Design, synthesis, spectroscopic characterizations, in vitro pancreatic lipase as well as tyrosinase inhibition evaluations and in silico analysis of novel aryl sulfonate-naphthalene hybrids

References

• Abbas, S., Nasir, H. H., Zaib, S., Ali, S., Mahmood, T., Ayub, K., Tahir, N. M., & Iqbal, J. (2018). Carbonic anhydrase inhibition of Schiff base derivative of imino-methyl-naphthalen-2-ol: Synthesis, structure elucidation, molecular docking, dynamic simulation and density functional theory calculations. Journal of Molecular Structure, 1156, 193–200. https://doi.org/10.1016/j.molstruc.2017.11.086
   Web of Science ®Google Scholar
• Akocak, S., Taslimi, P., Lolak, N., Işık, M., Durgun, M., Budak, Y., Türkeş, C., Gülçin, İ., & Beydemir, Ş. (2021). Synthesis, characterization, and inhibition study of novel substituted phenylureidosulfaguanidine derivatives as α‐glycosidase and cholinesterase inhibitors. Chemistry & Biodiversity, 18(4), e2000958. https://doi.org/10.1002/cbdv.202000958
   PubMed Web of Science ®Google Scholar
• Alanazi, M. M., Elkady, H., Alsaif, N. A., Obaidullah, A. J., Alanazi, W. A., Al-Hossaini, A. M., Alharbi, M. A., Eissa, I. H., & Dahab, M. A. (2022). Discovery of new quinoxaline-based derivatives as anticancer agents and potent VEGFR-2 inhibitors: Design, synthesis, and in silico study. Journal of Molecular Structure, 1253, 132220. https://doi.org/10.1016/j.molstruc.2021.132220
   Web of Science ®Google Scholar
• Ali, S. A., Awad, S. M., Said, A. M., Mahgoub, S., Taha, H., & Ahmed, N. M. (2020). Design, synthesis, molecular modelling and biological evaluation of novel 3-(2-naphthyl)-1-phenyl-1H-pyrazole derivatives as potent antioxidants and 15-Lipoxygenase inhibitors. Journal of Enzyme İnhibition and Medicinal Chemistry, 35(1), 847–863. https://doi.org/10.1080/14756366.2020.1742116
   PubMed Web of Science ®Google Scholar
• Aziz, H., Mahmood, A., Zaib, S., Saeed, A., El-Seedi, H. R., Pelletier, J., Sévigny, J., & Iqbal, J. (2021). Synthesis, characterization, alkaline phosphatase inhibition assay and molecular modelingstudies of 1-benzylidene-2-(4-tert-butylthiazol-2-yl) hydrazines. Journal of Biomolecular Structure and Dynamics, 39(16), 6140–6153. https://doi.org/10.1080/07391102.2020.1802336
   PubMed Web of Science ®Google Scholar
• Aziz, H., Mahmood, A., Zaib, S., Saeed, A., Shafiq, Z., Pelletier, J., Sévigny, J., & Iqbal, J. (2020). Synthesis, characterization, in vitro tissue-nonspecific alkaline phosphatase (TNAP) and intestinal alkaline phosphatase (IAP) inhibition studies and computational evaluation of novel thiazole derivatives. Bioorganic Chemistry, 102, 104088. https://doi.org/10.1016/j.bioorg.2020.104088
   PubMed Web of Science ®Google Scholar
• Behl, T., Kaur, D., Sehgal, A., Singh, S., Sharma, N., Zengin, G., Andronie-Cioara, F. L., Toma, M. M., Bungau, S., & Bumbu, A. G. (2021). Role of monoamine oxidase activity in Alzheimer’s disease: An insight into the therapeutic potential of inhibitors. Molecules, 26(12), 3724. https://doi.org/10.3390/molecules26123724
   PubMed Web of Science ®Google Scholar
• Biovia, Dassault Systèmes. (2017). “Discovery studio visualizer.” San Diego, CA, USA 936.
   Google Scholar
• Çakmak, R., Başaran, E., & Şentürk, M. (2022). Synthesis, characterization, and biological evaluation of some novel Schiff bases as potential metabolic enzyme inhibitors. Archiv der Pharmazie, 355, e2100430.
