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Complexes Coded As DH4 and DH5 in Human Ovarian Tumour Models

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Complexes Coded As DH4 and DH5 in Human Ovarian Tumour Models ANTICANCER RESEARCH 32: 5331-5336 (2012) Studies on the Activity of Two Trans-Planaramine Platinum(II) Complexes Coded as DH4 and DH5 in Human Ovarian Tumour Models NARJES DEQNAH1, JUN Q. YU1, PHILIP BEALE2 and FAZLUL HUQ1 1Discipline of Biomedical Science, Sydney Medical School, The University of Sydney, Sydney, Australia; 2Sydney Cancer Centre, Concord Hospital, Concord, Australia; 3School of Chemistry, The University of Sydney, Sydney, Australia Abstract. In this article, we report the synthesis and the in vitro synthesized a number of trans-planaramine platinum(II) activity of trans-bis(2-methylimidazole)dichloroplatinum(II) complexes with in vitro activity in ovarian tumour models, (coded as DH4) and trans-(ammino)(2,3-diaminopyridine) similar to or better than that of cisplatin (1, 2). We report dichloroplatinum(II) (coded as DH5) in the human ovarian here the synthesis, characterization, cytotoxic activity, cell tumour models. DH4 is less active than cisplatin against the uptake, and DNA binding of trans-dichlorobis(2- parental A2780 cell line but more active than cisplatin against methylimidazol)platinum(II) (coded as DH4) and trans- the resistant A2780cisR cell line, thus indicating that it is better dichloro(ammine)(2,3-diaminopyridine)platinum(II) (coded able to overcome mechanisms of resistance operating in the as DH5) (Figure 1). A2780cisR line. In contrast, DH5 is less active than cisplatin against all three cell lines. The higher activity of DH4 than Materials and Methods cisplatin in the A2780cisR cell line is in line with the associated higher platinum−DNA binding level. Whereas cisplatin binds Potassium tetrachloroplatinate (K2PtCl4), N,N-dimethylformamide (DMF), 2-methylimidazole and 2,3-diaminopyridine were obtained with DNA, forming mainly intrastrand 1,2-Pt(GG) and 1,2- from Sigma Chemical Company, St. Louis, Mo, USA; hydrochloric Pt(AG) adducts, DH4 and DH5 are expected to form more 1,2- acid was obtained from Asia Pacific Specialty Chemicals Ltd., interstrand Pt(GG) and monofunctional adducts. The results of (NSW, Australia); acetone and silver nitrate from Ajax Chemicals, interaction with pBR322 plasmid DNA combined with BamH1 (Auburn, NSW, Australia); silver acetate from Sigma Chemical digestion show that DH4 and DH5 are less able to prevent Company, Germany and charcoal from Sigma Aldrich Chemical BamH1 digestion than cisplatin, indicating that cisplatin causes Company (Milwaukee, WI, USA); 200 mM L-glutamine, 5.6% a greater conformational change in the DNA than do DH4 and sodium bicarbonate, foetal calf serum (FCS), RPMI-1640 from Trace Biosciences Pty Ltd. Australia; other chemicals were obtained DH5, although DH5 is more damaging to DNA. The difference from Sigma-Aldrich, Sydney, Australia. A2780, A2780CisR and in the activity of DH4 and DH5, with 2-methylimidazole and 2,3- A2780ZD0473R ovarian cancer cell lines were gifts from Ms. Mei diaminopyridine respectively as carrier ligands, can be seen to Zhang, Royal Prince Alfred Hospital, Sydney, Australia. Stock illustrate structure−activity relationships. solutions of platinum compounds (1 mM) were prepared in 1:1 DMF and milli Q water mixture. Currently much attention is given to platinum compounds that bind with DNA differently from cisplatin, with the idea Synthesis. Cisplatin: Cisplatin required for the synthesis of DH4 and DH5, and also used as a reference was prepared according to the that the difference in nature of binding with DNA may modified Dhara method (3). Briefly, to one millimol of translate into an altered spectrum of activity. We have tetrachloroplatinate dissolved in 5 ml of milli-Q water was added potassium iodide (4.12 mmol) dissolved in 1 ml of mQ water. The mixture left on a shaking water bath, at 37˚C, for 5 min, produced K2PtI4 which then reacted with 2 mmol of aqueous ammonia at Correspondence to: Fazlul Huq, Discipline of Biomedical Science, 37˚C for 1 h. The dark-yellow precipitate of cis-Pt(NH3)2I2 was School of Medical Sciences, Sydney Medical School, The washed with ice-cold water and ethanol and air dried. Silver nitrate University of Sydney, Cumberland Campus C42, 75 East Street, (2 mmol) and cis-Pt(NH3)2I2 (1 mmol) were mixed together Lidcombe, NSW 1825, Australia. Tel: +61 293519522, Fax: +61 followed by the addition of 4 ml of mQ water. The mixture was left 293519520, e-mail: [email protected] on a shaking water-bath at 37˚C for 30 min to produce cis- Pt(NH3)2(NO3)2 and solid silver