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Research Articles

Anticancer potential of Cu(II)prolinedithiocarbamate complex: design, synthesis, spectroscopy, molecular docking, molecular dynamic, ADMET, and in-vitro studies

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Pages 12938-12950 | Received 29 Oct 2022, Accepted 11 Jan 2023, Published online: 23 Jan 2023

References

  • Adeyemi, J. O., & Onwudiwe, D. C. (2018). Organotin(IV) dithiocarbamate complexes: Chemistry and biological activity. Molecules, 23(10), 2571. https://doi.org/10.3390/MOLECULES23102571
  • Adeyemi, J. O., Saibu, G. M., Olasunkanmi, L. O., Fadaka, A. O., Meyer, M., Sibuyi, N. R. S., Onwudiwe, D. C., & Oyedeji, A. O. (2021). Synthesis, computational and biological studies of alkyltin(IV) N-methyl-N-hydroxyethyl dithiocarbamate complexes. Heliyon, 7(8), e07693. https://doi.org/10.1016/j.heliyon.2021.e07693
  • Askari, B., Rudbari, H. A., Micale, N., Schirmeister, T., Maugeri, A., & Navarra, M. N. (2019). Anticancer study of heterobimetallic Platinum(II)-Ruthenium(II) and Platinum(II). Journal of Organometallic Chemistry, 900, 120918.
  • Bitencourt-Ferreira, G., & de Azevedo, W. F. J. (2019). Molegro virtual docker for docking. Methods in Molecular Biology (Clifton, N.J.), 2053, 149–167. https://doi.org/10.1007/978-1-4939-9752-7_10
  • Boschi, A., Martini, P., & Uccelli, L. (2017). Nitrido radiopharmaceuticals for radionuclide therapy. Pharmaceuticals, 10, 12.
  • Boschi, A., Uccelli, L., & Martini, P. (2019). Picture of modern Tc-99m radiopharmaceuticals: Production, chemistry, and applications in molecular imaging. Applied Sciences, 9, 2526.
  • Cardoso, F., Bedard, P. L., Winer, E. P., Pagani, O., Senkus-Konefka, E., Fallowfield, L. J., Kyriakides, S., Costa, A., Cufer, T., & Albain, K. S. (2009). International guidelines for management of metastatic breast cancer: Combination vs sequential single-agent chemotherapy. Journal of the National Cancer Institute, 101(17), 1174–1181. https://doi.org/10.1093/jnci/djp235
  • Cui, X., Qi, J. Tan, H. Chen, F. (2017). Comparison of ancient and modern Chinese based on complex weighted networks, PLoS ONE, 12 (11), e0187854.
  • Daina, A., Michielin, O., & Zoete, V. (2017). SwissADME: A free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules. Scientific Reports, 7(October 2016), 1–13. https://doi.org/10.1038/srep42717
  • Daniela, B., S. S. (2012). Dithiocarbamate-based coordination compounds as potent proteasome inhibitors in human cancer cells. Mini Reviews in Medicinal Chemistry, 12(12), 1193–1201.
  • Dorcier, A., Ang, W. H., Bolano, S., Gonsalvi, L., Juillerat-Jeannerat, L., Laurenczy, G., Peruzzini, M., Phillips, A. D., Zanobini, F., & Dyson, P. J. (2006). In vitro evaluation of rhodium and osmium RAPTA analogues: The case for organometallic anticancer drugs not based on ruthenium. Organometallics, 25(17), 4090–4096.
  • Ebrahimi, K. S., Ansari, M., Hosseyni Moghaddam, M. S., Ebrahimi, Z., Salehi, Z., Shahlaei, M., & Moradi, S. (2021). In silico investigation on the inhibitory effect of fungal secondary metabolites on RNA dependent RNA polymerase of SARS-CoV-II: A docking and molecular dynamic simulation study. Computers in Biology and Medicine, 135, 104613.
