Photodegradation of Bexarotene and Its Implication for Cytotoxicity

A detailed understanding of the stability of an active pharmaceutical ingredient and a pharmaceutical dosage form is essential for the drug-development process and for safe and effective use of medicines. Photostability testing as an inherent part of stability studies provides valuable knowledge on...

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Vydané v:	Pharmaceutics Ročník 13; číslo 8; s. 1220
Hlavní autori:	Kryczyk-Poprawa, Agata, Zupkó, István, Bérdi, Péter, Żmudzki, Paweł, Piotrowska, Joanna, Pękala, Elżbieta, Berdys, Aleksandra, Muszyńska, Bożena, Opoka, Włodzimierz
Médium:	Journal Article
Jazyk:	English
Vydavateľské údaje:	Basel MDPI AG 07.08.2021 MDPI
Predmet:	Acne Alzheimer's disease bexarotene Breast cancer Cancer therapies Cosmetics Drugs Ethanol Experiments Lung cancer Metastasis Ovarian cancer Particle size Pharmaceuticals Photodegradation photostability Reagents Skin third-generation retinoids Toxicity UV absorbers Zinc oxides Poland United States > US Europe Germany
ISSN:	1999-4923, 1999-4923
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Abstract	A detailed understanding of the stability of an active pharmaceutical ingredient and a pharmaceutical dosage form is essential for the drug-development process and for safe and effective use of medicines. Photostability testing as an inherent part of stability studies provides valuable knowledge on degradation pathways and structures of products generated under UV irradiation. Photostability is particularly important for topically administered drugs, as they are more exposed to UV radiation. Bexarotene is a more recent third-generation retinoid approved by the U.S. Food and Drug Administration and the European Medicines Agency as a topically applied anticancer agent. The present study aimed to assess bexarotene photostability, including the presence of UV filters, which have been permitted to be used in cosmetic products in Europe and the USA. The bexarotene photostability testing was performed in ethanol solutions and in formulations applied on PMMA plates. The UPLC-MS/MS technique was used to determine the tested substance. The presence of photocatalysts such as TiO2 or ZnO, as well as the organic UV filters avobenzone, benzophenone-3, meradimate, and homosalate, could contribute to degradation of bexarotene under UV irradiation. Four photocatalytic degradation products of bexarotene were identified for the first time. The antiproliferative properties of the degradation products of bexarotene were assessed by MTT assay on a panel of human adherent cancer cells, and concentration-dependent growth inhibition was evidenced on all tested cell lines. The cytotoxicity of the formed products after 4 h of UV irradiation was significantly higher than that of the parent compound (p < 0.05). Furthermore non-cancerous murine fibroblasts exhibited marked concentration-dependent inhibition by bexarotene, while the degradation products elicited more pronounced antiproliferative action only at the highest applied concentration.
AbstractList	A detailed understanding of the stability of an active pharmaceutical ingredient and a pharmaceutical dosage form is essential for the drug-development process and for safe and effective use of medicines. Photostability testing as an inherent part of stability studies provides valuable knowledge on degradation pathways and structures of products generated under UV irradiation. Photostability is particularly important for topically administered drugs, as they are more exposed to UV radiation. Bexarotene is a more recent third-generation retinoid approved by the U.S. Food and Drug Administration and the European Medicines Agency as a topically applied anticancer agent. The present study aimed to assess bexarotene photostability, including the presence of UV filters, which have been permitted to be used in cosmetic products in Europe and the USA. The bexarotene photostability testing was performed in ethanol solutions and in formulations applied on PMMA plates. The UPLC-MS/MS technique was used to determine the tested substance. The presence of photocatalysts such as TiO2 or ZnO, as well as the organic UV filters avobenzone, benzophenone-3, meradimate, and homosalate, could contribute to degradation of bexarotene under UV irradiation. Four photocatalytic degradation products of bexarotene were identified for the first time. The antiproliferative properties of the degradation products of bexarotene were assessed by MTT assay on a panel of human adherent cancer cells, and concentration-dependent growth inhibition was evidenced on all tested cell lines. The cytotoxicity of the formed products after 4 h of UV irradiation was significantly higher than that of the parent compound (p < 0.05). Furthermore non-cancerous murine fibroblasts exhibited marked concentration-dependent inhibition by bexarotene, while the degradation products elicited more pronounced antiproliferative action only at the highest applied concentration. A detailed understanding of the stability of an active pharmaceutical ingredient and a pharmaceutical dosage form is essential for the drug-development process and for safe and effective use of medicines. Photostability testing as an inherent part of stability studies provides valuable knowledge on degradation pathways and structures of products generated under UV irradiation. Photostability is particularly important for topically administered drugs, as they are more exposed to UV radiation. Bexarotene is a more recent third-generation retinoid approved by the U.S. Food and Drug Administration and the European Medicines Agency as a topically applied anticancer agent. The present study aimed to assess bexarotene photostability, including the presence of UV filters, which have been permitted to be used in cosmetic products in Europe and the USA. The bexarotene photostability testing was performed in ethanol solutions and in formulations applied on PMMA plates. The UPLC-MS/MS technique was used to determine