Synthesis, biological evaluation, and metabolic stability of phenazine derivatives as antibacterial agents

Krishnaiah, Maddeboina; Almeida, Nathália Rodrigues de; Udumula, Venkatareddy; Song, Zengqiang; Chhonker, Yashpal S.; Abdelmoaty, Mai Mohamed; Nascimento, Valter Aragão do; Murry, Daryl J.; Conda‐Sheridan, Martin

doi:10.1016/j.ejmech.2017.11.026

Cited by 40 publications

(29 citation statements)

References 26 publications

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“…Moreover, only few papers concern the synthesis of novel LAC-mediated coupling products from phenolics or well-known antibacterial chemicals [3,22,23]. From the broad variety of antimicrobial compounds, phenazines, acting as both electron donors and acceptors, are able to inhibit the growth of bacteria, fungi, parasites, insects, malaria agents, and other organisms; hence, they are promising new bioactive compounds [7,8]. Our results presented in this paper indicate possible laccase-mediated synthesis of new trimolecular phenazines, which exhibit both bioactive and dyeing properties.…”

Section: Discussionmentioning

confidence: 99%

“…In nature, phenazines with broad bioactivity are products of the idiophase of different bacteria, especially from Pseudomonas and Streptomyces strains [4,5]. Both natural and synthetic phenoxazines and phenazines known from the literature exhibit biological activities such as antibacterial [6][7][8], antitumoral [9], antiproliferative [10], and antioxidant [11] properties. The chemical route of phenazine synthesis requires the use of coupling agents and additives such as benzene, BBr 3 , DMF, and various other harsh, toxic, and mutagenic compounds [12].…”

Section: Introductionmentioning

confidence: 99%

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Structure and Bioactive Properties of Novel Textile Dyes Synthesised by Fungal Laccase

Polak

Wlizło

Pogni

et al. 2020

IJMS

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Novel sustainable processes involving oxidative enzymatic catalysts are considered as an alternative for classical organic chemistry. The unique physicochemical and bioactive properties of novel bio-products can be obtained using fungal laccase as catalyst. Among them are textile biodyes synthesised during oxidation of substrates belonging to the amine and methoxy organic derivatives. The process of synthesis occurs in mild conditions of pH, temperature, and pressure, and without using harmful oxidants. The effect of fungal laccase activity on the substrates mixture transformation efficiency was analysed in terms of antimicrobial dye synthesis on a large scale. Three new phenazine dyes, obtained in the presence of laccase from Cerrena unicolor, were studied for their structure and properties. The phenazine core structure of the products was a result of tri-molecular transformation of aminomethoxybenzoic acid and aminonaphthalene sulfonic acid isomers. One of the compounds from the synthesised dye, namely 10-((2-carboxy-6-methoxyphenyl)amino)-11-methoxybenzo[a]phenazine-8-carboxylic acid, was able to inhibit the growth of Staphylococcus aureus. The high concentration of substrates (5 g/L) was efficiently transformed during 72 h in the mild conditions of pH 4 with the use of laccase with an activity of 200 U per g of the substrates mixture. The new bioactive dye exhibited excellent dyeing properties with concomitant antibacterial and antioxidative activity. The proposed enzyme-mediated synthesis represents an alternative eco-friendly route for the synthesis of novel antimicrobial compounds with high importance for the medical textile industry.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Structure and Bioactive Properties of Novel Textile Dyes Synthesised by Fungal Laccase

Polak

Wlizło

Pogni

et al. 2020

IJMS

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“…The in‐vitro metabolism studies were performed utilizing human liver S9 fractions (XenoTech, LLC, Lenexa, KS, USA) for both phase I and phase II metabolism. The incubation was performed as described and all analyses were performed in triplicate (Gautam, Bathena, Chen, Natarajan, & Alnouti, ; Gautam, Thakare, Rana, Natarajan, & Alnouti, ; Krishnaiah et al, ). The in vitro metabolic stability of MOX was determined using human liver S9 fractions following standard protocols.…”

