Antimicrobial azo molecules: a review

Banaszak-Léonard, Estelle; Fayeulle, Antoine; Franche, Antoine; Sagadevan, Suresh; Billamboz, Muriel

doi:10.1007/s13738-021-02238-4

Cited by 12 publications

(7 citation statements)

References 96 publications

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“…Due to their wide range of potential uses, nitrogenous compounds are presently the most vital and fascinating area of research. Antimicrobial [8][9][10][11], antitubercular [12], antiinflammatory [13], anticancer [14], antidiabetic [15], and antiviral [16] are only a few of the biological activities shown by hydrazine-containing ( N NH ) molecules.…”

Section: Introductionmentioning

confidence: 99%

“…Due to their wide range of potential uses, nitrogenous compounds are presently the most vital and fascinating area of research. Antimicrobial [8–11], antitubercular [12], anti‐inflammatory [13], anticancer [14], antidiabetic [15], and antiviral [16] are only a few of the biological activities shown by hydrazine‐containing (NNH) molecules. Recent years have seen a surge in the study of aromatic azo compounds, which have many potential medical uses and are easy to study because of their low cost, relative simplicity, and high repeatability.…”

Section: Introductionmentioning

confidence: 99%

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Indeno[1,2‐b]pyridin‐5‐one derivatives containing azo groups and their hydrazonal precursors: Synthesis, antimicrobial profile, DNA gyrase binding affinity, and molecular docking

Kassab,

Muhammad,

Al‐Hussain

et al. 2023

Journal of Heterocyclic Chem

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The prevalence of germs that are resistant to many antibiotics is rising rapidly the world over. There is a large group of researchers actively looking for better medicines. Here, we designed two series of hydrazonal and indeno[1,2‐b]pyridin‐5‐one bearing hydrazone and azo‐groups to test their antimicrobial activity. Molecular structures of all derivatives were assured based on their spectral data and elemental analyses. Results of the antimicrobial activity of the tested hydrazone and azo compounds showed promising potential for several derivatives. The minimum inhibitory concentrations (MICs) of hydrazones4a‐hand6a‐gdisplayed good antibacterial reactivities with a range of 3.91–250 μg/mL and moderate antifungal activity with a range of 15.6–500 μg/mL. The most promising hydrazone4fand azo‐6acompounds demonstrated MIC values againstStreptococcus faecalisandEscherichia coliequal to 3.91 and 7.81 μg/mL, respectively. Moreover, azo compound6ashowed MIC value equal to 3.91 μg/mL againstEnterobacter cloacaespecies. Additionally, derivative4fexhibited a significant inhibitory profile against theE. coligyrase A enzyme (IC50 = 5.53 μg/mL). On the other hand, compound6a(IC5014.05 μg/mL) exhibited the lowest DNA gyrase inhibitory activity as compared to compounds4fand reference standard drug novobiocin, IC505.53 and 1.88 μg/mL, respectively. Pharmacokinetic and pharmacodynamic profiles and molecular docking studies for the two most promising molecules4fand6awere computed and revealed that both compounds have good ADME profiles and high binding affinity to DNA gyrase binding site.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Indeno[1,2‐b]pyridin‐5‐one derivatives containing azo groups and their hydrazonal precursors: Synthesis, antimicrobial profile, DNA gyrase binding affinity, and molecular docking

Kassab,

Muhammad,

Al‐Hussain

et al. 2023

Journal of Heterocyclic Chem

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“…The rotation results in the -C-N-C- dihedral angle changing, while an -N-N-C- angle remains fixed at 120°. In the inversion mechanism, an -N=N-C- angle increases to 180°, while the -C-N=N-C- dihedral angle remains fixed; this results in a transition state in which a nitrogen atom will be hybridized sp [ 7 , 8 ].…”

Section: Introductionmentioning

confidence: 99%

Azobenzene as Antimicrobial Molecules

et al. 2022

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Azo molecules, characterized by the presence of a -N=N- double bond, are widely used in various fields due to their sensitivity to external stimuli, ch as light. The emergence of bacterial resistance has pushed research towards designing new antimicrobial molecules that are more efficient than those currently in use. Many authors have attempted to exploit the antimicrobial activity of azobenzene and to utilize their photoisomerization for selective control of the bioactivities of antimicrobial molecules, which is necessary for antibacterial therapy. This review will provide a systematic and consequential approach to coupling azobenzene moiety with active antimicrobial molecules and drugs, including small and large organic molecules, such as peptides. A selection of significant cutting-edge articles collected in recent years has been discussed, based on the structural pattern and antimicrobial performance, focusing especially on the photoactivity of azobenzene and the design of smart materials as the most targeted and desirable application.

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“…The azo-incorporating compounds in Figure could target not only bacterial strains but also fungus, , which means a broader spectrum of microbicide. Interestingly, a review was reported to compile some examples of proper azobenzene dyes as antimicrobials. And azobenzene dusts , were reported to be particularly effective against red spider mite and the Mexican bean beetle in the 1940s.…”

Section: Introductionmentioning

confidence: 99%

Azo-incorporating Increases Inhibitory Activity of Succinate Dehydrogenase

Yuan

et al. 2021

J. Agric. Food Chem.

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Diversity of pesticide discovery provided a solution to resistance. Here, we presented a strategy of azo-incorporating to promote the diverse developments of fungicide. A series of novel fungicides were synthesized by incorporating azobenzene derivatives into fluxapyroxad. Much better in vitro fungicidal activity increases for compound 9d were observed compared to the positive control, fluxapyroxad against Botrytis cinerea and Rhizoctonia solani. Compound 9d (IC50 = 0.03 μM) also had a great enzyme-inhibiting activity increase toward succinate dehydrogenase in comparison with fluxapyroxad (IC50 = 4.40 μM). A comparatively equivalent biological activity was observed between compounds 8a and 9d. SEM analysis helped us to observe clearly the morphology of the fungi before and after active ingredient delivery. Our results of molecular docking analysis, fluorescence quenching analysis, and enzymatic assays demonstrated that compound 8a and 9d act on SDH. An increase in inhibitory activity could be occurring after incorporation of azobenzene, which provided a new strategy for molecular design in pesticide discovery.

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Antimicrobial azo molecules: a review

Cited by 12 publications

References 96 publications

Indeno[1,2‐b]pyridin‐5‐one derivatives containing azo groups and their hydrazonal precursors: Synthesis, antimicrobial profile, DNA gyrase binding affinity, and molecular docking

Indeno[1,2‐b]pyridin‐5‐one derivatives containing azo groups and their hydrazonal precursors: Synthesis, antimicrobial profile, DNA gyrase binding affinity, and molecular docking

Azobenzene as Antimicrobial Molecules

Azo-incorporating Increases Inhibitory Activity of Succinate Dehydrogenase

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