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Issue 10, 2010
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Photophysical characterization of atorvastatin (Lipitor®) ortho-hydroxy metabolite: role of hydroxyl group on the drug photochemistry

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Abstract

The influence of the phenolic hydroxyl group of ortho-hydroxy atorvastatin metabolite (Ato-OH) on the photochemistry of atorvastatin (Ato) has been evaluated by steady and time-resolved experiments. Direct excitation of Ato and Ato-OH led to phenanthrene-like intermediate formation, being ∼30% for Ato-OH less efficient than that for its parent compound in methanol. Both, Ato and Ato-OH are able to quench benzophenone (ET ∼69 kcal mol−1) and xanthone (ET ∼74 kcal mol−1) triplet excited state with rate constants close to diffusion limit control which suggest energy transfer mechanism is taking place. In fact, lower triplet energies ∼63 kcal mol−1 and π,π* character, were confirmed by DFT calculations for both compounds. Interestinlgy, only Ato-OH can act as a hydrogen donor towards triplet benzil excited state (ET ∼ 54 kcal mol−1) due to the presence of the phenolic hydroxyl group. Nevertheless, the presence of this group in Ato-OH does not modify to a significant degree the compound reactivity toward singlet oxygen. The importance of triplet energy transfer in biological systems to form Ato and Ato-OH triplet excited state as well as the hydrogen donor capacity of Ato-OH toward triplet excited state are discussed in the present communication.

Graphical abstract: Photophysical characterization of atorvastatin (Lipitor®) ortho-hydroxy metabolite: role of hydroxyl group on the drug photochemistry

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Publication details

The article was received on 28 Apr 2010, accepted on 09 Aug 2010 and first published on 27 Aug 2010


Article type: Paper
DOI: 10.1039/C0PP00102C
Citation: Photochem. Photobiol. Sci., 2010,9, 1378-1384
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    Photophysical characterization of atorvastatin (Lipitor®) ortho-hydroxy metabolite: role of hydroxyl group on the drug photochemistry

    E. Alarcón, M. González-Béjar, S. Gorelsky, R. Ebensperger, C. Lopez-Alarcón, J. C. Netto-Ferreira and J. C. Scaiano, Photochem. Photobiol. Sci., 2010, 9, 1378
    DOI: 10.1039/C0PP00102C

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