Photostability Testing of a Third-Generation Retinoid—Tazarotene in the Presence of UV Absorbers
Exposure of a drug to UV irradiation could affect its physicochemical properties. Hence, photostability testing is essential for topically administered drugs. Tazarotene, a receptor-selective, third-generation retinoid, is commonly used to treat acne vulgaris and psoriasis. In the present study, an...
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| Published in: | Pharmaceutics Vol. 12; no. 9; p. 899 |
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| Main Authors: | , , , , , , |
| Format: | Journal Article |
| Language: | English |
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| ISSN: | 1999-4923, 1999-4923 |
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| Abstract | Exposure of a drug to UV irradiation could affect its physicochemical properties. Hence, photostability testing is essential for topically administered drugs. Tazarotene, a receptor-selective, third-generation retinoid, is commonly used to treat acne vulgaris and psoriasis. In the present study, an in-depth analysis of the photostability of tazarotene in ethanolic solution in the presence of zinc oxide and/or titanium dioxide as well as benzophenone-type UV filters was performed. Eleven presumed products were derived from the photocatalytic degradation of tazarotene using ultra-performance liquid chromatography–tandem mass spectrometry, and transformation pathways were proposed. The degradation process mainly affected the 4,4-dimethyl-3,4-dihydro-2H-thiopyran moiety. The fragments most susceptible to oxidation were the methyl groups and the sulfur atom. Moreover, in the presence of sulisobenzone, under UV irradiation, tazarotene was subjected to a degradation process, which resulted in two photodecomposition products. In silico studies performed by OSIRIS Property Explorer demonstrated that five of the degradation products could be harmful in terms of the reproductive effects, which are associated with 3,4-dihydro-6-methyl-2H-1-benzothiopyran 1,1-dioxide, while one of them demonstrated potential irritant activity. The cytotoxic properties of the degradation products of tazarotene were assessed by MTT assay on a panel of human adherent cancer cells. Time- and concentration-dependent growth inhibition was evidenced in ovary (A2780) and breast (MDA-MB-231) cancer cell lines. The potential implication of the outcomes of the present research requires further studies mainly concerning the photostability of tazarotene in the topical formulations. |
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| AbstractList | Exposure of a drug to UV irradiation could affect its physicochemical properties. Hence, photostability testing is essential for topically administered drugs. Tazarotene, a receptor-selective, third-generation retinoid, is commonly used to treat acne vulgaris and psoriasis. In the present study, an in-depth analysis of the photostability of tazarotene in ethanolic solution in the presence of zinc oxide and/or titanium dioxide as well as benzophenone-type UV filters was performed. Eleven presumed products were derived from the photocatalytic degradation of tazarotene using ultra-performance liquid chromatography–tandem mass spectrometry, and transformation pathways were proposed. The degradation process mainly affected the 4,4-dimethyl-3,4-dihydro-2H-thiopyran moiety. The fragments most susceptible to oxidation were the methyl groups and the sulfur atom. Moreover, in the presence of sulisobenzone, under UV irradiation, tazarotene was subjected to a degradation process, which resulted in two photodecomposition products. In silico studies performed by OSIRIS Property Explorer demonstrated that five of the degradation products could be harmful in terms of the reproductive effects, which are associated with 3,4-dihydro-6-methyl-2H-1-benzothiopyran 1,1-dioxide, while one of them demonstrated potential irritant activity. The cytotoxic properties of the degradation products of tazarotene were assessed by MTT assay on a panel of human adherent cancer cells. Time- and concentration-dependent growth inhibition was evidenced in ovary (A2780) and breast (MDA-MB-231) cancer cell lines. The potential implication of the outcomes of the present research requires further studies mainly concerning the photostability of tazarotene in the topical formulations. Exposure of a drug to UV irradiation could affect its physicochemical properties. Hence, photostability testing is essential for topically administered drugs. Tazarotene, a receptor-selective, third-generation retinoid, is commonly used to treat acne vulgaris and psoriasis. In the present study, an in-depth analysis of the photostability of tazarotene in ethanolic solution in the presence of zinc oxide and/or titanium dioxide as well as benzophenone-type UV filters was performed. Eleven presumed products were derived from the photocatalytic degradation of tazarotene using ultra-performance liquid chromatography-tandem mass spectrometry, and transformation pathways were proposed. The degradation process mainly affected the 4,4-dimethyl-3,4-dihydro-2H-thiopyran moiety. The fragments most susceptible to oxidation were the methyl