374
Views
16
CrossRef citations to date
0
Altmetric
Articles

Synthesis, crystal structure and anticancer activity of the dibutyltin(IV)oxide complexes containing substituted salicylaldehyde-o-aminophenol Schiff base with appended donor functionality

, , , , , & show all
Pages 486-494 | Received 10 Dec 2017, Accepted 02 Jan 2019, Published online: 22 Feb 2019

References

  • Jimenez-Perez, V. M.; Garcia-Lopez, M. C.; Munoz-Flores, B. M.; Chan-Navarro, R.; Berrones-Reyes, J. C.; Dias, H. V. R.; Moggio, I.; Arias, E.; Serrano-Mireles, J. A.; Chavez-Reyes, A. New Application of Fluorescent Organotin Compounds Derived from Schiff Bases: Synthesis, X-ray Structures, Photophysical Properties, Cytotoxicity and Fluorescent Bioimaging. J. Mater. Chem. B 2015, 3, 5731–5745. DOI: 10.1039/C5TB00717H.
  • Chandrasekhar, V.; Mohapatra, C. 2D-Coordination Polymer Containing Interconnected 82-Membered Organotin Macrocycles. Cryst. Growth Des. 2013, 13, 4655–4658. DOI: 10.1021/cg401363p.
  • Rivera, J. M.; Reyes, H.; Cortés, A.; Santillan, R.; Lacroix, P. G.; Lepetit, C.; Nakatani, K.; Farfán, N. Second-Harmonic Generation within the P212121 Space Group, in a Series of Chiral (Salicylaldiminato)tin Schiff Base Complexes. Chem. Mater. 2006, 18, 1174–1183.
  • Yin, H.; Hong, M.; Xu, H.; Gao, Z.; Li, G.; Wang, D. Self-Assembly of Organotin(IV) Moieties with the Schiff-Base Ligands Pyruvic Acid Isonicotinyl Hydrazone and Pyruvic Acid Salicylhydrazone: Synthesis, Characterization, and Crystal Structures of Monomeric or Polymeric Complexes. Eur. J. Inorg. Chem. 2005, 2005, 4572–4581. DOI: 10.1002/ejic.200500412.
  • Hazra, S.; Paul, A.; Sharma, G.; Koch, B.; da Silva, M. F. C. G.; Pombeiro, A. J. L. Sulfonated Schiff Base Sn(IV) complexes as Potential Anticancer Agents. J. Inorg. Biochem. 2016, 162, 83–95.
  • Hong, M.; Yin, H.; Zhang, X.; Li, C.; Yue, C.; Cheng, S. Di- and Tri-organotin(IV) complexes with 2-hydroxy-1-naphthaldehyde 5-chloro-2-hydroxybenzoylhydrazone: Synthesis, characterization and in Vitro Antitumor Activities. J. Organomet. Chem. 2013, 724, 23–31. DOI: 10.1016/j.jorganchem.2012.10.031.
  • Shujah, S.; Zia Ur, R.; Muhammad, N.; Ali, S.; Khalid, N.; Tahir, M. N. New Dimeric and Supramolecular Organotin(IV) complexes with a Tridentate Schiff Base as Potential Biocidal Agents. J. Organomet. Chem. 2011, 696, 2772–2781.
  • Singh, R. V.; Chaudhary, P.; Chauhan, S.; Swami, M. Microwave-assisted Synthesis, characterization and Biological Activities of Organotin (IV) complexes with Some Thio Schiff Bases. Spectrochim. Acta A 2009, 72, 260–268. DOI: 10.1016/j.saa.2008.09.017.
  • Lee, S. M.; Sim, K. S.; Lo, K. M. Synthesis, characterization and Biological Studies of Diorganotin(IV) complexes with Tris [(Hydroxymethyl)aminomethane] Schiff Bases. Inorg. Chim. Acta 2015, 429, 195–208. DOI: 10.1016/j.ica.2015.01.017.
