Tyrosinase inhibition potency of phthalimide derivatives: crystal structure, Hirshfeld surface analysis and molecular docking studies

Li Yee Then; Huey Chong Kwong; Ching Kheng Quah; C.S. Chidan Kumar; Tze Shyang Chia; Qin Ai Wong; Siddegowda Chandraju; Thangavel Karthick; Yip-Foo Win; Shaida Fariza Sulaiman; Nurul Shafiqah Hashim; Kheng Leong Ooi

doi:10.1515/zkri-2018-2090

Article

Tyrosinase inhibition potency of phthalimide derivatives: crystal structure, Hirshfeld surface analysis and molecular docking studies

Li Yee Then , Huey Chong Kwong , Ching Kheng Quah , C.S. Chidan Kumar , Tze Shyang Chia , Qin Ai Wong , Siddegowda Chandraju , Thangavel Karthick , Yip-Foo Win , Shaida Fariza Sulaiman , Nurul Shafiqah Hashim and Kheng Leong Ooi

Published/Copyright: May 22, 2018

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From the journal Zeitschrift für Kristallographie - Crystalline Materials Volume 233 Issue 11

Abstract

A new series of seven 2-((pyridinylamino)methyl)isoindoline-1,3-dione derivatives were synthesized under mild condition and characterized by spectroscopy analysis. The crystal structures of these derivatives were further determined using single crystal X-ray diffraction technique. All derivatives adopt a V-shape conformation. The dihedral angle between phthalimide and pyridine rings increases as the torsion angle C1–N1–C9–N2 between phthalimide ring and methylene group increases. The torsion angles and molecular conformations are comparable to those related structures from the Cambridge Structural Database (CSD). Furthermore, the intermolecular interactions of all studied crystal structures were quantified and analyzed using Hirshfeld surface (HS) analysis. The quantitative data on the percentage contributions of overall interactions in all compounds are calculated by the two-dimensional (2D) fingerprint plots from the HS analysis. These compounds were evaluated for their antioxidant and antityrosinase properties. Noteworthy, 2-(((6-methoxypyridin-3-yl)amino)methyl)isoindoline-1,3-dione (compound g) exhibited higher tyrosinase inhibitory activity (EC₅₀=753 μg/mL) than the positive control ‘arbutin’ (EC₅₀=403 μg/mL). The inhibitory effect of compound g was further confirmed by computational molecular docking studies and the result revealed the 6-methoxypyridin-3-yl substituent has a better binding affinity toward tyrosinase.

Keywords: Hirshfeld surface analysis; molecular docking; phthalimide; spectroscopic analysis; X-ray diffraction analysis

Acknowledgements

LYT thanks Universiti Sains Malaysia for USM Fellowship Scheme and Malaysian Government for MyBrain15 (MyMaster) scholarship. HCK thanks Malaysian Government for MyBrain15 (MyPhD) scholarship. TK thanks University Grants Commission, New Delhi for Dr. D. S. Kothari postdoctoral fellowship. The authors thank the Malaysian Government and Universiti Sains Malaysia (USM) for the Fundamental Research Grant Scheme (FRGS) (203/PFIZIK/6711563). Authors extend their appreciation to Vidya Vikas Research & Development Centre for the facilities and encouragement.

References

[1] G. Brahmachari, Green Synthetic Approaches for Biologically Relevant Heterocycles. 1st ed. USA, Elsevier, 2014.10.1016/B978-0-12-800070-0.00001-3Search in Google Scholar

[2] R. Dua, S. Shrivastava, S. Sonwane, S. Srivastava, Adv. Biol. Res.2011, 5, 120.Search in Google Scholar

[3] W. Du, Tetrahedron2003, 59, 8649.10.1016/S0040-4020(03)01203-1Search in Google Scholar

[4] H. Chen, J. Wang, S.-B. Zhou, H. Liu, J. Org. Chem.2014, 79, 7872.10.1021/jo501571jSearch in Google Scholar

[5] L. Ji, S.-H. Xiang, W.-L. Leng, L. M. H. Kim, X.-W. Liu, Org. Lett.2015, 17, 1357.10.1021/ol5037437Search in Google Scholar