the tested substance. The presence of photocatalysts such as TiO2 or ZnO, as well as the organic UV filters avobenzone, benzophenone-3, meradimate, and homosalate, could contribute to degradation of bexarotene under UV irradiation. Four photocatalytic degradation products of bexarotene were identified for the first time. The antiproliferative properties of the degradation products of bexarotene were assessed by MTT assay on a panel of human adherent cancer cells, and concentration-dependent growth inhibition was evidenced on all tested cell lines. The cytotoxicity of the formed products after 4 h of UV irradiation was significantly higher than that of the parent compound (p < 0.05). Furthermore non-cancerous murine fibroblasts exhibited marked concentration-dependent inhibition by bexarotene, while the degradation products elicited more pronounced antiproliferative action only at the highest applied concentration.A detailed understanding of the stability of an active pharmaceutical ingredient and a pharmaceutical dosage form is essential for the drug-development process and for safe and effective use of medicines. Photostability testing as an inherent part of stability studies provides valuable knowledge on degradation pathways and structures of products generated under UV irradiation. Photostability is particularly important for topically administered drugs, as they are more exposed to UV radiation. Bexarotene is a more recent third-generation retinoid approved by the U.S. Food and Drug Administration and the European Medicines Agency as a topically applied anticancer agent. The present study aimed to assess bexarotene photostability, including the presence of UV filters, which have been permitted to be used in cosmetic products in Europe and the USA. The bexarotene photostability testing was performed in ethanol solutions and in formulations applied on PMMA plates. The UPLC-MS/MS technique was used to determine the tested substance. The presence of photocatalysts such as TiO2 or ZnO, as well as the organic UV filters avobenzone, benzophenone-3, meradimate, and homosalate, could contribute to degradation of bexarotene under UV irradiation. Four photocatalytic degradation products of bexarotene were identified for the first time. The antiproliferative properties of the degradation products of bexarotene were assessed by MTT assay on a panel of human adherent cancer cells, and concentration-dependent growth inhibition was evidenced on all tested cell lines. The cytotoxicity of the formed products after 4 h of UV irradiation was significantly higher than that of the parent compound (p < 0.05). Furthermore non-cancerous murine fibroblasts exhibited marked concentration-dependent inhibition by bexarotene, while the degradation products elicited more pronounced antiproliferative action only at the highest applied concentration.
Author	Kryczyk-Poprawa, Agata Berdys, Aleksandra Zupkó, István Opoka, Włodzimierz Muszyńska, Bożena Pękala, Elżbieta Żmudzki, Paweł Bérdi, Péter Piotrowska, Joanna
AuthorAffiliation	3 Interdisciplinary Centre for Natural Products, University of Szeged, H-6720 Szeged, Hungary 1 Department of Inorganic and Analytical Chemistry, Jagiellonian University Medical College, 30-688 Kraków, Poland; joanna.piotrowska@uj.edu.pl (J.P.); wlodzimierz.opoka@uj.edu.pl (W.O.) 5 Department of Pharmaceutical Biochemistry, Jagiellonian University Medical College, 30-688 Kraków, Poland; elzbieta.pekala@uj.edu.pl 4 Department of Medicinal Chemistry, Jagiellonian University Medical College, 30-688 Kraków, Poland; pawel.zmudzki@uj.edu.pl 7 Department of Pharmaceutical Botany, Jagiellonian University Collegium Medicum, 30-688 Kraków, Poland; muchon@poczta.fm 2 Department of Pharmacodynamics and Biopharmacy, University of Szeged, H-6720 Szeged, Hungary; zupko@pharm.u-szeged.hu (I.Z.); berdi.peter@pharm.u-szeged.hu (P.B.) 6 Independent Researchers, 30-688 Kraków, Poland; oberdys20@gmail.com
AuthorAffiliation_xml	– name: 2 Department of Pharmacodynamics and Biopharmacy, University of Szeged, H-6720 Szeged, Hungary; zupko@pharm.u-szeged.hu (I.Z.); berdi.peter@pharm.u-szeged.hu (P.B.) – name: 7 Department of Pharmaceutical Botany, Jagiellonian University Collegium Medicum, 30-688 Kraków, Poland; muchon@poczta.fm – name: 3 Interdisciplinary Centre for Natural Products, University of Szeged, H-6720 Szeged, Hungary – name: 6 Independent Researchers, 30-688 Kraków, Poland; oberdys20@gmail.com – name: 5 Department of Pharmaceutical Biochemistry, Jagiellonian University Medical College, 30-688 Kraków, Poland; elzbieta.pekala@uj.edu.pl – name: 1 Department of Inorganic and Analytical Chemistry, Jagiellonian University Medical College, 30-688 Kraków, Poland; joanna.piotrowska@uj.edu.pl (J.P.); wlodzimierz.opoka@uj.edu.pl (W.O.) – 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: Joanna surname: Piotrowska fullname: Piotrowska, Joanna – sequence: 6 givenname: Elżbieta orcidid: 0000-0002-1260-4253 surname: Pękala fullname: Pękala, Elżbieta – sequence: 7 givenname: Aleksandra surname: Berdys fullname: Berdys, Aleksandra – sequence: 8 givenname: Bożena orcidid: 0000-0002-5007-1486 surname: Muszyńska fullname: Muszyńska, Bożena – sequence: 9 givenname: Włodzimierz surname: Opoka fullname: Opoka, Włodzimierz
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CitedBy_id	crossref_primary_10_1016_j_jpba_2024_116201 crossref_primary_10_3390_molecules27051510 crossref_primary_10_1016_j_lfs_2025_123664 crossref_primary_10_3390_app15158124 crossref_primary_10_3390_pharmaceutics14020351
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SubjectTerms	Acne Alzheimer's disease bexarotene Breast cancer Cancer therapies Cosmetics Drugs Ethanol Experiments Lung cancer Metastasis Ovarian cancer Particle size Pharmaceuticals Photodegradation photostability Reagents Skin third-generation retinoids Toxicity UV absorbers Zinc oxides
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Title	Photodegradation of Bexarotene and Its Implication for Cytotoxicity
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