyl group. This investigation included a theoretical survey of the effects of rotamerization of the pyridine moiety, the puckering of the pyrrolidinone ring and the internal rotation of the methyl group. The experimental work examined the rotational spectrum of the molecule in a supersonic expansion, using both broadband chirped‐pulse excitation techniques and cavity microwave spectrometers. Two conformers were observed for cotinine, and the fine and hyperfine structures arising from the two quadrupolar 14N nuclei and the methyl internal rotor were fully analyzed. The two observed conformers share the same twisted conformation of the five‐membered ring, but differ in a roughly 180° rotamerization around the C−C bond connecting the two rings. The energy barriers for the internal rotation of the methyl group in cotinine (4.55(4) and 4.64(3) kJ mol−1, respectively) are much lower than in nicotine (estimated in 16.5 kJ mol−1). The combination of different intramolecular electronic effects, hydrogen bonding and possible binding differences to receptor molecules arising from the carbonyl group could explain the lower affinity of cotinine for nAChRs.

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Language(s): eng - English
 Dates: 2017-01-032017-03-272017-03-29
 Publication Status: Published in print
 Pages: 7
 Publishing info: -
 Table of Contents: -
 Rev. Method: Peer
 Identifiers: DOI: 10.1002/chem.201700023
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Project name : Financialsupport from the MICINN and MINECO (CTQ-2014- 54464-R, CTQ-2015-68148), the BasqueGovernment (Consoli- dated Groups, IT520-10) and the UPV/EHU(UFI11/23) is grate- fully acknowledged.I.U. acknowledges an FPU contractfrom the MECD. Computational resources and laser facilities of the UPV/EHU were used in this work (SGIkerand I2Basque)and Eu- ropeanfunding(ERDF andESF)
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Title: Chemistry – A European Journal
  Other : Chem. – Eur. J.
  Other : Chem. Eur. J.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 23 (30) Sequence Number: - Start / End Page: 7238 - 7244 Identifier: ISSN: 0947-6539
CoNE: /journals/resource/954926979058