Organotin(IV) Complexes as Promising Potential Drug Candidates in the Field of Cancer Chemotherapy: A Narrative Review

Abeer Erfan; Emad Yousif; Ahmed Neama Alshanon; Dina Saadi Ahmed; Muna Bufaroosha; Gamal El-Hiti

doi:10.54133/ajms.v5i.146

المؤلفون

Abeer Erfan Department of Chemistry, College of Science, Al-Nahrain University, Baghdad 64021, Iraq
Emad Yousif Department of Chemistry, College of Science, Al-Nahrain University, Baghdad, Iraq https://orcid.org/0000-0003-1458-4724
Ahmed Neama Alshanon Center of Biotechnology Researches, University of Al-Nahrain, Baghdad, Iraq
Dina Saadi Ahmed Department of Chemical Industries, Institute of Technology, Middle Technical University, Baghdad, Iraq
Muna Bufaroosha Department of Chemistry, College of Science, UAE University, Al-Ain, United Arab Emirates
Gamal El-Hiti Department of Optometry, College of Applied Medical Sciences, King Saud University, Riyadh 11433, Saudi Arabia https://orcid.org/0000-0001-6675-3126

DOI:

https://doi.org/10.54133/ajms.v5i.146

الكلمات المفتاحية:

Organotin complexes; Cephalexin; anticancer; antioxidants, medicinal and pharmaceutical applications.

الملخص

Organotin(IV) complexes have a wide range of different applications. They are highly involved in pharmaceutical applications and have shown anticancer activity against various cancer cell lines. They act as antioxidants and can scavenge free radical species. The biological activity of organotin complexes depends on the organic moiety, type of substituents, number, type, and content of heteroatoms, and their geometry. The current review aimed to discuss using organotin complexes against different cancer cells.

التنزيلات

بيانات التنزيل غير متوفرة بعد.

المراجع

Jamil K, Wajid R, Bakhtiar M, Danish M. Biologically active organotin(IV) Schiff base complexes. J Iran Chem Soc. 2010;7:495-499. doi: 10.1007/BF03246037. DOI: https://doi.org/10.1007/BF03246037

Predarska, I, Saoud, M, Morgan, I, Lönnecke, P, Kaluđerović, GN, Hey-Hawkins E. Triphenyltin (IV) carboxylates with exceptionally high cytotoxicity against different breast cancer cell lines. Biomolecules. 2023;13:595. doi: 10.3390/biom13040595. DOI: https://doi.org/10.3390/biom13040595

Gielen M, Davies AI, Pannell K, Tiekink E, (Eds.), Tin Chemistry: Fundamentals, Frontiers, and Applications, John Wiley and Sons, 2008, 1-4. DOI: https://doi.org/10.1002/9780470758090

Veith M, Recktenwald O, (Eds.), Organotin Compounds: Structure and Reactivity of Monomeric, Molecular Tin (II) Compounds, Springer-Verlag, Berlin Heidelberg, New York, 1982, 1-3. DOI: https://doi.org/10.1515/9783112597569-001

Hadi AG, Jawad KH, El-Hiti GA, Alotaibi MH, Ahmed AA, Yousif E, et al. Photostabilization of poly (vinyl chloride) by organotin(IV) compounds against photodegradation. Molecules. 2019;24:3557. doi: 10.3390/molecules24193557. DOI: https://doi.org/10.3390/molecules24193557

Ghazi D, Rasheed Z, Yousif E. A review of organotin compounds: Chemistry and applications. Arch Org Inorg Chem Sci. 2018;3:344-352. doi: 10.32474/AOICS.2018.03.000161. DOI: https://doi.org/10.32474/AOICS.2018.03.000161

Rabiee, N, Safarkhani, M, Amini, MM. Investigating the structural chemistry of organotin (IV) compounds: recent advances. Rev Inorg Chem. 2019;39:13-45. Doi:10.1515/revic-2018-0014. DOI: https://doi.org/10.1515/revic-2018-0014

Hadi AG, Jawad KH, Ahmed DS, Yousif E. Synthesis and biological activities of organotin (IV) carboxylates: A review. Syst Rev Pharm. 2019;10:26-31. doi: 10.5530/srp.2019.1.5. DOI: https://doi.org/10.5530/srp.2019.1.5