groups and the sulfur atom. Moreover, in the presence of sulisobenzone, under UV irradiation, tazarotene was subjected to a degradation process, which resulted in two photodecomposition products. In silico studies performed by OSIRIS Property Explorer demonstrated that five of the degradation products could be harmful in terms of the reproductive effects, which are associated with 3,4-dihydro-6-methyl-2H-1-benzothiopyran 1,1-dioxide, while one of them demonstrated potential irritant activity. The cytotoxic properties of the degradation products of tazarotene were assessed by MTT assay on a panel of human adherent cancer cells. Time- and concentration-dependent growth inhibition was evidenced in ovary (A2780) and breast (MDA-MB-231) cancer cell lines. The potential implication of the outcomes of the present research requires further studies mainly concerning the photostability of tazarotene in the topical formulations.Exposure of a drug to UV irradiation could affect its physicochemical properties. Hence, photostability testing is essential for topically administered drugs. Tazarotene, a receptor-selective, third-generation retinoid, is commonly used to treat acne vulgaris and psoriasis. In the present study, an in-depth analysis of the photostability of tazarotene in ethanolic solution in the presence of zinc oxide and/or titanium dioxide as well as benzophenone-type UV filters was performed. Eleven presumed products were derived from the photocatalytic degradation of tazarotene using ultra-performance liquid chromatography-tandem mass spectrometry, and transformation pathways were proposed. The degradation process mainly affected the 4,4-dimethyl-3,4-dihydro-2H-thiopyran moiety. The fragments most susceptible to oxidation were the methyl groups and the sulfur atom. Moreover, in the presence of sulisobenzone, under UV irradiation, tazarotene was subjected to a degradation process, which resulted in two photodecomposition products. In silico studies performed by OSIRIS Property Explorer demonstrated that five of the degradation products could be harmful in terms of the reproductive effects, which are associated with 3,4-dihydro-6-methyl-2H-1-benzothiopyran 1,1-dioxide, while one of them demonstrated potential irritant activity. The cytotoxic properties of the degradation products of tazarotene were assessed by MTT assay on a panel of human adherent cancer cells. Time- and concentration-dependent growth inhibition was evidenced in ovary (A2780) and breast (MDA-MB-231) cancer cell lines. The potential implication of the outcomes of the present research requires further studies mainly concerning the photostability of tazarotene in the topical formulations. |
| Author | Kryczyk-Poprawa, Agata Zupkó, István Opoka, Włodzimierz Muszyńska, Bożena Żmudzki, Paweł Bérdi, Péter Popiół, Justyna |
| AuthorAffiliation | 6 Department of Pharmaceutical Botany, Jagiellonian University Collegium Medicum, 30-688 Kraków, Poland; muchon@poczta.fm 4 Department of Medicinal Chemistry, Jagiellonian University Medical College, 30-688 Kraków, Poland; pawel.zmudzki@uj.edu.pl 2 Department of Pharmacodynamics and Biopharmacy, University of Szeged, 6720 Szeged, Hungary; zupko@pharm.u-szeged.hu (I.Z.); berdi.peter@pharm.u-szeged.hu (P.B.) 1 Department of Inorganic and Analytical Chemistry, Jagiellonian University Medical College, 30-688 Kraków, Poland; wlodzimierz.opoka@uj.edu.pl 3 Interdisciplinary Center for Natural Products, University of Szeged, 6720 Szeged, Hungary 5 Department of Pharmaceutical Biochemistry, Jagiellonian University Medical College, 30-688 Kraków, Poland; justyna.popiol@uj.edu.pl |
| AuthorAffiliation_xml | – name: 3 Interdisciplinary Center for Natural Products, University of Szeged, 6720 Szeged, Hungary – name: 5 Department of Pharmaceutical Biochemistry, Jagiellonian University Medical College, 30-688 Kraków, Poland; justyna.popiol@uj.edu.pl – name: 6 Department of Pharmaceutical Botany, Jagiellonian University Collegium Medicum, 30-688 Kraków, Poland; muchon@poczta.fm – name: 1 Department of Inorganic and Analytical Chemistry, Jagiellonian University Medical College, 30-688 Kraków, Poland; wlodzimierz.opoka@uj.edu.pl – name: 2 Department of Pharmacodynamics and Biopharmacy, University of Szeged, 6720 Szeged, Hungary; zupko@pharm.u-szeged.hu (I.Z.); berdi.peter@pharm.u-szeged.hu (P.B.) – name: 4 Department of Medicinal Chemistry, Jagiellonian University Medical College, 30-688 Kraków, Poland; pawel.zmudzki@uj.edu.pl |
| Author_xml | – sequence: 1 givenname: Agata orcidid: 0000-0001-9125-250X surname: Kryczyk-Poprawa fullname: Kryczyk-Poprawa, Agata – sequence: 2 givenname: István orcidid: 0000-0003-3243-5300 surname: Zupkó fullname: Zupkó, István – sequence: 3 givenname: Péter surname: Bérdi fullname: Bérdi, Péter – sequence: 4 givenname: Paweł orcidid: 0000-0003-3594-1241 surname: Żmudzki fullname: Żmudzki, Paweł – sequence: 5 givenname: Justyna orcidid: 0000-0002-9825-4302 surname: Popiół fullname: Popiół, Justyna – sequence: 6 givenname: Bożena orcidid: 0000-0002-5007-1486 surname: Muszyńska fullname: Muszyńska, Bożena – sequence: 7 givenname: Włodzimierz surname: Opoka fullname: Opoka, Włodzimierz |
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