The objective of this research was to elucidate the
biological effect of novel compounds derived from natural product of
syringaldehyde through novelsemi-synthetic method in order to investigate the physicochemical
properties and biological activities by using DPPH and FRAP techniques and its
antibacterial
activities against Klebsiella spp., Pseudomonas aeruginosa, Bacillus
cereus, and Staphylococcus aureus. Moreover, to examine its ability
against breast cancer cell line (MCF-7). The results showed that the
syringaldehyde hydrazonate copper complexes possessed the covalent bonds with
square-planar structure. In terms of antioxidant DPPH activities, it was found
that syringaldehyde hydrazone possessed high potency against DPPH free
radicals, with respect to syringaldehyde hydrazonate copper complexes. On the
other hand, all compounds possessed low reducing properties for changing Fe3+ to Fe2+ in FRAP technique. For antibacterial activitiesrevealed that the ligand L1 and L5 possessed high effect onPseudomonas
aeruginosa, but for all copper complexes possessed high potent
antibacterial susceptibility to four bacteria with concentration dependence. For anti-breast cancer cell line (MCF-7), it
was found that all compounds possessed high potent anticancer susceptibility with low IC50, especially, compound exhibit highly potency effective
is C5 (IC50 9.75 μM). The tendency of anticancer effect from
high to low was C5 > C2 > C1 > C4 > C3.
Therefore, all synthetic compounds obtained from the present research possibly
develop as the antibacterial drugs and the drugs for curing the diseases caused
by free radicals, including breast cancer in metastatic phase. The most
important feature of these drugs was the high specificity to the target and
harmless to the normal cells.
References
[1]
Carpenter, D.O. and Bushkin-Bedient, S. (2013) Exposure to Chemicals and Radiation during Childhood and Risk for Cancer Later in Life. Journal of Adolescent Health, 52, S21-S29. https://doi.org/10.1016/j.jadohealth.2013.01.027
[2]
Sugimura, T. (2000) Nutrition and Dietary Carcinogens. Carcinogenesis, 21, 387-395. https://doi.org/10.1093/carcin/21.3.387
[3]
Molina-Montes, E., Ubago-Guisada, E., Petrova, D., Amiano, P., Chirlaque, M.-D., Agudo, A. and Sánchez, M.-J. (2021) The Role of Diet, Alcohol, BMI and Physical Activity in Cancer Mortality: Summary Findings of the EPIC Study. Nutrients, 13, Article 4293. https://doi.org/10.3390/nu13124293
[4]
Basu, A.K. (2018) DNA Damage, Mutagenesis and Cancer. International Journal of Molecular Sciences, 19, Article 970. https://doi.org/10.3390/ijms19040970
[5]
Datta, N., Chakraborty, S., Basu, M. and Ghosh, M.K. (2020) Tumer Suppressors having Oncogenic Functions: The Double Agents. Cells, 10, Article 46. https://doi.org/10.3390/cells10010046
[6]
Barrios, C.H. (2022) Global Challenges in Breast Cancer Detection and Treatment. The Breast, 62, S3-S6. https://doi.org/10.1016/j.breast.2022.02.003
[7]
Brierley, J., O’Sullivan, B., Asamura, H., Burd, D., Huang, S.H., Lee, A., Piñeros, M., Mason, M., Moraes, F.Y., Rösler, W., Rous, B., Torode, J., Krieken, J.H.V. and Gospodarowicz, M. (2019) Global Consultation on Cancer Staging: Promoting Consistent Understanding and Use. Nature Reviews Clinical Oncology, 16, 763-771. https://doi.org/10.1038/s41571-019-0253-x