Ruisi G, Giudice MT, Hubert F, VornefeIdt M. Di- and tri-organotin(1V) complexes of N-acetyltriglycine and N-benzoyltriglycine: Synthesis and spectroscopic characterization. Appl Organometal Chem. 1996;10:779-790. doi: 10.1002/(SICI)1099-0739(199612)10:10<779::AID-AOC517>3.0.CO;2-7. DOI: https://doi.org/10.1002/(SICI)1099-0739(199612)10:10<779::AID-AOC517>3.0.CO;2-7

Holland FS. The direct synthesis of triorgano tin compounds. Appl Organometal Chem. 1987;1:185-187. doi: 0268-2605/87/01209185/S03.50. DOI: https://doi.org/10.1002/aoc.590010210

Kerk GJ, Luijten JG. Investigation on organotin compounds: The preparation of butyltin compounds by a Wurts reaction. J Appl Chem. 1954;4:301-307. doi: 10.1002/jctb.5010040605 DOI: https://doi.org/10.1002/jctb.5010040605

Ali M, Yousif E. Chemistry and applications of organotin(IV) complexes: A review. Res J Pharm Biol Chem Sci. 2016;7:2611.

Ghani H, Yousif E. Chemistry of some organotin compounds. Al-Nahrain J Sci. 2021;24:9-15. doi: 10.22401/ANJS2. DOI: https://doi.org/10.22401/ANJS.24.3.02

Debnath P, Debnath P, Roy M, Siero L, Maniukiewicz W, Aktar T, et al. Novel organotin(IV) complexes of 2-[4-hydroxy-3-((2-hydroxyethylimino)methyl)phenylazo]benzoic acid: Synthesis, structure, noncovalent interactions and in vitro antibacterial activity. Crystals. 2022;12:1582. doi: 10.3390/cryst12111582. DOI: https://doi.org/10.3390/cryst12111582

Pantelic ND, Zmejkovski BB, Zizak Z, N. Banjac NR, Bozic BD, Stanojkovic TP, et al. Design and in vitro biological evaluation of a novel organotin(IV) complex with 1-(4-Carboxyphenyl)-3-ethyl-3-methylpyrrolidine-2,5-dione. J Chem. 2019;2019: 2905840. doi: 10.1155/2019/2905840. DOI: https://doi.org/10.1155/2019/2905840

Graisa AM, Zainulabdeen KH, Salman I, Al-Ani A, Mohammed R, Hairunisa N, et al. Toxicity and anti-tumour activity of organotin (IV) compounds. Baghdad J Biochem Appl Biol Sci. 2022;3:99-108. doi: 10.47419/bjbabs.v3i02.131. DOI: https://doi.org/10.47419/bjbabs.v3i02.131

Baul TS, Basu S, de Vos D, Linden A. Amino acetate functionalized Schiff base organotin(IV) complexes as anticancer drugs: synthesis, structural characterization, and in vitro cytotoxicity studies. Invest New Drugs. 2009;27:419-431. doi: 10.1007/s10637-008-9189-1. DOI: https://doi.org/10.1007/s10637-008-9189-1

Agiorgiti MS, Evangelou A, Vezyraki P, Hadjikakou SK, Kalfakakou V, Tsanaktsidis I, et al. Cytotoxic effect, antitumour activity and toxicity of organotin derivatives with ortho- or para-hydroxy-benzoic acids. Med Chem Res. 2018;27:1122-1130. doi: 10.1007/s00044-018-2135-7. DOI: https://doi.org/10.1007/s00044-018-2135-7

Gómez-Ruiz G, Zizak Z, Erovic GNK. Structural studies and cytotoxic activity against human cancer cell lines of mono and dinuclear tin(IV) complexes with the a,a’-dimercapto-o-xylene ligand. Inorg Chim Acta. 2014;1-6. doi: 10.1016/j.ica.2014.04.023. DOI: https://doi.org/10.1016/j.ica.2014.04.023

Muhammad N, Ahmad M, Sirajuddin M, Ali Z, Tumanov N, Wouters J, et al. Synthesis, characterization, biological activity and molecular docking studies of novel organotin(IV) carboxylates. Front Pharmacol. 2022;13:864336. doi: 10.3389/fphar.2022.864336. DOI: https://doi.org/10.3389/fphar.2022.864336

