188674-57-9Relevant articles and documents
Pyrogallol and its analogs can antagonize bacterial quorum sensing in Vibrio harveyi
Ni, Nanting,Choudhary, Gaurav,Li, Minyong,Wang, Binghe
, p. 1567 - 1572 (2008)
Bacteria can coordinate community-wide behaviors through quorum sensing, that is, the secretion and sensing of autoinducer (AI) molecules. Bacterial quorum sensing is implicated in the regulation of pathologically relevant events such as biofilm formation, bacterial virulence, and drug resistance. Inhibitors of bacterial quorum sensing could therefore be useful therapeutics. Herein we report for the first time the discovery of several pyrogallol compounds as single digit micromolar inhibitors of bacterial quorum sensing in Vibrio harveyi.
Inhibition of Pseudomonas aeruginosa quorum sensing by AI-2 analogs
Ganin, Hadas,Tang, Xu,Meijler, Michael M.
, p. 3941 - 3944 (2009)
Autoinducer-2 (AI-2) has been suggested to serve as a universal interspecies quorum sensing signaling molecule. We have synthesized a set of AI-2 analogs with small incremental changes in alkyl substitution on C-2 and evaluated them for their agonistic and antagonistic potential as quorum sensing (QS) attenuators in two different bacterial species: Pseudomonas aeruginosa and Vibrio harveyi. Unexpectedly, several of the analogs were found to function as synergistic QS agonists in V. harveyi, while two of these analogs inhibit QS in P. aeruginosa.
Synthesis and biological validation of a ubiquitous quorum-sensing molecule
Meijler, Michael M.,Hom, Louis G.,Kaufmann, Gunnar F.,McKenzie, Kathleen M.,Sun, Chengzao,Moss, Jason A.,Matsushita, Masayuki,Janda, Kim D.
, p. 2106 - 2108 (2004)
Chemical communication ("quorum sensing") amongst bacteria has been studied by the synthesis and study of enantiopure (R)-4,5-dihydroxy-2,3- pentanedione (DPD, see scheme). Bioactivity assays with DPD have shown that chelation of boron by the cyclic form of DPD appears to be essential for full induction of bioluminescence, which is an example of quorum-sensing-controlled behavior.
5-(2-Aminoethyl)dithio-2-nitrobenzoate as a more base-stable alternative to ellman's reagent
Zhu, Jinge,Dhimitruka, Ilirian,Pei, Dehua
, p. 3809 - 3812 (2004)
(Chemical Equation Presented) 5-(2-Aminoethyl)dithio-2-nitrobenzoate (ADNB) reacts with free thiols with kinetics similar to those of Ellman's reagent but has dramatically improved stability under alkaline conditions, making it an excellent alternative to Ellman's reagent for the quantitation of thiol contents and enzymatic assays under basic pH conditions.
Maillard Browning Inhibition by Ellagic Acid via Its Adduct Formation with the Amadori Rearrangement Product
Cui, Heping,Hayat, Khizar,Ho, Chi-Tang,Ma, Mengyu,Wang, Ziyan,Xu, Yan,Zhang, Qiang,Zhang, Xiaoming
, p. 9924 - 9933 (2021/09/11)
The Maillard reaction performed under a stepwise increase of temperature was applied for researching the inhibition of Maillard browning caused by ellagic acid. Ellagic acid was found effective for the inhibition of melanoidin formation in the xylose-glycine Maillard reaction but depended on its dosage and the point of time it was added in the reaction system. The lightest color of the Maillard reaction products was observed when ellagic acid was added at the 90th min, which was the point of time when the Amadori rearrangement product (ARP) developed the most. LC-ESI-MS/MS analysis results showed a significant tendency of the ellagic acid hydrolysis product to react with the predominant intermediate ARP to yield an adduct. The adduct stabilized the ARP and delayed its decomposition and inhibited the downstream reactions toward browning. After the ARP was depleted, ellagic acid also showed an effect on scavenging some short-chain dicarbonyls which contributed to the inhibition of Maillard browning.
A versatile strategy for the synthesis of 4,5-dihydroxy-2,3-pentanedione (DPD) and related compounds as potential modulators of bacterial quorum sensing
Stotani, Silvia,Gatta, Viviana,Medda, Federico,Padmanaban, Mohan,Karawajczyk, Anna,Tammela, P?ivi,Giordanetto, Fabrizio,Tzalis, Dimitrios,Collina, Simona
, (2018/10/20)
Resistance to antibiotics is an increasingly serious threat to global public health and its management translates to significant health care costs. The validation of new Gram-negative antibacterial targets as sources for potential new antibiotics remains a challenge for all the scientists working in this field. The interference with bacterial Quorum Sensing (QS) mechanisms represents a potentially interesting approach to control bacterial growth and pursue the next generation of antimicrobials. In this context, our research is focused on the discovery of novel compounds structurally related to (S)-4,5-dihydroxy-2,3-pentanedione, commonly known as (S)-DPD, a small signaling molecule able to modulate bacterial QS in both Gram-negative and Gram-positive bacteria. In this study, a practical and versatile synthesis of racemic DPD is presented. Compared to previously reported syntheses, the proposed strategy is short and robust: it requires only one purification step and avoids the use of expensive or hazardous starting materials as well as the use of specific equipment. It is therefore well suited to the synthesis of derivatives for pharmaceutical research, as demonstrated by four series of novel DPD-related compounds described herein.