  • Feng, L., Geisselbrecht, Y., Blanck, S., Wilbuer, A., Atilla-Gokcumen, G. E., Filippakopoulos, P., Kräling, K., Celik, M. A., Harms, K., Maksimoska, J., Marmorstein, R., Frenking, G., Knapp, S., Essen, L.-O., & Meggers, E. (2011). Structurally sophisticated octahedral metal complexes as highly selective protein kinase inhibitors. Journal of the American Chemical Society, 133(15), 5976–5986.
  • Ferlay, J., Soerjomataram, I., Dikshit, R., Eser, S., Mathers, C., Rebelo, M., Parkin, D. M., Forman, D., & Bray, F. (2015). Cancer incidence and mortality worldwide: Sources, methods and major patterns in GLOBOCAN 2012. International Journal of Cancer, 136(5), E359–E386. https://doi.org/10.1002/ijc.29210
  • Ferraro, M.G., Piccolo, M., Misso, G., Santamaria, R., Irace, C. (2022). Bioactivity and Development of Small Non-Platinum Metal- Based Chemotherapeutics. Pharmaceutics, 14(5), 954. https://doi.org/10.3390/pharmaceutics14050954
  • Ferreira, I. P., de Lima, G. M., Paniago, E. B., Pinheiro, C. B., Wardell, J. L., & Wardell, S. M. S. V. (2015). Study of metal dithiocarbamate complexes, Part V. Metal complexes of [S2CN(CH2CH(OMe)2]: A standard dimeric zinc dithiocarbamate structural motive, a rare cadmium dithiocarbamate coordination polymer, and a hydrated sodium dithiocarbarmate complex, with a [Na2O2] core and chain. Inorganica Chimica Acta, 44, 137–145.
  • Gong, C., Yao, H., Liu, Q., Chen, J., Shi, J., Su, F., & Song, E. (2010). Markers of tumor-initiating cells predict chemoresistance in breast cancer. PloS one, 5(12), e15630.
  • Hadjiliadis, N. D., & Sletten, E. (2009). Metal complex-DNA interactions. Wiley.
  • Hassan, E. A., & Zayed, S. E. (2014). Dithiocarbamates as precursors in organic chemistry; synthesis and uses. Phosphorus, Sulfur, and Silicon and the Related Elements, 189(3), 300–323. https://doi.org/10.1080/10426507.2013.797416
  • Hodge, H. C., & Sterner, J. H. (1949). Tabulation of toxicity classes. American Industrial Hygiene Association Quarterly, 10(4), 93–96. https://doi.org/10.1080/00968204909344159
  • Hong, M., Geng, H., Niu, M., Wang, F., Li, D., Liu, J., & Yin, H. (2014). Organotin(IV) complexes derived from Schiff base N′-[(1E)-(2-hydroxy-3-methoxyphenyl)methylidene]pyridine-4-carbohydrazone: Synthesis, in vitro cytotoxicities and DNA/BSA interaction. European Journal of Medicinal Chemistry, 86, 550–561. https://doi.org/10.1016/J.EJMECH.2014.08.070
  • Irfandi, R., Raya, I., Ahmad, A., Fudholi, A., Natsir, H., Kartina, D., Karim, H., Santi, S., & Salnus, S. (2022). Review on anticancer activity of essential metal dithiocarbamate complexes. Indonesian Journal of Chemistry, 22(6), 1722–1736. https://doi.org/10.22146/ijc.73738
  • Irfandi, R., Riswandi, R., Raya, I., Ahmad, A., Fudholi, A., Jarre, S., Tirto Sari, D. R., Santi, S., Wijaya, R. I., & Prihantono, P. (2022). A new complex design of Fe(II) isoleucine dithiocarbamate as a novel anticancer and antivirus against SARSCOV-2. Asian Pacific Journal of Cancer Prevention, 23(9), 3113–3123. https://doi.org/10.31557/APJCP.2022.23.9.3113
  • Irfandi, R., Santi, S., Raya, I., Ahmad, A., Fudholi, A., Sari, D. R. T., & Prihantono. (2022). Study of new Zn(II)prolinedithiocarbamate as a potential agent for breast cancer: Characterization and molecular docking. Journal of Molecular Structure, 1252, 132101. https://doi.org/10.1016/j.molstruc.2021.132101
  • Kalia, S. B., Kaushal, G., Kumar, M., Cameotra, S. S., Sharma, A., Verma, M. L., & Kanwar, S. S. (2009). Antimicrobial and toxicological studies of some metal complexes of 4- methylpiperazine-1-carbodithioate and phenanthroline mixed ligands. Brazilian Journal of Microbiology, 40(4), 916–922.