  • Rehman, W.; Haq, S.; Rahim, F.; Khan, S.; Waseem, M.; Nawaz, M.; Abid, O.-U.-R.; Qursehi, M. T.; Guo, C.-Y. Synthesis, Characterization and Antibacterial Screening of Diorganotin(IV) Complexes Derived from 2-[(4-Dimethylamino-Benzylidene)Amino] Phenol. Pharm. Chem. J. 2017, 51, 115–118.
  • Cozzi, P. G. Metal-Salen Schiff Base Complexes in Catalysis: practical Aspects. Chem. Soc. Rev. 2004, 33, 410–421.
  • Jiang, W. J.; Kuang, D. Z.; Feng, Y. L.; Yu, J. X.; Zhang, F. X.; Zhu, X. M. Microwave-Assisted Synthesis, Characterization and Fluorescence Properties of the Salicylaldehyde-o-aminophenol Schiff Base with Appended Donor Functionality and Their n-Butyltin(IV) Complexes. Chin. J. Org. Chem. 2014, 34, 2288–2295. DOI: 10.6023/cjoc201404037.
  • Tan, Y.-X.; Zhang, Z.-J.; Liu, Y.; Yu, J.-X.; Zhu, X.-M.; Kuang, D.-Z.; Jiang, W.-J. Synthesis, crystal Structure and Biological Activity of the Schiff Base Organotin(IV) complexes Based on Salicylaldehyde-o-Aminophenol. J. Mol. Struct. 2017, 1149, 874–881. DOI: 10.1016/j.molstruc.2017.08.058.
  • Tan, Y.; Zhang, Z.; Tan, Y.; Kuang, D.; Yu, J.; Zhu, X.; Jiang, W. Syntheses, crystal Structures and Biological Activity of the Dialkytin Complexes Based on 2-oxo-3-phenylpropionic Acid Salicyloylhydrazone. J. Coord. Chem. 2017, 70, 2606–2624. DOI: 10.1080/00958972.2017.1355460.
  • Tan, Y.-X.; Zhang, Z.-J.; Feng, Y.-L.; Yu, J.-X.; Zhu, X.-M.; Zhang, F.-X.; Kuang, D.-Z.; Jiang, W.-J. Syntheses, Crystal Structures and Biological Activity of the 1D Chain Benzyltin Complexes Based on 2-Oxo-Propionic Acid Benzoyl Hydrazone. J. Inorg. Organomet. Polym. 2017, 27, 342–352. P. DOI: 10.1007/s10904-016-0477-5.
  • Zhang, Z. J.; Kuang, D. Z.; Jiang, W. J.; Yu, J. X.; Zhu, X. M.; Zhang, F. X. Synthesis, Crystal Structure, and Thermal Stability of a Dibutyltin Complex {[4-Et2NC6H3(O)C = NC6H3(O)-5-NO2](n-Bu2Sn)}2 and Its Interaction with DNA. Chinese J. Struct. Chem. 2014, 09, 1319–1325.
  • Jiang, W. J.; Wu, X. M.; Liu, C.; Yu, J. X.; Zhu, X. M.; Feng, Y. L.; Zhang, F. X.; Kuang, D. Z. Syntheses, Crystal Structures and Biological Activity of Schiff Base Organotin Complexes Based on o-Vanillin and 2-Amino-4-Nitrophenol. Chinese J. Inorg. Chem. 2015, 07, 1321–1328.
  • Sheldrick, G. M. SHELXL-97. A Program for Crystal Structure Refinement, University of Geöttingen, Germany, 1997.
  • Farrugia, L. J. WINGX: A Windows Program for Crystal Structure Analysis, University of Glasgow, Germany, 1988.
