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Abstract

Breast cancer still remains one of the precarious ailments among humans globally. The vulnerability of this ailment in homeopathic world remains colossal and this has drawn the attention of seasoned researchers to find lasting solution to this hazard. Therefore, 10 novel 1,2,4-thiadiazole-1,2,4-triazole derivatives were studied so as to explore their anti-breast cancer activities. The studied compounds were optimized using Spartan 14 and the QSAR study was executed by using Gretl and MATLAB. Also, docking study was observed using Pymol (for treating downloaded protein), Autodock Tool (for locating binding site in the downloaded protein and for converting ligand and receptor to .pdbqt format from .pdb format), Auto dock vina (for docking calculation) and discovery studio (for viewing the non-bonding interaction between the docked complexes). The selected descriptors were used to developed effective QSAR model and it was observed that the developed QSAR model using artificial neural network (ANN) predicted better than the prediction made by multiple linear regression (MLR). More so, the calculated binding affinity revealed that compound g (-11.4 kcal/mol) possess ability to inhibit 3α-hydroxysteroid dehydrogenase type 3 (PDB ID: 4xo6) than other studied compounds as well as etoposide (Standard).

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4-Thiadiazole 4-Triazole Breast cancer QSAR DFT.

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Abel Kolawole, O., Sunday Adewale, A., Simon N., O., Oluwatoba Emmanuel, O., & Banjo, S. (2021). Theoretical Bioevaluation of 1,2,4-Thiadiazole-1,2,4-triazole Derivatives via Molecular Modelling Approach. Asian Journal of Organic & Medicinal Chemistry, 6(1), 40–46. https://doi.org/10.14233/ajomc.2021.AJOMC-P307
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References

  1. A. Jemal, F. Bray, M.M. Center, J. Ferlay, E. Ward and D. Forman, Global Cancer Statistics, CA Cancer J. Clin., 61, 69 (2011); https://doi.org/10.3322/caac.20107
  2. O.A. Kolawole, F. Olatomide A and S. Banjo, Anti-Gastric Cancer Activity of 1,2,3-Triazolo[4,5-d]pyrimidine Hybrids (1,2,3-TPH): QSAR and Molecular Docking Approaches, Heliyon, 6, e03561 (2020); https://doi.org/10.1016/j.heliyon.2020.e03561
  3. J.Y. Zhang, Apoptosis-Based Anticancer Drugs, Nat. Rev. Drug Discov., 1, 101 (2002); https://doi.org/10.1038/nrd742
  4. J.K. Buolamwini, Novel Anticancer Drug Discovery, Curr. Opin. Chem. Biol., 3, 500 (1999); https://doi.org/10.1016/S1367-5931(99)80073-8
  5. G. Charitos, D.T. Trafalis, P. Dalezis, C. Potamitis, P. Zoumpoulakis, V. Sarli and C. Camoutsis, Synthesis and Anticancer Activity of Novel 3,6-Disubstituted 1,2,4-Triazolo[3,4-b]1,3,4-thiadiazole Derivatives, Arab. J. Chem., 12, 4784 (2019); https://doi.org/10.1016/j.arabjc.2016.09.015