[8]
Pourrahmat, M.-M., Kim, A., Kansal, A.R., Hux, M., Pushkarna, D., Fazeli, M.S. and Chung, K.C. (2021) Health State Utility Values by Cancer Stage: A Systematic Literature Review. European Journal of Health Economics, 22, 1275-1288. https://doi.org/10.1007/s10198-021-01335-8
[9]
Riggio, A.I., Varley, K.E. and Welm, A.L. (2021) The Lingering Mysteries of Metastatic Recurrence in Breast Cancer. British Journal of Cancer, 124, 13-26. https://doi.org/10.1038/s41416-020-01161-4
[10]
Tilsed, C.M., Fisher, S.A., Nowak, A.K., Lake, R.A. and Lesterhuis, W.J. (2022) Cancer Chemotherapy: Insights into Cellular and Tumor Microenvironmental Mechanisms of Action. Frontiers in Oncology, 12, Article 960317. https://doi.org/10.3389/fonc.2022.960317
[11]
Schirrmacher, V. (2019) From Chemotherapy to Biological Therapy: A Review of Novel Concept to Reduce the Side Effects of Systemic cancer Treatment. International Journal of Oncology, 54, 407-419. https://doi.org/10.3892/ijo.2018.4661
[12]
Housman, G., Byler, S., Heerboth, S., Lapinska, K., Longacre, M., Snyder, N. and Sarkar, S. (2014) Drug Resistance in Cancer: An Overview. Cancers, 6, 1769-1792. https://doi.org/10.3390/cancers6031769
[13]
Baker, R.E., Mahmud, A.S., Miller, I.F., Rajeev, M., Rasambainarivo, F., Rice, B.L., Takahashi, S., Tatem, A.J., Wagner, C.E., Wang, L.-F., Wesolowski, A. and Metcalf, C.J.E. (2022) Infectious Disease in an Era Global Change. Nature Reviews, 20, 193-205. https://doi.org/10.1038/s41579-021-00639-z
[14]
Lee, A.S., Lencastre, H.D., Garau, J., Kluytmans, J., Malhotra-Kumar, S., Peschel, A. and Harbarth, S. (2018) Methicillin-Resistant Staphylococcus aureus. Nature Reviews, 4, Article No. 18033. https://doi.org/10.1038/nrdp.2018.33
[15]
Sharma, N.K., Dey, S. and Prasad, R. (2007) In Vitro Antioxidant Potential Evaluation of Euphorbia hirta L. pharmacologyonline, 1, 91-98.
[16]
Melha, K.A. (2008) Antimicrobial, Spectral, Magnetic and Thermal Studies of Cu(II), Ni(II), Co(II), UO2(VI) and Fe(III) Complexes of the Schiff Base Derived from Oxalylhydrazide. Journal of Enzyme Inhibition and Medicinal Chemistry, 23, 285-295. https://doi.org/10.1080/14756360701448073
[17]
Vyas, A., Patitungkho, S., Jamadar, A., Adsule, S., Padhye, S., Ahmad, A. and Sarkar, F.H. (2012) ATRA-Hydrazonate Derivatives and Their Copper Complexes against Hormone-Dependent (MCF-7), Hormone-Independent (MDA-MB-231 and BT-20) Breast Cancer and Androgen-Independent (PC3) Prostate Cancer Cell lines. Inorganic Chemistry Communications, 23, 17-20. https://doi.org/10.1016/j.inoche.2012.05.027
[18]
Patitungkho, S., Adsule, S., Dandawate, P., Padhye, S., Ahmad, A. and Sarkar, F.H. (2011) Synthesis, Characterization and Anti-Tumor Activity of Moxifloxacin-Copper Complexes against Breast Cancer Cell Lines. Bioorganic Medicinal Chemistry Letters, 21, 1802-1806. https://doi.org/10.1016/j.bmcl.2011.01.061
[19]
Chaviara, A.T., Cox, P.J., Repana, K.H., Pantazaki, A.A., Papazisis, K.T., Kortsaris, A.H., Kyriakidis, D.A., Nikolov, G.S. and Bolos, C.A. (2005) The Unexpected Formation of Biologically Active Cu(II) Schiff Mono-Base Complexes with 2-Thiophene-Carboxaldehyde and Dipropylenetriamine: Crystal and Molecular Structure of CudptaSCl2. Journal of Inorganic Biochemistry. 99, 467-476. https://doi.org/10.1016/j.jinorgbio.2004.10.026
