Antibacterial, Antioxidant and DNA Cleavage Activity Evaluation of Substituted Phenylureido Sulfaguanidine and Sulfamethazine Derivatives

Tekeli, Yener; Lolak, Nabih; Sönmez, Görkem Deniz; Tekeli, Tuba; Akocak, Süleyman

doi:10.1007/s11094-022-02654-7

Cited by 6 publications

(17 citation statements)

References 31 publications

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“…Each inhibitor concentration was tested in triplicate, and the reported values represent the mean of these results. The inhibition constants were calculated using nonlinear least‐squares methods, employing the Cheng‐Prusoff equation, as previously reported, and are the average of at least three separate determinations [43–53] …”

Section: Methodsmentioning

confidence: 99%

“…The inhibition constants were calculated using nonlinear least-squares methods, employing the Cheng-Prusoff equation, as previously reported, and are the average of at least three separate determinations. [43][44][45][46][47][48][49][50][51][52][53] . All CA isozymes used in this study were recombinant proteins previously obtained by our research group.…”

Section: Ca Inhibitionmentioning

confidence: 99%

“…All CA isozymes used in this study were recombinant proteins previously obtained by our research group. [43][44][45][46][47][48][49][50][51][52][53]…”

Section: Ca Inhibitionmentioning

confidence: 99%

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Exploring the potency of diazo‐coumarin containing hybrid molecules: Selective inhibition of tumor‐associated carbonic anhydrase isoforms IX and XII

Yapar,

Lolak,

Bonardi

et al. 2024

ChemMedChem

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This study introduces a series of ten hybrid molecules DK(1‐10), which combine diazo and coumarin moieties along with diverse aromatic substitutions. The primary objective was to evaluate the inhibitory capabilities of these compounds against four prominent isoforms: the cytosolic hCA I and II, as well as the tumor‐associated membrane‐bound hCA IX and XII. Impressively, the majority of the tested compounds exhibited significant inhibition activity against the tumor‐associated isoforms hCA IX and XII, with KI values ranging from 29.2 to 293.3 nM. Notably, compound DK‐8 displayed particularly robust inhibitory activity against the tumor‐associated membrane‐bound isoforms, hCA IX and XII, yielding KI values of 32.5 and 29.2 nM, respectively. Additionally, another derivative, DK‐9, containing a primary sulfonamide, exhibited notable inhibition against hCA XII with a KI value of 36.4 nM. This investigation aimed to explore the structure‐activity relationships within these compounds, shedding light on how various substitutions and structural components influence their inhibitory potential. As a result, these compounds present promising candidates for further exploration in medicinal and pharmacological research. Their ability to selectively inhibit specific isoforms, particularly those associated with hypoxic tumors, suggests their potential as foundational compounds for the development of novel therapeutic agents.

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Section: Methodsmentioning

confidence: 99%

Section: Ca Inhibitionmentioning

confidence: 99%

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Exploring the potency of diazo‐coumarin containing hybrid molecules: Selective inhibition of tumor‐associated carbonic anhydrase isoforms IX and XII

Yapar,

Lolak,

Bonardi

et al. 2024

ChemMedChem

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show abstract

“…The antibacterial activity of freshly synthesized bis‐ureido‐substituted sulfonamides was evaluated against four pathogenic bacterial strains, encompassing both Gram‐positive ( Staphylococcus aureus ATCC 29213, Enterococcus faecalis ATCC 29212) and Gram‐negative ( Pseudomonas aeruginosa ATCC 10231, Escherichia coli ATCC 25912) bacteria. The antibacterial analyses were conducted using the modified method introduced by Al‐Blewi et al., [52] which has been proven effective in previous studies conducted by our research team [53–55] . This innovative approach has consistently demonstrated its reliability and accuracy in assessing the antibacterial properties of various compounds, setting a robust foundation for our current investigations.…”

Section: Methodsmentioning

confidence: 99%

“…Recently, our research team demonstrated the highly effective inhibition of carbonic anhydrase by a group of aromatic bis‐ureido‐substituted benzenesulfonamide derivatives [49] . These compounds exhibited remarkable potency in inhibiting human carbonic anhydrase IX and XII (hCA IX and XII), which are membrane‐bound isozymes of the carbonic anhydrase enzyme overexpressed in tumors.…”

