Investigation of Biochemical Properties of Acetone O-(4-chlorophenylsulfonyl)oxime and Acetone O-(2-naphthylsulfonyl)oxime

Yıl 2024, Cilt: 1 Sayı: 1, 7 - 11, 26.04.2024

Pınar Yalçın , Abdurrahman Dündar , Veysi Okumuş

https://doi.org/10.5281/zenodo.11068908

Öz

The purpose of this study is to survey if acetone O-(4 chlorophenylsulfonyl) oxime and acetone O-(2-naphtylsülphonyl)oxime compounds have antimicrobial and antioxidant properties or not. For this purpose, the antioxidant activity of the compounds was tested using the DPPH free radical method and the method of determining the antibacterial activity of newly synthesized compounds. As a result, compound 1a shows better antioxidant activity than compound 2a at all tested concentrations. The antibacterial activities of sulfonate derivatives on Staphylococcus aureus, Bacillus sps, Escherichia coli, and Klebsiella pneumoniae strains were investigated and it was determined that all compounds showed partial antibacterial activity for S. aureus, E. coli, and K. pneumoniae strains.

Anahtar Kelimeler

Acetone O-(4-chlorophenylsulfonyl)oxime, Acetone O-(2-naphtylsülphonyl)Oxime, Antimicrobial activity, Antioxidant activity, Docking, ADMET

Aseton O-(4-klorofenilsülfonil)oksim ve Aseton O-(2-naftilsülfonil)oksimin Biyokimyasal Özelliklerinin Araştırılması

Öz

Bu çalışmanın amacı, aseton O-(4 klorofenilsülfonil) oksim ve aseton O-(2-naftilsülfonil)oksim bileşiklerinin antimikrobiyal ve antioksidan özelliklere sahip olup olmadığını araştırmaktır. Bu amaçla bileşiklerin antioksidan aktiviteleri DPPH serbest radikal yöntemi ile antioksidan ve antibakteriyel aktivitelerinin belirlenmiştir. Sonuç olarak bileşik 1a, test edilen tüm konsantrasyonlarda bileşik 2a'dan daha iyi antioksidan aktivite gösterir. Sülfonat türevlerinin Staphylococcus aureus, Bacillus sps, Escherichia coli ve Klebsiella pneumoniae suşları üzerindeki antibakteriyel aktiviteleri araştırılmış ve tüm bileşiklerin S. aureus, E. coli ve K. pneumoniae suşlarına karşı kısmi antibakteriyel aktivite gösterdiği tespit edilmiştir.

Anahtar Kelimeler

Aseton, Aseton oksim, Antimikrobiyal aktivite, Antioksidan aktivite, Docking, ADMET

