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Your search keyword '"protocatechuic acid alkyl esters"' showing total 2 results
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2 results on '"protocatechuic acid alkyl esters"'

1. Abilities of protocatechuic acid and its alkyl esters, ethyl and heptyl protocatechuates, to counteract UVB-induced oxidative injuries and photoaging in fibroblasts L929 cell line.

Author

Daré, Regina G., Oliveira, Mariana M., Truiti, Maria C.T., Nakamura, Celso V., Ximenes, Valdecir F., and Lautenschlager, Sueli O.S.

Subjects
*CELL lines, *SKIN aging, *ESTERS, *MITOCHONDRIAL membranes, *PREMATURE aging (Medicine)
Abstract

Ultraviolet B (UVB) radiation triggers the activation of many reactive oxygen species (ROS)-sensitive signaling pathways, resulting in the induction of skin damage that can progress to premature skin aging with long-term exposure. Even after the cessation of UVB radiation, the activated photosensitizers can still cause cellular injury. Thus, the use of photoprotectors that inhibit or prevent intracellular ROS production during or after UV exposure is one alternative to counteract UV-induced oxidative damage. The present study investigated the photoprotective activity of protocatechuic acid (P0) and its alkyl esters ethyl protocatechuate (P2) and heptyl protocatechuate (P7) against UVB-induced damage in L929 fibroblasts by evaluating biomarkers of oxidative stress and photoaging. P0, P2 and P7 markedly increased cell viability after UVB exposure. This protective effect was related to the ability of these compounds to absorb UVB and restore cellular redox balance even 24 h after UVB exposure. P0, P2 and P7 also decreased oxidative damage to membrane lipids, mitochondrial membrane potential, and DNA. They also inhibited the nuclear translocation of NF-κB p65 and downregulated the expression of the photoaging-related proteins matrix metalloproteinases-1 and -9 and cyclooxygenase-2. As the lipophilicity of the P0 derivatives increased, their antioxidant potency increased, but more pronounced cytotoxic effects were also detected. In summary, P0 and P2 may be promising candidates for the prevention and treatment of UVB-induced skin photodamage and photoaging. Unlabelled Image • P0, P2 and P7 exhibited antioxidant and anti-wrinkle potentials. • P0, P2 and P7 protected L929 fibroblasts against UVB-induced cytotoxicity. • P0, P2 and P7 prevented UVB-induced photodamages in L929 fibroblasts. • P0, P2 and P7 down regulated MMP-1, MMP-9 and COX-2 expressions via NF-kB pathway. • P0 and P2 were potential candidates for dermatological administration. [ABSTRACT FROM AUTHOR]

Published
2020
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2. Alkyl hydroxybenzoic acid derivatives that inhibit HIV-1 protease dimerization

Author

Vanderlan da Silva Bolzani, Michèle Reboud-Ravaux, Dulce Helena Siqueira Silva, Laure Dufau, Maicon Segalla Petrônio, Luis Octávio Regasini, Otavio Flausino, Thierry Rose, Smithsonian Institution National Museum of Natural History (NMNH), Vieillissement Cellulaire Intégré et Inflammation (VCII), Adaptation Biologique et Vieillissement = Biological Adaptation and Ageing (B2A), Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Biologie Paris Seine (IBPS), Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Biologie Paris Seine (IBPS), Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), Centre National de la Recherche Scientifique (CNRS)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Biologie Paris Seine (IBPS), Institut National de la Santé et de la Recherche Médicale (INSERM)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Biologie Paris Seine (IBPS), and Institut National de la Santé et de la Recherche Médicale (INSERM)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Models, Molecular, Hydroxybenzoic acid, Proteases, Stereochemistry, medicine.medical_treatment, protein-protein interactions, non-peptide inhibitors, Biochemistry, fluorescent probe binding, Protocatechuic acid, aromatic ring substitutions, intermolecularβ-sheet inhibitors, chemistry.chemical_compound, Structure-Activity Relationship, HIV-1 protease, HIV Protease, Gallic Acid, Drug Discovery, protocatechuic acid alkyl esters, medicine, [CHIM]Chemical Sciences, Humans, Gallic acid, Alkyl, Alkyl Hydroxybenzoic Acid, Pharmacology, chemistry.chemical_classification, Protease, biology, Chemistry, Organic Chemistry, gallic acid alkyl esters, Active site, HIV Protease Inhibitors, biology.protein, Molecular Medicine, Protein Multimerization, dimerization inhibitors, HIV-1 protease inhibition
Abstract

International audience; The therapeutic potential of gallic acid and its derivatives as anti-cancer, antimicrobial and antiviral agents is well known. We have examined the mechanism by which natural gallic acid and newly synthesized gallic acid alkyl esters and related protocatechuic acid alkyl esters inhibit HIV-1 protease to compare the influence of the aromatic ring substitutions on inhibition. We used Zhang-Poorman’s kinetic analysis and fluorescent probe binding to demonstrate that several gallic and protecatechuic acid alkyl esters inhibited HIV-1 protease by preventing the dimerization of this obligate homodimeric aspartic protease rather than targeting the active site. The tri-hydroxy substituted benzoic moiety in gallates was more favorable than the di-substituted one in protocatechuates. In both series, the type of inhibition, its mechanism and the inhibitory efficiency dramatically depended on the length of the alkyl chain: no inhibition with alkyl chains less than 8 carbon atoms long. Molecular dynamics simulations corroborated the kinetic data and propose that gallic esters are intercalated between the two N- and C-monomer ends. They complete the β-sheet and disrupt the dimeric enzyme. The best gallic ester (14 carbon atoms, Kid of 320 nM) also inhibited the multi-mutated protease MDR-HM. These results will aid the rational design of future generations of non-peptide inhibitors of HIV-1 protease dimerization that inhibit multi-mutated proteases. Finally, our work suggests the wide use of gallic and protocatechuic alkyl esters to dissociate intermolecular β-sheets involved in protein-protein interactions. - See more at: http://www.eurekaselect.com/103137/article#sthash.FvTzAG3y.dpuf

Published
2012
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