Section: Introductionmentioning

confidence: 99%

Bis‐Ureido‐Substituted Benzenesulfonamides: Evaluation of Their Antibacterial, Anticholinesterase, and Cytotoxicity Properties

Tekeli,

Lolak,

Tekeli

et al. 2024

ChemistrySelect

Self Cite

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In this study, we present the re‐synthesis of a series of twelve bis‐ureido‐substituted benzenesulfonamides, focusing on their potential as antibacterial, anticholinesterase, and cytotoxic agents. First, the antibacterial assessment of these compounds indicated varying activity levels across different bacterial strains, with S. aureus displaying resistance to all compounds, while compounds 9 and 11 exhibited promise against E. faecalis with a MIC value of 31.25 μg/mL. Additionally, P. aeruginosa showed resistance to compounds containing 4‐aminobenzene sulfonamides, whereas derivatives such as (8–11) and compound 19 displayed notable activity against E. coli, comparable to Ampicillin. Second, their anticholinesterase activities were examined, with a focus on their potential role in addressing neurological disorders, particularly Alzheimer′s disease. The findings indicated that all synthesized compounds showed a significant inhibitory effect on both AChE and BChE enzymes. Compound 11 demonstrated the most effective inhibition on the AChE enzyme with an IC50 value of 0.2160±0.09 nM, while compound 18 exhibited the most potent inhibition on the BChE enzyme with an IC50 value of 0.2257±0.06 nM. Finally, cytotoxicity studies were conducted across various cell lines, including breast, lung, and prostate cancer cells and normal cells. The results revealed that compound 12 emerged as the most potent tested compound against breast cancer cells with no cytotoxic effect on CRL‐4010 normal breast epithelial cells. The research presented here not only highlights the multifaceted pharmacological potential of bis‐ureido‐substituted benzenesulfonamides, but also indicates their potential as versatile compounds for antibacterial, anticholinesterase, and cytotoxicity applications, opening up new avenues for drug discovery and development.

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In‐vitro and in‐silico investigations of SLC‐0111 hydrazinyl analogs as human carbonic anhydrase I, II, IX, and XII inhibitors

Sharma,

Vats,

Giovannuzzi

et al. 2024

Archiv der Pharmazie

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Two novel series of hydrazinyl‐based benzenesulfonamides 9a–j and 10a–j were designed and synthesized using SLC‐0111 as the lead molecule. The newly synthesized compounds were evaluated for their inhibitory activity against four different human carbonic anhydrase (hCA) isoforms I, II, IX, and XII. Both the series reported here were practically inactive against the off‐target isozyme hCA I. Notably, derivative 10a exhibited superior potency (Ki of 10.2 nM) than acetazolamide (AAZ) against the cytosolic isoform hCA II. The hCA IX and XII isoforms implicated in tumor progression were effectively inhibited with Kis in the low nanomolar range of 20.5–176.6 nM and 6.0–127.5 nM, respectively. Compound 9g emerged as the most potent and selective hCA IX and XII inhibitor with Ki of 20.5 nM and SI of 200.1, and Ki of 6.0 nM and SI of 683.7, respectively, over hCA I. Furthermore, six compounds (9a, 9h, 10a, 10g, 10i, and 10j) exhibited significant inhibition toward hCA IX (Kis = 27.0, 41.1, 27.4, 25.9, 40.7, and 30.8 nM) relative to AAZ and SLC‐0111 (Kis = 25.0 and 45.0 nM, respectively). These findings underscore the potential of these derivatives as potent and selective inhibitors of hCA IX and XII over the off‐target hCA I and II.

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Antibacterial, Antioxidant and DNA Cleavage Activity Evaluation of Substituted Phenylureido Sulfaguanidine and Sulfamethazine Derivatives

Cited by 6 publications

References 31 publications

Exploring the potency of diazo‐coumarin containing hybrid molecules: Selective inhibition of tumor‐associated carbonic anhydrase isoforms IX and XII

Exploring the potency of diazo‐coumarin containing hybrid molecules: Selective inhibition of tumor‐associated carbonic anhydrase isoforms IX and XII

Bis‐Ureido‐Substituted Benzenesulfonamides: Evaluation of Their Antibacterial, Anticholinesterase, and Cytotoxicity Properties

In‐vitro and in‐silico investigations of SLC‐0111 hydrazinyl analogs as human carbonic anhydrase I, II, IX, and XII inhibitors

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