[6] E. Grunberg, E. H. Titsworth, Annu. Rev. Microbiol.1973, 27, 317.10.1146/annurev.mi.27.100173.001533Search in Google Scholar

[7] M. Hosseinnezhad, K. Gharanjig, S. Moradian, S. Tafaghodi, Arab. J. Chem.2015, in press.Search in Google Scholar

[8] E. Butuc, G. M. Gherasim, J. Polym. Sci. Part A: Polym. Chem.1984, 22, 503.10.1002/pol.1984.170220220Search in Google Scholar

[9] K. M. Amin, A. H. El-masry, N. A. Mohamed, G. E. A. Awad, B. S. Habib, Der Pharm. Chem.2013, 5, 97.Search in Google Scholar

[10] T. Ito, H. Ando, H. Handa, Cell. Mol. Life Sci.2011, 68, 1569.10.1007/s00018-010-0619-9Search in Google Scholar

[11] S. K. Teo, K. E. Resztak, M. A. Scheffler, K. A. Kook, J. B. Zeldis, D. I. Stirling, S. D. Thomas, Microbes Infect.2002, 4, 1193.10.1016/S1286-4579(02)01645-3Search in Google Scholar

[12] L. M. Fu, C. S. Fu-Liu, Int. J. Tuberc. Lung Dis.2002, 6, 569.Search in Google Scholar

[13] Z.-L. Zhang, Z.-S. Liu, Q. Sun, World J. Gastroenterol.2005, 11, 216.10.3748/wjg.v11.i2.216Search in Google Scholar

[14] M. T. Miller, K. Strömland, Teratology1999, 60, 306.10.1002/(SICI)1096-9926(199911)60:5<306::AID-TERA11>3.0.CO;2-YSearch in Google Scholar

[15] A. A.-M. Abdel-Hafez, Arch. Pharm. Res.2004, 27, 495.10.1007/BF02980121Search in Google Scholar

[16] R. A. Pophale, M. N. Deodhar, Der Pharm. Chem.2010, 2,185.Search in Google Scholar

[17] O. Fhid, T. H. Zeglam, S. E. A. Saad, T. Elmoug, A. Eswayah, M. Zitouni, W. Sdera, A. A. Edeep, A. Ebzabez, Der Pharm. Chem.2014, 6, 234.Search in Google Scholar

[18] C. Pessoa, P. M. P. Ferreira, L. V. C. Lotufo, M. O. de Moraes, S. M. T. Cavalcanti, L. C. D. Coêlho, M. Z. Hernandes, A. C. L. Leite, C. A. De Simone, V. M. A. Costa, V. M. O. Souza, ChemMedChem.2010, 5, 523.10.1002/cmdc.200900525Search in Google Scholar PubMed

[19] B. Natsume, S. Suzuki, N. Minami, O. Ikeda, Patent US: 6365753, 2002.Search in Google Scholar

[20] J. Koh, H. Kim, J. Park, Fibers Polym.2008, 9, 143.10.1007/s12221-008-0024-2Search in Google Scholar

[21] M. H. Nasirtabrizi, Z. M. Ziaei, A. P. Jadid, L. Z. Fatin, Int. J. Ind. Chem.2013, 4, 1.10.1186/2228-5547-4-1Search in Google Scholar

[22] J. M. Bohen, G. H. Reifenberg, D. L. Stein, Patent US: 4904795, 1990.Search in Google Scholar

[23] M. T. H. Khan, Pure Appl. Chem.2007, 79, 2277.10.1351/pac200779122277Search in Google Scholar

[24] A. Di Petrillo, A. M. González-Paramás, B. Era, R. Medda, F. Pintus, C. Santos-Buelga, A. Fais, BMC Complement. Altern. Med.2016, 16, 453.10.1186/s12906-016-1442-0Search in Google Scholar PubMed PubMed Central

[25] M. R. Loizzo, R. Tundis, F. Menichini, Compr. Rev. Food Sci. Food Saf.2012, 11, 378.10.1111/j.1541-4337.2012.00191.xSearch in Google Scholar

[26] C. S. Chidan Kumar, W.-S. Loh, S. Chandraju, Y.-F. Win, W. K. Tan, C. K. Quah, H.-K. Fun, PLoS One.2015, 10, e0119440.10.1371/journal.pone.0119440Search in Google Scholar PubMed PubMed Central

