European Journal of Chemistry 2016, 7(1), 1-7. doi:10.5155/eurjchem.7.1.1-7.1354

Synthesis, structural and spectral characterization, and in vitro nuclease activity of new thiosemicarbazone derivatives


Mouayed Abdulaali Hussein (1,*) , Teoh Siang Guan (2)

(1) Department of Chemistry, College of Science, University of Basrah, Basrah, 61001, Iraq
(2) School of Chemical Science, Universiti Sains Malaysia, Minden, Pulau Pinang, 11800, Malaysia
(*) Corresponding Author

Received: 01 Nov 2015, Accepted: 18 Nov 2015, Published: 31 Mar 2016

Abstract


Two new compounds, (E)-2-(3-ethoxy-2-hydroxybenzylidene)hydrazinecarbothioamide (1) and (E)-N-ethyl-2-((2-hydroxynaphthalen-1-yl)methylene)hydrazinecarbothioamide (2) have been synthesized. The prepared compounds have been characterized by CHN analysis, FT-IR, UV-Vis, 1H and 13C NMR spectroscopic techniques as well as the fluorescence emission spectroscopy. The molecular structures of the compounds have also been determined by X-ray single crystal diffraction analysis. The crystal structures revealed that the compounds are remain as a thione form in the solid state and are different in their geometrical, conformational and symmetrical structures. The nuclease activity of compounds to cleave pBR 322 has been investigated using agarose gel electrophoresis assay. The compound 2 revealed a significant nuclease activity which was attributed to the lipophilic properties that provided by substituent moieties of the compound.


Keywords


DNA cleavage; Gel electrophoresis; Thiosemicarbazone; Electronic transition; Fluorescence emission; X-ray single crystal structure

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DOI: 10.5155/eurjchem.7.1.1-7.1354

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References

[1]. Leigh, M.; Castillo, C. E.; Raines, D. J.; Duhme-Klair, A. K. Chem. Med. Chem. 2011, 6, 612-616.
http://dx.doi.org/10.1002/cmdc.201000429

[2]. Hussein, M. A.; Guan, T. S.; Haque, R. A.; Ahamed, M. B. K.; Majid, A. M. S. A. Polyhedron 2015, 85, 93-103.
http://dx.doi.org/10.1016/j.poly.2014.02.048

[3]. Ali, A. Q.; Teoh, S. G.; Eltayeb, N. E.; Ahamed, M. B. K.; Majid, A. M. S. A. Polyhedron 2014, 74, 6-15.
http://dx.doi.org/10.1016/j.poly.2014.02.025

[4]. Ngan, N. K.; Lo, K. M.; Wong, C. S. R. Polyhedron 2012, 33, 235-251.
http://dx.doi.org/10.1016/j.poly.2011.11.057

[5]. Hussein, M. A.; Iqbal, M. A.; Asif, M.; Haque, R. A.; Ahamed, M. B. K.; Majid, A. M. S. A.; Guan, T. A. Phosphorus, Sulfur Silicon Relat. Elem. 2015, 190, 1498-1508.
http://dx.doi.org/10.1080/10426507.2014.995299

[6]. Argueelles, M. C. R.; Touceda, P. T.; Cao, R.; Deibe, A. M. G.; Pelagatti, P.; Pelizzi, C.; Zani, F. J. Inorg. Biochem. 2009, 103, 35-42.
http://dx.doi.org/10.1016/j.jinorgbio.2008.08.015

[7]. Ferrari, M. B.; Bisceglie, F.; Pelosi, G.; Tarasconi, P.; Albertini, R.; Pinelli, S. J. Inorg. Biochem. 2001, 87, 137-147.
http://dx.doi.org/10.1016/S0162-0134(01)00321-X

[8]. Kowol, C. R.; Berger, R.; Eichinger, R.; Roller, A.; Jakupec, M. A.; Schmidt, P. P.; Arion, V. B. Keppler, B. K. J. Med. Chem. 2007, 50, 1254-1265.
http://dx.doi.org/10.1021/jm0612618

[9]. Osman, H.; Arshad, A.; Lam, C. K.; Bagley M. C. Chem. Cent. J. 2012, 6, 32-42.
http://dx.doi.org/10.1186/1752-153X-6-32

[10]. Mendes, I. C.; Soares, M. A.; Dos Santos, R. G.; Pinheiro, C.; Beraldo, H. Eur. J. Med. Chem. 2009, 44, 1870-1877.
http://dx.doi.org/10.1016/j.ejmech.2008.11.006

[11]. Bernhardt, P. V.; Sharpe, P. C.; Islam, M.; Lovejoy, D. B.; Kalinowski, D. S.; Richardson, D. R. J. Med. Chem. 2009, 52, 407-415.
http://dx.doi.org/10.1021/jm801012z

[12]. Baldini, M.; Ferrari, M. B.; Bisceglie, F.; Pelosi, G.; Pinelli, S. Inorg. Chem. 2003, 42, 2049-2055.
http://dx.doi.org/10.1021/ic026131d

[13]. Bisceglie, F.; Baldini, M.; Belicchi-Ferrari, M.; Buluggiu, E.; Careri, M.; Pelosi, G.; Pinelli, S.; Tarasconi, P. Eur. J. Med. Chem. 2007, 42, 627-634.
http://dx.doi.org/10.1016/j.ejmech.2006.12.019

[14]. Baodui, W.; Zhengyin, Y.; Minghua, L.; Jun, H.; Qin, W.; Zhongnig, C. J. Organomet. Chem. 2009, 694, 4069-4075.
http://dx.doi.org/10.1016/j.jorganchem.2009.08.024

