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Anti-Cancer Agents in Medicinal Chemistry

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ISSN (Print): 1871-5206
ISSN (Online): 1875-5992

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Research Article

The Development of Organotin(IV) N-Ethyl-N-Benzyldithiocarbamate Complexes: A Study on Their Synthesis, Characterization, and Cytocidal Effects on A549 Cell Line

Author(s): Nurul Amalina Abd Aziz, Normah Awang*, Nurul Farahana Kamaludin, Nur Najmi Mohamad Anuar, Asmah Hamid, Kok Meng Chan and Suhana Arshad

Volume 24, Issue 12, 2024

Published on: 15 April, 2024

Page: [942 - 953] Pages: 12

DOI: 10.2174/0118715206309421240402093335

Price: $65

Abstract

Background: Organotin(IV) complexes of dithiocarbamate are vital in medicinal chemistry, exhibiting potential in targeting cancer cells due to their unique properties that enhance targeted delivery. This study aimed to synthesize and characterize organotin(IV) N-ethyl-N-benzyldithiocarbamate complexes (ONBDCs) and evaluate their cytotoxicity against A549 cells, which are commonly used as a model for human lung cancer research.

Methods: The two ONBDC derivatives – ONBDC 1 (dimethyltin(IV) N-ethyl-N-benzyldithiocarbamate) and ONBDC 2 (triphenyltin(IV) N-ethyl-N-benzyldithiocarbamate) – were synthesized via the reaction of tin(IV) chloride with N-ethylbenzylamine in the presence of carbon disulfide. A range of analytical techniques, including elemental analysis, IR spectroscopy, NMR spectroscopy, UV-Vis spectrometry, TGA/DTA analysis, and X-ray crystallography, was conducted to characterize these compounds comprehensively. The cytotoxic effects of ONBDCs against A549 cells were evaluated using MTT assay.

Results: Both compounds were synthesized and characterized successfully via elemental and spectroscopies analysis. MTT assay revealed that ONBDC 2 demonstrated remarkable cytotoxicity towards A549 cells, with an IC50 value of 0.52 μM. Additionally, ONBDC 2 displayed significantly higher cytotoxic activity against the A549 cell line when compared to the commercially available chemotherapeutic agent cisplatin (IC50: 32 μM).

Conclusion: Thus, it was shown that ONBDC 2 could have important anticancer properties and should be further explored as a top contender for creating improved and specialized cancer treatments.

Keywords: Organotin(IV), dithiocarbamate, synthesis, elemental, spectroscopy, cytotoxicity, A549 cells.