  6. Y.-H. Wu, T.-H. Chang, Y.-F. Huang, H.-D. Huang and C.-Y. Chou, COL11A1 Promotes Tumor Progression and Predicts Poor Clinical Outcome in Ovarian Cancer, Oncogene, 33, 3432 (2014); https://doi.org/10.1038/onc.2013.307
  7. J.R. Molina, P. Yang, S.D. Cassivi, S.E. Schild and A.A. Adjei, Non-Small Cell Lung Cancer: Epidemiology, Risk Factors, Treatment and Survivorship, Mayo Clin. Proc., 83, 584 (2008); https://doi.org/10.1016/S0025-6196(11)60735-0
  8. B. Ljepoja, J. García-Roman, A.-K. Sommer, E. Wagner and A. Roidl, Breast, 43, 31 (2019); https://doi.org/10.1016/j.breast.2018.10.007
  9. S.P. Helmrich, S. Shapiro, L. Rosenberg, D.W. Kaufman, D. Slone, C. Bain, O.S. Miettinen, P.D. Stolley, N.B. Rosenshein, R.C. Knapp, T. Leavitt Jr., D. Schottenfeld, R.L. Engle Jr. and M. Levy, Risk Factors for Breast Cancer, Am. J. Epidemiol., 117, 35 (1983); https://doi.org/10.1093/oxfordjournals.aje.a113513
  10. L.A. Keogh, E. Steel, P. Weideman, P. Butow, I.M. Collins, J.D. Emery, G.B. Mann, A. Bickerstaffe, A.H. Trainer, L.J. Hopper and K. Phillips, Consumer and Clinician Perspectives on Personalising Breast Cancer Prevention Information, Breast, 43, 39 (2019); https://doi.org/10.1016/j.breast.2018.11.002
  11. M. Berliere, F. Roelants, C. Watremez, M.A. Docquier, N. Piette, S. Lamerant, V. Megevand, A. Van Maanen, P. Piette, A. Gerday and F.P. Duhoux, The Advantages of Hypnosis Intervention on Breast Cancer Surgery and Adjuvant therapy, Breast, 37, 114 (2018); https://doi.org/10.1016/j.breast.2017.10.017
  12. A.K. Kaur, S. Kumar and P.K. Sharma, Hepatoprotective Activity of Inula cappa DC. Aqueous Extract against Carbon Tetrachloride induced Hepatotoxicity in Wistar Rats, Int. Res. J. Pharm., 8, 14 (2017); https://doi.org/10.7897/2230-8407.08013
  13. B. Kaproñ, J.J. Luszczki, A. Plaziñska, A. Siwek, T. Karcz, A. Grybos, G. Nowak, A. Makuch-Kocka, K. Walczak, E. Langner, K. Szalast, S. Marciniak, M. Paczkowska, J. Cielecka-Piontek, L.M. Ciesla and T. Plech, Development of the 1,2,4-Triazole-based Anticonvulsant Drug Candidates Acting on the Voltage-gated Sodium Channels. Insights from in-vivo, in-vitro and in-silico Studies, Eur. J. Pharm. Sci., 129, 42 (2019); https://doi.org/10.1016/j.ejps.2018.12.018
  14. A.T. Mavrova, D. Wesselinova, J.A. Tsenov and L.A. Lubenov, Synthesis and Antiproliferative Activity of Some New Thieno[2,3-d]-pyrimidin-4(3H)-ones Containing 1,2,4-Triazole and 1,3,4-Thiadiazole Moiety, Eur. J. Med. Chem., 86, 676 (2014); https://doi.org/10.1016/j.ejmech.2014.09.032
  15. F. Lazrak, E.M. Essassi, Y.K. Rodi, K. Misbahi and M. Pierrot, Synthese De Nouveaux Systemes Condenses Renfermant Le 1,2,4-triazole, La 1,3-thiazine, La 1,3-thiazepine Et La 1,3,5,7-dithiadiazocine, Phosphorus Sulfur Silicon Rel. Elem., 179, 1799 (2004); https://doi.org/10.1080/10426500490466526
  16. F. Lazrak, N.H. Ahabchane, A. Keita, E.M. Essassi and M. Pierrot, Synthesis and Crystal Structure of 3-Methoxycarbonyl-5-methyl-1-p-tolyl-1,2,4-triazolo[3,4-c]-1,2,4-triazole, J. Indian Chem., 41B, 821 (2002).