   PubMed Web of Science ®Google Scholar
• Cetin, A., Türkan, F., Bursal, E., & Murahari, M. (2021). Synthesis, characterization, enzyme ınhibitory activity, and molecular docking analysis of a new series of thiophene-based heterocyclic compounds. Russian Journal of Organic Chemistry, 57(4), 598–604. https://doi.org/10.1134/S107042802104014X
   Web of Science ®Google Scholar
• Chen, W., Yao, S., Wan, J., Tian, Y., Huang, L., Wang, S., Akter, F., Wu, Y., Yao, Y., & Zhang, X. (2021). BBB-crossing adeno-associated virus vector: An excellent gene delivery tool for CNS disease treatment. Journal of Controlled Release, 333, 129–138. https://doi.org/10.1016/j.jconrel.2021.03.029
   PubMed Web of Science ®Google Scholar
• Ciupak, O., Daśko, M., Biernacki, K., Rachon, J., Masłyk, M., Kubiński, K., Martyna, A., & Demkowicz, S. (2021). New potent steroid sulphatase inhibitors based on 6-(1-phenyl-1 H-1, 2, 3-triazol-4-yl) naphthalen-2-yl sulphamate derivatives. Journal of Enzyme Inhibition and Medicinal Chemistry, 36(1), 239–248. https://doi.org/10.1080/14756366.2020.1858820
   Web of Science ®Google Scholar
• Demir, Y., Taslimi, P., Koçyiğit, Ü. M., Akkuş, M., Özaslan, M. S., Duran, H. E., Budak, Y., Tüzün, B., Gürdere, M. B., Ceylan, M., Taysi, S., Gülçin, İ., & Beydemir, Ş. (2020). Determination of the inhibition profiles of pyrazolyl–thiazole derivatives against aldose reductase and α‐glycosidase and molecular docking studies. Archiv Der Pharmazie, 353(12), 2000118. https://doi.org/10.1002/ardp.202000118
   PubMed Web of Science ®Google Scholar
• Dennington, R., Keith, T., & Millam, J. (2009). GaussView, Version. GaussView, Version 5.0.8.
   Google Scholar
• Elkady, H., Elwan, A., El-Mahdy, H. A., Doghish, A. S., Ismail, A., Taghour, M. S., Elkaeed, E. B., Eissa, I. H., Dahab, M. A., Mahdy, H. A., & Khalifa, M. M. (2022). New benzoxazole derivatives as potential VEGFR-2 inhibitors and apoptosis inducers: Design, synthesis, anti-proliferative evaluation, flowcytometric analysis, and in silico studies. Journal of Enzyme Inhibition and Medicinal Chemistry, 37(1), 403–416. https://doi.org/10.1080/14756366.2021.2015343
   Web of Science ®Google Scholar
• Erdoğan, M., Polat Köse, L., Eşsiz, S., & Gülçin, İ. İ (2021). Synthesis and biological evaluation of some 1‐naphthol derivatives as antioxidants, acetylcholinesterase, and carbonic anhydrase inhibitors. Archiv Der Pharmazie, 354(8), 2100113. https://doi.org/10.1002/ardp.202100113
   Web of Science ®Google Scholar
• Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Scalmani, G., Barone, V., Petersson, G. A., Nakatsuji, H., Li, X., Caricato, M., Marenich, A., Bloino, J., Janesko, B. G., Gomperts, R., Mennucci, B., Hratchian, H. P., Ortiz, J. V., … Fox, D. J. (2016). Gaussian 09, Rev. D.01, Gaussian Inc.