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[1]
Upadhyay, A. Cancer: An unknown territory; rethinking before going ahead. Genes Dis., 2021, 8(5), 655-661.
[http://dx.doi.org/10.1016/j.gendis.2020.09.002] [PMID: 34291136]
[2]
Chhikara, B.S.; Parang, K. Global cancer statistics 2022: The trends projection analysis. Chem. Biol. Lett., 2023, 10(1), 451.
[3]
Ferlay, J.; Colombet, M.; Soerjomataram, I.; Parkin, D.M.; Piñeros, M.; Znaor, A.; Bray, F. Cancer statistics for the year 2020: An overview. Int. J. Cancer, 2021, 149(4), 778-789.
[http://dx.doi.org/10.1002/ijc.33588] [PMID: 33818764]
[4]
Guo, Q.; Liu, L.; Chen, Z.; Fan, Y.; Zhou, Y.; Yuan, Z.; Zhang, W. Current treatments for non-small cell lung cancer. Front. Oncol., 2022, 12, 945102.
[http://dx.doi.org/10.3389/fonc.2022.945102] [PMID: 36033435]
[5]
Debela, D.T.; Muzazu, S.G.Y.; Heraro, K.D.; Ndalama, M.T.; Mesele, B.W.; Haile, D.C.; Kitui, S.K.; Manyazewal, T. New approaches and procedures for cancer treatment: Current perspectives. SAGE Open Med., 2021, 9.
[http://dx.doi.org/10.1177/20503121211034366] [PMID: 34408877]
[6]
Dasari, S.; Tchounwou, B.P. Cisplatin in cancer therapy: Molecular mechanisms of action. Eur. J. Pharmacol., 2014, 740, 364-378.
[http://dx.doi.org/10.1016/j.ejphar.2014.07.025] [PMID: 25058905]
[7]
Lee, N.; Spears, M.E.; Carlisle, A.E.; Kim, D. Endogenous toxic metabolites and implications in cancer therapy. Oncogene, 2020, 39(35), 5709-5720.
[http://dx.doi.org/10.1038/s41388-020-01395-9] [PMID: 32709924]
[8]
Ong, M.S.; Deng, S.; Halim, C.E.; Cai, W.; Tan, T.Z.; Huang, R.Y.J.; Sethi, G.; Hooi, S.C.; Kumar, A.P.; Yap, C.T. Cytoskeletal proteins in cancer and intracellular stress: A therapeutic perspective. Cancers, 2020, 12(1), 238.
[http://dx.doi.org/10.3390/cancers12010238] [PMID: 31963677]
[9]
Karpinich, N.O.; Tafani, M.; Rothman, R.J.; Russo, M.A.; Farber, J.L. The course of etoposide-induced apoptosis from damage to DNA and p53 activation to mitochondrial release of cytochrome c. J. Biol. Chem., 2002, 277(19), 16547-16552.
[http://dx.doi.org/10.1074/jbc.M110629200] [PMID: 11864976]
[10]
Bunn, P.A., Jr The expanding role of cisplatin in the treatment of non-small-cell lung cancer. Semin. Oncol., 1989, 16(4), 10-21.
[PMID: 2548280]
[11]
Aldossary, S.A. Review on pharmacology of cisplatin: Clinical use, toxicity and mechanism of resistance of cisplatin. Biomed. Pharmacol. J., 2019, 12(1), 07-15.
[http://dx.doi.org/10.13005/bpj/1608]
[12]
Yusof, E.N.M.; Azam, M.; Sirat, S.S.; Ravoof, T.B.S.A.; Page, A.J.; Veerakumarasivam, A.; Karunakaran, T.; Razali, M.R. Dithiocarbazate ligand-based Cu(II), Ni(II), and Zn(II) complexes: Synthesis, structural investigations, cytotoxicity, dna binding, and molecular docking studies. Bioinorg. Chem. Appl., 2022, 2022, 1-13.
[http://dx.doi.org/10.1155/2022/2004052] [PMID: 35959229]
[13]
Ndagi, U.; Mhlongo, N.; Soliman, M. Metal complexes in cancer therapy – An update from drug design perspective. Drug Des. Devel. Ther., 2017, 11, 599-616.
[http://dx.doi.org/10.2147/DDDT.S119488] [PMID: 28424538]
[14]
Awang, N.; Mohd Yousof, N.S.A.; Rajab, N.F.; Kamaludin, N.F. In vitro cytotoxic activity of new triphenyltin (IV) alkyl-isopropyl-di-thiocarbamate compounds on human acute T-lymphoblastic cell line. J. Appl. Pharm. Sci., 2015, 5, 7-11.
[http://dx.doi.org/10.7324/JAPS.2015.54.S2]
[15]