  • Kamaludin, N. F., Awang, N., Baba, I., Hamid, A., & Meng, C. K. (2013). Synthesis, characterization and crystal structure of organotin(IV) N-Butyl-N-phenyldithiocarbamate compounds and their cytotoxicity in human leukemia cell lines. Pakistan journal of Biological Sciences, 16(1), 12–21. https://doi.org/10.3923/PJBS.2013.12.21
  • Khan, S. Z., Amir, M. K., Abbasi, R., Tahir., & M. N., Zia-Ur-Rehman. (2016). New 3D and 2D supramolecular heteroleptic Palladium(II) dithiocarbamates as potent anticancer agents. Journal of Coordination Chemistry, 69(20), 2999–3009., https://doi.org/10.1080/00958972.2016.1225198
  • Khemalapure, S. S., Katti, V. S., Hiremath, C. S., Hiremath, S. M., Basanagouda, M., & Radder, S. B. (2019). Spectroscopic (FT-IR, FT-Raman, NMR and UV–vis), ELF, LOL, NBO, and Fukui function investigations on (5-bromo-benzofuran-3-yl)-acetic acid hydrazide (5BBAH): Experimental and theoretical approach. Journal of Molecular Structure. 1196, 280–290. https://doi.org/10.1016/j.molstruc.2019.06.078
  • Krieger, E., & Vriend, G. (2015). New ways to boost molecular dynamics simulations. Journal of Computational Chemistry, 36(13), 996–1007.
  • Kumar, A., Naaz, A., Prakasham, A. P., Gangwar, M. K., Butcher, R. J., Panda, D., & Ghosh, P. (2017). Potent anticancer activity with high selectivity of a chiral palladium N-heterocyclic carbene complex. ACS Omega, 2(8), 4632–4646. https://doi.org/10.1021/acsomega.7b00688
  • Kumar, L. V., & Nath, R. G. (2018). Synthesis and characterization studies of cobalt (II), nickel (II), copper (II) and zinc (II) complexes of carboxymethyl-N-methyl-N-phenyl dithiocarbamate. Oriental Journal of Chemistry, 34(6), 3064.
  • Kumar, L. V., & Nath, R. G. (2019). Synthesis and characterization studies of cobalt (II), nickel (II), copper (II) and zinc (II) complexes of carboxymethyl-N-methyl-N-phenyl dithiocarbamate. Oriental Journal of Chemistry, 34(Ii), 4–9.
  • Luzzati, V., Masson, F., & Lerman, L. S. (1961). Interaction of DNA and proflavine: A small-angle X-ray scattering study. Journal of Molecular Biology, 3(5), 634–639. https://doi.org/10.1016/S0022-2836(61)80026-0
  • Malaguarnera, L., Pilastro, M. R., Scifo, C., Renis, M., Mazzarino, M. C., & Messina, A. (2003). Cell death in human acute myelogenousleukemia cells induced bypyrrolidinedithiocarbamate. Apoptosis, 5, 539–545.
  • Moussa, Y.E., and Wheate, N.J. (2018). The side effects of platinum-based chemotherapy drugs: A review of chemists, Dalton Trans., 47 (19), 6645– 6653.
  • Mudasir, M., Wijaya, K., Wahyuni, E. T., & Inoue, H. (2010). Interaction of iron(ii) mixed-ligand complexes with DNA: Base-pair specificity and thermal denaturation studies. Indonesian Journal of Chemistry, 4(3), 174–179. https://doi.org/10.22146/IJC.21849
  • Muttaqin, F. Z. (2019). Molecular docking and molecular dynamic studies of stilbene derivative compounds as Sirtuin-3 (Sirt3) histone deacetylase inhibitor on melanoma skin cancer and their toxicities prediction. Journal of Pharmacopolium, 2(2), 112–121.
