Synthesis, Characterization and Cytotoxic Activity of N-(5-indanyl(methylene)anthranilic acid(5-indanyl methylene)-hydrazide and Its Pt(II) Complex

Main Article Content

Nasser Mohammed Hosny
Lamiaa A. A. Barakat


Since the discovery of the platinum based complex, cisplatin, medicinal inorganic chemistry has attracted much more attention and a large number of platinum complexes with promising pharmacological properties have been synthesized. In this work a new platinum complex of N-(5-indanyl(methylene)anthranilic acid(5-indanyl methylene)-hydrazide (HL) has been synthesized and characterized by physical and spectral techniques, as elemental analysis, IR, EI-MS, 1H-NMR, thermal analysis, transmittance electron microscope (TEM) and magnetic moment. The results indicated that the ligand binds to Pt(II) in the enol form. Square-planar stereochemistry was suggested for the Pt(II) complex. The morphological characterization showed nano-sized spherical particles with average size 92 nm of the isolated complex. The synthesized Pt(II) complex exhibited a significant cytotoxic activity against HCT116 and HEPG2. Also in vivo study of the Pt(II) complex showed cytotoxic activity towards Ehrlich ascites carcinoma (EAC).

Synthesis, Pt(II) complex, cytotoxic activity

Article Details

How to Cite
Hosny, N., & Barakat, L. (2019). Synthesis, Characterization and Cytotoxic Activity of N-(5-indanyl(methylene)anthranilic acid(5-indanyl methylene)-hydrazide and Its Pt(II) Complex. Asian Journal of Research in Biochemistry, 4(3), 1-12.
Original Research Article


Zhukova OS, Dobrynin IV. Current results and perspectives of the use of human tumor cell lines for antitumor drug screening. Voprosy Onkologii. 2001;47:706.

Divsalar A, Zhila I, Saboury AA, Nabiuni M, Razmi M, Mansuri-Torshizi H. Cytotoxic and spectroscopic studies on binding of a new synthesized bipyridine ethyl dithiocarbamate Pt(II) nitrate complex to the milk carrier protein of BLG. Journal of Iranian Chemical Society. 2013;10:951.
DOI: 10.1007/s13738-013-0232-6

Kostova I. Platinum complexes as anticancer agents, Recent Patents on Anti-Cancer Drug Discovery. 2006;1:1.

Grunicke H, Doppler W, Helliger W. Tumor biochemistry as basis for advances in tumor chemotherapy. Archive Geschwulst Forsch. 1986;156:193.

Noordhui P, Laan A, Born K, Losekoot N, Kathmann I, Peters G. Oxaliplatin activity in selected and unselected human ovarian and colorectal cancer cell lines. Biochemical Pharmacology. 2008;76: 53.
DOI: 10.1016/j.bcp.2008.04.007

Sönmez M, Celebi M, Yardim Y, Sentürk Z. Palladium(II) and platinum(II) complexes a symmetric Schiff base derived from 2,6,diformyl-4-methylphenol with N-aminopyrimidine: Synthesis, characterization and detection of DNA interaction by voltammetry. European Journal of Medicinal Chemistry. 2010;45:4215.
DOI: 10.1016/j.ejmech.2010.06.016

Sakurai H, Kojima Y, Yoshikawa Y, Kawabe K, Yasui H. Antidiabetic vanadium(IV) and zinc(II) complexes. Coordination Chemistry Review. 2002;226:187.

Jain A, Jain SK, Ganesh N. Design and development of ligand-appended polysaccharidie nanoparticles for the delivery of oxaliplatin in colorectal cancer, Nanomedicine Nanotechnology Biology and Medicine. 2010;6:179.
DOI: 10.1016/j.nano.2009.03.002

Ehrsson H, Wallin I, Yachnin J. Pharmacokinetics of oxaliplatin in humans. Medical Oncology. 2002;16:261.
DOI: 10.1385/MO:19:4:261

Al-Jibori SA, Al-Jibori GH, Al-Hayaly LJ, Wagner C, Schmidt H, Timur S, Barlas FB, Subasi E, Ghosh S, Hogarth G. Combining anti-cancer drugs with artificial sweeteners: Synthesis and anti-cancer activity of saccharinate (sac) and thiosaccharinate (tsac) complexes cis-[Pt(sac)2(NH3)2] and cis-[Pt(tsac)2(NH3)2]. Journal of Inorganic Biochemistry. 2014;141:55.
DOI: 10.1016/j.jinorgbio.2014.07.017

Tabrizi L, Chiniforoshan H. Cytotoxicity and cellular response mechanisms of water-soluble platinum(II) complexes of lidocaine and phenylcyanamide derivatives. Bio Metals. 2017;30:59.
DOI: 10.1007/s10534-016-9986-5

Wang B, Wang Z, Ai F, Tang WK, Zhu G. A monofunctional platinum(II)-based anticancer agent from a salicylanilide derivative: Synthesis, antiproliferative activity and transcription inhibition. Journal of Inorganic Biochemistry. 2015;142:118.

Wang Q, Yang L, Wu J, Wang H, Song J, Tang X. Four mononuclear platinum(II) complexes: Synthesis, DNA/BSA binding, DNA cleavage and cytotoxicity. BioMetals. 2017;30:17.
DOI: 10.1007/s10534-016-9984-7

Fujio N, Tomoaki F. Substituted naphthyl anthranilic acids. United States Patents, 3989746A; 1976.