Gielen, M. Review: Organotin compounds and their therapeutic potential: A report from the Organometallic Chemistry Department of the Free University of Brussels. Appl. Organomet. Chem., 2002, 16(9), 481-494.
[http://dx.doi.org/10.1002/aoc.331]
[16]
Hamid, A.; Azmi, M.A.; Rajab, N.F.; Awang, N.; Jufri, N.F. Cytotoxic effects of organotin(IV) dithiocarbamate compounds with different functional groups on leukemic cell line, K-562. Sains Malays., 2020, 49(6), 1421-1430.
[http://dx.doi.org/10.17576/jsm-2020-4906-20]
[17]
Ramirez, V.A.; Costanzo, M.; Carrasco, Y.P.; Pannell, K.H.; Aguilera, R.J. Cytotoxic effects of two organotin compounds and their mode of inflicting cell death on four mammalian cancer cells. Cell Biol. Toxicol., 2011, 27(3), 159-168.
[http://dx.doi.org/10.1007/s10565-010-9178-y] [PMID: 21069563]
[18]
Awang, N.; Kamaludin, N.F.; Hamid, A.; Mokhtar, N.W.N.; Rajab, N.F. Cytotoxicity of triphenyltin(IV) methyl- and ethylisopropyldithiocarbamate compounds in chronic myelogenus leukemia cell line (K-562). Pak. J. Biol. Sci., 2012, 15(17), 833-838.
[http://dx.doi.org/10.3923/pjbs.2012.833.838] [PMID: 24163967]
[19]
Devi, J.; Pachwania, S. Recent advancements in DNA interaction studies of organotin(IV) complexes. Inorg. Chem. Commun., 2018, 91, 44-62.
[http://dx.doi.org/10.1016/j.inoche.2018.03.012]
[20]
Attanzio, A.; D’Agostino, S.; Busà, R.; Frazzitta, A.; Rubino, S.; Girasolo, M.A.; Sabatino, P.; Tesoriere, L. Cytotoxic activity of organotin(IV) derivatives with triazolopyrimidine containing exocyclic oxygen atoms. Molecules, 2020, 25(4), 859.
[http://dx.doi.org/10.3390/molecules25040859] [PMID: 32075253]
[21]
Syed Annuar, S.N.; Kamaludin, N.F.; Awang, N.; Chan, K.M. Cellular basis of organotin(IV) derivatives as anticancer metallodrugs: A review. Front Chem., 2021, 9, 657599.
[http://dx.doi.org/10.3389/fchem.2021.657599] [PMID: 34368075]
[22]
Fuertes, M.; Castilla, J.; Alonso, C.; Pérez, J. Cisplatin biochemical mechanism of action: From cytotoxicity to induction of cell death through interconnections between apoptotic and necrotic pathways. Curr. Med. Chem., 2003, 10(3), 257-266.
[http://dx.doi.org/10.2174/0929867033368484] [PMID: 12570712]
[23]
Adeyemi, J.; Onwudiwe, D. Organotin(IV) dithiocarbamate complexes: Chemistry and biological activity. Molecules, 2018, 23(10), 2571.
[http://dx.doi.org/10.3390/molecules23102571] [PMID: 30304779]
[24]
Adeyemi, J.O.; Onwudiwe, D.C.; Ekennia, A.C.; Okafor, S.N.; Hosten, E.C. Organotin(IV) N-butyl-N-phenyldithiocarbamate complexes: Synthesis, characterization, biological evaluation and molecular docking studies. J. Mol. Struct., 2019, 1192, 15-26.
[http://dx.doi.org/10.1016/j.molstruc.2019.04.097]
[25]
Awang, N.; Kamaludin, N.; Baba, I.; Chan, K.; Rajab, N.; Hamid, A. Synthesis, characterization, and antitumor activity of new organotin(IV) methoxyethyldithiocarbamate complexes. Orient. J. Chem., 2016, 32(1), 101-107.
[http://dx.doi.org/10.13005/ojc/320110]
[26]
Haezam, F.N.; Awang, N.; Kamaludin, N.F.; Mohamad, R. Synthesis and cytotoxic activity of organotin(IV) diallyldithiocarbamate compounds as anticancer agent towards colon adenocarcinoma cells (HT-29). Saudi J. Biol. Sci., 2021, 28(5), 3160-3168.
[http://dx.doi.org/10.1016/j.sjbs.2021.02.060] [PMID: 34025187]
[27]
Nath, M. Toxicity and the cardiovascular activity of organotin compounds: A review. Appl. Organomet. Chem., 2008, 22(10), 598-612.
[http://dx.doi.org/10.1002/aoc.1436]