  • Nabipour, H., Ghammamy, S., Ashuri, S., & Aghbolagh, Z. S. (2010). Synthesis of a new dithiocarbamate compound and study of its biological properties. Journal of Organic Chemistry, 2, 75–80.
  • Peter, A., Ajidabe, F. P., Andrew, A. A., & Fatoun, A. E. O. (2021). Synthesis, characterization and in vitro screening for anticancer potential of Mn(II), Co(II), Zn(II), and Pt(II) methoxyphenyl dithiocarbamate complexes. Journal of Moleculer Structure, 1230, 129894.
  • Pires, D. E. V., Blundell, T. L., & Ascher, D. (2015). pkCSM: Predicting small-molecule pharmacokinetic and toxicity properties using graph-based signatures. Journal of Medicinal Chemistry, 58(9), 4066–4072. https://doi.org/10.1021/acs.jmedchem.5b00104
  • Prayong, P., Barusrux, S., Weerapreeyakul, N. (2008). Cytotoxic activity screening of some indigenous Thai plants, Fitoterapia, 79 (7–8), 598–601.
  • Prihantono, P., Irfandi, R., & Raya, I. (2021). The comparison of Zn(II) arginine dithiocarbamate cytotoxicity in T47D breast cancer and fibroblast cells. Breast Disease, 40(S1), S55–S61. https://doi.org/10.3233/BD-219008
  • Prihantono, Irfandi, R., Raya, I., & Warsinggih. (2020). Potential anticancer activity of Mn (II) complexes containing arginine dithiocarbamate ligand on MCF-7 breast cancer cell lines. Annals of Medicine and Surgery (2012), 60(October), 396–402. https://doi.org/10.1016/j.amsu.2020.11.018
  • Prosser, K. E., Leung, A. W. Y., Harrypersad, S., Lewis, A. R., Bally, M. B., & Walsby, C. J. (2018). Transition metal ions promote the bioavailability of hydrophobic therapeutics: Cu and Zn interactions with RNA polymerase I inhibitor CX5461. Chemistry—A European Journal, 24, 6334.
  • Radisavljevic, S., Bratsos, I., Scheurer, A., Korzekwa, J., Masnikosa, R., Tot, A., Gligorijevic, N., Radulovic, S., & Simovic, A. R. (2018). New gold pincer-type complexes: Synthesis, characterization, DNA binding studies and cytotoxicity. Dalton Transactions, 47(38), 13696–13712.
  • Rau, T., Alsfasser, R., Zahl, A., & van Eldik, R. (1998). Structural and kinetic studies on the formation of Platinum(II) and Palladium(II) complexes with L-cysteine-derived ligands. Inorganic Chemistry, 37(17), 4223–4230.
  • Raya, I., Baba, I., & Yamin, B. M. (2006). New mixed ligands complexes of Samarium(III) with dithiocarbamates and 1,10-phenanthroline. Malaysia Journal of Analytical Sciences, 10(1), 93–98.
  • Ritacco, I., Russo, N., & Sicilia, E. (2015). DFT Investigation of the mechanism of action of Organoiridium(III) complexes as anticancer agents. Inorganic Chemistry, 54(22), 10801–10810. https://doi.org/10.1021/acs.inorgchem.5b01832
  • Rogachev, I., Gusis, V., Gusis, A., Cortina, J. L., Gressel, J., & Warshawsky, A. (1999). Spectrophotometric determination of copper complexation properties of new amphiphilic dithiocarbamates. Reactive and Functional Polymers, 42(3), 243–254. https://doi.org/10.1016/S1381-5148(98)00083-2
  • Ruswanto, S., Richa, M., Tita, N., & Tresna, L. (2017). Molecular docking of 1-benzoyl-3-methylthiourea as anti cancer candidate and its absorption, distribution, and toxicity prediction. Journal of Pharmaceutical Science and Research, 9(5), 680–684.