   Google Scholar
• George, G., Auti, P. S., & Paul, A. T. (2021). Design, synthesis and biological evaluation of N‐substituted indole‐thiazolidinedione analogues as potential pancreatic lipase inhibitors. Chemical Biology & Drug Design, 98(1), 49–59. https://doi.org/10.1111/cbdd.13846
   PubMed Web of Science ®Google Scholar
• Gümüş, M., Babacan, ŞN., Demir, Y., Sert, Y., Koca, İ., & Gülçin, İ. (2022). Discovery of sulfadrug–pyrrole conjugates as carbonic anhydrase and acetylcholinesterase inhibitors. Archiv Der Pharmazie, 355(1), 2100242. https://doi.org/10.1002/ardp.202100242
   PubMed Web of Science ®Google Scholar
• Halder, A. K., Adhikary, N., Maity, M. K., & Jha, T. (2010). Synthesis, pharmacological activity and comparative QSAR modeling of 1, 5-N, N′-substituted-2-(substituted naphthalenesulphonyl) glutamamides as possible anticancer agents. European Journal of Medicinal Chemistry, 45(5), 1760–1771. https://doi.org/10.1016/j.ejmech.2010.01.008
   PubMed Web of Science ®Google Scholar
• Hanwell, M. D., Curtis, D. E., Lonie, D. C., Vandermeersch, T., Zurek, E., & Hutchison, G. R. (2012). Avogadro: An advanced semantic chemical editor, visualization, and analysis platform. Journal of Cheminformatics, 4(1), 17. https://doi.org/10.1186/1758-2946-4-17
   PubMed Web of Science ®Google Scholar
• Huo, P.-C., Hu, Q., Shu, S., Zhou, Q.-H., He, R.-J., Hou, J., Guan, X.-Q., Tu, D.-Z., Hou, X.-D., Liu, P., Zhang, N., Liu, Z.-G., & Ge, G.-B. (2021). Design, synthesis and biological evaluation of novel chalcone-like compounds as potent and reversible pancreatic lipase inhibitors. Bioorganic & Medicinal Chemistry, 29, 115853. https://doi.org/10.1016/j.bmc.2020.115853
   PubMedGoogle Scholar
• Kim, B. H., Park, K. C., Park, J. H., Lee, C. G., Ye, S. K., & Park, J. Y. (2016). Inhibition of tyrosinase activity and melanin production by the chalcone derivative 1-(2-cyclohexylmethoxy-6-hydroxy-phenyl)-3-(4-hydroxymethyl-phenyl)-propenone. Biochemical and Biophysical Research Communications, 480(4), 648–654. https://doi.org/10.1016/j.bbrc.2016.10.110
   PubMed Web of Science ®Google Scholar
• Korkmaz, A. (2022). Synthesis, characterization, ADMET prediction and molecular docking studies of novel coumarinsulfonate derivatives. Journal of the Institute of Science and Technology, 12, 918–932. https://doi.org/10.21597/jist.1089701
   Google Scholar
• Korkmaz, A., & Bursal, E. (2022a). Synthesis, biological activity and molecular docking studies of novel sulfonate derivatives bearing salicylaldehyde. Chemistry and Biodiversity, 19, e20220014.
   Web of Science ®Google Scholar
• Korkmaz, A., & Bursal, E. (2022b). Benzothiazolesulfonate derivatives bearing azomethine: Synthesis, characterization, enzyme inhibition, and molecular docking study. Journal of Molecular Structure, 1257, 132641. https://doi.org/10.1016/j.molstruc.2022.132641
   Web of Science ®Google Scholar
• Korkmaz, A., & Bursal, E. (2022c). 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. https://doi.org/10.1016/j.molstruc.2022.132734
   Web of Science ®Google Scholar
• Korkmaz, A., Rhyman, L., & Ramasami, P. (2022). Synthesis, characterization, DFT and molecular docking studies of acetone O-((2,5-dichlorophenyl)sulfonyl) oxime. Physical Sciences Reviews. https://doi.org/10.1515/psr-2021-0230
   Google Scholar
• Kumar, A., & Chauhan, S. (2021). Pancreatic lipase inhibitors: The road voyaged and successes. Life Sciences, 271, 119115. https://doi.org/10.1016/j.lfs.2021.119115
   PubMed Web of Science ®Google Scholar
• Lee, S. K., Kang, Y., Chang, G. S., Lee, I. H., Park, S. H., & Park, J. (2017). Bioinformatics and molecular design research center. Yonsei University, Seoul https://preadmet.bmdrc.kr.
