Exploring the Bioactive Sites of New Sulfonamide Metal Chelates for Multi-Drug Resistance: An Experimental Versus Theoretical Design

Hassan, Ali; Sumrra, Sajjad Hussain

doi:10.1007/s10904-021-02135-6

Cited by 45 publications

(15 citation statements)

References 66 publications

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“…All of the optimized geometrical structures of synthetic compounds, at their ground-state energies, were considered using Gaussian 09 software and the density functional theory (DFT) methodology. The B3LYP approach with LanL2DZ basis sets was utilized to optimize geometries such that ligands and complexes might have the minimum energy-feasible structures 41 (Figure 1). The benzene (C−C) system conceded DFT-optimized bonding distances of 1.41−1.42, 1.32−1.33, 1.33−1.35, 1.37−1.38, 1.32−1.34, and 1.32−1.33 Å.…”

Section: Resultsmentioning

confidence: 99%

Aminothiazole-Linked Metal Chelates: Synthesis, Density Functional Theory, and Antimicrobial Studies with Antioxidant Correlations

Noreen

Sumrra

2021

ACS Omega

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During the current study, the new aminothiazole Schiff base ligands (S 1 ) and (S 2 ) were designed by reacting 1,3thiazol-2-amine and 6-ethoxy-1,3-benzothiazole-2-amine separately with 3-methoxy-2-hydroxybenzaldehyde in good yields (68−73%). The ligands were characterized through various analytical, physical, and spectroscopic (FT-IR, UV−Vis, 1 H and 13 C NMR, and MS) methods. The ligands were exploited in lieu of chelation with bivalent metal (cobalt, nickel, copper, and zinc) chlorides in a 1:2 (M:L) ratio. The spectral (UV−Vis, FT-IR, and MS), as well as magnetic, results suggested their octahedral geometry. The theoretically optimized geometrical structures were examined using the M06/6-311G+(d,p) function of density function theory. Their bioactive nature was designated by global reactivity parameters containing a high hardness (η) value of 1.34 eV and a lower softness (σ) value of 0.37 eV. Different microbial species were verified for their potency (in vitro), revealing a strong action. The Gram-positive Micrococcus luteus and Gram-negative Escherichia coli gave the highest activities of 20 and 21 mm for compounds (8) and ( 7), respectively. The antifungal activity against the Aspergillus niger and Aspergillus terreus species gave the highest activities of 20 and 18 mm for compounds ( 7) and ( 6), respectively. The antioxidant activity, evaluated as DPPH and ferric reducing power, gave the highest inhibition (%) as 72.0 ± 0.11% (IC 50 = 144 ± 0.11 μL) and 66.3% (IC 50 = 132 ± 0.11 μL) for compounds (3) and (8), respectively. All metal complexes were found to be more biocompatible than free ligands due to their chelation phenomenon. The energies of LUMOs had a link with their activities. ■ HIGHLIGHTS• A facile synthesis of aminothiazole-containing Schiff bases and their metal chelates. • Combined experimental and theoretical exploration to decide their medicinal role. • Geometry optimization studies at the M06/6-311G +(d,p) level of density function theory. • The relative order of medicinal studies was as follows:reference drugs > metal chelates > ligands.

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Section: Resultsmentioning

confidence: 99%

Aminothiazole-Linked Metal Chelates: Synthesis, Density Functional Theory, and Antimicrobial Studies with Antioxidant Correlations

Noreen

Sumrra

2021

ACS Omega

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“…These ligands and their metal chelates were shown to have antioxidant- and enzyme-inhibiting abilities. Antibacterial and antifungal screenings have shown that the chelates were more efficient in that sense than the free ligands [ 49 ]. Furthermore, the studies have also shown that multi-drug resistance may be combated in the future via metal-based medicines derived from several commonly used pharmaceuticals such as sulfonamides [ 49 , 113 ].…”

Section: Sulfonamidesmentioning

confidence: 99%

“…Antibacterial and antifungal screenings have shown that the chelates were more efficient in that sense than the free ligands [ 49 ]. Furthermore, the studies have also shown that multi-drug resistance may be combated in the future via metal-based medicines derived from several commonly used pharmaceuticals such as sulfonamides [ 49 , 113 ]. One study presented the synthesis of a new derivative of N-carboxamide compound bearing sulfonamide group and its Zn 2+ , Ni 2+ , Mn 2+ , Cu 2+ , Co 2+ , and Pd 2+ complexes [ 114 ].…”