Mohammed A, Makia R, Ali M, Raheem R, Yousif E. Cytotoxic effects of valsartan organotin(IV) complexes on human lung cancer cells. Platinum Open Access J. 2021;11:8156-8164. doi: 10.33263/BRIAC111.81568164. DOI: https://doi.org/10.33263/BRIAC111.81568164

Hong M, Yin H, Zhang X, Li CH, Yue C, Cheng SH. Di- and tri-organotin(IV) complexes with 2-hydroxy-1-naphthaldehyde 5-chloro- 2-hydroxybenzoylhydrazone: Synthesis, characterization and in vitro antitumor activities. J Organometal Chem. 2013;724:23-31. doi: 10.1016/j.jorganchem.2012.10.031. DOI: https://doi.org/10.1016/j.jorganchem.2012.10.031

Nguyen C, Toubia I, Diring S, Kaddour KH, Bobo MG, Kobeissi M, et al. Synergetic anticancer activity of gold porphyrin appended to phenyl tin malonate organometallic complexes. Dalton Trans. 2021;50:4583-4592. doi: 10.1039/d0dt03792c. DOI: https://doi.org/10.1039/D0DT03792C

Al-Rikabi EH, Al-Refai RAK, Baqir SJ, Hadi AG, Al-Qayyim AK. Synthesis, structure, and in vitro cytotoxic activity of two organotin complexes of 2-[(2,3-dimethylphenyl)amino]benzoic acid. J Med Chem Sci. 2023;6:1230-1238. doi: 10.26655/JMCHEMSCI.2023.6.3. DOI: https://doi.org/10.26655/JMCHEMSCI.2023.6.3

Liu Q, Xie B, Lin S, Liao Q, Deng R, Zhaohua Y. Silicon-containing diorganotin complexes with salicylaldehyde thiosemicarbazone and their anticancer activity, J Chem Sci. 2019;131:73. doi: 10.1007/s12039-019-1650-5. DOI: https://doi.org/10.1007/s12039-019-1650-5

Haezam FN, Awang N, Kamaludin NF, 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;28:3160-3168. doi: 10.1016/j.sjbs.2021.02.060. DOI: https://doi.org/10.1016/j.sjbs.2021.02.060

Xiaoa X, Lia C, Laia H, Hec Y, Jianga T, Shia N, et al. Drumlike p-methylphenyltin carboxylates: the synthesis, characterization, antitumor activities and fluorescence. J Mol Struct. 2019;1190:116-124. doi: 10.1016/j.molstruc.2019.04.047. DOI: https://doi.org/10.1016/j.molstruc.2019.04.047

Pantelića ND, Zmejkovskid BB, Božiće B, Dojčinovićd B, Banjacb NR, Wessjohannc LA, et al. Synthesis, characterization and in vitro biological evaluation of novel organotin(IV) compounds with derivatives of 2-(5-arylidene-2,4-dioxothiazolidin-3-yl)propanoic acid. J Inorg Biochem. 2020;211: 111207. doi: 10.1016/j.jinorgbio.2020.111207. DOI: https://doi.org/10.1016/j.jinorgbio.2020.111207

Antonenko TA, Gracheva YA, Shpakovsky DB, Vorobyev MA, Mazur DM, Tafeenko VA, et al. Biological activity of novel organotin compounds with a Schiff base containing an antioxidant fragment. Int J Mol Sci. 2023;24:2024. doi: 10.3390/ijms24032024. DOI: https://doi.org/10.3390/ijms24032024

Dahmani M, Ettouhami A, El Bali B, Yahyi A, Wilson C, Ullah K, et al. Organotin (IV) derivative of piperic acid and phenylthioacetic acid: Synthesis, crystal structure, spectroscopic characterizations and biological activities. Moroccan J Chem. 2020;8:244-263.

Panteli ND, Boži B, Zmejkovski BB, Banjac NR, Dojcinovi B, Wessjohann LA, et al. In vitro evaluation of antiproliferative properties of novel organotin(IV) carboxylate compounds with propanoic acid derivatives on a panel of human cancer cell lines. Molecules. 2021;26:3199. doi: 10.3390/molecules26113199. DOI: https://doi.org/10.3390/molecules26113199

Baul TS, Hlychho B, Addepalli MR, Kundu S, Vos D, Linden A. Design, synthesis and cytotoxic evaluation in tumor cell lines of organotin(IV) complexes with heteroditopic hydroxo-carboxylato polyaromatic ligands. Res Sequare. 2022. Preprint. doi:10.21203/rs.3.rs-2131319/v1. DOI: https://doi.org/10.21203/rs.3.rs-2131319/v1