[28]
Awang, N.; Baba, I.; Yamin, B.M.; Othman, M.S.; Kamaludin, N.F. Synthesis, characterization and biological activities of organotin (IV) methylcyclohexyldithiocarbamate compounds. Am. J. Appl. Sci., 2011, 8(4), 310-317.
[http://dx.doi.org/10.3844/ajassp.2011.310.317]
[29]
Adeyemi, J.; Onwudiwe, D. Antimicrobial and cytotoxicity studies of some organotin(IV) N-ethyl-N-phenyl dithiocarbamate complexes. Pol. J. Environ. Stud., 2020, 29(4), 2525-2532.
[http://dx.doi.org/10.15244/pjoes/111231]
[30]
Tiekink, E.R.T. Tin dithiocarbamates: Applications and structures. Appl. Organomet. Chem., 2008, 22(9), 533-550.
[http://dx.doi.org/10.1002/aoc.1441]
[31]
Syed Annuar, S.N.; Kamaludin, N.F.; Awang, N.; Chan, K.M. Triphenyltin(IV) dithiocarbamate compound induces genotoxicity and cytotoxicity in K562 human erythroleukemia cells primarily via mitochondria-mediated apoptosis. Food Chem. Toxicol., 2022, 168, 113336.
[http://dx.doi.org/10.1016/j.fct.2022.113336] [PMID: 35963475]
[32]
Abd Aziz, N.A.; Awang, N.; Chan, K.M.; Kamaludin, N.F.; Anuar, M.N.N. Organotin (IV) dithiocarbamate compounds as anticancer agents: A review of syntheses and cytotoxicity studies. Molecules, 2023, 28(15), 5841.
[http://dx.doi.org/10.3390/molecules28155841] [PMID: 37570810]
[33]
Khan, H.N.; Ali, S.; Shahzadi, S.; Helliwell, M. Synthesis and spectral characterization of chloro-organotin(IV) complexes of S-donor ligand: Crystal structure of chloro-t-dibutyltin[4-methyl-1-piperidine]thiocarboxylate. Russ. J. Inorg. Chem., 2012, 57(5), 665-670.
[http://dx.doi.org/10.1134/S0036023612050117]
[34]
Awang, N.; Zakri, N.H.; Zain, N.M. Antimicrobial activity of organotin(IV) alkylisopropildithiocarbamate compounds. J. Chem. Pharm. Res., 2016, 8, 862-866.
[35]
Kadu, R.; Roy, H.; Singh, V.K. Diphenyltin(IV) dithiocarbamate macrocyclic scaffolds as potent apoptosis inducers for human cancer HEP 3B and IMR 32 cells: synthesis, spectral characterization, density functional theory study and in vitro cytotoxicity. Appl. Organomet. Chem., 2015, 29(11), 746-755.
[http://dx.doi.org/10.1002/aoc.3362]
[36]
Awang, N.; Mohktar, S.M.; Zin, N.M.; Kamaludin, N.F. Evaluation of antimicrobial activities of organotin (IV) alkylphenyl dithiocarbamate compounds. Asian J. Appl. Sci., 2015, 8(2), 165-172.
[http://dx.doi.org/10.3923/ajaps.2015.165.172]
[37]
Adeyemi, J.O.; Onwudiwe, D.C.; Nundkumar, N.; Singh, M.; Nundkumar, N.; Singh, M. Diorganotin(iv) benzyldithiocarbamate complexes: synthesis, characterization, and thermal and cytotoxicity study. Open Chem., 2020, 18(1), 453-462.
[http://dx.doi.org/10.1515/chem-2020-0037]
[38]
Awang, N.; Aziz, Z.A.; Kamaludin, N.F.; Chan, K.M. Cytotoxicity and mode of cell death induced by triphenyltin (IV) compounds in vitro. Online J. Biol. Sci., 2014, 14(2), 84-93.
[http://dx.doi.org/10.3844/ojbsci.2014.84.93]
[39]
Yin, H.D.; Xue, S.C. Synthesis and characterization of organotin complexes with dithiocarbamates and crystal structures of (4‐NCC6H4CH2)2Sn(S2CNEt2)2 and (2‐ClC6H4CH2)2Sn(Cl)S2CNBz2. Appl. Organomet. Chem., 2006, 20(4), 283-289.
[http://dx.doi.org/10.1002/aoc.1048]
[40]
Rasli, N.R.; Hamid, A.; Awang, N.; Kamaludin, N.F. Series of organotin(IV) compounds with different dithiocarbamate ligands induced cytotoxicity, apoptosis and cell cycle arrest on jurkat E6.1, T acute lymphoblastic leukemia cells. Molecules, 2023, 28(8), 3376.
