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Biscarbazole Derivatives: Synthesis, Characterization, Antimicrobial and Antitumor Activity, and Molecular Docking Study

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Abstract

New series of biscarbazole derivatives containing imine-amine groups was synthesized. Antimicrobial activity of newly synthesized compounds against bacterial strains and yeast isolates was determined. The effects of the synthesized test compounds on cell proliferation and NCI-60 survival parameter values were measured. In addition, in silico analysis against five different receptors with synthesized two compounds was carried out to see the necessary interactions responsible for anti-bacterial activity. The docking results of both compounds supported the antibacterial activity exhibiting high inhibition constants.

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REFERENCES

  1. Çiçek, B., Çalısır, Ü., Tavaslı, M., and Tülek, R., J. Mol. Struct., 2018, vol. 1153, p. 4. https://doi.org/10.1016/j.molstruc.2017.09.109

    Article  CAS  Google Scholar 

  2. Kharanekoa, A.O., and Kharanekoa, O.I., Russ. J. Org. Chem., 2019, vol. 55, p. 291. https://doi.org/10.1134/S1070428019030023

  3. Zhang, F.F., Gan, L.L., and Zhou, C.H., Bioorg. Med. Chem. Lett., 2010, vol. 20, p. 1881. https://doi.org/10.1016/j.bmcl.2010.01.159

    Article  CAS  PubMed  Google Scholar 

  4. Głuszynska, A., Eur. J. Med. Chem., 2015, vol. 94, p. 405. https://doi.org/10.1016/j.ejmech.2015.02.059

    Article  CAS  PubMed  Google Scholar 

  5. Chakraborty, A., Saha, C., Podder, G., Chowdhury, B.K., and Bhattacharyya, P., Phytochemistry, 1995, vol. 38, p. 787. https://doi.org/10.1016/0031-9422(94)00666-h

    Article  CAS  PubMed  Google Scholar 

  6. Choi, T.A., Czerwonka, R., Fröhner, W., Krahl, M.P., Reddy, K.R., and Franzblau, S.G., Chem. Med. Chem., 2006, vol. 1, p. 812. https://doi.org/10.1002/cmdc.200600002

  7. Archer, S. and Ross, B.S., Eur. J. Med. Chem., 1987, vol. 30, p. 1204. https://doi.org/10.1021/jm00390a014

    Article  CAS  Google Scholar 

  8. Yamamoto, S., Shirai, J., Fukase, Y., Tomata, Y., Sato, A., Ochida, A., Yonemori, K., Nakagawa, H., Patent Japan WO2013/042782, 2013.

  9. Sakano, K.I., Ishimaru, K., and Nakamura, S., J. Antibiotics., 1980, vol. 33, p. 683. https://doi.org/10.7164/antibiotics.33.683

    Article  CAS  Google Scholar 

  10. Arbiser, J.L., Govindarajan, B., Barrle, T.E., Lynch, R., Frank, D.A., and UshioFukai, M., J. Invest. Dermatol., 2006, vol. 126, p. 1396. https://doi.org/10.1038/sj.jid.5700276

    Article  CAS  PubMed  Google Scholar 

  11. Pozharskii, A.F., Soldatenkov, A.T., and Katritzky, A.R., Technology, Medicine and Agriculture, Chichester: John Wiley and Sons, 1997.

  12. Liger, F., Popowycz, F., Besson, T., Picot, L., Galmarini, C. M., and Joseph, B., Bioorg. Med. Chem., 2007, vol. 16, p. 5615. https://doi.org/10.1016/j.bmc.2007.05.033

  13. Lee, C., Yang, W., and Parr, R.G., Phys. Rev. (B), 1988, vol. 37, p. 785. https://doi.org/10.1103/physrevb.37.785

    Article  CAS  Google Scholar 

  14. Mas-Torrent, M. and Rovira, C., J. Mater. Chem., 2006, vol. 16, p. 433. https://doi.org/10.1039/B510121B

    Article  CAS  Google Scholar 

  15. Forrest, S.R., Nature, 2004, vol. 428, p. 911. https://doi.org/10.1038/nature02498

    Article  CAS  PubMed  Google Scholar 

  16. Mullen, K. and Scherf, U., Organic Light-Emitting Devices, Weinheim: Wiley-VCH, 2006.

  17. Choukri, H., Fischer, A., Forget, S., Chenais, S., Castex, M.C., and Geffroy, B., Synth. Metals, 2007, vol. 157, p. 198. https://doi.org/10.1016/j.synthmet.2007.01.005

    Article  CAS  Google Scholar 

  18. Zhuang, J., Su, W., Li, W., Zhou, Y., Shen, Q., and Zhou, M., Org. Electron., 2012, vol. 13, p. 2210. https://doi.org/10.1016/j.orgel.2012.06.025

    Article  CAS  Google Scholar 

  19. Dongcai, G., Panliang, W., Hui, T., Long, X., and Wenhui, Z., J. Lumin., 2011, vol. 131, p. 1272.

    Article  Google Scholar 

  20. Unver, Y., Sancak, K., Çelik, F., Birinci, E., Küçük, M., Soylu, M.S., and Arslan, N.B., Eur. J. Med. Chem., 2014, vol. 84, p. 639. https://doi.org/10.1016/j.ejmech.2014.01.014