iodide. The mixture was Key Words: Cisplatin, platinum−DNA binding, apoptosis, ovarian centrifuged. The supernatant consisting of cis-Pt(NH3)2(NO3)2 in cancer, drug resistance, pBR322 plasmid. solution was collected. Potassium chloride (0.11 g, 1.5 mmol) was 0250-7005/2012 $2.00+.40 5331 ANTICANCER RESEARCH 32: 5331-5336 (2012) Figure 1. Structures of DH4 (a) and DH5 (b). added to the filtrate. The mixture was left on a water bath at 37˚C Molar Conductivity: The limiting molar conductivity value (in –1 2 –1 for 30 min for crystals of cisplatin to form. ohm cm mol ) at zero concentration (Λ0) for DH4, DH5 and DH4: Although synthesis of DH4 was reported earlier (4), no cisplatin are 254, 470 and 304 respectively, indicating that the work on the activity of the compound has been performed. Briefly degree of ionization is slightly less than that of cisplatin, but that of the method of synthesis was as follows: 1 mmol (0.415 g) of DH5 is much greater than that of cisplatin. potassium tetrachloroplatinate was dissolved in 4 ml of mQ water Spectral studies: Infrared, mass and 1H (NMR) spectra were to which 0.25 ml of concentrated hydrochloric acid were added. The used to aid in the structural characterization of DH4 and DH5. solution was heated to 50˚C. 10 mmol (0.82 g) of 2- methylimidazole, dissolved in 2 ml of DMF, were slowly added to IR (KBr). IR spectrum was collected using a Bruker IFS66 the solution of potassium tetracholoroplatinate. The temperature of spectrometer equipped with a Spectra-Tech Diffuse Reflectance the solution was increased to 65˚C and maintained at that Accessory (DRA) (Bruker Australia Pty Ltd Bruker Sydney NSW temperature for 1 h while the solution was stirred. The volume of Australia), an air-cooled DTGS detector and a KBr beam splitter. the solution was reduced to about 5 ml, following which 40 ml of 6 Spectrum was recorded at a resolution of 4 cm–1, with the addition M hydrochloric acid were added and the mixture was heated under of 128 scans and a Blackman-Harris 3-term apodization function reflux for 24 h at 90˚C. The mixture was cooled to room was applied. The peaks listed below can be seen to provide support temperature, resulting in the formation of dark-purple precipitate of for the suggested structures of DH4 and DH5. DH4, which was collected by filtration, giving a yield of 35%. DH4: 3367.4 and 3121.8.4 cm–1: N-H stretch; 1621.5 and DH5: From the reaction of 1 mmol (0.3 g) of cisplatin with 1426.3 cm–1: C=N stretch; 1283.7 cm–1: imidazole ring stretch; 2 mmol (0.218 g) of 2,3-diaminopyridine, synthesis of 1 mmol of 539.4 cm-1: Pt−N stretch. trans-dichloro(ammino)(2,3-diaminopyridine)platinum(II) was DH5: 3307 and 3121.8.4 cm–1: N-H stretch; 1623.5 and 1584.1 attempted, giving a yield of 45%. The method of synthesis was as cm–1: C=N and C=C stretch; 1222.4 cm–1: ring stretch; 449.4 cm-1: follows: Cisplatin (0.300 g, 1 mmol) was added to 8 ml of milli-Q Pt−N stretch. water. 2,3-Diaminopyridine (0.218 g, 2 mmol), dissolved in 2 ml Mass: The mass spectrum of DH3 was obtained using a Finnigan of DMF, was added to the cisplatin suspension. The mixture was LCQ ion trap mass spectrometer (Thermo Scientific Massachusetts heated under reflux for 1 h at 70˚C to cause 2,3-diaminopyridine USA) in which fragmentation was produced by electrospray ligand to replace chloro-ligands. The mixture was cooled to room ionization (EIS). temperature to stop the reaction. Concentrated hydrochloric acid MH4: (EIS-MS) (milli Q water) (m/z: M=428). The peak at (1.22 ml, 12.2 mmol) was added to the mixture, followed by m/z=427 corresponds to (M–H)). heating to 70˚C under reflux, to produce dark-black crystals of MH5: (EIS-MS) (milli Q water) (m/z: M=392). The peak at DH5. The crystals of DH5 formed were collected by filtration, m/z=316 corresponds to (Pt (C5H7N3)(NH3)–5H). washed with ice-cold water and ice-cold ethanol, and air dried, giving a yield of 45%. 1H-NMR. 1H-NMR spectra of DH4 and DH5 dissolved in DMSO were recorded in a Bruker DPX400 spectrometer (Bruker Australia Characterization. Microanalyses: Pt was determined by graphite Pty Ltd Sydney NSW Australia) using a 5mm high precision furnace atomic absorption spectroscopy (AAS) using a Varian Wilmad NMR tube. Spectra-20 Atomic Absorption Spectrophotometer. C, H, N, and Cl DH4: 1H-NMR DMSO δ ppm: 12.42 (d, due to CH); 11.34 (d, were determined at the Australian National University. due to CH); 6.66 (s, due to CH3); 5.70 (s, due to NH); 4.63 (s, due DH4: Calc.% C: 22.4; H: 2.4, N: 13.1; Cl: 16.6; Pt: 45.6; Obs.%: to NH-Pt); 2.50 (due to DMSO). C: 22.3±0.4, H: 2.8±0.4, N: 13.1±0.4, Cl: 16.4±0.4, Pt: 45.2±1.0.
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