[http://dx.doi.org/10.3390/molecules28083376] [PMID: 37110610]
[41]
Adokoh, C.K. Therapeutic potential of dithiocarbamate supported gold compounds. RSC Advances, 2020, 10(5), 2975-2988.
[http://dx.doi.org/10.1039/C9RA09682E] [PMID: 35496096]
[42]
Cattaruzza, L.; Fregona, D.; Mongiat, M.; Ronconi, L.; Fassina, A.; Colombatti, A.; Aldinucci, D. Antitumor activity of gold(III)‐dithiocarbamato derivatives on prostate cancer cells and xenografts. Int. J. Cancer, 2011, 128(1), 206-215.
[http://dx.doi.org/10.1002/ijc.25311] [PMID: 20209498]
[43]
Kamaludin, N.F.; Awang, N. Synthesis and characterisation of organotin(IV) Nethyl- N-phenyldithiocarbamate compounds and the crystal structures of dibutyl- and triphenyltin(IV) nethyl- N-phenyldithiocarbamate. Res. J. Chem. Environ., 2014, 18, 90-98.
[44]
Odularu, A.T.; Ajibade, P.A. Dithiocarbamates: Challenges, control, and approaches to excellent yield, characterization, and their biological applications. Bioinorg. Chem. Appl., 2019, 2019, 1-15.
[http://dx.doi.org/10.1155/2019/8260496] [PMID: 30881441]
[45]
Mosmann, T. Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays. J. Immunol. Methods, 1983, 65(1-2), 55-63.
[http://dx.doi.org/10.1016/0022-1759(83)90303-4] [PMID: 6606682]
[46]
Muthalib, A.F.A.; Baba, I. New mono-organotin (IV) dithiocarbamate complexes. AIP Conf. Proc., 2014, 1614, 237-243.
[http://dx.doi.org/10.1063/1.4895202]
[47]
Sainorudin, M.H.; Sidek, N.M.; Ismail, N.; Rozaini, M.Z.H.; Harun, N.A.; Anuar, S.T.T.N.; Azmi, A.R.A.A.; Yusoff, F. Synthesis, characterization and biological activity of organotin(IV) complexes featuring di-2-ethylhexyldithiocarbamate and n-methylbutyldithiocarbamate as ligands. GSTF Journal of Chemical Sciences, 2015, 2(1), 2.
[http://dx.doi.org/10.7603/s40837-015-0002-3]
[48]
Ghaffar, A.; Khan, N. Biological and electronic transition studies of the previously reported organotin (IV) dithiocarbamates of p-Fluoro-Nmethylbenzylaminedithiocarbamate. Pure Appl. Biol., 2019, 8(1), 672-679.
[http://dx.doi.org/10.19045/bspab.2019.80007]
[49]
Nurazzi, N.M.; Asyraf, M.R.M.; Rayung, M.; Norrrahim, M.N.F.; Shazleen, S.S.; Rani, M.S.A.; Shafi, A.R.; Aisyah, H.A.; Radzi, M.H.M.; Sabaruddin, F.A.; Ilyas, R.A.; Zainudin, E.S.; Abdan, K. Thermogravimetric analysis properties of cellulosic natural fiber polymer composites: A review on influence of chemical treatments. Polymers, 2021, 13(16), 2710.
[http://dx.doi.org/10.3390/polym13162710] [PMID: 34451248]
[50]
Adeyemi, J.O.; Onwudiwe, D.C.; Hosten, E.C. Organotin(IV) complexes derived from N -ethyl- N -phenyldithiocarbamate: Synthesis, characterization and thermal studies. J. Saudi Chem. Soc., 2018, 22(4), 427-438.
[http://dx.doi.org/10.1016/j.jscs.2017.08.004]
[51]
Kartina, D.; Wahab, A.W.; Ahmad, A.; Irfandi, R.; Raya, I. In vitro antibacterial and anticancer activity of Zn(II)Valinedithiocarbamate complexes. J. Phys. Conf. Ser., 2019, 1341(3), 032042.
[http://dx.doi.org/10.1088/1742-6596/1341/3/032042]
[52]
Awang, N.; Baba, I. Diorganotin(IV) alkylcyclohexyldithiocarbamate compounds: Synthesis, characterization and biological activities. Sains Malays., 2012, 41, 977-982.
[53]
Brown, D.A.; Glass, W.K.; Burke, M.A. The general use of i.r. spectral criteria in discussions of the bonding and structure of metal dithiocarbamates. Spectrochim. Acta A, 1976, 32(1), 137-143.
[http://dx.doi.org/10.1016/0584-8539(76)80059-1]