    Article  CAS  PubMed  Google Scholar 

  21. Gündüzalp, A.B. and Özbay, H.F., Russ. J. Inorg. Chem., 2012, vol. 57, p. 257. https://doi.org/

    Article  Google Scholar 

  22. Süleymanoglu, N., Ustabas, R., Direkel, S., Alpaslan, Y.B., and Ünver, Y., J. Mol. Struct., 2017, vol. 1150, p. 82. https://doi.org/10.1016/j.molstruc.2017.08.075

    Article  CAS  Google Scholar 

  23. Ünver, Y., and Bektaş, E., Lett. Drug Des. Discov., 2018, vol. 14, p. 706. https://doi.org/10.2174/1570180814666171012163651

    Article  CAS  Google Scholar 

  24. Ünver, Y., Tuluk, M., Kahriman, N., Emirik, M., Bektaş, E., and Direkel, Ş., Russ. J. Gen. Chem., 2019, vol. 89, p. 794. https://doi.org/10.1134/S107036321904025X

    Article  Google Scholar 

  25. Süleymanoğlu, N., Demir, E.E., Direkel, Ş., and Ünver, Y., J. Mol. Struct., 2020, vol. 1218, p. 128522. https://doi.org/10.1016/j.molstruc.2020.128522

    Article  CAS  Google Scholar 

  26. Ünver, Y., Ünlüer, D., Direkel, Ş., and Durdaği, S., Turk. J. Chem., 2020, vol. 44, p. 1164. https://doi.org/10.3906/kim-2004-78

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  27. Chen, D., Ozguen, N., Urvil, P., Ferguson, C., Dann, S.M., and Savidge, T.C., Sci. Adv., 2016, vol. 2, p. 1501240. https://doi.org/10.1126/sciadv.1501240

    Article  CAS  Google Scholar 

  28. Raj, S., Sasidharan, S., Dubey, V.K., and Saudagar, P., PloS One, 2019, vol. 14, p. 0221331.

    Article  Google Scholar 

  29. Bachmann, K.A., and Lewis, J.D., Ann. Pharmacother., 2015, vol. 39, no. 6, p. 1064. https://doi.org/10.1345/aph.1E508

    Article  CAS  Google Scholar 

  30. Ghooi, R.B., and Thatte, S.M., Med. Hypotheses, 1995, vol. 44, p. 127. https://doi.org/10.1016/0306-9877(95)90085-3;

    Article  CAS  PubMed  Google Scholar 

  31. Subbaiah, S.G., Dakappa, S.S., and Lakshmikantha, R.Y., Res. J. Phytochem., 2017, vol. 11, p. 28. https://doi.org/10.3923/rjphyto.2017.28.34

    Article  CAS  Google Scholar 

  32. Hussain, M., Qadri, T., Hussain, Z., Saeed, A., Channar, P., Shehzadi, S.A., Hassan, M., Larik, F., Mahmood, A., and Malik, A., Heliyon, 2019, vol. 11, p. 02812. https://doi.org/10.1016/j.heliyon.2019.e02812

    Article  Google Scholar 

  33. Atay, Ç., Ti̇lki̇, K., and Dede, T., Süleyman Demirel Üniversitesi Fen Edebiyat Fakültesi Fen Dergisi, 2019, vol. 14, p. 150. https://doi.org/10.29233/sdufeffd.544174

    Article  CAS  Google Scholar 

  34. Gulluce, M., Adiguzel, A., Ogutcu, H., Sengul, M., and Sahin, F., Phytother Res., 2004, vol. 18, p. 208. https://doi.org/10.1002/ptr.1419

    Article  CAS  PubMed  Google Scholar 

  35. Morris, G.M., Huey, R., Lindstrom, W., Sanner, M.F., Belew, R.K., Goodsell, D.S., and Olson, A.J., J. Comput. Chem., 2009, vol. 30, p. 2785. https://doi.org/10.1002/jcc.21256

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  36. Guex, N., Peitsch, M.C., and Schwede, T., Electrophoresis Jun., 2009, vol. 30, p. 162. https://doi.org/10.1002/elps.200900140

    Article  Google Scholar 

  37. O’Boyle, M., Banck, M., James, C.A., Morley, C., Vandermeersch, T., and Hutchison, G.R., J. Cheminf., 2011, vol. 3, p. 33. https://doi.org/10.1186/1758-2946-3-33

    Article  CAS  Google Scholar 

  38. Hanwell, M.D., J. Cheminformatics, 2012, vol. 4, p. 1. https://doi.org/10.1186/1758-2946-4-17

    Article  CAS  Google Scholar 

  39. Dassault Systèmes BIOVIA, Discovery Studio Modeling Environment, Release 2017, San Diego: Dassault Systèmes, 2016.

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ACKNOWLEDGMENTS

This work was supported by the Scientific research Project of Karadeniz Technical University (grant no. FBS-2021-9685).

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Sciences, Karadeniz Technical University, 61080, Trabzon, Turkey

    F. Çelik & Y. Ünver

  2. Department of Basic Medical Science, Faculty of Medicine, Bozok University, 66100, Yozgat, Turkey

    A. Aydın

  3. Department of Molecular Biology and Genetics, Karadeniz Technical University Faculty of Science, 61080, Trabzon, Turkey

    K. İ. Bektaş, H. İ. Güler & A. Nalçaoğlu

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  1. F. Çelik
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  2. A. Aydın
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Correspondence to Y. Ünver.

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Çelik, F., Aydın, A., Bektaş, K.İ. et al. Biscarbazole Derivatives: Synthesis, Characterization, Antimicrobial and Antitumor Activity, and Molecular Docking Study. Russ J Gen Chem 92, 2145–2160 (2022). https://doi.org/10.1134/S1070363222100279

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