  • Santi, Wahab, A. W., Raya, I., & Ahmad, A. (2020). Synthesis and interaction of adenosine-5’-triphosphate with rare earth metal Europium (Eu3+). AIP Conference Proceedings, 2296, 020074.
  • Schreck, R., Meier, B., Mannel, D. N., Droge, W., & Baeuerle, P. A. (1992). Dithiocarbamate as potent inhibitors of nuclear factor kappa B activation in intact cells. Journal of Experimental Medicine, 5, 1181–1194.
  • Shaheen, F., Sirajuddin, M., Ali, S., Zia-Ur-Rehman, Dyson, P. J., Shah, N. A., & Tahir, M. N. (2018). Organotin(IV) 4-(benzo[d][1,3]dioxol-5-ylmethyl)piperazine-1-carbodithioates: Synthesis, characterization and biological activities. Journal of Organometallic Chemistry, 856, 13–22.
  • Sharma, R., Nagar, M., Agarwal, M., & Sharma, H. (2009). Synthesis, characterization and antimicrobial activities of some mixed ligand complexes of Co(II) with thiosemicarbazones and N-protected amino acids. Journal of Enzyme Inhibition and Medicinal Chemistry, 24(1), 197–204. https://doi.org/10.1080/14756360802051263
  • Sorkun, M.C., Khetan, A., & Er, S. (2019). AqSolDB, a curated reference set of aqueous solubility and 2D descriptors for a diverse set of compounds. Scientific Data, 6(1), 143. https://doi.org/10.1038/s41597-019-0151-1
  • Torella, R., Moroni, E., Caselle, M., Morra, G., & Colombo, G. (2010). Investigating dynamic and energetic determinants of protein nucleic acid recognition: Analysis of the zinc finger zif268-DNA complexes. BMC structural Biology, 10(Md), 42. https://doi.org/10.1186/1472-6807-10-42
  • Tripathy, D., Nayak, B. S., Mohanty, B., & Mishra, B. (2019). Solid dispersion: A technology for improving aqueous solubility of drug. Journal Of Pharmaceutical Advanced Research, 2(7), 577–586.
  • Yang, L., Tan, J., Wang, B. C., & Zhu, L. C. (2014). Synthesis, characterization, and anti-cancer activity of emodin-Mn(II) metal complex. Chinese journal of Natural Medicines, 12(12), 937–942. https://doi.org/10.1016/S1875-5364(14)60137-0
  • YASARA Molecular Dynamics Trajectory Analysis for 4mbs [Internet]. (n.d.). [Cited 2022 Feb 21]. http://www.Yasara.Org/Mdreport/4mbs_report.Html.
  • Yeni, Y., & Rachmania, R. A. (2022). The prediction of pharmacokinetic properties of compounds in Hemigraphis alternata (Burm.F.) T. Ander Leaves Using pkCSM. Indonesian Journal of Chemistry, 22(4), 1081–1089. https://doi.org/10.22146/ijc.73117
  • Yi, J. T., Tan, Y. S., Yeo, C. I., Chew, J., & Tiekink, E. R. T. (2019). In vitro anti-bacterial and time kill evaluation of binuclear tricyclohexylphosphanesilver(I) dithiocarbamates, {Cy3PAg(S2CNRR′)}2. Journal of Inorganic Biochemistry, 192, 107–118. https://doi.org/10.1016/j.jinorgbio.2018.12.017
  • Zhang, W., Yang, R., Cieplak, P., Luo, R., Lee, T. C. J. (2003). A point-charge force field for molecular mechanics simulations of proteins based on condensed-phase. Journal of Computational Chemistry, 24(16), 1999–2012. https://doi.org/10.1002/jcc.10349
  • Zoroddu, M. A., Aaseth, J., Crisponi, G., Medici, S., Peana, M., & Nurchi, V. M. (2019). The essential metals for humans: A brief overview. Journal of Inorganic Biochemistry, 195, 120–129. https://doi.org/10.1016/j.jinorgbio.2019.03.013

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