  • Pyle, A. M.; Rehmann, J. P.; Meshoyrer, R.; Kumar, C. V.; Turro, N. J.; Barton, J. K. Mixed-ligand Complexes of Ruthenium(II): Factors Governing Binding to DNA. J. Am. Chem. Soc. 1989, 111, 3051–3058. DOI: 10.1021/ja00190a046.
  • Tan, C.; Liu, J.; Chen, L.; Shi, S.; Ji, L. Synthesis, structural Characteristics, DNA Binding Properties and Cytotoxicity Studies of a Series of Ru(III) Complexes. J. Inorg. Biochem. 2008, 102, 1644–1653. DOI: 10.1016/j.jinorgbio.2008.03.005.
  • Cinarli, A.; Gurbuz, D.; Tavman, A.; Birteksoz, A. S. Spectral Characterization and Antimicrobial Activity of Some Schiff Bases Derived from 4-Chloro-2-aminophenol and Various Salicylaldehyde Derivatives. Chin. J. Chem. 2012, 30, 449–459. DOI: 10.1002/cjoc.201180473.
  • Yadav, S.; Yousuf, I.; Usman, M.; Ahmad, M.; Arjmand, F.; Tabassum, S. Synthesis and Spectroscopic Characterization of Diorganotin(iv) complexes of N [prime or Minute]- (4-hydroxypent-3-en-2-ylidene) isonicotinohydrazide: chemotherapeutic Potential Validation by in Vitro Interaction Studies with DNA/HSA, DFT, molecular Docking and Cytotoxic Activity. RSC Adv. 2015, 5, 50673–50690. DOI: 10.1039/C5RA06953J.
  • Basu Baul, T. S.; Kehie, P.; Duthie, A.; Guchhait, N.; Raviprakash, N.; Mokhamatam, R. B.; Manna, S. K.; Armata, N.; Scopelliti, M.; Wang, R.; Englert, U. Synthesis, Photophysical Properties and Structures of Organotin-Schiff Bases Utilizing Aromatic Amino Acid from the Chiral Pool and Evaluation of the Biological Perspective of a Triphenyltin Compound. J. Inorg. Biochem. 2017, 168, 76–89. DOI: 10.1016/j.jinorgbio.2016.12.001.
  • Yang, Y.; Hong, M.; Xu, L.; Cui, J.; Chang, G.; Li, D.; Li, C-z. Organotin(IV) complexes Derived from Schiff Base N’-[(1E)-(2-hydroxy-3-methoxyphenyl)methylidene] pyridine-3 -carbohydrazone: Synthesis, in Vitro Cytotoxicities and DNA/BSA Interaction. J. Organomet. Chem. 2016, 804, 48–58. DOI: 10.1016/j.jorganchem.2015.12.041.
  • Nath, M.; Saini, P. K.; Kumar, A. Synthesis, structural Characterization, biological Activity and Thermal Study of Tri- and Diorganotin(IV) complexes of Schiff Base Derived from 2-Aminomethylbenzimidazole. Appl. Organometal. Chem. 2009, 23, 434–445. DOI: 10.1002/aoc.1537.
  • Hong, M.; Chang, G.; Li, R.; Niu, M. Anti-proliferative Activity and DNA/BSA Interactions of Five Mono- or di-organotin(iv) compounds Derived from 2-hydroxy-N[prime or Minute]-[(2-hydroxy-3-methoxyphenyl)methylidene]-Benzohydrazone. New J. Chem. 2016, 40, 7889–7900. DOI: 10.1039/C6NJ00525J.
  • Pretsch, E.; Buhlmann, P.; Martin, B. Structure Determina-tion of Organic Compounds, Tables of Spectral Data, 4th ed.; Springer-Verlag, Berlin Heidelberg, 2009.
  • Fulmer, G. R.; Miller, A. J. M.; Sherden, N. H.; Gottlieb, H. E.; Nudelman, A.; Stoltz, B. M.; Bercaw, J. E.; Goldberg, K. I. NMR Chemical Shifts of Trace Impurities: Common Laboratory Solvents, Organics, and Gases in Deuterated Solvents Relevant to the Organometallic Chemist. Organometallics 2010, 29, 2176–2179. DOI: 10.1021/om100106e.
