Substituent effect of side chains on the photochemical behavior of a new generation 1,4-dihydropyridine: Lercanidipine

Sebastián Cumsille, Javier Morales, Catalina Sandoval-Altamirano, Germán Günther, Andrés Vega, Nancy Pizarro

Resultado de la investigación: Contribución a la publicaciónArticle

Resumen

Lercanidipine (LERCA) is a third generation antihypertensive drug belonging to the 1,4-dihydropyridine's family, which has been reported to induce photoallergic and/or phototoxic effects in patients with long term treatment. The electronic nature of substituents on the 4-aryl moiety bonded to the 1,4-dihydropyridine ring has been described to strongly affect the photophysical and photochemical behavior of this family of compounds, which displays a typical absorption band around 360 nm. LERCA undergoes photodegradation after excitation, with a first order kinetic, in significant competition to the radiative path. The photodegradation quantum yields for LERCA are higher than for its homologue nimodipine (NIMO), thus indicating that the substituents on the 1,4-dihydropyridinic ring also affect their photophysical and photochemical properties. The media where the photodegradation takes place impacts on the product profile, in a homogeneous one the photoproducts obtained appear to be more polar than those obtained for a micro-heterogeneous one (micelles or bilayers mimicking biological media).

IdiomaEnglish
Páginas1-9
Número de páginas9
PublicaciónJournal of Photochemistry and Photobiology A: Chemistry
Volumen353
DOI
EstadoPublished - 15 feb 2018

Huella dactilar

Photodegradation
Nimodipine
rings
Micelles
Quantum yield
Antihypertensive Agents
Absorption spectra
micelles
drugs
absorption spectra
Kinetics
kinetics
products
profiles
electronics
excitation
1,4-dihydropyridine
lercanidipine

Keywords

    ASJC Scopus subject areas

    • Chemistry(all)
    • Chemical Engineering(all)
    • Physics and Astronomy(all)

    Citar esto

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    title = "Substituent effect of side chains on the photochemical behavior of a new generation 1,4-dihydropyridine: Lercanidipine",
    abstract = "Lercanidipine (LERCA) is a third generation antihypertensive drug belonging to the 1,4-dihydropyridine's family, which has been reported to induce photoallergic and/or phototoxic effects in patients with long term treatment. The electronic nature of substituents on the 4-aryl moiety bonded to the 1,4-dihydropyridine ring has been described to strongly affect the photophysical and photochemical behavior of this family of compounds, which displays a typical absorption band around 360 nm. LERCA undergoes photodegradation after excitation, with a first order kinetic, in significant competition to the radiative path. The photodegradation quantum yields for LERCA are higher than for its homologue nimodipine (NIMO), thus indicating that the substituents on the 1,4-dihydropyridinic ring also affect their photophysical and photochemical properties. The media where the photodegradation takes place impacts on the product profile, in a homogeneous one the photoproducts obtained appear to be more polar than those obtained for a micro-heterogeneous one (micelles or bilayers mimicking biological media).",
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    author = "Sebasti{\'a}n Cumsille and Javier Morales and Catalina Sandoval-Altamirano and Germ{\'a}n G{\"u}nther and Andr{\'e}s Vega and Nancy Pizarro",
    note = "Enviada a pago 02-02-2018",
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    Substituent effect of side chains on the photochemical behavior of a new generation 1,4-dihydropyridine : Lercanidipine. / Cumsille, Sebastián; Morales, Javier; Sandoval-Altamirano, Catalina; Günther, Germán; Vega, Andrés; Pizarro, Nancy.

    En: Journal of Photochemistry and Photobiology A: Chemistry, Vol. 353, 15.02.2018, p. 1-9.

    Resultado de la investigación: Contribución a la publicaciónArticle

    TY - JOUR

    T1 - Substituent effect of side chains on the photochemical behavior of a new generation 1,4-dihydropyridine

    T2 - Journal of Photochemistry and Photobiology A: Chemistry

    AU - Cumsille,Sebastián

    AU - Morales,Javier

    AU - Sandoval-Altamirano,Catalina

    AU - Günther,Germán

    AU - Vega,Andrés

    AU - Pizarro,Nancy

    N1 - Enviada a pago 02-02-2018

    PY - 2018/2/15

    Y1 - 2018/2/15

    N2 - Lercanidipine (LERCA) is a third generation antihypertensive drug belonging to the 1,4-dihydropyridine's family, which has been reported to induce photoallergic and/or phototoxic effects in patients with long term treatment. The electronic nature of substituents on the 4-aryl moiety bonded to the 1,4-dihydropyridine ring has been described to strongly affect the photophysical and photochemical behavior of this family of compounds, which displays a typical absorption band around 360 nm. LERCA undergoes photodegradation after excitation, with a first order kinetic, in significant competition to the radiative path. The photodegradation quantum yields for LERCA are higher than for its homologue nimodipine (NIMO), thus indicating that the substituents on the 1,4-dihydropyridinic ring also affect their photophysical and photochemical properties. The media where the photodegradation takes place impacts on the product profile, in a homogeneous one the photoproducts obtained appear to be more polar than those obtained for a micro-heterogeneous one (micelles or bilayers mimicking biological media).

    AB - Lercanidipine (LERCA) is a third generation antihypertensive drug belonging to the 1,4-dihydropyridine's family, which has been reported to induce photoallergic and/or phototoxic effects in patients with long term treatment. The electronic nature of substituents on the 4-aryl moiety bonded to the 1,4-dihydropyridine ring has been described to strongly affect the photophysical and photochemical behavior of this family of compounds, which displays a typical absorption band around 360 nm. LERCA undergoes photodegradation after excitation, with a first order kinetic, in significant competition to the radiative path. The photodegradation quantum yields for LERCA are higher than for its homologue nimodipine (NIMO), thus indicating that the substituents on the 1,4-dihydropyridinic ring also affect their photophysical and photochemical properties. The media where the photodegradation takes place impacts on the product profile, in a homogeneous one the photoproducts obtained appear to be more polar than those obtained for a micro-heterogeneous one (micelles or bilayers mimicking biological media).

    KW - Lercanidipine

    KW - Photolability

    KW - Substituent effect

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