Philips S, Rista S, Dominic S, Anne M, Jaames M, David V, Jonathan TW, Heidi B, Susan K, Michael RB. Newcoloremtric cytotoxicity assay for anti-cancer drug screening. Journal of National Cancer Institute. 1990;8:1107.
DOI: 10.1016/j.bcp.2008.04.007

Meier J, Theakston RD. Approximate LD50 determinations of snake venoms using eight to ten experimental animals. Toxicon Journal. 1986;24:395.

Crump KS, Hoel DG, Langley CH, Peto R. Fundamental carcinogenic processes and their implications for low dose risk assessment. Cancer Research. 1976;36:2973.

McLiman WF, Dairs EV, Glover FL, Rake GW. The submerged culture of mammalian cells: The spinner culture. Journal of Immunology. 1957;79:428.

Levesque R. SPSS: Programming and data management: A guide for SPSS and SAS users. Fourth Edition, SPSS INC Chicago III; 2007.

Nakamoto K (ed). Infrared spectra of inorganic and coordination compounds. John Wiley, New York; 1970.

Hosny NM. Cu(II) and Zr(IV) Complexes with (E)-N-(1-(Pyridine-4-yl)ethylidine)nicotinohydrazide. Synth. React. Inorg-Org Met Nano. 2010;6:391.
DOI: 10.1080/15533174.2010.492550

Hosny NM. Synthesis and charcterization of transition metal complexes derived from (E)-(N)-(1-(Pyridine-2-yl)ethylidiene)benzohydrazide (PEBH). Journal Molecular Structure. 2009;923:98.

Hosny NM, Shallaby AM. Spectroscopic characterization of some metal complexes derived from 4-acetylpyridine nicotinoylhydrazone, transition metal chemistry. 2007;32:1085.
DOI: 10.1007/s11243-007-0288-1

Hosny NM, Sherif YE. Synthesis, structural, optical and anti-rheumatic activity of metal complexes derived from (E)-2-amino-N-(1-(2-aminophenyl)ethylidene) benzohydrazide (2-AAB) with Ru(III), Pd(II) and Zr(IV). Spectrochimica Acta A. 2015;136:510.

Hussien MA, Nawar N, Radwan FM, Hosny NM. Spectral characterization, optical band gap calculations and DNA binding of some binuclear Schiff-base metal complexes derived from 2-amino-ethanoic acid and acetylacetone, J. Mol. Struct. 2015;1080:162.

Hosny NM, Hussien MA, Radwan FM, Nawar N. Synthesis, spectral characterization and DNA binding of Schiff-base metal complexes derived from 2-amino-3-hydroxyprobanoic acid and acetylacetone. Spectrochimica Acta A. 2014;132:121.
DOI: 10.1016/j.saa.2014.04.165

Hosny NM. Synthesis, characterization, theoretical calculations and catalase-like activity of mixed ligand complexes derived from alanine and 2-acetylpyridine. Transition Metal Chemistry. 2007;32: 117.
DOI: 10.1007/s11243-006-0132-z

Misbahur Rehman, Imran M, Arif M. Synthesis, Characterization and in vitro Antimicrobial studies of Schiff-bases derived from Acetylacetone and amino acids and their oxovanadium(IV) complexes. American Journal of Applied Chemistry. 2013;1:59.
DOI: 10.11648/j.ajac.20130104.13

Sherif YE, Hosny NM. Synthesis, characterization, and anti-rheumatic potential of phthalazine-1,4-dione and its Cu(II) and Zn(II) complexes. Medicinal Chemistry Research. 2014;23:2536.
DOI: 10.1007/s00044-013-0827-6

Hyperchem, developed by Hypercube Inc; 2002.

Dezső G, Evanics F, Dombi G, Bernáth G. 1H and 13C NMR Chemical shift assignments of a cyclopentane fused cis-azetidinone (cis-azabicyclo[3.2.0]heptan-7-one). Atheoretical and experimental investigation. ARKIVOC III. 2001;73.

Gołębiewski M, Cholewińska M. Synthesis and spectral studies of transition metal complexes of aryloy-lhydrazones of 5- methylsalicylaldehyde, Pestycydy. 2004;1-2:21.

Lever ABP. Inorganic electronic spectroscopy, Elsevier, Amsterdam; 1986.

Soliman AA, Mohamed GG, Hosny WM, El-Mawgood MA. Synthesis, Spectro-scopic and thermal characterization of new sulfasalazine metal complexes. Synth. React. Inorg. Met-Org Nano-Met. Chem. 2005;35:483.
DOI: 10.1081/SIM-200067043

Coats AW, Redfern JP. Kinetic parameters from thermogravimetric. Nature. 1964;201:68.
DOI: 10.1038/201068a0

Hussain J, Chakravrty AR. Photocytotoxic lanthanide complexes. Journal of Chemical Science. 2012;124:1327.

Hosny NM, El Morsy EA, Sherif YE. Synthesis, spectral, optical and anti-inflammatory activity of complexes derived from 2-aminobenzohydrazide with some rare earths. Journal of Rare Earths. 2015;33:758.

Luo LJ, Tao W, Hu XY, Xiao T, Heng BJ, Huang W, Wang H, Han HW, Jiang QK, Wang JB, Tan YW. Mesoporous F-doped ZnO prism arrays with significantly enhanced photovoltaic performance for dye-sensitized solar cells. Journal of Power Sources. 2011;196:10518.

Mohammadikish M. Green synthesis and growth mechanism of new nanomaterial: Zn (salen) nano-complex. Crystal Engineering Communication. 2014;16: 8020.