Synthesis and Physico-Chemical Characterizations of Novel Hydrazone Ligands and Their Metal Complexes against Hormone-Dependent and Independent Cancers
This work deals with the synthesis and physicochemical characterizations of a new group of novel retinoidal ligands and their metal complexes. Their in vitro anti-proliferative activities have shown that ligand L1 is effective against human breast cancer BT-20 and MCF-7 cell lines. At the same time, compound L2 exerts its effect on human prostate cancer PC-3 and human breast cancer MDA-MB-231 and MCF-7 cell lines respectively. The retinoid ligands exert their pleiotropic action toward retinoic acid receptors (RARs) than their metal complexes but all compounds exhibit concentration-dependent.
References
[1]
Sun, S.Y. and Lotan, R. (2002) Retinoids and Their Receptors in Cancer Development and Chemoprevention. Critical Reviews in Oncology/Hematology, 41, 41-55. https://doi.org/10.1016/s1040-8428(01)00144-5
[2]
Kovacs, J.A.J. and Shear, N.H. (1993) Therapeutic Efficacy of Retinoids. In: Koren, G., Ed., Retinoids in Clinical Pratice: The Risk-Benefit Ratio, CRC Press, New York, 1.
[3]
Tullio, V., Gasperi, V., Catani, M.V. and Savini, I. (2021) The Impact of Whole Grain Intake on Gastrointestinal Tumors: A Focus on Colorectal, Gastric, and Esophageal Cancers. Nutrients, 13, Article 81. https://doi.org/10.3390/nu13010081
[4]
Niles, R.M. (2004) Signaling Pathways in Retinoid Chemoprevention and Treatment of Cancer. Mutation Research, 555, 81-96. https://doi.org/10.1016/j.mrfmmm.2004.05.020
[5]
Jin, Y., Teh, S.S., Lau, H.L.N., Xiao, J. and Mah, S.H. (2022) Retinoids as Anti-Cancer Agents and Their Mechanisms of Action. American of Cancer Research, 12, 938-960.
[6]
Hunsu, V.O., Facey, C.O.B., Fields, J.Z. and Boman, B.M. (2021) Retinoids as Chemo-Preventive and Molecular-Targeted Anti-Cancer Therapies. International Journal of Molecular Sciences, 22, Article 7731. https://doi.org/10.3390/ijms22147731
[7]
Uray, I.P., Dmitrovsky, E. and Brown, P.H. (2016) Retinoids and Rexinoids in Cancer Prevention: From Laboratory to Clinic. Seminars Oncology, 43, 49-64. https://doi.org/10.1053/j.seminoncol.2015.09.002
[8]
Vernia, F., Longo, S., Stefanelli, G., Viscido, A. and Latella, G. (2021) Dietary Factors Modulating Colorectal Carcinogenesis. Nutrients, 13, Article 143. https://doi.org/10.3390/nu13010143
[9]
Altucci, L. and Gronemeyer, H. (2001) The Promise of Retinoids to Fight against Cancer. Nature Reviews, 1, 181-193. https://doi.org/10.1038/35106036
[10]
Sharma, N.K., Dey, S. and Prasad, R. (2007) In vitro Antioxidant Potential Evaluation of Euphorbia hirta L. Pharmacologyonline, 1, 91-98.
[11]
Vyas, A., Patitungkho, S., Jamadar, A., Adsule, S., Padhye, S., Ahmad, A. and Sakar, 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 Communication, 23, 17-20. https://doi.org/10.1016/j.inoche.2012.05.027
[12]
Patitungkho, S., Adsule, S., Dandawate, P., Padhyde, 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
[13]
Patitungkho, S. and Patitungkho, K. (2023) Physicochemical Properties and Biological Activities of Novel Hydrazonate Copper Complexes. Open Journal of Medicinal Chemistry, 13, 1-13. https://doi.org/10.4236/ojmc.2023.131001
[14]
Ambike, V., Adsule, S., Ahmed, F., Wang, Z., Afrasiabi, Z., Sinn, E., Sarkar, F. and Padhyde, 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
[15]
Patitungkho, S., Laeid-On, K. and Patitungkho, K. (2023) Biological Investigation of Nano-Organometallic Agents against Bacteria and Chilo polychrysus. Journal of Agricultural Chemistry and Environmental, 12, 238-249. https://doi.org/10.4236/jacen.2023123018
[16]
Yusuf, T.L., Oladipo, S.D., Zamisa, S., Kumalo, H.M., Lawal, I.A., Lawal, M.M. and Mabuba, N. (2021) Design of New Schiff-Base Copper(II) Complexes: Synthesis, Crystal Structures, DFT Study, and Biding Potency toward Cytochrome P450 3A4. ACS Omega, 6, 13704-13718. https://doi.org/10.1021/acsomega.1c00906
[17]
