Synthesis and evaluation of 1,3,5-triazine derivatives as sunscreens useful to prevent skin cancer

Detalhes bibliográficos
Autor(a) principal: Reis, Juliana Santana [UNESP]
Data de Publicação: 2019
Outros Autores: Corrêa, Marcos Antonio [UNESP], Ribeiro, Clovis Augusto [UNESP], Dos Santos, Jean Leandro [UNESP]
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da UNESP
Texto Completo: http://dx.doi.org/10.1016/j.bmcl.2019.126755
http://hdl.handle.net/11449/201333
Resumo: The incidence of skin cancers such as non-melanoma skin cancer and malignant melanoma has increased in the last few years mainly because of chronic exposure to ultraviolet (UV) radiation. Sunscreens protect the skin against harmful UV radiations; however, some limitations of these products justify the discovery of new UV filters. Novel 1,3,5-triazine derivatives (12a-h) obtained by the optimization of prototype resveratrol were synthesized and characterized. All compounds exhibited sun protection factor (SPF) and UVA protection factor (UVAPF) in the range of 3–17 and 3–13, respectively. These values were superior to resveratrol and the UV filter ethylhexyl triazone (EHT) currently available on the market. In addition, all compounds demonstrated in vitro antioxidant activity and thermal stability with the decomposition at temperatures above 236 °C. In conclusion, the novel 1,3,5-triazine derivatives have emerged as new UV filters with antioxidant effect useful to prevent skin cancer.
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spelling Synthesis and evaluation of 1,3,5-triazine derivatives as sunscreens useful to prevent skin cancer1,3,5-triazineAntioxidantEHTMolecular optimizationPhotoprotectionSkin cancerSunscreensUV filtersUV radiationThe incidence of skin cancers such as non-melanoma skin cancer and malignant melanoma has increased in the last few years mainly because of chronic exposure to ultraviolet (UV) radiation. Sunscreens protect the skin against harmful UV radiations; however, some limitations of these products justify the discovery of new UV filters. Novel 1,3,5-triazine derivatives (12a-h) obtained by the optimization of prototype resveratrol were synthesized and characterized. All compounds exhibited sun protection factor (SPF) and UVA protection factor (UVAPF) in the range of 3–17 and 3–13, respectively. These values were superior to resveratrol and the UV filter ethylhexyl triazone (EHT) currently available on the market. In addition, all compounds demonstrated in vitro antioxidant activity and thermal stability with the decomposition at temperatures above 236 °C. In conclusion, the novel 1,3,5-triazine derivatives have emerged as new UV filters with antioxidant effect useful to prevent skin cancer.Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)Universidade Estadual PaulistaSão Paulo State University (UNESP) School of Pharmaceutical ScienceSão Paulo State University (UNESP) Institute of ChemistrySão Paulo State University (UNESP) School of Pharmaceutical ScienceSão Paulo State University (UNESP) Institute of ChemistryFAPESP: 18/11079-0CNPq: 430172/2018-4Universidade Estadual Paulista (Unesp)Reis, Juliana Santana [UNESP]Corrêa, Marcos Antonio [UNESP]Ribeiro, Clovis Augusto [UNESP]Dos Santos, Jean Leandro [UNESP]2020-12-12T02:29:52Z2020-12-12T02:29:52Z2019-12-15info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://dx.doi.org/10.1016/j.bmcl.2019.126755Bioorganic and Medicinal Chemistry Letters, v. 29, n. 24, 2019.1464-34050960-894Xhttp://hdl.handle.net/11449/20133310.1016/j.bmcl.2019.1267552-s2.0-8507508572184983108918100820000-0002-7984-5908Scopusreponame:Repositório Institucional da UNESPinstname:Universidade Estadual Paulista (UNESP)instacron:UNESPengBioorganic and Medicinal Chemistry Lettersinfo:eu-repo/semantics/openAccess2024-06-24T13:46:11Zoai:repositorio.unesp.br:11449/201333Repositório InstitucionalPUBhttp://repositorio.unesp.br/oai/requestopendoar:29462024-08-05T21:05:11.996799Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)false
dc.title.none.fl_str_mv Synthesis and evaluation of 1,3,5-triazine derivatives as sunscreens useful to prevent skin cancer