   Google Scholar
• Li, S., Hu, X., Pan, J., Gong, D., & Zhang, G. (2021). Mechanistic insights into the inhibition of pancreatic lipase by apigenin: Inhibitory interaction, conformational change and molecular docking studies. Journal of Molecular Liquids, 335, 116505. https://doi.org/10.1016/j.molliq.2021.116505
   Web of Science ®Google Scholar
• Liu, T. T., Liu, X. T., Chen, Q. X., & Shi, Y. (2020). Lipase inhibitors for obesity: A review. Biomedicine & Pharmacotherapy = Biomedecine & Pharmacotherapie, 128, 110314. https://doi.org/10.1016/j.biopha.2020.110314
   PubMed Web of Science ®Google Scholar
• Li, Y., Xu, Y., Pan, C., Ren, Z., & Yang, X. (2020). TRIF is essential for the anti-inflammatory effects of Astragalus polysaccharides on LPS-infected Caco2 cells. International Journal of Biological Macromolecules, 159, 832–838. https://doi.org/10.1016/j.ijbiomac.2020.05.005
   PubMed Web of Science ®Google Scholar
• Maya, A. B. S., Pérez-Melero, C., Mateo, C., Alonso, D., Fernández, J. L., Gajate, C., Mollinedo, F., Peláez, R., Caballero, E., & Medarde, M. (2005). Further naphthylcombretastatins.An investigation on the role of the naphthalene moiety. Journal of Medicinal Chemistry, 48(2), 556–568. https://doi.org/10.1021/jm0310737
   PubMed Web of Science ®Google Scholar
• Menteşe, E., Yılmaz, F., Emirik, M., Ülker, S., & Kahveci, B. (2018). Synthesis, molecular docking and biological evaluation of some benzimidazole derivatives as potent pancreatic lipase inhibitors. Bioorganic Chemistry, 76, 478–486. https://doi.org/10.1016/j.bioorg.2017.12.023
   PubMed Web of Science ®Google Scholar
• Mirzazadeh, R., Asgari, M. S., Barzegari, E., Pedrood, K., Mohammadi‐Khanaposhtani, M., Sherafati, M., Larijani, B., Rastegar, H., Rahmani, H., Mahdavi, M., Taslimi, P., Üç, E. M., & Gulçin, İ. (2021). New quinoxalin‐1, 3, 4‐oxadiazole derivatives: Synthesis, characterization, in vitro biological evaluations, and molecular modeling studies. Archiv Der Pharmazie, 354(9), 2000471. https://doi.org/10.1002/ardp.202000471
   Web of Science ®Google Scholar
• Molinspiration, C. (2011). http://www.molinspiration.com/cgi-bin/properties.
   Google Scholar
• Moussa, G., Alaaeddine, R., Alaeddine, L. M., Nassra, R., Belal, A. S. F., Ismail, A., El Yazbi, A. F., Abdel, Ghany, Y. S., & Hazzaa, A. (2018). Novel click modifiable thioquinazolinones as anti-inflammatory agents: Design, synthesis, biological evaluation and docking study. European Journal of Medicinal Chemistry, 144, 635–650. https://doi.org/10.1016/j.ejmech.2017.12.065
   PubMed Web of Science ®Google Scholar
• Oja, M., & Maran, U. (2018). pH-permeability profiles for drug substances: Experimental detection, comparison with human intestinal absorption and modelling. European Journal of Pharmaceutical Sciences, 123, 429–440. https://doi.org/10.1016/j.ejps.2018.07.014
   PubMed Web of Science ®Google Scholar
• Pettersen, E. F., Goddard, T. D., Huang, C. C., Couch, G. S., Greenblatt, D. M., Meng, E. C., & Ferrin, T. E. (2004). UCSF Chimera—A visualization system for exploratory research and analysis. Journal of Computational Chemistry, 25(13), 1605–1612. https://doi.org/10.1002/jcc.20084
   PubMed Web of Science ®Google Scholar
• Pillaiyar, T., Manickam, M., & Namasivayam, V. (2017). Skin whitening agents: Medicinal chemistry perspective of tyrosinase inhibitors. Journal of Enzyme İnhibition and Medicinal Chemistry, 32(1), 403–425. https://doi.org/10.1080/14756366.2016.1256882
   PubMed Web of Science ®Google Scholar
• Schrödinger LLC. (2021). The PyMOL molecular graphics system, version 2.5.2.