[27] H. C. Kwong, C. S. Chidan Kumar, S. H. Mah, T. S. Chia, C. K. Quah, Z. H. Loh, S. Chandraju, G. K. Lim, PLoS One.2017, 12, e0170117.10.1371/journal.pone.0170117Search in Google Scholar PubMed PubMed Central

[28] Bruker. APEX2, SAINT and SADABS. Bruker AXS Inc.: Madison, Wisconsin, USA, 2012.Search in Google Scholar

[29] G. M. Sheldrick, Acta Crystallogr. C2015, 71, 3.10.1107/S2053229614024218Search in Google Scholar PubMed PubMed Central

[30] S. K. Wolff, D. J. Grimwood, J. J. Mac Kimon, M. J. Turner, D. Jayatilaka, A. M. Spackman, Crystal Explorer Ver. 3.1: University of Western Australia, Perth, Australia, 2013.Search in Google Scholar

[31] J. J. McKinnon, M. A. Spackman, A. S. Mitchell, Acta Crystallogr. B2004, 60, 627.10.1107/S0108768104020300Search in Google Scholar PubMed

[32] M. A. Spackman, J. J. McKinnon, D. Jayatilaka, CrystEngComm.2008, 10, 377.Search in Google Scholar

[33] K. L. Ooi, T. S. Tengku Muhammad, M. L. Tan, S. F. Sulaiman, J. Ethnopharmacol.2011, 135, 685.10.1016/j.jep.2011.04.001Search in Google Scholar

[34] A. Vanni, D. Gastaldi, G. Giunta, Ann. Chim.1990, 80, 35.Search in Google Scholar

[35] G. M. Morris, R. Huey, W. Lindstrom, M. F. Sanner, R. K. Belew, D. S. Goodsell, A. J. Olson, J. Comput. Chem.2009, 30, 2785.10.1002/jcc.21256Search in Google Scholar

[36] Dassault Systèmes BIOVIA. Discovery Studio Modeling Environment. Release 4.5 ed. Dassault Systèmes: San Diego, 2015.Search in Google Scholar

[37] C. R. Groom, I. J. Bruno, M. P. Lightfoot, Acta Crystallogr. B2016, 72, 171.10.1107/S2052520616003954Search in Google Scholar

[38] S. Franklin, D. Tamilvendan, G. Venkatesa Prabhu, T. Balasubramanian, J. Chem. Crystallogr.2011, 41, 1120.10.1007/s10870-011-0055-1Search in Google Scholar

[39] V. L. M. Sena, R. M. Srivastava, C. A. de Simone, S. M. da Cruz Gonçalves, R. O. Silva, M. A. Pereira, J. Braz. Chem. Soc.2007, 18, 1224.10.1590/S0103-50532007000600018Search in Google Scholar

[40] M. A. Spackman, D. Jayatilaka, CrystEngComm.2009, 11, 19.10.1039/B818330ASearch in Google Scholar

[41] G. M. Morris, D. S. Goodsell, R. S. Halliday, R. Huey, W. E. Hart, R. K. Belew, A. J. Olson, J. Comput. Chem.1998, 19, 1639.10.1002/(SICI)1096-987X(19981115)19:14<1639::AID-JCC10>3.0.CO;2-BSearch in Google Scholar

[42] T.-S. Chang, Int. J. Mol. Sci.2009, 10, 2440.10.3390/ijms10062440Search in Google Scholar

[43] W.-C. Chen, T.-S. Tseng, N.-W. Hsiao, Y.-L. Lin, Z.-H. Wen, C.-C. Tsai, Y.-C. Lee, H.-H. Lin, K.-C. Tsai, Sci. Rep.2015, 5, 7995.10.1038/srep07995Search in Google Scholar

Supplementary Material

The online version of this article offers supplementary material (https://doi.org/10.1515/zkri-2018-2090).

Received: 2018-04-19

Accepted: 2018-04-23

Published Online: 2018-05-22

Published in Print: 2018-10-25

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Keywords for this article

Hirshfeld surface analysis; molecular docking; phthalimide; spectroscopic analysis; X-ray diffraction analysis