Design and synthesis of novel 1H-tetrazol-5-amine based potent antimicrobial agents: DNA topoisomerase IV and gyrase affinity evaluation supported by molecular docking studies

Szulczyk, Daniel; Dobrowolski, Michał A.; Roszkowski, Piotr; Bielenica, Anna; Stefańska, Joanna; Koliński, Michał; Kmiecik, Sebastian; Jóźwiak, Michał; Wrzosek, Małgorzata; Olejarz, Wioletta; Struga, Marta

doi:10.1016/j.ejmech.2018.07.041

Cited by 34 publications

(19 citation statements)

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“…The strong dependence between cytotoxic activity and the presence of electronegative elements on the phenyl moiety or an alkyl linker at the thiourea part, was proven by our team previously [ 5 , 6 , 7 , 8 , 9 , 12 , 13 , 14 , 15 , 16 , 17 ].…”

Section: Resultsmentioning

confidence: 80%

“…First, transition from thiourea to tetrazole derivative practically does not change molar weight, but has impact on lipophilicity. Second, our previous studies showed that this transition is extremely profitable in terms of designed pharmacological action [ 16 , 17 ]. It was decided to synthesize only one tetrazole compound at the first stage of studies to compare cytotoxicity results between thiourea and tetrazole derivative.…”

Section: Resultsmentioning

confidence: 99%

“…Most of these compounds showed significant biological activity. In some of reported studies, researchers were using thiourea derivatives as substrates to replace thiourea motif by heterocyclic arrangement [ 14 , 15 , 16 , 17 ]. Wide spectra of biological activities are reported continuously for thiourea-based compounds [ 18 , 19 , 20 , 21 ].…”

Section: Introductionmentioning

confidence: 99%

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Cytotoxicity Evaluation of Novel bis(2-aminoethyl)amine Derivatives

et al. 2020

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Seven novel derivatives of bis(2-aminoethyl)amine were synthesized. For compounds 1 and 7 single crystals were isolated and X-ray diffraction experiments were done. Lipophilicity and drug likeness were calculated in the initial stage of research. All compounds were screened for their in vitro cytotoxic activity against a panel of human cancer cell lines, which is contrary to normal (HaCaT) cell lines, by using the MTT method. Studies were followed by lactate dehydrogenase assay, apoptotic activity, and interleukin-6 assay. Within the studied group, compound 6 showed the most promising results in all biological studies. The strongest influence in A549 cells was denoted for derivative 4, which inhibited interleukin release almost tenfold, as compared to the control.

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Section: Resultsmentioning

confidence: 80%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Cytotoxicity Evaluation of Novel bis(2-aminoethyl)amine Derivatives

et al. 2020

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“…The docking was carried out in two stages. First to the binding site targeted by fluoroquinolones (e.g., Ciprofloxacin, see our previous works [ 34 ]. The fluoroquinolones bind to the DNA–enzyme complex and stabilize it in the cleaved DNA state.…”

Section: Resultsmentioning

confidence: 99%

Novel Tetrazole-Based Antimicrobial Agents Targeting Clinical Bacteria Strains: Exploring the Inhibition of Staphylococcus aureus DNA Topoisomerase IV and Gyrase

Roszkowski

Szymańska-Majchrzak

Koliński

et al. 2021

IJMS

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Eleven novel imide-tetrazoles were synthesized. In the initial stage of research, in silico structure-based pharmacological prediction was conducted. All compounds were screened for antimicrobial activity using standard and clinical strains. Within the studied group, compounds 1–3 were recognized as leading structures with the most promising results in antimicrobial studies. Minimal inhibitory concentration values for compounds 1, 2, 3 were within the range of 0.8–3.2 μg/mL for standard and clinical Gram-positive and Gram-negative bacterial strains, showing in some cases higher activity than the reference Ciprofloxacin. Additionally, all three inhibited the growth of all clinical Staphylococci panels: Staphylococcus aureus (T5592; T5591) and Staphylococcus epidermidis (5253; 4243) with MIC values of 0.8 μg/mL. Selected compounds were examined in topoisomerase IV decatenation assay and DNA gyrase supercoiling assay, followed by suitable molecular docking studies to explore the possible binding modes. In summary, the presented transition from substrate imide-thioureas to imide-tetrazole derivatives resulted in significant increase of antimicrobial properties. The compounds 1–3 proposed here provide a promising basis for further exploration towards novel antimicrobial drug candidates.

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“…Tetrazole, an important five-membered heterocycle, is well employed in medicinal chemistry due to its N-donor characteristics. Tetrazole derivatives have been reported to possess a broad spectrum of biological activities, such as antibacterial [5,6], anticancer [7,8], anti-Alzheimers's disease [9,10], antitubercular [11,12], antimalarial [13,14], and antifungal [15,16] properties. Moreover, many tetrazole-based drugs such as Tedizolid, Cilostazol, Cefamandole and Irbesartan have already been used in clinical practice for the treatment of various diseases.…”

Section: Commentmentioning

confidence: 99%

The crystal structure of 5-bromo-2-(1-methyl-1H-tetrazol-5-yl)pyridine, C₇H₆BrN₅

Tang

Xu²,

Wang

et al. 2019

Zeitschrift Für Kristallographie - New Crystal Structures

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Design and synthesis of novel 1H-tetrazol-5-amine based potent antimicrobial agents: DNA topoisomerase IV and gyrase affinity evaluation supported by molecular docking studies

Cited by 34 publications

References 38 publications

Cytotoxicity Evaluation of Novel bis(2-aminoethyl)amine Derivatives

Cytotoxicity Evaluation of Novel bis(2-aminoethyl)amine Derivatives

Novel Tetrazole-Based Antimicrobial Agents Targeting Clinical Bacteria Strains: Exploring the Inhibition of Staphylococcus aureus DNA Topoisomerase IV and Gyrase

The crystal structure of 5-bromo-2-(1-methyl-1H-tetrazol-5-yl)pyridine, C₇H₆BrN₅

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Design and synthesis of novel 1H-tetrazol-5-amine based potent antimicrobial agents: DNA topoisomerase IV and gyrase affinity evaluation supported by molecular docking studies

Cited by 34 publications

References 38 publications

Cytotoxicity Evaluation of Novel bis(2-aminoethyl)amine Derivatives

Cytotoxicity Evaluation of Novel bis(2-aminoethyl)amine Derivatives

Novel Tetrazole-Based Antimicrobial Agents Targeting Clinical Bacteria Strains: Exploring the Inhibition of Staphylococcus aureus DNA Topoisomerase IV and Gyrase

The crystal structure of 5-bromo-2-(1-methyl-1H-tetrazol-5-yl)pyridine, C7H6BrN5

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The crystal structure of 5-bromo-2-(1-methyl-1H-tetrazol-5-yl)pyridine, C₇H₆BrN₅