Antimicrobial azobenzene compounds and their potential use in biomaterials

Sessa, Lucia; Concilio, Simona; Iannelli, Pio; Santis, Felice De; Porta, Amalia; Piotto, Stefano

doi:10.1063/1.4945973

Cited by 17 publications

(12 citation statements)

References 11 publications

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“…Many of these compounds exhibit biomedical activity because they exhibit various properties such as anti-inflammatory activity, antibacterial activity, cell protection, protease inhibitors (enzymes that play functions in many pathological disorders), or have anti-HIV activity [19,20,21]. Also, it was proved recently that azo-benzene based compounds showed a killing effect on bacteria or fungi through the interaction with their protein receptors, rather than an interaction with membrane [22,23]. On the other hand, the molecular hybridization is specialized with synthesis new compounds from combination of biologically active substances for the production of a new hybrid compound.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antimicrobial Evaluation of Novel Pyrazolopyrimidines Incorporated with Mono- and Diphenylsulfonyl Groups

2019

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A novel series of pyrazolo[1,5-a]pyrimidine ring systems containing phenylsulfonyl moiety have been synthesized via the reaction of 2-(phenylsulfonyl)-1-(4-(phenylsulfonyl) phenyl)ethan-1-one, 2-benzenesulfonyl-1-(4-benzenesulfonyl-phenyl)-3-dimethylamino-propenone and 3-(dimethylamino)-1-(4-(phenylsulfonyl)phenyl)prop-2-en-1-one each with various substituted aminoazopyrazole derivatives in one pot reaction strategy. The proposed structure as well as the mechanism of their reactions were discussed and proved with all possible spectral data. The results of antimicrobial activities of the new sulfone derivatives revealed that several derivatives showed activity exceeding the activity of reference drug. Contrary to expectations, we found that derivatives containing one sulfone group are more effective against all bacteria and fungi used than those contain two sulfone groups.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Antimicrobial Evaluation of Novel Pyrazolopyrimidines Incorporated with Mono- and Diphenylsulfonyl Groups

2019

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“…Azocompounds are one of the largest types of organically synthesized compounds, which are effective both as drugs and cosmetics [12]. Also, they are extensively used in the field of dyeing textiles, biomedical studies, advanced applications in organic synthesis, and remarkable biological activities including antibacterial activity [13][14][15][16][17][18][19][20]. A number of azocompounds were synthesized comprising a drug moiety in their skeleton [21].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Cytotoxic Evaluation of Some Newly Substituted Diazene Candidates

El-Naggar

El‐Shorbagi

Elnaggar

et al. 2018

Journal of Chemistry

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A series of azocompounds containing methyl salicylate 4a–k and 1-naphthyl moiety 6–8 was synthesized and tested as anticancer agents. Nitrosation of methyl 5-amino-2-hydroxybenzoate or 1-aminonaphthalene by using NaNO2 in the presence of HCl afforded diazonium salt derivatives 2 and 5, which were treated with substituted imino or substituted amino derivatives, to give the corresponding substituted amino-pent-2-en-3-yl-diazenylbenzoate 4a–k or 2-substituted-1-(naphthalen-1-yl)diazene derivatives 6a–h, 7a,b, and 8a,b. All the synthesized compounds were elucidated by elemental analysis and spectroscopic evidence.

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“…This feature is widely-used in light-responsive materials [ 1 , 2 , 3 , 4 , 5 ], liquid crystals [ 6 , 7 ], electronic devices [ 8 , 9 , 10 , 11 ], or in NLO chromophores [ 12 , 13 ]. In recent papers, we reported a series of azobenzene-based molecules with antimicrobial properties [ 14 , 15 , 16 , 17 ]. For example, studies carried out in our labs showed that A4 ( Figure 1 ) is one of the most active of the series of compounds synthesized so far, showing antimicrobial activity against Staphylococcus aureus (MIC 100 20 μg/mL, the Minimum Inhibitory Concentration required to inhibit the growth of 100% of bacteria), against Candida albicans (MIC 0 17 μg/mL, the Minimum Inhibitory Concentration required to inhibit the growth of 100% of fungi), and Listeria monocytogenes (MIC 100 25 μg/mL) [ 16 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antimicrobial Studies of New Antibacterial Azo-Compounds Active against Staphylococcus aureus and Listeria monocytogenes

et al. 2017

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Some novel (phenyl-diazenyl)phenols (4a–m) were designed and synthesized to be evaluated for their antibacterial activity. Starting from an active previously-synthesized azobenzene chosen as lead compound, we introduced some modifications and optimization of the structure, in order to improve solubility and drug conveyance. Structures of all newly-synthesized compounds were confirmed by 1H nuclear magnetic resonance (NMR), mass spectrometry, and UV-Vis spectroscopy. Antibacterial activity of the new compounds was tested with the dilution method against the bacteria strains Listeria monocytogenes, Staphylococcus aureus, Escherichia coli, and Pseudomonas aeruginosa PAO1. All the compounds were selectively active against Gram-positive bacteria. In particular, compounds 4d, 4h, and 4i showed the highest activity against S. aureus and Listeria monocytogenes, reaching remarkable MIC100 values of 4 μg/mL and 8 μg/mL. The relationship between antimicrobial activity and compound structure has suggested that the presence of hydroxyl groups seems to be essential for antimicrobial activity of phenolic compounds.

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Antimicrobial azobenzene compounds and their potential use in biomaterials

Cited by 17 publications

References 11 publications

Synthesis and Antimicrobial Evaluation of Novel Pyrazolopyrimidines Incorporated with Mono- and Diphenylsulfonyl Groups

Synthesis and Antimicrobial Evaluation of Novel Pyrazolopyrimidines Incorporated with Mono- and Diphenylsulfonyl Groups

Synthesis, Characterization, and Cytotoxic Evaluation of Some Newly Substituted Diazene Candidates

Synthesis and Antimicrobial Studies of New Antibacterial Azo-Compounds Active against Staphylococcus aureus and Listeria monocytogenes

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