title Synthesis and evaluation of 1,3,5-triazine derivatives as sunscreens useful to prevent skin cancer
spellingShingle Synthesis and evaluation of 1,3,5-triazine derivatives as sunscreens useful to prevent skin cancer
Reis, Juliana Santana [UNESP]
1,3,5-triazine
Antioxidant
EHT
Molecular optimization
Photoprotection
Skin cancer
Sunscreens
UV filters
UV radiation
title_short Synthesis and evaluation of 1,3,5-triazine derivatives as sunscreens useful to prevent skin cancer
title_full Synthesis and evaluation of 1,3,5-triazine derivatives as sunscreens useful to prevent skin cancer
title_fullStr Synthesis and evaluation of 1,3,5-triazine derivatives as sunscreens useful to prevent skin cancer
title_full_unstemmed Synthesis and evaluation of 1,3,5-triazine derivatives as sunscreens useful to prevent skin cancer
title_sort Synthesis and evaluation of 1,3,5-triazine derivatives as sunscreens useful to prevent skin cancer
author Reis, Juliana Santana [UNESP]
author_facet Reis, Juliana Santana [UNESP]
Corrêa, Marcos Antonio [UNESP]
Ribeiro, Clovis Augusto [UNESP]
Dos Santos, Jean Leandro [UNESP]
author_role author
author2 Corrêa, Marcos Antonio [UNESP]
Ribeiro, Clovis Augusto [UNESP]
Dos Santos, Jean Leandro [UNESP]
author2_role author
author
author
dc.contributor.none.fl_str_mv Universidade Estadual Paulista (Unesp)
dc.contributor.author.fl_str_mv Reis, Juliana Santana [UNESP]
Corrêa, Marcos Antonio [UNESP]
Ribeiro, Clovis Augusto [UNESP]
Dos Santos, Jean Leandro [UNESP]
dc.subject.por.fl_str_mv 1,3,5-triazine
Antioxidant
EHT
Molecular optimization
Photoprotection
Skin cancer
Sunscreens
UV filters
UV radiation
topic 1,3,5-triazine
Antioxidant
EHT
Molecular optimization
Photoprotection
Skin cancer
Sunscreens
UV filters
UV radiation
description The incidence of skin cancers such as non-melanoma skin cancer and malignant melanoma has increased in the last few years mainly because of chronic exposure to ultraviolet (UV) radiation. Sunscreens protect the skin against harmful UV radiations; however, some limitations of these products justify the discovery of new UV filters. Novel 1,3,5-triazine derivatives (12a-h) obtained by the optimization of prototype resveratrol were synthesized and characterized. All compounds exhibited sun protection factor (SPF) and UVA protection factor (UVAPF) in the range of 3–17 and 3–13, respectively. These values were superior to resveratrol and the UV filter ethylhexyl triazone (EHT) currently available on the market. In addition, all compounds demonstrated in vitro antioxidant activity and thermal stability with the decomposition at temperatures above 236 °C. In conclusion, the novel 1,3,5-triazine derivatives have emerged as new UV filters with antioxidant effect useful to prevent skin cancer.
publishDate 2019
dc.date.none.fl_str_mv 2019-12-15
2020-12-12T02:29:52Z
2020-12-12T02:29:52Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://dx.doi.org/10.1016/j.bmcl.2019.126755
Bioorganic and Medicinal Chemistry Letters, v. 29, n. 24, 2019.
1464-3405
0960-894X
http://hdl.handle.net/11449/201333
10.1016/j.bmcl.2019.126755
2-s2.0-85075085721
8498310891810082
0000-0002-7984-5908
url http://dx.doi.org/10.1016/j.bmcl.2019.126755
http://hdl.handle.net/11449/201333
identifier_str_mv Bioorganic and Medicinal Chemistry Letters, v. 29, n. 24, 2019.
1464-3405
0960-894X
10.1016/j.bmcl.2019.126755
2-s2.0-85075085721
8498310891810082
0000-0002-7984-5908
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Bioorganic and Medicinal Chemistry Letters
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.source.none.fl_str_mv Scopus
reponame:Repositório Institucional da UNESP
instname:Universidade Estadual Paulista (UNESP)
instacron:UNESP
instname_str Universidade Estadual Paulista (UNESP)
instacron_str UNESP
institution UNESP
reponame_str Repositório Institucional da UNESP
collection Repositório Institucional da UNESP
repository.name.fl_str_mv Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)
repository.mail.fl_str_mv
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