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A mechanistic hypot...
A mechanistic hypothesis for the cytochrome P450-catalyzed cis-trans isomerization of 4-hydroxytamoxifen : an unusual redox reaction
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- Gao, Li (författare)
- Örebro universitet,Akademin för naturvetenskap och teknik,Örebro Life Science Center, School of Science and Technology, Örebro University
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- Tu, Yaoquan (författare)
- Örebro universitet,Akademin för naturvetenskap och teknik
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- Wegman [Palmebäck-Wegman], Pia (författare)
- Örebro universitet,Hälsoakademin
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- Wingren, Sten (författare)
- Örebro universitet,Hälsoakademin
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Eriksson, Leif A. (författare)
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(creator_code:org_t)
- 2011-09-13
- 2011
- Engelska.
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Ingår i: Journal of Chemical Information and Modeling. - : American Chemical Society (ACS). - 1549-9596 .- 1549-960X. ; 51:9, s. 2293-2301
- Relaterad länk:
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https://urn.kb.se/re...
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https://doi.org/10.1...
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https://urn.kb.se/re...
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Abstract
Ämnesord
Stäng
- We provide a detailed description of the cis-trans isomerization of 4-hydroxytamoxifen/endoxifen catalyzed by several isoforms from the cytochrome P450 (CYP) superfamily, including CYP1B1, CYP2B6, and CYP2C19. We show that the reactions mainly involve redox processes catalyzed by CYP, DFT calculation results strongly suggest that the isomerization occurs via a cationic intermediate. The cationic cis-isomer is more than 3 kcal/mol more stable than the trans form, resulting in an easier conversion from trans-to-cis than cis-to-trans. The cis-trans isomerization is a rarely reported CYP reaction and is ascribed to the lack of a second abstractable proton on the ethenyl group of the triarylvinyl class of substrates. The cationic intermediates thus formed instead of the stable dehydrogenation products allow for isomerization to occur. As a comparison, the reactions for the tamoxifen derivatives are compared to those of other substrates, 4-hydroxyacetanilide and raloxifene, for which the stable dehydrogenation products are formed.
Ämnesord
- NATURVETENSKAP -- Kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences (hsv//eng)
- MEDICIN OCH HÄLSOVETENSKAP -- Medicinsk bioteknologi -- Biomedicinsk laboratorievetenskap/teknologi (hsv//swe)
- MEDICAL AND HEALTH SCIENCES -- Medical Biotechnology -- Biomedical Laboratory Science/Technology (hsv//eng)
Nyckelord
- Chemistry
- Kemi
- Biomedicin
- Biomedicine
Publikations- och innehållstyp
- ref (ämneskategori)
- art (ämneskategori)
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