Kaynakça

• Sørensen, M., Neilson, E.H., Møller, B.L., “Oximes: unrecognized chameleons in general and specialized plant metabolism”, Molecular Plant, Vol. 11, Issue 1, Pages 95-117, 2018.
• Mahadevan, S., “Role of oximes in nitrogen metabolism in plants”, Annual Review of Plant Physiology, Vol. 24, Issue 1, Pages 69-88, 1973.
• Korkmaz, A., Bursalı, E., “An in vitro and in silico study on the synthesis and characterization of novel bis (sulfonate) derivatives as tyrosinase and pancreatic lipase inhibitors”, Journal of Molecular Structure, 1259, 132734, 2022.
• Asif, M., Imran, MA., “Mini-Reviews in Organic Chemistry, A Mini-Review on Pharmacological Importance of Benzothiazole Scaffold”, Vol. 18, Issue 8, Pages 1086-1097, 2021.
• Korkmaz, A., Bursalı, E., “Benzothiazole sulfonate derivatives bearing azomethine: Synthesis, characterization, enzyme inhibition, and molecular docking study”, Journal of Molecular Structure, 1257, 132641, 2022.
• Taslimi, P., Işık, M., Türkan, F., Durgun, M., Türkeş, C., Gülçin, İ., Beydemir, Ş., “Benzenesulfonamide derivatives as potent acetylcholinesterase, α-glycosidase, and glutathione S-transferase inhibitors: biological evaluation and molecular docking studies”, Journal of Biomolecular Structure and Dynamics, Vol. 39, Issue 15, Pages 5449-5460, 2021.
• Yetişsin, F., Kardeş, İ., “Could acetone O-(4-chlorophenylsulfonyl) oxime be a copper chelating and antioxidative molecule on maize seedlings?”, International Journal of Phytoremediation, Vol. 24, Issue 7, Pages 721-729, 2022.
• Yetişsin F., Karakaya A., “Investigation of the effects of acetone o-(4 chlorophenylsulfonyl) oxime pre-application on biochemical parameters of maize seedlings under salt stress”, Artvin Coruh University Journal of Forestry Faculty, Vol. 23, Issue 1, Pages 74-83, 2022.
• Yetişsin, F., “Exogenous acetone O-(2-naphthylsulfonyl) oxime improves the adverse effects of excess copper by copper detoxification systems in maize”, International Journal of Phytoremediation, Vol. 25, Issue 14, Pages 2001-2013, 2023.
• Demiralay, M., “Exogenous acetone O-(4-chlorophenylsulfonyl) oxime alleviates Cd stress-induced photosynthetic damage and oxidative stress by regulating the antioxidant defense mechanism in Zea mays”, Physiology and Molecular Biology of Plants, Vol. 28, Issue 11, Pages 2069-2083, 2022.
• Mishra, V.R., Ghanavatkar, C.W., Mali, S.N., Chaudhari, H.K., Sekar, N., “Schiff base clubbed benzothiazole: synthesis, potent antimicrobial and MCF-7 anticancer activity, DNA cleavage and computational study”, Journal of Biomolecular Structure and Dynamics, 1621213, 2019.
• Venugopala, K.N., Chandrashekharappa, S., Pillay, M., Bhandary, S., Kandeel, M., Mahomoodally, F.M., Morsy, M.A., Chopra, D., Aldhubiab, B.E., Attimarad, M., “Synthesis and Structural Elucidation of Novel Benzothiazole Derivatives as Anti-tubercular Agents: In-silico Screening for Possible Target Identification”, Medicinal Chemistry, Vol. 15, Issue 3, Pages 311-326, 2019.
• Gabr, M.T., El-Gohary, N.S., El-Bendary, E.R., El-Kerdawy, M.M., Ni, N., Shaaban, M.I., “Synthesis, antimicrobial, antiquorum-sensing and cytotoxic activities of new series of benzothiazole derivatives”, Chinese Chemical Letters, Vol. 26, Issue 12, Pages 1522-1528, 2015.
• Ke, S., Wei, Y., Yang, Z., Wang, K., Liang, Y. Shi, L., “Novel cycloalkylthiophene–imine derivatives bearing benzothiazole scaffold: Synthesis, characterization and antiviral activity evaluation”, Bioorganic Medicinal Chemistry Letters, Vol. 23, Issue 18, Pages 5131-5134, 2013.
• Joseph, J., Janaki, G.B., “Copper complexes bearing 2-aminobenzothiazole derivatives as potential antioxidant: Synthesis, characterization”, Journal of Photochemistry and Photobiology B, 162, Pages 86-92, 2016.
• Hazra, A., Mondal, S., Maity, A., Naskar, S., Saha, P., Paira, R., Mondal, N.B., “Amberlite–IRA-402 (OH) ion exchange resin mediated synthesis of indolizines, pyrrolo [1, 2-a] quinolines and isoquinolines: Antibacterial and antifungal evaluation of the products”, European Journal of Medicinal Chemistry, Vol. 46, Issue 6, Pages 2132-2140, 2011.