[54]
Nomura, R.; Takabe, A.; Matsuda, H. Facile synthesis of antimony dithiocarbamate complexes. Polyhedron, 1987, 6(3), 411-416.
[http://dx.doi.org/10.1016/S0277-5387(00)81000-1]
[55]
Jung, O-S.; Sohn, Y-S. Coordination chemistry of organotin(IV) dithiocarbamate complexes. Bull. Korean Chem. Soc., 1988, 9, 365-368.
[56]
Bonati, F.; Ugo, R. Organotin(IV) N,N-disubstituted dithiocarbamates. J. Organomet. Chem., 1967, 10(2), 257-268.
[http://dx.doi.org/10.1016/S0022-328X(00)93085-7]
[57]
Alverdi, V.; Giovagnini, L.; Marzano, C.; Seraglia, R.; Bettio, F.; Sitran, S.; Graziani, R.; Fregona, D. Characterization studies and cytotoxicity assays of Pt(II) and Pd(II) dithiocarbamate complexes by means of FT-IR, NMR spectroscopy and mass spectrometry. J. Inorg. Biochem., 2004, 98(6), 1117-1128.
[http://dx.doi.org/10.1016/j.jinorgbio.2004.03.011] [PMID: 15149823]
[58]
Mohamad, R.; Awang, N.; Kamaludin, N.F. Synthesis and characterisation of new organotin (IV)(2-Methoxyethyl)-methyldithiocarbamate complexes. Res. J. Pharm. Biol. Chem. Sci., 2016, 7, 1920-1925.
[59]
Kamaludin, N.F.; Awang, N.; Baba, I.; Hamid, A.; Meng, C.K. Synthesis, characterization and crystal structure of organotin(IV) N-butyl-N-phenyldithiocarbamate compounds and their cytotoxicity in human leukemia cell lines. Pak. J. Biol. Sci., 2012, 16(1), 12-21.
[http://dx.doi.org/10.3923/pjbs.2013.12.21] [PMID: 24199481]
[60]
Adeyemi, J.O.; Onwudiwe, D.C.; Singh, M. Synthesis, characterization, and cytotoxicity study of organotin(IV) complexes involving different dithiocarbamate groups. J. Mol. Struct., 2019, 1179, 366-375.
[http://dx.doi.org/10.1016/j.molstruc.2018.11.022]
[61]
Khan, S.; Nami, S.A.A.; Siddiqi, K.S. Mononuclear indolyldithiocarbamates of SnCl4 and R2SnCl2: Spectroscopic, thermal characterizations and cytotoxicity assays in vitro. J. Organomet. Chem., 2008, 693(6), 1049-1057.
[http://dx.doi.org/10.1016/j.jorganchem.2007.12.026]
[62]
Onwudiwe, D.C.; Nthwane, Y.B.; Ekennia, A.C.; Hosten, E. Synthesis, characterization and antimicrobial properties of some mixed ligand complexes of Zn(II) dithiocarbamate with different N-donor ligands. Inorg. Chim. Acta, 2016, 447, 134-141.
[http://dx.doi.org/10.1016/j.ica.2016.03.033]
[63]
Adeyemi, J.O.; Onwudiwe, D.C.; Hosten, E.C. Synthesis, characterization and the use of organotin(IV) dithiocarbamate complexes as precursor to tin sulfide nanoparticles by heat up approach. J. Mol. Struct., 2019, 1195, 395-402.
[http://dx.doi.org/10.1016/j.molstruc.2019.05.115]
[64]
Sirajuddin, M.; Ali, S.; Tahir, M.N. Pharmacological investigation of mono-, di- and tri-organotin(IV) derivatives of carbodithioates: Design, spectroscopic characterization, interaction with SS-DNA and POM analyses. Inorg. Chim. Acta, 2016, 439, 145-158.
[http://dx.doi.org/10.1016/j.ica.2015.10.017]
[65]
Jung, O.S.; Hwa Jeong, J.; Soo Sohn, Y. Preparation, properties and structures of estertin(IV) sulphides. Polyhedron, 1989, 8(21), 2557-2563.
[http://dx.doi.org/10.1016/S0277-5387(00)81156-0]
[66]
Muthalib, A.F.A.; Baba, I.; Farina, Y.; Samsudin, M.W. Synthesis and characterization of diphenyltin(IV) dithiocarbamate compounds. Malays. J. Anal. Sci., 2011, 15, 106-112.
[67]
Mamba, S.M. Synthesis, characterization and applications of dithiocarbamate transition metal complexes. University of Johannesburg; South Africa: ProQuest Dissertations Publishing, 2011.
[68]