Section: Methodsmentioning

confidence: 99%

Bioanalytical method development and validation of moxidectin in plasma by LC–MS/MS: Application to in vitro metabolism

Chhonker

Murry

2018

Biomedical Chromatography

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Moxidectin (MOX) has recently been approved by the US Food and Drug Administration for the treatment of river blindness in select populations. It is also being evaluated as an alternative for the use of ivermectin, widespread resistance to which is becoming a global health issue. Moreover, MOX is becoming increasingly used as a prophylactic antiparasitic in the cattle industry. In this study, we developed and validated an LC–MS/MS method of MOX in human, monkey and mouse plasma. The separation was achieved on an ACE C18 (50 × 3.0 mm, 3 μm) column with isocratic elution using 0.1% acetic acid and methanol–acetonitrile (1:1, v/v) as mobile phase. MOX was quantitated using MS/MS with an electrospray ionization source operating in negative multiple reaction monitoring mode. The multiple reaction monitoring precursor ion → product ion transitions for MOX and abamectin (IS) were m/z 638.40 → 236.30 and m/z 871.50 → 565.35 respectively. The MS/MS response was linear over the concentration range 0.1–1000 ng/mL in plasma with a correlation coefficient (r2) of 0.997 or better. The within‐ and between‐day precision (relative standard deviation, RSD) and accuracy were within the acceptable limits per US Food and Drug Administration guidelines. The method was successfully applied to an in vitro metabolic stability study of MOX.

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“…The lead molecules bearing sulphonamide structure exhibited diverse biological properties viz. antibacterial [12,13], diuretics, carbonic anhydrase (CA) inhibitors [14], antithyroid, antidiabetic [11,15,16], anticancer [17], antitubercular [18], selective Cox II inhibitors [19], anti-inflammatory [20], aldose reductase inhibitor [21], anti-oxidant [22], and anticancer [20] etc. Benzamides are the carbonic acid amide of benzoic acid and have also been described for exhibiting various biological activities i.e.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, molecular docking and molecular dynamic simulation studies of 2-chloro-5-[(4-chlorophenyl)sulfamoyl]-N-(alkyl/aryl)-4-nitrobenzamide derivatives as antidiabetic agents

et al. 2020

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A series of 2-chloro-5-[(4-chlorophenyl)sulfamoyl]-N-(alkyl/aryl)-4-nitrobenzamide derivatives (5a-5v) has been synthesized and confirmed by physicochemical(R f , melting point) and spectral means (IR, 1 HNMR, 13 CNMR). The results of in vitro antidiabetic study against α-glucosidase indicated that compound 5o bearing 2-CH 3-5-NO 2 substituent on phenyl ring was found to be the most active compound against both enzymes. The electron donating (CH 3) group and electron withdrawing (NO 2) group on a phenyl ring highly favoured the inhibitory activity against these enzymes. The docking simulations study revealed that these synthesized compounds displayed hydrogen bonding, electrostatic and hydrophobic interactions with active site residues. The structure activity relationship studies of these compounds were also corroborated with the help of molecular modeling studies. Molecular dynamic simulations have been done for top most active compound for validating its α-glucosidase and α-amylase inhibitory potential, RMSD analysis of ligand protein complex suggested the stability of top most active compound 5o in binding site of target proteins. In silico ADMET results showed that synthesized compounds were found to have negligible toxicity, good solubility and absorption profile as the synthesized compounds fulfilled Lipinski's rule of 5 and Veber's rule.

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Synthesis, biological evaluation, and metabolic stability of phenazine derivatives as antibacterial agents

Cited by 40 publications

References 26 publications

Structure and Bioactive Properties of Novel Textile Dyes Synthesised by Fungal Laccase

Structure and Bioactive Properties of Novel Textile Dyes Synthesised by Fungal Laccase

Bioanalytical method development and validation of moxidectin in plasma by LC–MS/MS: Application to in vitro metabolism

Synthesis, molecular docking and molecular dynamic simulation studies of 2-chloro-5-[(4-chlorophenyl)sulfamoyl]-N-(alkyl/aryl)-4-nitrobenzamide derivatives as antidiabetic agents

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