Heavy Metal Complexes of 1, 2, 3-Triazole derivative: Synthesis, Characterization, and Cytotoxicity Appraisal Against Breast Cancer Cell Lines (MDA-MB-231)

Main Article Content

Jihan Hameed Abdulameer
https://orcid.org/0000-0003-2850-8458
Mahasin F. Alias
https://orcid.org/0000-0002-3375-1797

Abstract

     New chelating ligand derived from triazole and its complexes with metal ions Rhodium, Platinum and Gold were synthesized. Through a copper (I)-catalyzed click reaction, the ligand produced 1,3-dipolar cycloaddition between 2,6-bis((prop-2-yn-1-yloxy) methyl) pyridine and 1-azidododecane. All structures of these new compounds were rigorously characterized in the solid state using spectroscopic techniques like: 1HNMR, 13CNMR, Uv-Vis, FTIR, metal and elemental analyses, magnetic susceptibility and conductivity measurements at room temperature, it was found that the ligand acts as a penta and tetradentate chelate through N3O2, N2O2, and the geometry of the new complexes are identified as octahedral for (Rh & Pt) complexes and for (Au) complex square planner. The newly prepared compounds were designed and efficiently synthesized to be used to investigation of their toxicity bioassay (in vitro) as anticancer agent towards MDA cell lines. From the results obtained from cytotoxic assay, it can be concluded that the synthesized compounds are promising as new anticancer candidates in future especially in high concentration.

Downloads

Download data is not yet available.

Article Details

How to Cite
1.
Abdulameer JH, Alias MF. Heavy Metal Complexes of 1, 2, 3-Triazole derivative: Synthesis, Characterization, and Cytotoxicity Appraisal Against Breast Cancer Cell Lines (MDA-MB-231). Baghdad Sci.J [Internet]. 2022 Dec. 5 [cited 2023 Jan. 28];19(6(Suppl.):1410. Available from: https://bsj.uobaghdad.edu.iq/index.php/BSJ/article/view/7178
Section
article

References

El Azab IH, El-Sheshtawy HS, Bakr RB, AA Elkanzi N. New 1, 2, 3-triazole-containing hybrids as antitumor candidates: design, click reaction synthesis, DFT calculations, and molecular docking study. Molecules. 2021 Jan; 26(3): 708.

Xu Z, Cheng G, Yang H, Zhang J, Shreeve JN. Synthesis and Characterization of 4‐(1, 2, 4‐Triazole‐5‐yl) furazan Derivatives as High Performance Insensitive Energetic Materials. Chem Eur J. 2018 Jul 20; 24(41): 10488-97.

El Azab IH, Elkanzi NA. An efficient synthetic approach towards Benzo [b] pyrano [2, 3-e][1, 4] diazepines, and their cytotoxic activity. Molecules. 2020 Jan; 25(9): 2051.

Rani P, Lal K, Shrivastava R, Ghule VD. Synthesis and characterization of 1, 2, 3-triazoles-linked urea hybrid sensor for selective sensing of fluoride ion. J Mol Struct.. 2020 Mar 5; 1203: 127437.

Farrer NJ, Griffith DM. Exploiting azide–alkyne click chemistry in the synthesis, tracking and targeting of platinum anticancer complexes. Curr Opin Chem Biol. 2020 Apr 1; 55: 59-68.

El Azab IH, Elkanzi NA, Gobouri AA. Design and Synthesis of Some New Quinoxaline Based Heterocycles. J Heterocycl Chem. 2018 Jan; 55(1): 65-76.

Riddell IA, Lippard SJ. Cisplatin and oxaliplatin: our current understanding of their actions. Met Ions Life Sci. 2018 Feb 5; 18: 1-42.

Kitteringham E, Zhou Z, Twamley B, Griffith DM. Au (III) and Pt (II) complexes of a novel and versatile 1, 4-disubstituted 1, 2, 3-triazole-based ligand possessing diverse secondary and tertiary coordinating groups. Inorg Chem. 2018 Sep 7; 57(19): 12282-90.

Jihan HA, Mahasin FA. Synthesis, Characterization and Antimicrobial Activity of Cu(II), Pt(IV) and Au(III) Complexes with 2,6-bis(((1-decyl-1H-1,2,3- triazole-4-yl)methoxy)methyl)pyridine. Chem Methodol. 2022; 6(3): 184-196.

Al-Radadi NS, Zayed EM, Mohamed GG, Abd El Salam HA. Synthesis, Spectroscopic Characterization, Molecular Docking, and Evaluation of Antibacterial Potential of Transition Metal Complexes Obtained Using Triazole Chelating Ligand. Hindawi. 2020 February 24; 1-12.

Ibrahim AA, Kareem MM, Al-Noor TH, Al-Muhimeed T, AlObaid AA, Albukhaty S, et al. Pt (II)-Thiocarbohydrazone complex as cytotoxic agent and apoptosis inducer in Caov-3 and HT-29 cells through the P53 and Caspase-8 pathways. Pharmaceuticals. 2021 Jun; 14(6): 509.

Yao K, Bertran A, Howarth A, Goicoechea JM, Hare SM, Rees NH, et al. A visible-light photoactivatable di-nuclear Pt IV triazolato azido complex. Chem Comm. 2019; 55(75): 11287-90.

Savaş B, Öztürk T, Meyvacı E, Hazer B. Synthesis and characterization of comb-type graft copolymers by redox polymerization and" click" chemistry method. SN Appl Sci. 2020 Feb; 2(2): 1-8.

