title: Photoprotective effect and acute oral systemic toxicity evaluation of the novel heterocyclic compound LQFM048.
abstract: The new heterocyclic derivative LQFM048 (3) (2,4,6-tris ((E)-ethyl 2-cyano-3-(4-hydroxy-3-methoxyphenyl)acrylate)-1,3,5-triazine) was originally designed through the molecular hybridization strategy from Uvinul® T 150 (1) and (E)-ethyl 2-cyano-3-(4hydroxy-3-methoxyphenyl)acrylate (2) sunscreens, using green chemistry approach. This compound was obtained in global yields (80%) and showed an interesting redox potential. In addition, it is thermally stable up to temperatures around 250°C. It was observed that LQFM048 (3) showed a low degradation after 150min of sunlight exposure at 39°C, whereas the extreme radiation conditions induced a considerable photodegradation of the LQFM048 (3), especially when irradiated by VIS and VIS+UVA. During the determination of sun protection factor, LQFM048 (3) showed interesting results, specially as in association with other photoprotective compounds and commercial sunscreen. Additionally, the compound (3) did not promote cytotoxicity for 3T3 fibroblasts. Moreover, it was not able to trigger acute oral systemic toxicity in mice, being classified as a compound with low acute toxicity hazard (2.000mg/kg>LD50<5.000mg/kg). Therefore, this compound synthesized using green chemistry approach is promising showing potential to development of a new sunscreen product with advantage of presenting redox potential, indicating antioxidant properties.
authors.affiliation: Laboratório de Química Farmacêutica Medicinal (LQFM), Faculdade de Farmácia, Universidade Federal de Goiás, Goiânia, GO, Brazil.
authors.forename: Daniela C
authors.initials: DC
authors.lastname: Vinhal
authors.affiliation: Laboratório de Farmacologia e Toxicologia Celular, LFTC/FarmaTec, Faculdade de Farmácia, Universidade Federal de Goiás, Goiânia, GO, Brazil.
authors.forename: Renato Ivan
authors.initials: RI
authors.lastname: de Ávila
authors.affiliation: Laboratório de Farmacologia e Toxicologia Celular, LFTC/FarmaTec, Faculdade de Farmácia, Universidade Federal de Goiás, Goiânia, GO, Brazil.
authors.forename: Marcelo S
authors.initials: MS
authors.lastname: Vieira
authors.affiliation: Laboratório de Ressonância Magnética Nuclear, Instituto de Química, Universidade Federal de Goiás, Goiânia, GO, Brazil.
authors.forename: Rangel M
authors.initials: RM
authors.lastname: Luzin
authors.affiliation: Laboratório de Ressonância Magnética Nuclear, Instituto de Química, Universidade Federal de Goiás, Goiânia, GO, Brazil.
authors.forename: Michelle P
authors.initials: MP
authors.lastname: Quintino
authors.affiliation: Instituto de Química, Universidade Federal de Goiás, Goiânia, GO, Brazil.
authors.forename: Liliane M
authors.initials: LM
authors.lastname: Nunes
authors.affiliation: Instituto de Química, Universidade Federal de Goiás, Goiânia, GO, Brazil.
authors.forename: Antonio Carlos Chaves
authors.initials: AC
authors.lastname: Ribeiro
authors.affiliation: Instituto de Química, Universidade Federal de Goiás, Goiânia, GO, Brazil.
authors.forename: Henrique Santiago
authors.initials: HS
authors.lastname: de Camargo
authors.affiliation: Laboratório de Espectrometria de Massas, LABEM, Universidade Federal do Rio de Janeiro, Rio de Janeiro, RJ, Brazil.
authors.forename: Angelo C
authors.initials: AC
authors.lastname: Pinto
authors.affiliation: Laboratório de Espectrometria de Massas, LABEM, Universidade Federal do Rio de Janeiro, Rio de Janeiro, RJ, Brazil.
authors.forename: Helvécio M
authors.initials: HM
authors.lastname: Dos Santos Júnior
authors.affiliation: Laboratório de Cosmetologia, LaCos, Departamento de Fármacos e Medicamentos, Faculdade de Ciências Farmacêuticas, Universidade Estadual Paulista Júlio de Mesquita Filho, Araraquara, SP, Brazil.
authors.forename: Bruna G
authors.initials: BG
authors.lastname: Chiari
authors.affiliation: Laboratório de Cosmetologia, LaCos, Departamento de Fármacos e Medicamentos, Faculdade de Ciências Farmacêuticas, Universidade Estadual Paulista Júlio de Mesquita Filho, Araraquara, SP, Brazil.
authors.forename: Vera
authors.initials: V
authors.lastname: Isaac
authors.affiliation: Laboratório de Farmacologia e Toxicologia Celular, LFTC/FarmaTec, Faculdade de Farmácia, Universidade Federal de Goiás, Goiânia, GO, Brazil. Electronic address: marizeufg@gmail.com.
authors.forename: Marize C
authors.initials: MC
authors.lastname: Valadares
authors.affiliation: Instituto de Química, Universidade Federal de Goiás, Goiânia, GO, Brazil.
authors.forename: Tatiana Duque
authors.initials: TD
authors.lastname: Martins
authors.affiliation: Laboratório de Ressonância Magnética Nuclear, Instituto de Química, Universidade Federal de Goiás, Goiânia, GO, Brazil.
authors.forename: Luciano M
authors.initials: LM
authors.lastname: Lião
authors.affiliation: Laboratório de Espectrometria de Massas, LABEM, Universidade Federal do Rio de Janeiro, Rio de Janeiro, RJ, Brazil.
authors.forename: Eric
authors.initials: E
authors.lastname: de S Gil
authors.affiliation: Laboratório de Química Farmacêutica Medicinal (LQFM), Faculdade de Farmácia, Universidade Federal de Goiás, Goiânia, GO, Brazil. Electronic address: rm_rj@yahoo.com.
authors.forename: Ricardo
authors.initials: R
authors.lastname: Menegatti
mesh_terms: D016475:3T3 Cells; D000818:Animals; D000975:Antioxidants / Q000737:chemistry / Q000494:pharmacology / Q000633:toxicity; D017209:Apoptosis / Q000187:drug effects*; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects; D055664:Electrochemical Techniques; D006571:Heterocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D008297:Male; D051379:Mice; D008968:Molecular Conformation; D010782:Photolysis / Q000528:radiation effects; D059405:Sun Protection Factor; D013473:Sunscreening Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013818:Thermogravimetry; D014227:Triazines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D014466:Ultraviolet Rays
chemical_list: D000975:Antioxidants; D006571:Heterocyclic Compounds; D013473:Sunscreening Agents; D014227:Triazines
keywords: Green chemistry; Heterocyclic derivative; Molecular hybridization; Photoprotection; Sunscreen