  17. Q. Zhang, Y. Peng, X.I. Wang, S.M. Keenan, S. Arora and W.J. Welsh, Highly Potent Triazole-Based Tubulin Polymerization Inhibitors, J. Med. Chem., 50, 749 (2007); https://doi.org/10.1021/jm061142s
  18. R. Singh, S.K. Kashaw, V.K. Mishra, M. Mishra, V. Rajoriya and V. Kashaw, Design and Synthesis of New Bioactive 1,2,4-Triazoles, Potential Antitubercular and Antimicrobial Agents, Indian J. Pharm. Sci., 80, 36 (2018); https://doi.org/10.4172/pharmaceutical-sciences.1000328
  19. M.T.M. El Wassimy, M. Abdel-Rahman, A.B.A.G. Ghattas and O.A.A. Abdallah, Synthesis and Reactions of N-Chloromethyl-1,2,4-triazoles with Sulfur and Oxygen Nucleophiles, Phosphorus Sulfur Silicon Rel. Elem., 70, 99 (1992); https://doi.org/10.1080/10426509208049156
  20. M.-X. Song and X.-Q. Deng, Recent Developments on Triazole Nucleus in Anticonvulsant Compounds: A Review, J. Enzyme Inhib. Med. Chem., 33, 453 (2018); https://doi.org/10.1080/14756366.2017.1423068
  21. H. Kumar, A.S. Javed, A.S. Khan and M. Amir, 1,3,4-Oxadiazole/Thiadiazole and 1,2,4-Triazole Derivatives of Biphenyl-4-yloxy Acetic Acid: Synthesis and Preliminary Evaluation of Biological Properties, Eur. J. Med. Chem., 43, 2688 (2008); https://doi.org/10.1016/j.ejmech.2008.01.039
  22. N.K. Basu and F.L. Rose, S-Triazolopyridazines: Synthesis as Potential Therapeutic Agents, J. Chem. Soc., 5660 (1963); https://doi.org/10.1039/jr9630005660
  23. G. Wu, Y. Gao, D. Kang, B. Huang, Z. Huo, H. Liu, V. Poongavanam, P. Zhan and X. Liu, Design, Synthesis and Biological Evaluation of Tacrine-1,2,3-triazole Derivatives as Potent Cholinesterase Inhibitors, MedChemComm, 9, 149 (2018); https://doi.org/10.1039/C7MD00457E
  24. A. Aliabadi, E. Eghbalian and A. Kiani, Synthesis and Evaluation of the Cytotoxicity of a Series of 1,3,4-Thiadiazole Based Compounds as Anticancer Agents, Iran. J. Basic Med. Sci., 16, 1133 (2013).
  25. N. Kushwaha, S.K.S. Kushwaha and A.K. Rai, Biological Activities of Thiadiazole Derivatives: A Review, Int. J. Chem. Res., 4, 517 (2012).
  26. S.M. Gomha, T.A. Salah and A.O. Abdelhamid, Synthesis, Characteri-zation and Pharmacological Evaluation of Some Novel Thiadiazoles and Thiazoles Incorporating Pyrazole Moiety as Anticancer Agents, Monatsh. Chem., 146, 149 (2015); https://doi.org/10.1007/s00706-014-1303-9
  27. S.M. Gomha and H.M. Abdel-Aziz, Synthesis and Antitumor Activity of 1,3,4-Thiadiazole Derivatives Bearing Coumarine Ring, Heterocycles, 91, 583 (2015); https://doi.org/10.3987/COM-14-13146
  28. N. Siddiqui, P. Ahuja, W. Ahsan, S.N. Pandeya and M.S. Alam, Thiadiazoles: Progress Report on Biological Activities, J. Chem. Pharm. Res., 1, 19 (2009).
