WoS İndeksli Yayınlar Koleksiyonu
Permanent URI for this collectionhttps://hdl.handle.net/20.500.14627/6
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Article Citation - WoS: 1Citation - Scopus: 2Synthesis of New 4-Aminobenzoic Acid (paba) Hydrazide-hydrazone/Sulfonate Hybrids and Antimicrobial Evaluation With Ascorbic Acid/Salicylic Acid/<i>n< Cysteine Combinations(Taylor & Francis Ltd, 2024) Han, M. Ihsan; Ince, Ufuk; Coskun, G. Pelin; Birgul, Kaan; Dogan, Sengul Dilem; Ashoorzadeh, Amir; Kucukguzel, S. GuenizOne of the most serious threats to human health is the increasing prevalence of drug-resistant pathogens. The development of new antibiotics capable of combating drug resistance is critical. In various bacteria and plant species, 4-aminobenzoic acid (PABA) is produced and used as a substrate for folate generation. In this study, a new series of PABA analogs were synthesized and evaluated for their antimicrobial activity. Thirteen novel compounds were prepared by linking PABA hydrazide to sulfonate esters via a hydrazone bridge (4a-m). The structures of these compounds were characterized by H-1 and C-13 NMR and FT-IR spectroscopy as well as by LC-MS. Following structural characterization, all compounds were tested for their antimicrobial activity against Staphylococcus aureus (ATCC 29213), Enterococcus faecium (ATCC 19434), Escherichia coli (ATCC 25922), Pseudomonas aeruginosa (ATCC 27853), and Candida albicans (ATCC 10231) strains. Four compounds were found to have moderate antimicrobial activity against the P. aeruginosa strain. These compounds, including 4e, 4f, 4g, and 4m, containing a hydrazide-hydrazone sulfonate functionality, showed the best MIC value of 64 mu g/mL. In addition, synergistic effects of ascorbic acid, salicylic acid, and N-acetyl cysteine (NAC) with synthesized compounds were also investigated. It was observed that the combination of compounds 4f and 4g with NAC showed antipseudomonal activity with MIC values of 32 mu g/mL and 16 mu g/mL, respectively, against the P. aeuriginosa strain. The antimicrobial activity of 4f and 4g was enhanced by two folds in combination with NAC. Our findings in this study can be crucial for the development of new potent antimicrobial agents. [GRAPHICS]Review Citation - WoS: 15Citation - Scopus: 11Thioethers: an Overview(Bentham Science Publ Ltd, 2022) Han, M. Ihsan; Kucukguzel, S. GunizSpreading rapidly in recent years, cancer has become one of the causes of the highest mortality rates after cardiovascular diseases. The reason for cancer development is still not clearly understood despite enormous research activities in this area. Scientists are now working on the biology of cancer, especially on the root cause of cancer development. The aim is to treat the cancer disease and thus cure the patients. The continuing efforts for the development of novel molecules as potential anti-cancer agents are essential for this purpose. The main aim of this review was to present a survey on the medicinal chemistry of thioethers and provide practical data on their cytotoxicities against various cancer cell lines. The research articles published between 2001-2020 were consulted to prepare this review article; however, patent literature has not been included. The thioether-containing heterocyclic compounds may emerge as a new class of potent and effective anti-cancer agents in the future.Article Citation - WoS: 11Citation - Scopus: 11Synthesis, Antimicrobial Evaluation, and Molecular Modeling Studies of New Thiosemicarbazide-Triazole Hybrid Derivatives of (<i>s</I>)-naproxen(Wiley-v C H verlag Gmbh, 2022) Han, M. Ihsan; Ince, Ufuk; Gunduz, Miyase Gozde; Kucckguzel, S. Guniz; Küçükgüzel, Ş. GünizThe 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, H-1-NMR, C-13-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.Article Citation - WoS: 14Citation - Scopus: 17Design, Synthesis, and <i>in Vitro</I> and <i>in Vivo</I> Anticancer Activity Studies of New (<i>s</I>)-naproxen Thiosemicarbazide/1,2,4-triazole Derivatives(Royal Soc Chemistry, 2022) Han, M. Ihsan; Tunc, Cansu Umran; Atalay, Pinar; Erdogan, Omer; Unal, Gokhan; Bozkurt, Mehmet; Kucukguzel, S. GunizIn this study, a series of novel (S)-Naproxen derivatives bearing a thiosemicarbazide/1,2,4-triazole moiety were designed, synthesized, and evaluated for anticancer activity. The structures of these compounds were characterized by spectral (H-1-C-13 NMR, FT-IR, and HR-MS analyses) methods. All of the synthesized compounds (3a-m, 4a-j) were screened for anticancer activity against human breast cancer cell line MDA-MB-231. Among them, (S)-4-(2,4-dichlorophenyl)-5-[1-(6-methoxynaphthalen-2-yl)ethyl]-4H-1,2,4-triazole-3-thione (4b) showed the most potent anticancer activity with a good selectivity (IC50= 9.89 +/- 2.4 mu M). Inhibition of anti-apoptotic protein Bcl-2 was investigated in MDA-MB-231 cells treated with compound 4b using Western Blotting. Apoptosis was also detected by AO/EB and JC-1 staining. Furthermore, activation of caspase-3 enzyme activity demonstrated apoptosis. The flow cytometric analysis results showed that compound 4b decreases the number of cells in the G2/M phase and increases the cells in the S phase in a dose-dependent manner. The anticancer activity of compound 4b was also investigated. In the Ehrlich acid tumor model, a well-validated in vivo ectopic breast cancer model, compound 4b had anticancer activity and reduced the tumor volume at both low (60 mg kg(-1)) and high (120 mg kg(-1)) doses in mice, according to our in vivo results.Article Citation - WoS: 41Citation - Scopus: 39Synthesis and Anticancer Activity of Novel Hydrazone Linkage-Based Aryl Sulfonate Derivatives as Apoptosis Inducers(Springer Birkhauser, 2022) Senkardes, Sevil; Han, M. Ihsan; Gurboga, Merve; Ozakpinar, Ozlem Bingol; Kucukguzel, S. Guniz; Güniz Küçükgüzel, Ş.; İhsan Han, M.In the present study, the various 28 hybrid molecules containing hydrazone and sulfonate moieties were synthesized and characterized by FTIR, H-1-NMR, C-13-NMR spectroscopy and LC-MS spectrometry, besides elemental analysis. The compounds were evaluated for their antiproliferative effects against six cancer cell lines, namely A549 (non-small cell lung cancer), MCF-7 (breast cancer), HT-29 (colorectal adenocarcinoma cancer), PC-3 (androgen-independent prostate adenocarcinoma), Hep3B (hepatocellular carcinoma cancer), and HeLa (epitheloid cervix carcinoma cancer). Among all the target compounds, compounds 4g and 4h exhibited more promising effects on MCF-7 cell lines (IC50 = 17.8 mu M and 21.2 mu M, respectively) with high selectivity. Further mechanistic studies proposed that compounds 4g and 4h induced apoptosis is mediated through the intrinsic apoptotic pathway with changes in mitochondrial membrane potential by finally activating caspase-9 and caspase-3. The results have been encouraging enough to merit further investigation. [GRAPHICS] .