Dzeikala, A. and Sykula, A. (2018) Schiff Bases as Important Class of Pharmacological Agents. Journal of Pharmacy and Pharmacology, 6, 989-1009. https://doi.org/10.17265/2328-2150/2018.12.002
[18]
Mandal, S. and Bharadwa, P.K. (1992) Hexa-Coordinated Copper(II) Complexes Having CuN2S2*S2 (S*=Thioether) Chromophore: Synthesis, Electrochemistry and Spectroscopy. Polyhedron, 11, 1037-1042. https://doi.org/10.1016/S0277-5387(00)84471-X
[19]
Hitchman, M.A. and Waite, T.D. (1976) Electronic Spectrum of Hexaaquocopper(2) Ion. Inorganic Chemistry, 15, 2150-2154. https://doi.org/10.1021/ic50163a030
[20]
Rao, C.R.K. and Zacharias, P.S. (1997) Synthesis & Magnetic Properties of Dithiooxamide-Bridged Ni(II) Complexes. Polyhedron, 16, 1201-1209. https://doi.org/10.1016/S0277-5387(96)00364-6
[21]
Ramesh, G.N., Prathima, B., Rao, Y.S., Reddy, Y.P., Pai, K.S.R. and Reddy, A.V. (2016) Synthesis, Spectroscopic and Anti-Tumor Studies on Copper(II) Complex of Orthohydroxypropiophenoneisonicoti Noylhydrazone. Arabian Journal of Chemistry, 9, S404-S410. http://dx.doi.org/10.1016/j.arabjc.2011.05.008
[22]
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
[25]
West, D.X., Ives, J.S., Bain, G.A., Liberta, A.E., Valdės-Martinez, J., Ebert, K.H. and Hernandez-Ortega, S. (1997) Copper(II) and Nickel(II) Complexes of 2,3-Butanedione Bis(N(3)-Substituted Thiosemicarbazone). Polyhedron, 16, 1895-1905. https://doi.org/10.1016/S0277-5387(96)00468-8
[26]
Krishna, P.M., Reddy, K.H., Pandey, J.P. and Siddavattam, D. (2008) Synthsis, Characterization, DNA Binding and Nuclease Activity of Binuclear Copper(II) Complexes of Cuminaldehyde Thiosemicarbazones. Transition Metal Chemistry, 33, 661-668. https://doi.org/10.1007/s11243-008-90947
[27]
Minner, E., Lovy, D. and Bill, H. (1993) Electron Paramagnetic Resonance and Relaxation Study of Copper(II) and Silver(II) in CsCdF3 Single Crystals. Journal of Chemical Physics, 99, 6378-6383. https://doi.org/10.1063/1.465876
[28]
Patole, J., Dutta, S., Padhye, S. and Sinn, E. (2001) Tuning up Superoxide Dismutase Activity of Copper Complex of Salicylaldehyde Semicarbazone by Heterocyclic Bases Pyridine and N-Methy Limidazole. Inorganica Chimica Acta, 318, 207-211. https://doi.org/10.1016/S0020-1693(01)00416-9
[29]
Prabhu, A., Shanker, K., Muthukrishna, P. and Kathiresan, A. (2016) Electrochemical Studies of Biosynthesized Silver Nanoparticles by Using Setaria Verticillate Plant. Journal of Advanced Chemical Sciences, 2, 302-304.
[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-Flu-orophenyl)Imino]Methyl}Phenol Metal (II) Complexes. Journal of Chemistry, 2020, Article ID: 1745236. https://doi.org/10.1155/2020/1745236
[31]
Azieana, J., Zainon, M.N., Noriham, A. and Rohana, M.N. (2017) Total Phenolic and Flavonoid Content and Antioxidant Activities of Ten Malaysian Wild Mushrooms. Open Access Library Journal, 4, e3987. https://doi.org/10.4236/oalib.1103987
[32]
Hong, W.K. and Sporn, M.B. (1997) Recent Advances in Chemoprevention of Cancer. Science, 278, 1073-1077. https://doi.org/10.1126/science.278.5340.1073
[33]
Zasada, M. and Budzisz, E. (2019) Retinoids: Active Molecules Influencing Skin Structure Formation in Cosmetic and Dermatological Treatments. Advances in Dermatology and Allergology, 36, 392-397. https://doi.org/10.5114/ada.2019.87443
[34]
Fontana, J.A. and Rishi, A.K. (2002) Classical and Novel Retinoids: Their Targets in Cancer Therapy. Leukemia, 16, 463-472. https://doi.org/10.1038/sj.leu.2402414
[35]
Kuroda, Y., Miyazaki, R., Shimonishi, D., Nakane, D. and Akitsu, T. (2023) Coordination and Photoisomerization of Azobenzene-Amino Acid Schiff Base Copper(II) Complexes to Lysozyme. Journal of Material Science Chemical Engineering, 11, 34-44. https://doi.org/10.4236/msce.2023.113003
[36]
Lisic, E., Grossarth, S., Bowman, S., Hill, J., Beck, M., Deweese, J. and Jiang, X. 2022) New Copper(II), Palladium(II), and Platinum(II) 2-Acetylpyrazine Tert-Bu-tylthiosemicarbazone Complexes: Inhibition of Human Topoisomerase IIα and Activity against Breast Cancer Cells. Open Journal of Medicinal Chemistry, 12, 1-13. https://doi.org/10.4236/ojmc.2023.121001
