Open Access
Issue
Published:
26 February 2020
Anti-Proliferative Activity and Tubulin Targeting of Novel Micro and Nanoparticles Complexes of 4-Amino-3-Thion-1, 2, 4-Triazole Derivatives
),
Download citation
621
Views
81
Downloads
7
Crossref
N/A
WoS
6
Scopus
N/A
CSCD
In this study, novel micro and nanoparticle complexes of Ag(Ⅰ), Ni(Ⅱ), and Pd(Ⅱ) ion with new asymmetrical Schiff base triazole ligand (4-(((3-mercapto-5-(naphthalen-1-ylmethyl)-4H-1, 2, 4-triazol-4-yl)imino)methyl)phenol) were prepared. The Schiff base micro complexes were identified using Fourier-transform infrared spectroscopy (FTIR), Ultraviolet–visible spectroscopy (UV-Vis), flame atomic absorption, elemental analysis C.H.N.S, conductivity measurements and magnetic susceptibility. New nanoparticles Schiff base triazole ligand (4-(((3-mercapto-5-(naphthalen-1-ylmethyl)-4H-1, 2, 4-triazol-4-yl)imino)methyl)phenol) ligand and Ag(Ⅰ), Ni(Ⅱ) and Pd(Ⅱ) complexes were synthesized as a novel compounds by using sonication method, and were fully characterized by using FTIR, atomic force microscopy (AFM), scanning electron microscope (SEM), and X-ray powder diffraction (XRD). The antioxidant activity of tested compounds was tested using DPPH assay. The effect of synthetic novel compounds on cancer cell line MCF-7 proliferation was measured by MTT assay. The ability of synthetic novel compounds in induction of apotosis was achieved using acridine orange/ethidium bromide (AO/EB) stains. We found that the synthetic novel compounds had the potential to inhibit growth of cancer cell at low concentrations. The effect of synthetic compounds on cell growth and proliferation of MCF-7 cells was associated with cell cycle arrest, and increased apoptosis. Our results showed that the synthetic novel compounds inhibited cancer cell line proliferation with a mechanism of action similar to that of other tubulin inhibitors. In conclusion, the results of this study indicate that synthetic novel compounds represent a new chemo type with a novel mechanisms of action and that it has the potential to be developed for tumor therapy.
menu
Anti-Proliferative Activity and Tubulin Targeting of Novel Micro and Nanoparticles Complexes of 4-Amino-3-Thion-1, 2, 4-Triazole Derivatives
),
Abstract
In this study, novel micro and nanoparticle complexes of Ag(Ⅰ), Ni(Ⅱ), and Pd(Ⅱ) ion with new asymmetrical Schiff base triazole ligand (4-(((3-mercapto-5-(naphthalen-1-ylmethyl)-4H-1, 2, 4-triazol-4-yl)imino)methyl)phenol) were prepared. The Schiff base micro complexes were identified using Fourier-transform infrared spectroscopy (FTIR), Ultraviolet–visible spectroscopy (UV-Vis), flame atomic absorption, elemental analysis C.H.N.S, conductivity measurements and magnetic susceptibility. New nanoparticles Schiff base triazole ligand (4-(((3-mercapto-5-(naphthalen-1-ylmethyl)-4H-1, 2, 4-triazol-4-yl)imino)methyl)phenol) ligand and Ag(Ⅰ), Ni(Ⅱ) and Pd(Ⅱ) complexes were synthesized as a novel compounds by using sonication method, and were fully characterized by using FTIR, atomic force microscopy (AFM), scanning electron microscope (SEM), and X-ray powder diffraction (XRD). The antioxidant activity of tested compounds was tested using DPPH assay. The effect of synthetic novel compounds on cancer cell line MCF-7 proliferation was measured by MTT assay. The ability of synthetic novel compounds in induction of apotosis was achieved using acridine orange/ethidium bromide (AO/EB) stains. We found that the synthetic novel compounds had the potential to inhibit growth of cancer cell at low concentrations. The effect of synthetic compounds on cell growth and proliferation of MCF-7 cells was associated with cell cycle arrest, and increased apoptosis. Our results showed that the synthetic novel compounds inhibited cancer cell line proliferation with a mechanism of action similar to that of other tubulin inhibitors. In conclusion, the results of this study indicate that synthetic novel compounds represent a new chemo type with a novel mechanisms of action and that it has the potential to be developed for tumor therapy.
References(36)
N. Seelam, S.P. Shrivastava., S. Prasanthi, et al., Synthesis and in vitro study of some fused 1, 2, 4-triazole derivatives as antimycobacterial agents. Journal of Saudi Chemical Society, 2016, 20(4): 411-418.