[20]
Nawar, N. and Hosney, N.M. (2000) Synthesis, Spectral and Antimicrobial Activity Studies of o-Aminoacetophenone o-Hydroxybenzoylhydrazone Complexes. Transition Metal Chemistry, 25, 1-8. https://doi.org/10.1023/A:1007080122211
[21]
Nakamoto, K. (2009) Infrared and Raman Spectra of Inorganic and Coordination Compounds Part A: Theory and Applications in Inorganic Chemistry. 6th Edition, John Wiley & Sons, New Jersey. https://doi.org/10.1002/9780470405840
Hathaway, B.J. and Billing, D.E. (1970) The Electronic Properties and Stereochemistry of Mono-Nuclear Complexes of the Copper(II) Ion. Coordination Chemistry Reviews, 5, 143-207. https://doi.org/10.1016/S0010-8545(00)80135-6
[24]
Kivelson, D. and Neiman, R. (1961) ESR Studies on the Bonding in Copper Complexes. The Journal of Chemical Physics, 35, 149-155. https://doi.org/10.1063/1.1731880
[25]
Yallur, B.C., Krishna, P.M. and Challa, M. (2021) Bivalent Ni(II), Co(II) and Cu(II) Complexes of [(E)-[(2-Methyl-1,3-Thiazol-5-yl)Methylidene]Amino]Thiourea: Synthesis, Spectral Characterization, DNA and in Vitro Anti-Bacterial Studies. Heliyon, 7, e06838. https://doi.org/10.1016/j.heliyon.2021.e06838
[26]
Salama, Z.A., Baz, F.K.E., Gaafar, A.A. and Zaki, M.F. (2015) Antioxidant Activities of Phenolics, Flavonoids and Vitamin C in Two Cultivars of Fennel (Foeniculum vulgare Mill.) in Responses to Organic and Bio-Organic Fertilizers. Journal of the Saudi Society of Agriculture Sciences, 14, 91-99. https://doi.org/10.1016/j.jssas.2013.10.004
[27]
Azieana, J., Zainon, M.N., Noriham, A. and Rohana, M.N. (2017) Total Phenolic and Flavonoid Content and Antioxidant Activities of Ten Malasian Wild Mushrooms. Open Access Library, 4, e3987. https://doi.org/10.4236/oalib.1103987
[28]
Ghasemzadeh, A., Jaafar, H.Z.E. and Rahmat, A. (2010) Antioxidant Activities, Total Phenolics and Flavonoids Content in Two Varieties of Malasia Young Ginger (Zingiber officinale Roscoe). Molecules, 15, 4324-4333. https://doi.org/10.3390/molecules15064324
[29]
Christodoulou, M.C., Palacios, J.C.O., Hesami, G., Jafarzadeh, S., Lorenzo, J.M., Domìnguez, R., Moreno, A. and Hadidi, M. (2022) Spectrophotometric Methods for Measurement of Antioxidant Activity in Food and Pharmaceuticals. Antioxidants, 11, Article 2213. https://doi.org/10.3390/antiox11112213
[30]
Ommenya, F.K., Nyawade, E.A., Andala, D.M. and Kinyua, J. (2020) Synthesis, Characterization and Antibacterial Activity of Schiff Base, 4-Chloro-2-{E-[(4-Fluorophenyl)Imino]Methyl}Phenol Metal (II) Complexes. Journal of Chemistry, 2020, Article ID: 1745236. https://doi.org/10.1155/2020/1745236
[31]
Zambre, A., Kulkarni, V.M., Padhye, S., Sandur, S.K. and Aggarwal, B.B. (2006) Novel Curcumin Analogs Targeting TNF-Induced NF-κB Activation and Proliferation in Human Leukemic KBM-5 Cells. Bioorganic Medicinal Chemistry, 14, 7196-7204. https://doi.org/10.1016/j.bmc.2006.06.056
[32]
Ambike, V., Adsule, S., Ahmed, F., Wang, Z., Afrasiabi, Z., Sinn, E., Sarkar, F. and Padhye, S. (2007) Copper Conjugates of Nimsulide Schiff Bases Targeting VEGF, COX and Bcl-2 in Pancreatic Cancer Cells. Journal of Inorganic Biochemistry, 101, 1517-1524. https://doi.org/10.1016/j.jinorgbio.2007.06.028