  • Arjmand, F.; Yousuf, I. Synthesis, characterization and in Vitro DNA Binding of Chromone Schiff Base Organotin(IV) Complexes. J. Organomet. Chem. 2013, 743, 55–62. DOI: 10.1016/j.jorganchem.2013.06.018.
  • Nath, M.; Saini, P. K. Chemistry and Applications of Organotin(IV) Complexes of Schiff Bases. Dalton Trans. 2011, 42, 7077. DOI: 10.1039/c0dt01426e.
  • Basu, S.; Masharing, C.; Das, B. Diorganotin(IV) complexes of Polyaromaticazo-azomethine Ligand Derived from Salicylaldehyde and Ortho-aminophenol: Synthesis, Characterization, and Molecular Structures. Heteroatom Chem. 2012, 23, 457–465. DOI: 10.1002/hc.21037.
  • Chandrasekhar, V.; Gopal, K.; Sasikumar, P.; Thirumoorthi, R. Organooxotin Assemblies from Sn-C Bond Cleavage Reactions. Coord. Chem. Rev. 2005, 249, 1745–1765. DOI: 10.1016/j.ccr.2005.03.028.
  • Beltrán, H. I.; Damian-Zea, C.; Hernández-Ortega, S.; Nieto-Camacho, A.; Ramı´Rez-Apan, M. T. Synthesis and Characterization of di-phenyl-tinIV-salicyliden-ortho-aminophenols: Analysis of in Vitro Antitumor/antioxidant Activities and Molecular Structures. J. Inorg. Biochem. 2007, 101, 1070–1085. DOI: 10.1016/j.jinorgbio.2007.04.002.
  • Çelebier, M.; Şahin, E.; Ancın, N.; Öztaş, N. A.; Öztaş, S. G. Synthesis and Characterization of Diorganotin(IV) complexes of Schiff Bases with ONO-type Donors and Crystal Structure of [N-(2-hydroxy-4-nitrophenyl)-3-ethoxysalicylideneiminato] diphenyltin(IV). Appl. Organometal. Chem 2007, 21, 913–918.
  • Asadi, Z.; Asadi, M.; Setoodehkhah, M. Thermodynamics of Adduct Formation of Cobalt(II) tetraaza Schiff Base Complexes with Organotin(IV)Trichlorides. Spectrochim. Acta A Mol. Biomol. Spectrosc. 2013, 112, 214–218.
  • Chang, J. H.; Dong, Q. G. Spectral Theory and Analysis; Science Press, Beijing, 2012.
  • Zhao, G.; Shi, X.; J. Liu, J, Z.; Xiao, H.; L. Synthesis, S. Crystal Structures and Biological Activity of Transition Metalcomplexes of 2-phenyl-4-selenazole Carboxylic Acid. Sci. China Chem 2010, 40, 1525–1534.
  • Xu, J. G.; Wang, Z. B. Fluorescence Analysis, 3rd ed.; Science Press, Beijing, 2006.
  • Yan, C.; Zhang, J.; Liang, T.; Li, Q. Diorganotin (IV) complexes with 4-nitro-N-phthaloyl-glycine: Synthesis, characterization, antitumor Activity and DNA-binding Studies. Biomed. Pharmacother. 2015, 71, 119–127. DOI: 10.1016/j.biopha.2015.02.027.
  • Hussain, S.; Ali, S.; Shahzadi, S.; Tahir, M. N.; Shahid, M. Synthesis, characterization, biological Activities, Crystal Structure and DNA Binding of Organotin(IV) 5-Chlorosalicylates. J. Coord. Chem. 2015, 68, 2369–2387. DOI: 10.1080/00958972.2015.1046849.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.