Small azobenzene derivatives active against bacteria and fungi

Piotto, Stefano; Concilio, Simona; Sessa, Lucia; Porta, Amalia; Calabrese, Elena Concetta; Varcamonti, Mario; Iannelli, Pio

doi:10.1016/j.ejmech.2013.07.030

Cited by 40 publications

(46 citation statements)

References 22 publications

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“…Nevertheless, they still possess antimicrobial and antifungal activity, even if at concentrations higher than A4. 3c and 3d compounds lose antibacterial and antifungal activity and all analogues do not exhibit antimicrobial activity against P. aeruginosa, as already observed for previously synthesized similar compounds [9]. Interestingly, all the compounds show antibacterial activity only against Gram-positive bacteria.…”

Section: Preprints (Wwwpreprintsorg) | Not Peer-reviewed | Posted: supporting

confidence: 53%

“…Consequently, the increased resistance of microorganisms to the currently used antimicrobials has led to the evaluation of other agents that might have antimicrobial activity [7,8]. Recently, our research group described the synthesis and properties of some azobenzene-based compounds and their antimicrobial properties both as single molecules [9] and dispersed in a polymer matrix [10][11][12]. In one of this works, we also selected the best candidates by preliminary in silico test of ADMET properties and then we synthesized the azo compounds with lowest in silico toxicity values according to the classic scheme of diazocopulation reaction [9,13].…”

Section: Introductionmentioning

confidence: 99%

“…Recently, our research group described the synthesis and properties of some azobenzene-based compounds and their antimicrobial properties both as single molecules [9] and dispersed in a polymer matrix [10][11][12]. In one of this works, we also selected the best candidates by preliminary in silico test of ADMET properties and then we synthesized the azo compounds with lowest in silico toxicity values according to the classic scheme of diazocopulation reaction [9,13]. The majority of synthesized compounds exhibited high antibacterial activity against S. aureus and antifungal activity against C. albicans, but they were inactive against Gram-negative bacteria such as Pseudomonas aeruginosa and Salmonella typhimurium.…”

Section: Introductionmentioning

confidence: 99%

“…We chose A4 from ref [9], one the best antibacterial azo-compound we synthesized, as lead compound to synthesize several analogues (see Figure 1). The choice of A4 is related to both activity and synthetic easiness.…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Structure Modification of an Active Azo-Compound as a Route to New Antimicrobial Compounds

Concilio¹,

Sessa²,

Petrone³

et al. 2017

Preprint

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Some novel (phenyl-diazenyl)phenols (3a-g) were designed and synthesized to be evaluated for their antimicrobial activity. A previously synthesized molecule, active against bacteria and fungi, was used as lead for modifications and optimization of the structure, by introduction/removal or displacement of hydroxyl groups on the azobenzene rings. The aim of this work was to evaluate the consequent changes of the antimicrobial activity and to validate the hypothesis that, for these compounds, a plausible mechanism could involve an interaction with protein receptors, rather than an interaction with membrane. All newly synthesized compounds were analyzed by 1 H nuclear magnetic resonance (NMR), DSC thermal analysis and UV-Vis spectroscopy. The in vitro minimal inhibitory concentrations (MIC) of each compound was determined against Gram-positive and Gram-negative bacteria and Candida albicans. Compounds 3b and 3g showed the highest activity against S. aureus and C. albicans, with remarkable MIC values of 10 µg/mL and 3 µg/mL, respectively. Structure-activity relationship studies were capable to rationalize the effect of different substitutions on the phenyl ring of the azobenzene on antimicrobial activity.

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Section: Preprints (Wwwpreprintsorg) | Not Peer-reviewed | Posted: supporting

confidence: 53%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Structure Modification of an Active Azo-Compound as a Route to New Antimicrobial Compounds

Concilio¹,

Sessa²,

Petrone³

et al. 2017

Preprint

Self Cite

View full text Add to dashboard Cite

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“…There are different approaches to impart antimicrobial activity into polymers [5]. We have synthesized a class of active compounds with azobenzene structure exhibiting strong activity against Gram+ bacteria and fungi [1]. Our strategy was to insert antimicrobial azo compounds (indicated as A3, A4 and A5) into polymer materials to provide composites having good processability, low cost of production, stability, antimicrobial potential and low cytotoxicity.…”

Section: Introductionmentioning

confidence: 99%

Antimicrobial azobenzene compounds and their potential use in biomaterials

Sessa

Concilio

Iannelli

et al. 2016

AIP Conference Proceedings

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Photo‐Stimuli Smart Supramolecular Self‐Assembly of Azobenzene/β‐Cyclodextrin Inclusion Complex for Controlling Plant Bacterial Diseases

Yang

Xiang

et al. 2023

Adv Funct Materials

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Controllable and on‐demand delivery of supramolecular systems have received considerable attention in modern agricultural management, especially for managing intractable plant diseases. Here, an intelligent photoresponsive pesticide delivery system is reported based on β‐cyclodextrin (β‐CD) and azobenzene, which overcomes the resistance of phytopathogens caused by the irrational use of conventional pesticides. Antibacterial bioassays illustrated that designed azobenzene derivative 3a possesses the most efficient bioactivity with EC50 values of 0.52–25.31 µg mL−1 toward three typical phytopathogens. Moreover, the assembly of the supramolecular binary complex 3a@β‐CD is successfully elucidated and displays exceptional inhibitory activity on biofilm formation. Of note, this supramolecular binary complex significantly improves the water solubility, foliar surface wettability, and shows marked light‐responsive properties. In vivo anti‐Xoo assays reveal that 3a@β‐CD has excellent control efficiency (protective activity: 51.22%, curative activity: 48.37%) against rice bacterial blight pathogens, and their control efficiency can be elevated to values of 55.84% (protective activity) and 52.05% (curative activity) by UV–vis exposure. In addition, the 3a@β‐CD are non‐toxic toward various non‐target organisms. This study therefore offers new insights into the potential of host‐guest complexes as a feasible pesticide discovery strategy characterized by a safe, biocompatible, light‐responsive release, and antibiofilm properties for overcoming intractable plant bacterial diseases.

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Small azobenzene derivatives active against bacteria and fungi

Cited by 40 publications

References 22 publications

Structure Modification of an Active Azo-Compound as a Route to New Antimicrobial Compounds

Structure Modification of an Active Azo-Compound as a Route to New Antimicrobial Compounds

Antimicrobial azobenzene compounds and their potential use in biomaterials

Photo‐Stimuli Smart Supramolecular Self‐Assembly of Azobenzene/β‐Cyclodextrin Inclusion Complex for Controlling Plant Bacterial Diseases

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