C. Tratrat, M. Haroun, A. Paparisva, et al., Design, synthesis and biological evaluation of new substituted 5-benzylideno-2-adamantylthiazol[3, 2-b][1, 2, 4] triazol-6 (5H) ones. Pharmacophore models for antifungal activity. Arabian Journal of Chemistry, 2018, 11(4): 573-590.
C. Kuş, G. Ayhan-Kılcıgil, S. Özbey, et al., Synthesis and antioxidant properties of novel N-methyl-1, 3, 4-thiadiazol-2-amine and 4-methyl-2H-1, 2, 4-triazole-3 (4H)-thione derivatives of benzimidazole class. Bioorganic & Medicinal Chemistry, 2008, 16(8), 4294-4303.
Ali, A.A., & Al-Abdali, B. I. (2015). Synthesis and characterization of 4-(((3-mercapto-5-phenyl-4H-1, 2, 4-triazole-4-yl) imino) methyl)-2-methoxyphenol and its complexes with Zr (Ⅳ), Cd (Ⅱ) and Sn (Ⅱ) ions. Iraqi Journal of Science, 56(2B), 1274-1288.
Singh, A.K., & Kandel, K.R. (2012). Synthesis of Triazole derivative: [4-(benzylideneamino)-5-phenyl-4H-1, 2, 4-triazole-3-thiol]. Journal of Nepal Chemical Society, 30, 174-177.
Bekircan, O., & Bektas, H. (2006). Synthesis of new bis-1, 2, 4-triazole derivatives. Molecules , 11(6), 469-477.
Wu, Q., Yang, Z., Nie, Y., Shi, Y., & Fan, D. (2014). Multi-drug resistance in cancer chemotherapeutics: mechanisms and lab approaches. Cancer letters, 347(2), 159-166.
Ślusarczyk, S., Hajnos, M., Skalicka-Woźniak, K., & Matkowski, A. (2009). Antioxidant activity of polyphenols from Lycopuslucidus Turcz. Food Chemistry, 113(1), 134-138.
N. Karal, Ö. Güzel, N. Özsoy, et al., Synthesis of new spiroindolinones incorporating a benzothiazole moiety as antioxidant agents. European Journal of Medicinal Chemistry, 2010, 45(3): 1068-1077.
F. Bray, J. Ferlay, I. Soerjomataram, et al., Global cancer statistics 2018: GLOBOCAN estimates of incidence and mortality worldwide for 36 cancers in 185 countries. CA Cancer J Clin, 2018, 68: 394-424.
A. Schrofel, G. Kratosova, I. Safarik, et al., Applications of biosynthesized metallic nanoparticles - A re-view. Acta Biomaterialia, 2014, 10: 4023-4042.
J. Zhou, D. Wu, and D. Guo, Optimization of the production of thiocarbohydrazide using the Taguchi method. Journal of Chemical Technology & Biotechnology, 2010, 85(10): 1402-1406.
A.Y. Hassan, Synthesis and reactions of new fused heterocycles derived from 5-substituted-4-amino-3-mercapto-(4H)-1, 2, 4-triazole with biological interest. Phosphorus, Sulfur, and Silicon, 2009, 184(11): 2759-2776.
Z. Li, Z. Gu, K. Yin, et al., Synthesis of substituted-phenyl-1, 2, 4-triazol-3-thione analogues with modified d-glucopyranosyl residues and their antiproliferative activities. European Journal of Medicinal Chemistry, 2009, 44(11): 4716-4720.
M.S. Jabir, A.A. Taha, and U.I. Sahib, Linalool loaded on glutathione-modified gold nanoparticles: a drug delivery system for a successful antimicrobial therapy. Artif. Cells, Nanomedicine Biotechnol, 2018.
S.H. Ali, G.M. Sulaiman, M.M. Al-Halbosiy, et al., Fabrication of hesperidin nanoparticles loaded by poly lactic co-Glycolic acid for improved therapeutic efficiency and cytotoxicity. Artificial Cells, Nanomedicine, and Biotechnology, 2019, 47(1): 378-394.
H.A. Kadhem, S.A. Ibraheem, M.S. Jabir, et al., Zinc oxide nanoparticles induces apoptosis in human breast cancer cells via Caspase-8 and P53 pathway, Nano Biomed. Eng. , 2019, 1: 35-43.
I. Alsaedi, Z.J. Taqi, A Hussien, et al., Graphene nanoparticles induces apoptosis in MCF-7 cells through mitochondrial damage and NF-KB pathway. Materials Research Express, 2019, 6: 095413.
K.S. Khashan, M.S. Jabir, and F.A. Abdulameer, Carbon nanoparticles decorated with cupric oxide Nanoparticles prepared by laser ablation in liquid as an antibacterial therapeutic agent. Materials Research Express, 2018, 5(3): 035003.
W.K. Kadhim, U.M. Nayef, and M.S. Jabir, Polyethylene glycol-functionalized magnetic (Fe3O4) nanoparticles: a good method for a successful antibacterial therapeutic agent via damage DNA molecule. Surface Review and Letters, 2019: 1950079.
