Tyrosinase inhibition potency of phthalimide derivatives: crystal structure, Hirshfeld surface analysis and molecular docking studies
-
Li Yee Then
,
C.S. Chidan Kumar
,
Tze Shyang Chia
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.
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/B978-0-12-800070-0.00001-3Suche in Google Scholar
[2] R. Dua, S. Shrivastava, S. Sonwane, S. Srivastava, Adv. Biol. Res.2011, 5, 120.Suche in Google Scholar
[3] W. Du, Tetrahedron2003, 59, 8649.10.1016/S0040-4020(03)01203-1Suche in Google Scholar
[4] H. Chen, J. Wang, S.-B. Zhou, H. Liu, J. Org. Chem.2014, 79, 7872.10.1021/jo501571jSuche 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/ol5037437Suche in Google Scholar
[6] E. Grunberg, E. H. Titsworth, Annu. Rev. Microbiol.1973, 27, 317.10.1146/annurev.mi.27.100173.001533Suche in Google Scholar
[7] M. Hosseinnezhad, K. Gharanjig, S. Moradian, S. Tafaghodi, Arab. J. Chem.2015, in press.Suche in Google Scholar
[8] E. Butuc, G. M. Gherasim, J. Polym. Sci. Part A: Polym. Chem.1984, 22, 503.10.1002/pol.1984.170220220Suche 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.Suche in Google Scholar
[10] T. Ito, H. Ando, H. Handa, Cell. Mol. Life Sci.2011, 68, 1569.10.1007/s00018-010-0619-9Suche 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)01645-3Suche in Google Scholar
[12] L. M. Fu, C. S. Fu-Liu, Int. J. Tuberc. Lung Dis.2002, 6, 569.Suche in Google Scholar
[13] Z.-L. Zhang, Z.-S. Liu, Q. Sun, World J. Gastroenterol.2005, 11, 216.10.3748/wjg.v11.i2.216Suche 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-YSuche in Google Scholar
[15] A. A.-M. Abdel-Hafez, Arch. Pharm. Res.2004, 27, 495.10.1007/BF02980121Suche in Google Scholar
[16] R. A. Pophale, M. N. Deodhar, Der Pharm. Chem.2010, 2,185.Suche 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.Suche 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.200900525Suche in Google Scholar PubMed
[19] B. Natsume, S. Suzuki, N. Minami, O. Ikeda, Patent US: 6365753, 2002.Suche in Google Scholar
[20] J. Koh, H. Kim, J. Park, Fibers Polym.2008, 9, 143.10.1007/s12221-008-0024-2Suche in Google Scholar
[21] M. H. Nasirtabrizi, Z. M. Ziaei, A. P. Jadid, L. Z. Fatin, Int. J. Ind. Chem.2013, 4, 1.10.1186/2228-5547-4-1Suche in Google Scholar
[22] J. M. Bohen, G. H. Reifenberg, D. L. Stein, Patent US: 4904795, 1990.Suche in Google Scholar
[23] M. T. H. Khan, Pure Appl. Chem.2007, 79, 2277.10.1351/pac200779122277Suche 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/s12906-016-1442-0Suche 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.xSuche 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.0119440Suche 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.0170117Suche in Google Scholar PubMed PubMed Central
[28] Bruker. APEX2, SAINT and SADABS. Bruker AXS Inc.: Madison, Wisconsin, USA, 2012.Suche in Google Scholar
[29] G. M. Sheldrick, Acta Crystallogr. C2015, 71, 3.10.1107/S2053229614024218Suche 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.Suche in Google Scholar
[31] J. J. McKinnon, M. A. Spackman, A. S. Mitchell, Acta Crystallogr. B2004, 60, 627.10.1107/S0108768104020300Suche in Google Scholar PubMed
[32] M. A. Spackman, J. J. McKinnon, D. Jayatilaka, CrystEngComm.2008, 10, 377.Suche 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.2011.04.001Suche in Google Scholar
[34] A. Vanni, D. Gastaldi, G. Giunta, Ann. Chim.1990, 80, 35.Suche 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.21256Suche in Google Scholar
[36] Dassault Systèmes BIOVIA. Discovery Studio Modeling Environment. Release 4.5 ed. Dassault Systèmes: San Diego, 2015.Suche in Google Scholar
[37] C. R. Groom, I. J. Bruno, M. P. Lightfoot, Acta Crystallogr. B2016, 72, 171.10.1107/S2052520616003954Suche in Google Scholar
[38] S. Franklin, D. Tamilvendan, G. Venkatesa Prabhu, T. Balasubramanian, J. Chem. Crystallogr.2011, 41, 1120.10.1007/s10870-011-0055-1Suche 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/S0103-50532007000600018Suche in Google Scholar
[40] M. A. Spackman, D. Jayatilaka, CrystEngComm.2009, 11, 19.10.1039/B818330ASuche 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-BSuche in Google Scholar
[42] T.-S. Chang, Int. J. Mol. Sci.2009, 10, 2440.10.3390/ijms10062440Suche 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/srep07995Suche in Google Scholar
Supplementary Material
The online version of this article offers supplementary material (https://doi.org/10.1515/zkri-2018-2090).
©2018 Walter de Gruyter GmbH, Berlin/Boston
Artikel in diesem Heft
- Frontmatter
- Graphical Synopsis
- A new disodium hafnium borate Na2Hf(BO3)2: synthesis, crystal structure, DFT calculations and luminescent properties
- Crystal structures and Hirshfeld surface analyses of seven 7-aryl-4,7-dioxoheptanoic acids: differing carboxylic acid interactions leading to dimers, chains and three-dimensional arrays
- Molecular arrangements in crystals of racemic and enantiopure forms of N-carbamoyl-2-phenylbutyramide and 2-phenylbutyramide: differences and similarities
- Red photo- and electroluminescent half-lantern cyclometalated dinuclear platinum(II) complex
- Tyrosinase inhibition potency of phthalimide derivatives: crystal structure, Hirshfeld surface analysis and molecular docking studies
Artikel in diesem Heft
- Frontmatter
- Graphical Synopsis
- A new disodium hafnium borate Na2Hf(BO3)2: synthesis, crystal structure, DFT calculations and luminescent properties
- Crystal structures and Hirshfeld surface analyses of seven 7-aryl-4,7-dioxoheptanoic acids: differing carboxylic acid interactions leading to dimers, chains and three-dimensional arrays
- Molecular arrangements in crystals of racemic and enantiopure forms of N-carbamoyl-2-phenylbutyramide and 2-phenylbutyramide: differences and similarities
- Red photo- and electroluminescent half-lantern cyclometalated dinuclear platinum(II) complex
- Tyrosinase inhibition potency of phthalimide derivatives: crystal structure, Hirshfeld surface analysis and molecular docking studies