[15]. Lobana, T. S.; Sharma, R.; Bava, G.; Khanna, S. Coord. Chem. Rev. 2009, 253, 977-1055.
http://dx.doi.org/10.1016/j.ccr.2008.07.004

[16]. Anderson, B. J.; Shalit, Z. A.; Jasinski, J. P. Acta Cryst. E 2014, 70, o732-o732.
http://dx.doi.org/10.1107/S1600536814012057

[17]. Casas, J. S.; Garcia, T. M. S.; Sordo, J. Coord. Chem. Rev. 2000, 209, 197-261.
http://dx.doi.org/10.1016/S0010-8545(00)00363-5

[18]. Beraldo, H.; Gambino, D. Mini-Rev. Med. Chem. 2004, 4, 31-39.
http://dx.doi.org/10.2174/1389557043487484

[19]. Dilovic, I.; Rubcic, M.; Vrdoljak, V.; Pavelic, S. K.; Kralj, M.; Piantanida, I.; Cindric, M. Bioorg. Med. Chem. 2008, 16, 5189-5198.
http://dx.doi.org/10.1016/j.bmc.2008.03.006

[20]. Hussein, M. A.; Guan, T. S.; Haque, R. A.; Ahamed, M. B. K.; Majid, A. M. S. A. J. Coord. Chem. 2014, 67, 714-727.
http://dx.doi.org/10.1080/00958972.2014.893430

[21]. Gomez-Saiz, P.; Gil-Garcia, R.; Maestro, M. A.; Pizarro, J. L.; Arriortua, M. I.; Lezama, L.; Rojo, T.; Gonzalez-Alvarez, M.; Borras, J.; Garcia-Tojal, J. Inorg. Biochem. 2008, 102, 1910-1920.

[22]. Lu, J.; Guo, H.; Zeng, X.; Zhang, Y.; Zhao, P.; Jiang, J.; Zang, L. Inorg. Biochem. 2012, 112, 39-48.
http://dx.doi.org/10.1016/j.jinorgbio.2012.02.034

[23]. Aguirre, Y. C.; Borras, J.; Castineiras, A.; Garcia-Monteagudo, J. M.; Garcia- Santos, I.; Niclos, J.; West, D. X. Eur. J. Inorg. Chem. 2006, 2006, 1231-1244.

[24]. Lobana, T. S.; Kumari, P.; Butcher, R. J. Inorg. Chem. Commun. 2008, 11, 11-14.
http://dx.doi.org/10.1016/j.inoche.2007.10.001

[25]. Lhuachan, S.; Siripaisarnpipat, S.; Chaichit, N. Eur. J. Inorg. Chem. 2003, 2003, 263- 267.
http://dx.doi.org/10.1002/ejic.200390035

[26]. Sheldrick, G. M. Acta Cryst. 2008, A64, 112-122.
http://dx.doi.org/10.1107/S0108767307043930

[27]. Yeung A. S.; Frank, C. W.; Singer, R. E. Polymer 1990, 31, 1092-1099.
http://dx.doi.org/10.1016/0032-3861(90)90257-Y

[28]. Bains, G. K.; Kim, S. H.; Sorin, E. J.; Narayanaswami, V. Biochemistry 2012, 51, 6207- 6219.
http://dx.doi.org/10.1021/bi3005285

[29]. Ardakani, A. A.; Kargar, H.; Kia, R.; Tahir, M. N. Acta Cryst. E 2012, 68, o340-o341.
http://dx.doi.org/10.1107/S1600536812000487

[30]. Ok, M. K.; Chi, E. O.; Halasyamani, S. Chem. Soc. Rev. 2006, 35, 710-717.
http://dx.doi.org/10.1039/b511119f

[31]. Hussein, M. A.; Guan, T. S.; Haque, R. A.; Ahamed, M. B. K.; Majid, A. M. S. A. Spectrochim. Acta A 2015, 136, 1355-1348.
http://dx.doi.org/10.1016/j.saa.2014.10.021

[32]. Gao, E. J.; Zhu, M. C.; Huang, Y.; Liu, L.; Ma, S.; Shi, C. Y. Eur. J. Med. Chem. 2010, 45, 1034-1041.
http://dx.doi.org/10.1016/j.ejmech.2009.11.048


How to cite


Hussein, M.; Guan, T. Eur. J. Chem. 2016, 7(1), 1-7. doi:10.5155/eurjchem.7.1.1-7.1354
Hussein, M.; Guan, T. Synthesis, structural and spectral characterization, and in vitro nuclease activity of new thiosemicarbazone derivatives. Eur. J. Chem. 2016, 7(1), 1-7. doi:10.5155/eurjchem.7.1.1-7.1354
Hussein, M., & Guan, T. (2016). Synthesis, structural and spectral characterization, and in vitro nuclease activity of new thiosemicarbazone derivatives. European Journal of Chemistry, 7(1), 1-7. doi:10.5155/eurjchem.7.1.1-7.1354
Hussein, Mouayed, & Teoh Siang Guan. "Synthesis, structural and spectral characterization, and in vitro nuclease activity of new thiosemicarbazone derivatives." European Journal of Chemistry [Online], 7.1 (2016): 1-7. Web. 21 Oct. 2019
Hussein, Mouayed, AND Guan, Teoh. "Synthesis, structural and spectral characterization, and in vitro nuclease activity of new thiosemicarbazone derivatives" European Journal of Chemistry [Online], Volume 7 Number 1 (31 March 2016)

DOI Link: https://doi.org/10.5155/eurjchem.7.1.1-7.1354

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