M.S. Jabir, U.M. Nayef, W.K. Abdulkadhim, et al., Supermagnetic Fe3O4-PEG nanoparticles combined with NIR laser and alternating magnetic field as potent anti-cancer agent against human ovarian cancer cells. Materials Research Express, 2019, 6: 115412.
M.S. Jabir, U.M. Nayef, and W.K.A. Kadhim, Polyethylene glycol-functionalized magnetic (Fe3O4) nanoparticles: a novel DNA-mediated antibacterial agent. Nano Biomedicine & Engineering, 2019, 11(1): 18-27.
E. Palaska, G. Şahin, P. Kelicen, et al., Synthesis and anti-inflammatory of 1-acylthiosemicarbazide, 1, 3, 4-oxadiazoles, 1, 3, 4-thiadiazoles and 1, 2, 4-triazole-3-thiones. Il Farmaco, 2002, 57(2): 101-107.
J. Singh, P. Singh, Synthesis, spectroscopic characterization, and in vitro antimicrobial studies of pyridine-2-carboxylic acid N'-(4-chloro-benzoyl)-hydrazide and its Co (Ⅱ), Ni (Ⅱ), and Cu (Ⅱ) complexes. Bioinorganic Chemistry and Applications, 2012.
G.B. Bagihalli, P.G. Avaji, S.A. Patil, et al., Synthesis, spectral characterization, in vitro antibacterial, antifungal and cytotoxic activities of Co (Ⅱ), Ni (Ⅱ) and Cu (Ⅱ) complexes with 1, 2, 4-triazole Schiff bases. European Journal of Medicinal Chemistry, 2008, 43(12): 2639-2649.
T.R. Rao, A. Prasad, Synthesis and spectral studies on 3 D metal complexes of mesogenic Schiff base ligands. Part 1. Complexes of N-(4-butylphenyl) salicylaldimine. Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry, 2005, 35(4): 299-304.
R.E. de Paiva, C. Abbehausen, A.F. Gomes, et al., Synthesis, spectroscopic characterization, DFT studies and antibacterial assays of a novel silver (Ⅰ) complex with the anti-inflammatory nimesulide. Polyhedron, 2012, 36(1): 112-119.
Y.N. Zhang, H. Wang, J.Q. Liu, et al., Novel silver (Ⅰ) compounds assembled from hybrid ligands based on linear or T-shaped coordination environment. Inorganic Chemistry Communications, 2009, 12(7): 611-614.
M. Haga, E.S. Dodsworth, A.B.P. Lever, et al., Synthesis, characterization, and charge distribution of bis (4-tert-butylpyridine) bis (3, 5-di-tert-butylquinone) ruthenium. Journal of the American Chemical Society, 1986, 108(23): 7413-7414.
R.A. Saleh, H.A. Mohammad, T.I. Gerber, et al., Synthesis and characterization of mono and mixed ligand, Ni (Ⅱ), Pd (Ⅱ) and Pt (Ⅱ) complexes of S-5-phenyl-1, 3, 4-oxadiazole-2-yl benzothioate with some tertiary diphosphines ligands. AIP Conference Proceedings, 2017, 1888(1): 020047.
M. Koparır, A. Çetin, and A. Cansız, 5-Furan-2yl[1, 3, 4] oxadiazole-2-thiol, 5-furan-2yl-4H[1, 2, 4] triazole-3-thiol and their thiol-thione tautomerism. Molecules, 2005, 10(2): 475-480.
S. Amer, N. El-Wakiel, and H. El-Ghamry, Synthesis, spectral, antitumor and antimicrobial studies on Cu (Ⅱ) complexes of purine and triazole Schiff base derivatives. Journal of Molecular Structure, 2013, 1049: 326-335.
A.K. Singh, O.P. Pandey, and S.K. Sengupta, Synthesis, spectral characterization and biological activity of zinc (Ⅱ) complexes with 3-substituted phenyl-4-amino-5-hydrazino-1, 2, 4-triazole Schiff bases. SpectrochimicaActa Part A: Molecular and Biomolecular Spectroscopy, 2012, 85(1): 1-6.
S.F. Barbuceanu, G. Saramet, G.L. Almajan, et al., New heterocyclic compounds from 1, 2, 4-triazole and 1, 3, 4-thiadiazole class bearing diphenylsulfone moieties. Synthesis, characterization and antimicrobial activity evaluation. European Journal of Medicinal Chemistry, 2012, 49: 417-423.
R.M. Silverstein, G.C. Bassler, and D.J. Kiemle, Spectrometric identification of organic compounds, 7th ed. John Wiley and Sons, 2005.
Publication history
Copyright
Rights and permissions
This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.
FEEDBACK 
TOP