   Google Scholar
• Shirinzadeh, H., Dilek, E., & Alım, Z. (2022). Evaluation of naphthalenylmethylen hydrazine derivatives as potent ınhibitors on, antiatherogenic enzymes, paraoxonase ı and acetylcholinesterase activities. ChemistrySelect, 7(5), e202104489. https://doi.org/10.1002/slct.202104489
   Web of Science ®Google Scholar
• Song, X., Ni, M., Zhang, Y., Zhang, G., Pan, J., & Gong, D. (2021). Comparing the inhibitory abilities of epigallocatechin-3-gallate and gallocatechingallate against tyrosinase and their combined effects with kojic acid. Food Chemistry, 349, 129172. https://doi.org/10.1016/j.foodchem.2021.129172
   PubMed Web of Science ®Google Scholar
• Trott, O., & Olson, A. J. (2010). Software news and update AutoDockVina: İmproving the speed and accuracy of docking with a new scoring function. efficient optimization, and multithreading. Journal of Computational Chemistry, 31(2), 455–461. https://doi.org/10.1002/jcc.21334
   PubMed Web of Science ®Google Scholar
• Turkan, F., Cetin, A., Taslimi, P., Karaman, H. S., & Gulcin, I. (2019). Synthesis, characterization, molecular docking and biological activities of novel pyrazoline derivatives. Archiv Der Pharmazie, 352(6), 1800359. https://doi.org/10.1002/ardp.201800359
   PubMed Web of Science ®Google Scholar
• Viana Nunes, A. M., das Chagas Pereira de Andrade, F., Filgueiras, L. A., de Carvalho Maia, O. A., Cunha, R. L. O. R., Rodezno, S. V. A., Maia Filho, A. L. M., de Amorim Carvalho, F. A., Braz, D. C., & Mendes, A. N. (2020). preADMET analysis and clinical aspects of dogs treated with the Organotellurium compound RF07: A possible control for canine visceral leishmaniasis? Environmental Toxicology and Pharmacology, 80, 103470.
   PubMed Web of Science ®Google Scholar
• Wang, G., Liu, W., Tang, J., Ma, X., Gong, Z., Huang, Y., Li, Y., & Peng, Z. (2020). Design, synthesis, and anticancer evaluation of benzophenone derivatives bearing naphthalene moiety as novel tubulin polymerization inhibitors. Bioorganic Chemistry, 104, 104265. https://doi.org/10.1016/j.bioorg.2020.104265
   PubMed Web of Science ®Google Scholar
• Whitty, A., Viarengo, L. A., & Zhong, M. (2017). Progress towards the broad use of non-peptide synthetic macrocycles in drug discovery. Organic & Biomolecular Chemistry, 15(37), 7729–7735. https://doi.org/10.1039/c7ob00056a
   PubMed Web of Science ®Google Scholar
• Yetişsin, F., & Kardeş, İ. (2022). Could acetone O-(4-chlorophenylsulfonyl) oxime be a copper chelating and antioxidative molecule on maize seedlings? International Journal of Phytoremediation, 24(7), 721–729. https://doi.org/10.1080/15226514.2021.1970101
   PubMed Web of Science ®Google Scholar
• Yuriev, E., Agostino, M., & Ramsland, P. A. (2011). Challenges and advances in computational docking: 2009 in review. Journal of Molecular Recognition: JMR, 24(2), 149–164. https://doi.org/10.1002/jmr.1077
   PubMed Web of Science ®Google Scholar
• Zhang, J., Yang, Y., Qian, X.-K., Song, P.-F., Zhao, Y.-S., Guan, X.-Q., Zou, L.-W., Bao, X., & Wang, H. (2021). Design, synthesis, and structure‐activity relationship study of pyrazolones as potent ınhibitors of pancreatic lipase. ChemMedChem. 16(10), 1600–1604. https://doi.org/10.1002/cmdc.202000850
   PubMed Web of Science ®Google Scholar
• Zolghadri, S., Bahrami, A., Hassan Khan, M. T., Munoz-Muno, J., Garcia-Molina, F., Garcia-Canovas, F., & Saboury, A. A. (2019). A comprehensive review on tyrosinase inhibitors. Journal of Enzyme İnhibition and Medicinal Chemistry, 34(1), 279–309. https://doi.org/10.1080/14756366.2018.1545767
   PubMed Web of Science ®Google Scholar