Englinger B, Pirker C, Heffeter P, Terenzi A, Kowol CR, Keppler BK, et al. Metal drugs and the anticancer immune response. Chem Rev. 2018 Nov 29; 119(2): 1519-624.

Samarasimhareddy M, Shamir M, Shalev DE, Hurevich M, Friedler A. A rapid and efficient building block approach for click cyclization of peptoids. Front Chem. 2020 May 19; 8: 405-420.

Saeed AA, Jassim AH, Ahmed MF. Determination of the Ratios of Ligands to Metal lon of some Metal Complexes of Triazoles by Using Electronic Spectra in Organic Solvents. Baghdad Sci J. 2004; 1(1): 110-115.

Peng K, Mawamba V, Schulz E, Löhr M, Hagemann C, Schatzschneider U. iClick reactions of square-planar palladium (II) and platinum (II) azido complexes with electron-poor alkynes: metal-dependent preference for N1 vs N2 triazolate coordination and kinetic studies with 1H and 19F NMR spectroscopy. Inorg Chem. 2019 Aug 8; 58(17): 11508-21.

El Malah T, Nour HF, Satti AA, Hemdan BA, El-Sayed WA. Design, synthesis, and antimicrobial activities of 1, 2, 3-triazole glycoside clickamers. Molecules. 2020 Jan; 25(4): 790.

Mohamad HA, AL-Kattan WT, AL-Daly ZM. Synthesis, Characterization and Cytotoxicity of Ni (II), Pd (II), Pt (II) Complexes with 6-Methoxy-2, 3, 4, 5-tetrahydropyridine (MTP). Chemistry. 2020 July 20; 36(5): 903-907.

Burke HM, Gallagher JF, Indelli MT, Vos JG. The synthesis and characterisation of Rh (III) complexes with pyridyl triazole ligands. Inorganica Chim Acta. 2004 Jul 20; 357(10): 2989-3000.

Burke HM, Gallagher JF, Indelli MT, Vos JG. The synthesis and characterisation of Rh (III) complexes with pyridyl triazole ligands. Inorganica Chim Acta. 2004 Jul 20; 357(10): 2989-3000.

Mohamad HA, Al-Kattan WT, Al-Daly ZM. Synthesis, Characterization and Cytotoxicity of Ni (II), Pd (II), Pt (II) Complexes with 6-Methoxy-2, 3, 4, 5-tetrahydropyridine (MTP). Chemistry. 2020 July 20; 36(5): 903-907.

Al-Hamdani AAS, Hamoodah RG. Transition metal complexes with tridentate ligand: preparation, spectroscopic characterization, thermal analysis and structural studies. Baghdad Sci J. 2016; 13(4): 770-781.

Shayma AS, Mohammed HA, Al-Hamdani AAS. Preparation, Physico-Chemical and Spectroscopic Investigation of Thiacetazone and Quinalizarin Complexes with Mn(II), Fe(II), Co(II), Ni(II), Cu(II), Zn(II), Cd(II) and Pb(II). Austr J Basic Appl.Sci. 2010;4(10): 5178-5183.

Zhang Y, Chu CW, Ma W, Takahara A. Functionalization of Metal Surface via Thiol–Ene Click Chemistry: Synthesis, Adsorption Behavior, and Postfunctionalization of a Catechol-and Allyl-Containing Copolymer. ACS Omega. 2020 Mar 26; 5(13): 7488-96.

Kollaschinski M, Sobotta J, Schalk A, Frischmuth T, Graf B, Serdjukow S. Efficient DNA Click Reaction Replaces Enzymatic Ligation. Bioconjug Chem. 2019 Dec 24;31(3):507-12.

Stefanetti G, Allan M, Usera A, Micoli F. Click chemistry compared to thiol chemistry for the synthesis of site-selective glycoconjugate vaccines using CRM197 as carrier protein. Glycoconj J. 2020 Oct; 37(5): 611-22.

Sharmin S, Rahaman M, Martorell M, Sastre-Serra J, Sharifi-Rad J, Butnariu M, et al. Cytotoxicity of synthetic derivatives against breast cancer and multi-drug resistant breast cancer cell lines: a literature-based perspective study. Cancer Cell Int. 2021 Dec; 21(1): 1-9.

AlSaady TA, Madlum KN, Obied HN. Effect of antioxidants on cisplatin-induced cytotoxicity and oxidative stress in colon cancer cells. Eur Asian J Biosci. 2020 Aug 1; 14(2).

Rocha AM, Sousa FS, Borba VM, Munchen TS, Leal JG, Rodrigues OE, et al. Evaluation of the effect of synthetic compounds derived from azidothymidine on MDA-MB-231 type breast cancer cells. Bioorganic Med Chem Lett. 2020 Sep 1; 30(17): 127365.

Liang T, Sun X, Li W, Hou G, Gao F. 1, 2, 3-Triazole-Containing Compounds as Anti–Lung Cancer Agents: Current Developments, Mechanisms of Action, and Structure–Activity Relationship. Front Pharmacol. 2021; 12.

Prasad B, Nayak VL, Srikanth PS, Baig MF, Reddy NS, Babu KS, et al. Synthesis and biological evaluation of 1-benzyl-N-(2-(phenylamino) pyridin-3-yl)-1H-1, 2, 3-triazole-4-carboxamides as antimitotic agents. Bioorganic Chem. 2019 Mar 1; 83: 535-48.