Design, synthesis and biological evaluation of 2-substituted 3-hydroxy-6-methyl-4H-pyran-4-one derivatives as Pseudomonas aeruginosa biofilm inhibitors

Li, Yibin; Huang, Zhi-Xing; Yu, Jiahui; Xu, Xiaofang; Sun, Ping‐Hua; Lin, Jing; Chen, Weimin

doi:10.1016/j.ejmech.2018.09.041

Cited by 26 publications

(12 citation statements)

References 33 publications

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“…The 4H-pyran core can be found in many natural products or pharmaceutical compounds, commonly as part of 4H-chromene skeletons (4H-1-benzopyrans) [1][2][3] . Their interesting pharmacological profile varies from antitumor, antiallergic, antimicrobial to antibacterial agent, among other properties [4][5][6][7][8][9][10] . By similarity with 1,4-dihydropyridines, 4H-pyrans have been also applied as calcium channel blockers 11 .…”

mentioning

confidence: 99%

Ultrasound-assisted multicomponent synthesis of 4H-pyrans in water and DNA binding studies

Auria‐Luna

Fernández‐Moreira

Marqués‐López

et al. 2020

Sci Rep

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A simple approach to synthesize new highly substituted 4H-pyran derivatives is described. Efficient et 3 n acts as a readily accessible catalyst of this process performed in pure water and with only a 20 mol% of catalyst loading. The extremely simple operational methodology, short reaction times, clean procedure and excellent product yields render this new approach extremely appealing for the synthesis of 4H-pyrans, as potentially biological scaffolds. Additionally, DNA interaction analysis reveals that 4H-pyran derivatives behave preferably as minor groove binders over major groove or intercalators. Therefore, this is one of the scarce examples where pyrans have resulted to be interesting DnA binders with high binding constants (K b ranges from 1.53 × 10 4 M −1 to 2.05 × 10 6 M −1).

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mentioning

confidence: 99%

Ultrasound-assisted multicomponent synthesis of 4H-pyrans in water and DNA binding studies

Auria‐Luna

Fernández‐Moreira

Marqués‐López

et al. 2020

Sci Rep

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“…This derivative showed an anti-pyocyanin activity (IC 50 of 3.65 µM in a P. aeruginosa PA14 strain) similar to the one of compound 41. The pyranone and pyridinone derivatives 42 and 43 described by Li et al were both able to inhibit biofilm formation without affecting bacterial growth with IC50s of 20.3 and 6.57 µM in a P. aeruginosa PAO1 strain, respectively (Scheme 10, Table 4) [117,118]. The compound 42 also revealed an anti-pyocyanin activity with 60% inhibition at 40 µM.…”

Section: Ilangovan Et Al Studied the Interactions Of Hhq Pqs And Othe...mentioning

confidence: 91%

Quorum Sensing Inhibitors to Quench P. aeruginosa Pathogenicity

2021

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The emergence and the dissemination of multidrug-resistant bacteria constitute a major public health issue. Among incriminated Gram-negative bacteria, Pseudomonas aeruginosa has been designated by the WHO as a critical priority threat. During the infection process, this pathogen secretes various virulence factors in order to adhere and colonize host tissues. Furthermore, P. aeruginosa has the capacity to establish biofilms that reinforce its virulence and intrinsic drug resistance. The regulation of biofilm and virulence factor production of this micro-organism is controlled by a specific bacterial communication system named Quorum Sensing (QS). The development of anti-virulence agents targeting QS that could attenuate P. aeruginosa pathogenicity without affecting its growth seems to be a promising new therapeutic strategy. This could prevent the selective pressure put on bacteria by the conventional antibiotics that cause their death and promote resistant strain survival. This review describes the QS-controlled pathogenicity of P. aeruginosa and its different specific QS molecular pathways, as well as the recent advances in the development of innovative QS-quenching anti-virulence agents to fight anti-bioresistance.

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“…2‐Heptyl‐3‐hydroxy‐4(1 H ) quinolone, known as Pseudomonas quinolone signal (PQS), is the third signaling molecule in the QS system, which can interact with the two AHL systems ( las and rhl ) and provide a regulatory link between these two AHL‐based QS systems . Currently, novel 2‐substituted 3‐hydroxy‐6‐methyl‐4 H ‐pyran‐4‐one derivatives such as compound 6a ( 81 ) as PQS pathway inhibitors suppress the production of PQS‐regulated QS virulence factors . In general, nonnatural AHLs remain the most extensively studied class of synthetic QS inhibitors.…”

Section: Pigments Of Representative Colored Pathogens and Their Inhibmentioning

confidence: 99%

“…162 Currently, novel 2-substituted 3-hydroxy-6-methyl-4H-pyran-4-one derivatives such as compound 6a (81) as PQS pathway inhibitors suppress the production of PQS-regulated QS virulence factors. 163 In general, nonnatural AHLs remain the most extensively studied class of synthetic QS inhibitors. However, the resulting side products are either inactive against QS or toxic, thus limiting the use of such molecules as pharmaceutical agents.…”

Section: Pyocyanin Inhibitors From a Natural Product Library And Drmentioning

confidence: 99%

Targeting virulence factors as an antimicrobial approach: Pigment inhibitors

et al. 2019

Medicinal Research Reviews

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The fascinating and dangerous colored pathogens contain unique chemically pigmented molecules, which give varied and efficient assistance as virulence factors to the crucial reproduction and growth of microbes. Therefore, multiple novel strategies and inhibitors have been developed in recent years that target virulence factor pigments. However, despite the importance and significance of this topic, it has not yet been comprehensively reviewed. Moreover, research groups around the world have made successful progress against antibacterial infections by targeting pigment production, including our serial works on the discovery of CrtN inhibitors against staphyloxanthin production in Staphylococcus aureus. On the basis of the previous achievements and recent progress of our group in this field, this article will be the first comprehensive review of pigment inhibitors against colored pathogens, especially S. aureus infections, and this article includes design strategies, representative case studies, advantages, limitations, and perspectives to guide future research.

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Design, synthesis and biological evaluation of 2-substituted 3-hydroxy-6-methyl-4H-pyran-4-one derivatives as Pseudomonas aeruginosa biofilm inhibitors

Cited by 26 publications

References 33 publications

Ultrasound-assisted multicomponent synthesis of 4H-pyrans in water and DNA binding studies

Ultrasound-assisted multicomponent synthesis of 4H-pyrans in water and DNA binding studies

Quorum Sensing Inhibitors to Quench P. aeruginosa Pathogenicity

Targeting virulence factors as an antimicrobial approach: Pigment inhibitors

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