Section: Sulfonamidesmentioning

confidence: 99%

“…More recently, sulfonamides and their metal-based (cobalt, copper, nickel, or zinc) compounds were synthesized and screened for in vitro antibacterial and antiparasitic activity [ 47 , 48 ]. Finally, in 2022, bidentate chelates of sulfonamide and metals (Co 2+ , Ni 2+ , Cu 2+ , Zn 2+ , and VO 2+ ) were synthesized and screened ( Figure 6 b), and some of these demonstrated antibacterial and antioxidative activities [ 49 ].…”

Section: Sulfonamidesmentioning

confidence: 99%

“…( b ) Chelation is not relevant in the classical sulfonamide mode of action, but the chelates of new-generation sulfonamide molecules with metal (M) cations (M = Co 2+ , Ni 2+ , Cu 2+ , Zn 2+ , and VO 2+ ) demonstrate antibacterial and antioxidative activities; inspired by ref. [ 49 ].…”

Section: Figurementioning

confidence: 99%

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Chelation in Antibacterial Drugs: From Nitroxoline to Cefiderocol and Beyond

et al. 2022

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In the era of escalating antimicrobial resistance, the need for antibacterial drugs with novel or improved modes of action (MOAs) is a health concern of utmost importance. Adding or improving the chelating abilities of existing drugs or finding new, nature-inspired chelating agents seems to be one of the major ways to ensure progress. This review article provides insight into the modes of action of antibacterial agents, class by class, through the perspective of chelation. We covered a wide scope of antibacterials, from a century-old quintessential chelating agent nitroxoline, currently unearthed due to its newly discovered anticancer and antibiofilm activities, over the commonly used antibacterial classes, to new cephalosporin cefiderocol and a potential future class of tetramates. We show the impressive spectrum of roles that chelation plays in antibacterial MOAs. This, by itself, demonstrates the importance of understanding the fundamental chemistry behind such complex processes.

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Photovoltaic and Optical Characterization of Organic Heterocyclic 6,6′‐Dibromoindigotin Crystal Under Changing Solvent Polarity by DFT Analysis

Hassan,

Sumrra,

2023

Cryst. Res. Technol.

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The photovoltaic and optical properties of 6,6′‐dibromoindigotin (DBI) crystal under changing solvent polarity are investigated through DFT analysis. It includes geometry optimization, global reactivity, UV–vis analysis, open circuit voltage (Voc), FMOs, and NBO analysis. The highest HOMO‐LUMO gap (Egap) value is found for the gaseous phase (1.82 eV), while the lowest Egap is found for dichloro methane (1.64 eV), and intermediate values with the other solvents. The molecule has a high IP of 2.48 eV, low EA of 0.74 eV, moderate polarity, and hardness (η). The maximum absorption wavelengths (λmax) of the compound in different solvents are dichloromethane and DMSO (373 nm), chloroform (372 nm), methanol and water (371 nm), toluene (367 nm), and gaseous (356 nm). Their Voc range is 0.2–0.28 eV. Among all, chloroform demonstrates the highest performance with a fill factor (FF) of 0.8630, normalized open circuit (Nor. Voc) of 31.69 eV, and Jsc of 26.47 mA cm−2. Toluene also shows promising results with an FF of 0.8060, Nor. Voc of 19.71 eV, and Jsc of 21.19 mA cm−2. Water, although not as effective as other solvents, still exhibits respectable values with an FF of 0.8315, Nor. Voc of 23.96 eV, and Jsc of 24.63 mA cm−2.

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Exploring the Bioactive Sites of New Sulfonamide Metal Chelates for Multi-Drug Resistance: An Experimental Versus Theoretical Design

Cited by 45 publications

References 66 publications

Aminothiazole-Linked Metal Chelates: Synthesis, Density Functional Theory, and Antimicrobial Studies with Antioxidant Correlations

Aminothiazole-Linked Metal Chelates: Synthesis, Density Functional Theory, and Antimicrobial Studies with Antioxidant Correlations

Chelation in Antibacterial Drugs: From Nitroxoline to Cefiderocol and Beyond

Photovoltaic and Optical Characterization of Organic Heterocyclic 6,6′‐Dibromoindigotin Crystal Under Changing Solvent Polarity by DFT Analysis

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