• Su, S., Zhou, Q., Tang, X., Peng, F., Liu, T., Liu, L., Xie, C., He, M., Xue, W., “Design, synthesis, and antibacterial activity of novel myricetin derivatives containing sulfonate”, Monatshefte für Chemie, Chemical Monthly, Vol. 152, Issue 3, Pages 345-356, 2021.
• Rajan, L., Palaniswamy, D., Mohankumar, S.K., “Targeting obesity with plant-derived pancreatic lipase inhibitors: A comprehensive review”, Pharmacological Research, Vol. 155, 104681, 2020. Kumar, A., Chauhan, S., “Pancreatic lipase inhibitors: The road voyaged and successes”, Life Sciences, Vol. 271, 119115, 2021.
• Riaz, R., Batool, S., Zucca, P., Rescigno, A., Peddio, S., Peddio, R., Saleem, S., “Plants as a promising reservoir of tyrosinase inhibitors”, Mini Revies in Organic Chemistry, Vol. 18, Issue 6, Pages 808-828, 2021.
• Gatley, S.J., “Activities of the enantiomers of cocaine and some related compounds as substrates and inhibitors of plasma butyrylcholinesterase”, Biochemical Pharmacology, Vol. 41, Issue 8, Pages 1249-1254, 1991.
• Li, Q., Yang, H., Chen, Y., Sun, H., “Recent progress in the identification of selective butyrylcholinesterase inhibitors for Alzheimer's disease”, European Journal of Medicinal Chemistry, Vol. 132, Pages 294-309, 2017.
• Korkmaz, A., Duran, S., “High yielding electrophilic amination with lower order and higher order organocuprates: Application of acetone O-(4-Chlorophenylsulfonyl) oxime in the construction of the C− N bond at room temperature”, Synthetic Communications, Vol. 51, Issue 14, Pages 2077-2087, 2021.
• Korkmaz, A., “Copper-Catalyzed Electrophilic Amination of Diarylcadmium Reagents Utilizing Acetone O-(4-chlorophenylsulphonyl) oxime and Acetone O-(2-naphthylsulphonyl) oxime as Amination Agent”, Journal of the Institute of Science and Technology, Vol. 11, Issue 3, Pages 2102-2111, 2021.
• Korkmaz, A., “Room-temperature copper-catalyzed electrophilic amination of arylcadmium iodides with ketoximes” Journal of the Iranian Chemical Society, Vol. 18, Issue 11, Pages 3119-3125, 2021.
• Gümüş, A., Okumuş, V., Gümüş, S., “Synthesis, biological evaluation of antioxidant-antibacterial activities and computational studies of novel anthracene- and pyrene-based Schiff base derivatives”, Turkish Journal of Chemistry, Vol. 44, Issue 4, Pages 1200-1215, 2020.
• Tarhan, T., Dündar, A., Okumuş, V., Çulha, M., “Synthesis and Characterization of Bionanomaterials and Evaluation of Their Antioxidant, Antibacterial and DNA Cleavage Activities”, Chemistry Select, Vol. 6, Issue 17, Pages 4217-4223, 2021.
• Gumus, A., Okumus, V. “Synthesis and biological evaluation of quinoline-triazole and quinolone-triazole conjugates”, Turkish Journal of Chemistry, Vol. 42, Issue 5, Pages 1344-1357, 2018.
• Ejidike, I.P., Ajibade, P.A., “Synthesis, characterization, and in vitro antioxidant and anticancer studies of ruthenium(III) complexes of symmetric and asymmetric tetradentate Schiff bases”, Journal of Coordination Chemistry, Vol. 68, Issue 14, Pages 2552-2564, 2015.
• United States Center of Disease Control and Prevention (CDC), Antibiotic resistance threat report, 2019. Zurcher, K., Zwahlen, M., Ballif, M., Rieder, H.L., Egger, M., Fenner, L., "Influenza pandemics and tuberculosismortality in 1889 and 1918: analysis of historica data from Switzerland", PLoS ONE, Vol. 11, Issue 10, e0162575, 2016.
• Hoagland, H.C., Gastineau, D.A., “Haematological complications of cancer chemotherapy”, The chemotherapy source book, Michael C Perry, 2nd edition: 559. 1992.
• Kahl, R., Kappus, H., “Toxicology of the synthetic antioxidants BHA and BHT in comparison with the natural antioxidant vitamin E”, Z Lebensm Unters Forsch., Vol. 196, Issue 4, Pages 329-338, 1993. Rang, H.P., Dale, M.M., Ritter, J.M., “Anticancer drugs, Text book of Pharmacology”, Elsevier; 7 th edition: 673-87, 2012.
• Kilic, A., Söylemez, R., Okumuş, V., “Design, spectroscopic properties and effects of novel catechol spiroborates derived from Schiff bases in the antioxidant, antibacterial and DNA binding activity”, Journal of Organometallic Chemistry, 122228, 2021.