  29. P. Bhattacharya, J.T. Leonard and K. Roy, Exploring QSAR of Thiazole and Thiadiazole Derivatives as Potent and Selective Human Adenosine A3 Receptor Antagonists using FA and GFA Techniques, Bioorg. Med. Chem., 13, 1159 (2005); https://doi.org/10.1016/j.bmc.2004.11.022
  30. A. Foroumadi, Z. Kargar, A. Sakhteman, Z. Sharifzadeh, M. Kazemi, R. Feyzmohammadi and A. Shafiee, Synthesis and Antimycobacterial Activity of Some Alkyl [5-(Nitroaryl)-1,3,4-thiadiazol-2-ylthio]propio-nates, Bioorg. Med. Chem. Lett., 16, 1164 (2006); https://doi.org/10.1016/j.bmcl.2005.11.087
  31. D. Kumar, N. Maruthi Kumar, K.-H. Chang and K. Shah, Synthesis and Anticancer Activity of 5-(3-Indolyl)-1,3,4-thiadiazoles, Eur. J. Med. Chem., 45, 4664 (2010); https://doi.org/10.1016/j.ejmech.2010.07.023
  32. B. Sharma, A. Verma, S. Prajapati and U.K. Sharma, Synthetic Methods, Chemistry, and the Anticonvulsant Activity of Thiadiazoles, Int. J. Med. Chem., 2013, 348948 (2013); https://doi.org/10.1155/2013/348948
  33. V. Mathew, J. Keshavayya, V.P. Vaidya and D. Giles, Studies on Synthesis and Pharmacological Activities of 3,6-Disubstituted-1,2,4-triazolo[3,4-b]1,3,4-thiadiazoles and their Dihydro Analogues, Eur. J. Med. Chem., 42, 823 (2007); https://doi.org/10.1016/j.ejmech.2006.12.010
  34. K. Jain, S. Sharma, A. Vaidya, V. Ravichandran and R.K. Agrawal, 1,3,4-Thiadiazole and its Derivatives: A Review on Recent Progress in Biological Activities, Chem. Biol. Drug Des., 81, 557 (2013); https://doi.org/10.1111/cbdd.12125
  35. B. Zhang, X.-J. Hu, X.-Q. Wang, J.-F. Th’eriault, D.-W. Zhu, P. Shang, F. Labrie and S.-X. Lin, Human 3a-Hydroxysteroid Dehydrogenase Type 3: Structural Clues of 5a-DHT Reverse Binding and Enzyme Down-Regulation Decreasing MCF7 Cell Growth, Biochem. J., 473, 1037 (2016); https://doi.org/10.1042/BCJ20160083
  36. Y.J. Pragathi, R. Sreenivasulu, D. Veronica and R.R. Raju, Design, Synthesis and Biological Evaluation of 1,2,4-Thiadiazole-1,2,4-Triazole Derivatives Bearing Amide Functionality as Anticancer Agents, Arab. J. Sci. Eng., 46, 225 (2021); https://doi.org/10.1007/s13369-020-04626-z
  37. A.K. Oyebamiji, I.O. Abdulsalami and B. Semire, Dataset on in silico Approaches for 3,4-Hihydropyrimidin-2(1H)-one Urea Derivatives as Efficient Staphylococcus aureus inhibitor, Data Brief, 32, 106195 (2020); https://doi.org/10.1016/j.dib.2020.106195
  38. R.O. Adegoke, A.K. Oyebamiji and B. Semire, Dataset on the DFT-QSAR and Docking Approaches for Anticancer Activities of 1,2,3-Triazole-Pyrimidine Derivatives Against Human Esophageal Carcinoma (EC-109), Data Brief, 31, 105963 (2020); https://doi.org/10.1016/j.dib.2020.105963
  39. A.K. Oyebamiji, G.F. Tolufashe, O.M. Oyawoye, T.A. Oyedepo and B. Semire, Biological Activity of Selected Compounds from Annona muricata Seed as Antibreast Cancer Agents: Theoretical Study, J. Chem., 2020, 6735232 (2020); https://doi.org/10.1155/2020/6735232
  40. A.I. Taourati, M. Ghamali, S. Chtita, H. Zaki, M. Benlyass, F. Guenoun, T. Lakhlifi and M. Bouachrine, QSAR Studies of the Inhibitory Activity of a Series of Substituted Indole and Derivatives Againt Isoprenyl-cysteine Carboxyl Methyltransferase (Icmt), Int. J. Pharm. Sci. Inven., 6, 6 (2017).
  41. H. Rachid, I.T. Abdelhafid, L. Majdouline, A. Azeddine, A. Abdelaziz, B. Mohammed and L. Tahar, Combining DFT and QSAR Result for Predicting the Biological Activity of the Phenylsuccinimide Derivatives, J. Chem. Pharm. Res., 5, 45 (2013).