147993-48-4Relevant articles and documents
Design of antibacterial agents: Alkyl dihydroxybenzoates against xanthomonas citri subsp. citri
Nazaré, Ana Carolina,Polaquini, Carlos Roberto,Anselmo, Daiane Bertholin,Regasini, Luis Octavio,Cavalca, Lúcia Bonci,Ferreira, Henrique,Zielinska, Aleksandra,Scheffers, Dirk-Jan,Saiki, Marilia de Freitas Calmon,Monteiro, Diego Alves,Rahal, Paula,Gomes, Eleni
, (2018/11/21)
Xanthomonas citri subsp. citri (Xcc) causes citrus canker, affecting sweet orange-producing areas around the world. The current chemical treatment available for this disease is based on cupric compounds. For this reason, the objective of this study was to design antibacterial agents. In order to do this, we analyzed the anti-Xcc activity of 36 alkyl dihydroxybenzoates and we found 14 active compounds. Among them, three esters with the lowest minimum inhibitory concentration values were selected; compounds 4 (52 μM), 16 (80 μM) and 28 (88 μM). Our study demonstrated that alkyl dihydroxybenzoates cause a delay in the exponential phase. The permeability capacity of alkyl dihydroxybenzoates in a quarter of MIC was compared to nisin (positive control). Compound 28 was the most effective (93.8), compared to compound 16 (41.3) and compound 4 (13.9) by percentage values. Finally, all three compounds showed inhibition of FtsZ GTPase activity, and promoted changes in protofilaments, leading to depolymerization, which prevents bacterial cell division. In conclusion, heptyl dihydroxybenzoates (compounds 4, 16 and 28) are promising anti-Xcc agents which may serve as an alternative for the control of citrus canker.
Mono-/dihydroxybenzoic acid esters and phenol pyridinium derivatives as inhibitors of the mammalian carbonic anhydrase isoforms I, II, VII, IX, XII and XIV
Carta, Fabrizio,Vullo, Daniela,Maresca, Alfonso,Scozzafava, Andrea,Supuran, Claudiu T.
supporting information, p. 1564 - 1569 (2013/04/10)
Using hydroxy-/dihydroxybenzoic acids as leads, a series of methyl, ethyl and iso-propyl esters of 4-hydroxy-benzoic acid, 2,4-, 2,5-, 2,6-, 3,4-, and 3,5-dihydroxybenzoic acids and of coumaric acid, were obtained and investigated for the inhibition of six mammalian carbonic anhydrase (CA, EC 4.2.1.1) isoforms, that is, the cytosolic CA I, II and VII, and the transmembrane CA IX, XII and XIV, many of which are established drug targets. Other compounds incorporating phenol/catechol moieties were obtained from dopamine by reaction with fluorescein isothiocyanate or with 2,4,6-trisubstituted pyrylium salts. Some aminophenols were also derivatized in a similar manner, by using pyrylium salts. Many of these compounds showed increased inhibitory action compared to the lead compounds from which they were obtained, with efficacy in the submicromolar range against most investigated CA isoforms. As phenols are a class of less investigated CA inhibitors (CAIs) compared to the sulfonamides, and their mechanism of inhibition is less well understood, compounds of the type designed here may be helpful in gaining more insights into these phenomena.
Inhibitors of mammalian melanocyte tyrosinase: In vitro comparisons of alkyl esters of gentisic acid with other putative inhibitors
Curto, Ernest V.,Kwong, Cecil,Hermersdoerfer, Heino,Glatt, Hansruedi,Santis, Chie,Virador, Victoria,Hearing Jr, Vincent J.,Dooley, Thomas P.
, p. 663 - 672 (2008/04/18)
To discover safe and effective topical skin-lightening agents, we have evaluated alkyl esters of the natural product gentisic acid (GA), which is related to our lead compound methyl gentisate (MG), and four putative tyrosinase inhibitors, utilizing mammalian melanocyte cell cultures and cell-free extracts. Desirable characteristics include the ability to inhibit melanogenesis in cells (ic50 50 ~ 11 and 20 μg/mL, respectively). For comparison, hydroquinone (HQ), a commercial skin 'bleaching' agent, was a less effective enzyme inhibitor (ic50 ~ 72 μg/mL), and was highly cytotoxic to melanocytes in vitro at concentrations substantially lower than the ic50 for enzymatic inhibition. Kojic acid was a potent inhibitor of the mammalian enzyme (ic50 ~ 6 μg/mL), but did not reduce pigmentation in cells. Both arbutin and magnesium ascorbyl phosphate were ineffective in the cell-free and cell-based assays. MG at 100 μg/mL exhibited a minimal inhibitory effect on DHICA oxidase (TRP-1) and no effect on DOPAchrome tautomerase (TRP-2), suggesting that MG inhibits melanogenesis primarily via tyrosinase inhibition. MG and GA were non-mutagenic at the hprt locus in V79 Chinese hamster cells, whereas HQ was highly mutagenic and cytotoxic. The properties of MG in vitro, including (1) pigmentation inhibition in melanocytes, (2) tyrosinase inhibition and selectivity, (3) reduced cytotoxicity relative to HQ, and (4) lack of mutagenic potential in mammalian cells, establish MG as a superior candidate skin-lightening agent. Copyright (C) 1999 Elsevier Science Inc.