Kamaludin NF, Ismail N, Awang N, Mohamad R, Pim NU. Cytotoxicity evaluation and the mode of cell death of K562 cells induced by organotin (IV) (2-methoxyethyl) methyldithiocarbamate compounds. J Appl Pharm Sci. 2019;9:10-15. doi: 10.7324/JAPS.2019.90602. DOI: https://doi.org/10.7324/JAPS.2019.90602

Dontha S. A review on antioxidant methods. Asian J Pharm Clin Res. 2016;9:14-32. doi: 10.22159/ajpcr.2016.v9s2.13092. DOI: https://doi.org/10.22159/ajpcr.2016.v9s2.13092

Nopitasari S, Suhartati T, Suharso B, Herasari D, Pandiangan KD, Hadi S. Synthesis, characterization, and antioxidant activity of some organotin(IV) 2-nitrobenzoate using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) method. J Physics. 2021;1751:012098. doi: 10.1088/1742-6596/1751/1/012098. DOI: https://doi.org/10.1088/1742-6596/1751/1/012098

Nikitin E, Mironova E, Shpakovsky D, Gracheva Y, Koshelev D, Utochnikova V, et al. Cytotoxic and luminescent properties of novel organotin complexes with chelating antioxidant ligand. Molecules. 2022;27:8359. doi: 10.3390/molecules27238359. DOI: https://doi.org/10.3390/molecules27238359

Shpakovsky DB, Banti CN, Mukhatova EM, Gracheva YA, Osipova VP, Berberova NT, et al. Comparison of ground state recovery trace between 640 and 650 nm components in intact PBS. Royal Soc. Chem. 2021. doi: 10.1039/b000000x/.

Hadi AG, Hassen TF, Mahdi IJ. Synthesis, characterization, and antioxidant material activities of organotin (IV) carboxylates with tin-para methoxy benzoic acid. Mater. Today. 2021;49:2797-2801. doi: 10.1016/j.matpr.2021.09.469. DOI: https://doi.org/10.1016/j.matpr.2021.09.469

Sirivibulkovit K, Nouanthavong S, Sameenoi Y. Paper-based DPPH assay for antioxidant activity analysis. Japan Soc Anal Chem. 2018;34:795-800. doi: 10.2116/analsci.18P014. DOI: https://doi.org/10.2116/analsci.18P014

Arraq RR, Hadi AG. Synthesis, identification, and anti-oxidant activity of di-organotin (IV)-cephalexin complexes. J Med Chem Sci. 2023;6:392-401. doi: 0000-0002-5396-7560. ffoi: 10.26655/JMCHEMSCI.2023.2.19.

Devi J, Yadav J, Singh N. Synthesis, characterization, in vitro antimicrobial, antioxidant and anti‑inflammatory activities of diorganotin(IV) complexes derived from salicylaldehyde Schiff bases. Res Chem Intermed. 2019;45, 3943–3968. doi: 10.1007/s11164-019-03830-3. DOI: https://doi.org/10.1007/s11164-019-03830-3

Hashim DJ, Hassen TF, Hadi AG. Enhanced antioxidant activity of di- and triorganotin complexes derived from mefenamic acid. Egypt J Chem. 2022;65:483-490. doi: 10.21608/ejchem.2021.82292.4056. DOI: https://doi.org/10.21608/ejchem.2021.82292.4056

Choudhary VK, Bhatt AK, Dash D, Sharma N. Synthesis, characterization, thermal, computational and biological activity studies of new potential bioactive diorganotin(IV) nitrosubstitutedhydroxamates-A comparative study. Appl Organometal Chem. 2020;34:e5360. doi: 10.1002/aoc.5360. DOI: https://doi.org/10.1002/aoc.5360

Sirajuddin M, Ali S, Shah FA, Ahmad M, Tahir N. Potential bioactive vanillin–Schiff base di- and tri-organotin(IV) complexes of 4-((3,5-dimethylphenylimino)methyl)-2-methoxyphenol: synthesis, characterization and biological screenings. Iran Chem Soc. 2014;11:297-313. doi: 10.1007/s13738-013-0301-x. DOI: https://doi.org/10.1007/s13738-013-0301-x