Chee, D.N.A.; Rodis, M.L.; Saat, N.; Ngaini, Z.; Halim, A.N.A. Synthesis and antibacterial study of organotin(IV) complexes containing hydrazinopyridine ligand. Malays. J. Anal. Sci., 2017, 21(5), 1143-1150.
[http://dx.doi.org/10.17576/mjas-2017-2105-17]
[69]
Adli, H.K.; Sidek, N.M.; Ismail, N.; Khairul, W.M. Several organotin (IV) complexes featuring 1-methylpiperazinedithiocarbamate and n-methylcyclohexyldithiocarbamate as ligands and their anti-microbial activity studies. J. Sci. Facul. Chiang Mai Uni., 2013, 40, 117-125.
[70]
Yusof, E.N.M.; Latif, M.A.M.; Tahir, M.I.M.; Sakoff, J.A.; Simone, M.I.; Page, A.J.; Veerakumarasivam, A.; Tiekink, E.R.T.; Ravoof, T.B.S.A. o-Vanillin derived schiff bases and their organotin(IV) compounds: Synthesis, structural characterisation, in silico studies and cytotoxicity. Int. J. Mol. Sci., 2019, 20(4), 854.
[http://dx.doi.org/10.3390/ijms20040854] [PMID: 30781445]
[71]
CrysAlis PRO User inspired software for single crystal x-ray diffractometers., 2018. Available from: https://www.rigaku.com/products/crystallography/crysalis
[72]
Sheldrick, G.M. A short history of SHELX. Acta Crystallogr. A, 2008, 64(1), 112-122.
[http://dx.doi.org/10.1107/S0108767307043930] [PMID: 18156677]
[73]
Spek, A.L. Structure validation in chemical crystallography. Acta Crystallogr. D Biol. Crystallogr., 2009, 65(2), 148-155.
[http://dx.doi.org/10.1107/S090744490804362X] [PMID: 19171970]
[74]
Awang, N.; Haezam, F.N.; Kamal, N.N.; Kamaludin, N.F.; Mohamad, R. Synthesis and characterization of organotin(IV) diisopropyldithiocarbamate compounds. J. Sci. Facult. Chiang Mai, 2021, 48, 1101-1110.
[75]
How, F.N.F.; Crouse, K.A.; Tahir, M.I.M.; Tarafder, M.T.H.; Cowley, A.R. Synthesis, characterization and biological studies of S-benzyl-β-N-(benzoyl) dithiocarbazate and its metal complexes. Polyhedron, 2008, 27(15), 3325-3329.
[http://dx.doi.org/10.1016/j.poly.2008.07.022]
[76]
Awang, N.; Baba, I.; Mohd Yousof, N.S.A.; Kamaludin, N.F. Synthesis and characterization of organotin(IV) N-Benzyl-N-isopropyldithiocarbamate compounds: Cytotoxic assay on human hepatocarcinoma cells (HepG2). Am. J. Appl. Sci., 2010, 7(8), 1047-1052.
[http://dx.doi.org/10.3844/ajassp.2010.1047.1052]
[77]
Zhuang, W.R.; Wang, Y.; Cui, P.F.; Xing, L.; Lee, J.; Kim, D.; Jiang, H.L.; Oh, Y.K. Applications of π-π stacking interactions in the design of drug-delivery systems. J. Control. Release, 2019, 294, 311-326.
[http://dx.doi.org/10.1016/j.jconrel.2018.12.014] [PMID: 30550939]
[78]
Liu, K.; Yan, H.; Chang, G.; Li, Z.; Niu, M.; Hong, M. Organotin(IV) complexes derived from hydrazone Schiff base: Synthesis, crystal structure, in vitro cytotoxicity and DNA/BSA interactions. Inorg. Chim. Acta, 2017, 464, 137-146.
[http://dx.doi.org/10.1016/j.ica.2017.05.017]
[79]
Cvek, B.; Dvorak, Z. Targeting of nuclear factor-kappaB and proteasome by dithiocarbamate complexes with metals. Curr. Pharm. Des., 2007, 13(30), 3155-3167.
[http://dx.doi.org/10.2174/138161207782110390] [PMID: 17979756]
[80]
Javed, F.; Sirajuddin, M.; Ali, S.; Khalid, N.; Tahir, M.N.; Shah, N.A.; Rasheed, Z.; Khan, M.R. Organotin(IV) derivatives of o-isobutyl carbonodithioate: Synthesis, spectroscopic characterization, X-ray structure, HOMO/LUMO and in vitro biological activities. Polyhedron, 2016, 104, 80-90.
[http://dx.doi.org/10.1016/j.poly.2015.11.041]

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