Antimicrobial, cytotoxicity, molecular modeling and DNA cleavage/binding studies of zinc-naproxen complex: switching DNA binding mode of naproxen by coordination to zinc ion

Khandar, Ali Akbar; Mirzaei-Kalar, Zeinab; Shahabadi, Nahid; Hadidi, Saba; Abolhasani, Hoda; Hosseini‐Yazdi, Seyed Abolfazl; Jouyban, Abolghasem

doi:10.1080/07391102.2020.1854858

Cited by 10 publications

(4 citation statements)

References 57 publications

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“…Naproxen, ( S )‐2‐(6‐methoxynaphthalen‐2‐yl)propionic acid ( Figure 1), is one of the most frequently utilized nonsteroidal anti‐inflammatory drugs providing an effective cure in inflammatory disorders and symptoms, such as pain and fever [4] . Besides these biological activities, naproxen and its derivatives have attracted great interest in recent years due to their anticancer and antimicrobial effects [5–7] …”

Section: Introductionmentioning

confidence: 99%

“…[4] Besides these biological activities, naproxen and its derivatives have attracted great interest in recent years due to their anticancer and antimicrobial effects. [5][6][7] Thiosemicarbazide (NH 2 À NHÀ (C=S)À NH 2 ) is the sulfur-counterpart of semicarbazide functionality and provides chemical versatility and varying biological Supporting information for this article is available on the WWW under https://doi.org/10.1002/cbdv.202100900 properties than semicarbazide due to the presence of the sulfur atom. [8] In addition to its wide range of pharmacological activities such as anticancer, antioxidant, and anti-inflammatory, [9][10][11] thiosemicarbazide is also a strategic functionality frequently used in the development of antimicrobial agents (Figure 2).…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Antimicrobial Evaluation, and Molecular Modeling Studies of New Thiosemicarbazide‐Triazole Hybrid Derivatives of (S)‐Naproxen

Han

İnce

Gündüz

et al. 2022

Chemistry & Biodiversity

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The discovery of new antimicrobial molecules is crucial for combating drug‐resistant bacterial and fungal infections that pose a dangerous threat to human health. In the current research, we applied a molecular hybridization approach to synthesize original thiosemicarbazide‐triazole derivatives starting from (S)‐naproxen (7a–7k). After structural characterization using FT‐IR, 1H‐NMR, 13C‐NMR, and HR‐MS, the obtained compounds were screened for their antimicrobial activities against Staphylococcus aureus ATCC 29213, Escherichia coli ATCC 25922, Candida albicans ATCC 10231 and their isolates, as well. Although all compounds were found to be moderate antimicrobial agents, in general, their antibacterial activities were better than antifungal effects. Among the tested compounds, 7j carrying nitrophenyl group on the thiosemicarbazide functionality represented the best MIC value against S. aureus isolate. Finally, molecular docking studies were performed in the active pocket of S. aureus flavohemoglobin to rationalize the obtained biological data.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis, Antimicrobial Evaluation, and Molecular Modeling Studies of New Thiosemicarbazide‐Triazole Hybrid Derivatives of (S)‐Naproxen

Han

İnce

Gündüz

et al. 2022

Chemistry & Biodiversity

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“… *Antibacterial activity. [251] 119-Ni pUC18, AGE *Cytotoxicity activity: MTT assay. Apoptosis induction studies.…”

Section: Amss In Pharma Studiesmentioning

confidence: 99%

Nuclease-like metalloscissors: Biomimetic candidates for cancer and bacterial and viral infections therapy

Anjomshoa

Amirheidari

2022

Coordination Chemistry Reviews

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Despite the extensive and rapid discovery of modern drugs for treatment of cancer, microbial infections, and viral illnesses; these diseases are still among major global health concerns. To take inspiration from natural nucleases and also the therapeutic potential of metallopeptide antibiotics such as the bleomycin family, artificial metallonucleases with the ability of promoting DNA/RNA cleavage and eventually affecting cellular biological processes can be introduced as a new class of therapeutic candidates. Metal complexes can be considered as one of the main categories of artificial metalloscissors, which can prompt nucleic acid strand scission. Accordingly, biologists, inorganic chemists, and medicinal inorganic chemists worldwide have been designing, synthesizing and evaluating the biological properties of metal complexes as artificial metalloscissors. In this review, we try to highlight the recent studies conducted on the nuclease-like metalloscissors and their potential therapeutic applications. Under the light of the concurrent Covid-19 pandemic, the human need for new therapeutics was highlighted much more than ever before. The nuclease-like metalloscissors with the potential of RNA cleavage of invading viral pathogens hence deserve prime attention.

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“…Naproxen (Hnap), a prominent member of NSAIDs, has been mainly used in the treatment of headaches and fevers based on its analgesic and antipyretic features [25][26][27][28]. There are several papers in which silver-naproxen complexes are synthesized and their biological properties evaluated, showing better biological activities than naproxen [29][30][31][32].…”

Section: Introductionmentioning

confidence: 99%

Trinuclear silver(I) complex of non-steroidal anti-inflammatory drug naproxen: Synthesis, characterization, and in vitro cytotoxicity

Çağlar

Altay

Harurluoglu

et al. 2021

Maced. J. Chem. Chem. Eng.

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Herein, a new silver(I) complex with the non-steroidal anti-inflammatory drug naproxen and nitrogen donor 3-picoline ligands was synthesized, characterized, and subsequently tested for its cytotoxicity against different types of cancer cell lines. Elemental analysis, Fourier transform infrared spectroscopy, thermal, and proton nuclear magnetic resonance techniques showed that the molecular formula of the prepared complex is bis(3-picoline)tris(-naproxenato)trisilver(I) and naproxen ligands bind to silver ions in a bridging bidentate mode. 2,3-bis-(2-methoxy-4-nitro-5-sulfophenyl)-2H-tetrazolium-5-carboxanilide (XTT) results revealed that silver salts and naproxen alone showed quite weak cytotoxic activity against human breast adenocarcinoma (MDA-MB-453), lung adenocarcinoma (A-549), and colorectal adenocarcinoma (HT-29) cell lines (IC50 > 250 µM), whereas the complex displayed dose dependent cytotoxicity against the aforementioned cell lines. The highest cytotoxicity was observed on MDA-MB-453 cells with an IC50 value of 11.73 µM. Moreover, the complex showed higher selectivity against the cancer cell lines compared to fibroblast 3T3-L1 cells. This study provides preliminary scientific data on the complex for further elucidation of its anticancer mechanism of action.

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Antimicrobial, cytotoxicity, molecular modeling and DNA cleavage/binding studies of zinc-naproxen complex: switching DNA binding mode of naproxen by coordination to zinc ion

Cited by 10 publications

References 57 publications

Synthesis, Antimicrobial Evaluation, and Molecular Modeling Studies of New Thiosemicarbazide‐Triazole Hybrid Derivatives of (S)‐Naproxen

Synthesis, Antimicrobial Evaluation, and Molecular Modeling Studies of New Thiosemicarbazide‐Triazole Hybrid Derivatives of (S)‐Naproxen

Nuclease-like metalloscissors: Biomimetic candidates for cancer and bacterial and viral infections therapy

Trinuclear silver(I) complex of non-steroidal anti-inflammatory drug naproxen: Synthesis, characterization, and in vitro cytotoxicity

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