Hydrosulfide adducts of organo-iridium anticancer complexes
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1 Hydrosulfide adducts of organo-iridium anticancer complexes Pavel Štarha, Abraha Habtemariam, Isolda Romero-Canelo n, Guy J. Clarkson, Peter J. Sadler*, Regional Centre of Advanced Technologies and Materials, Department of Inorganic Chemistry, Faculty of Science, Palacký University, 17. listopadu 12, Olomouc, Czech Republic Department of Chemistry, University of Warwick, Gibbet Hill Road, Coventry CV4 7AL, U.K. Supporting Information Synthesis of [(η 5 -Cp biph )Ir(phen)Cl]Cl and [(η 5 -Cp biph )Ir(bpy)Cl]Cl Tables S1 and S2 Figures S1 S12 S1
2 Synthesis [(η 5 -Cp biph )Ir(phen)Cl]Cl and [(η 5 -Cp biph )Ir(bpy)Cl]Cl Solutions of [(η 5 -Cp biph )IrCl 2 ] 2 (53.7 mg, 0.05 mmol) and 1,10-phenanthroline (21.6 mg, 0.12 mmol) or 2,2`-bipyridine (18.7 mg, 0.12 mmol) in 10 ml of methanol were heated for 1 min at 373 K in a microwave synthesizer. They were filtered and their volume was reduced to ca. 2 ml on a rotary evaporator. After cooling to ambient temperature, diethyl ether was added until light yellow precipitate formed. The products were collected by filtration, washed with diethyl ether and dried under vacuum (30 min). [(η 5 -Cp biph )Ir(phen)Cl]Cl: Yield: 65 mg (79%). 1 H NMR (400 MHz, DMSO-d 6 ): δ = 9.12 (d, 2H, J HH = 5.3 Hz), 8.99 (d, 2H, J HH = 8.3 Hz), 8.39 (s, 2H), 8.19 (dd, 2H, J HH = 8.2, 5.4 Hz), 7.83 (d, 2H, J HH = 8.0 Hz), 7.77 (d, 2H, J HH = 7.5 Hz), 7.66 (d, 2H, J HH = 8.3 Hz), 7.51 (t, 2H, J HH = 7.5 Hz), 7.42 (t, 1H, J HH = 7.5 Hz), 1.85 (s, 6H), 1.77 (s, 6H). [(η 5 -Cp biph )Ir(bpy)Cl]Cl: Yield: 58 mg (73%). 1 H NMR (400 MHz, DMSO-d 6 ): δ = 8.85 (d, 2H, J HH = 8.3 Hz), 8.75 (d, 2H, J HH = 5.8 Hz), 8.36 (t, 2H, J HH = 7.8 Hz), 7.84 (m, 4H), 7.77 (d, 2H, J HH = 7.5 Hz), 7.60 (d, 2H, J HH = 8.3 Hz), 7.50 (m, 2H), 7.42 (m, 1H), 1.78 (s, 6H), 1.72 (s, 6H). S2
3 Table S1. Crystal data and structure refinements for (η 5 -Cp*)Ir(phen)(SH)]BPh 4 (1`) Empirical formula C 46 H 44 BIrN 2 S Formula weight Temperature (K) 150(2) Crystal size (mm) Wavelength (Å) Crystal system, space group Triclinic, P-1 Unit cell dimensions a (Å) (2) b (Å) (3) c (Å) (4) α ( ) (2) β ( ) (2) γ ( ) (2) V (Å 3 ) (12) Z, D calc (g cm 3 ) 4, Absorption coefficient (mm 1 ) F (000) 1728 θ range for data collection ( ) θ Reflections collected/unique /21878 R int, R sigma , Final R indices [I>2σ(I)] R 1 = R indices (all data) wr 2 = Goodnes-of-fit S3
4 Table S2. Selected bond lengths (Å) and angles ( ) of (η 5 -Cp*)Ir(phen)(SH)]BPh 4 (1`) determined by a single-crystal X-ray analysis. Data are given for disordered (η 5 -Cp*)Ir(phen)(SH)] + cation found in the asymmetric unit of 1` (i.e. cation involving Ir2 and Ir2A atoms) Bond lengths (Å) Bond angles ( ) Ir N 2.107(7) / 2.28(3) N Ir N 76.6(3) / 70.1(12) 2.130(10) / 1.98(3) N Ir Cg 132.2(2) / 137.1(9) Ir C a 2.213(10) / 2.08(2) 131.6(2) / 123.6(8) 2.183(11) / 2.15(2) N Ir S 84.1(2) / 83.6(9) 2.150(12) / 2.10(2) 88.7(3) / 85.4(7) 2.181(12) / 1.99(2) S Ir Cg (8) / 133.6(2) 2.213(10) / 1.975(11) Ir Cg b (8) / 1.664(5) Ir S 2.384(3) / 2.428(5) a ) aromatic carbon atoms of Cp*ring b ) Cg = centroid of Cp* aromatic ring S4
5 Figure S1. ESI-MS monitoring of the synthesis of 1: variation of the reaction time. A = { (η 5 -Cp*)Ir(phen)] H} + (m/z = 507.2), B = (η 5 -Cp*)Ir(phen)(OH)] + (m/z = 525.2), C = (η 5 -Cp*)Ir(phen)(OCH 3 )] + (m/z = 539.2), (η 5 -Cp*)Ir(phen)(SH)] + (m/z = 541.1), (η 5 -Cp*)Ir(phen)(Cl)] + (m/z = 543.1) and D = (η 5 -Cp*)Ir(phen)(OTf)] + (m/z = 657.1). S5
6 Figure S2. ESI-MS monitoring of the synthesis of 1: variation of the molar ratio of the starting compounds (η 5 -Cp*)Ir(phen)Cl]Cl and NaSH xh 2 O (0.5, 1.0, 1.5 and 2.0 mol equiv). (a) shows (η 5 -Cp*)Ir(phen)Cl]Cl activated by AgOTf. A = (η 5 -Cp*)Ir(phen)(SH)] + (m/z = 541.1) and B = (η 5 -Cp*)Ir(phen)(OTf)] + (m/z = 657.1). S6
7 Figure S3. 1 H NMR spectra of the starting complex (η 5 -Cp*)Ir(bpy)Cl]Cl dissolved in DMSO-d 6 (A), the crude product (2*) dissolved in DMSO-d 6 (B) and CDCl 3 (C), and the final product, (η 5 - Cp*)Ir(bpy)(SH)]PF 6 (2), dissolved in DMSO-d 6 (D). S7
8 Figure S4. 1 H NMR spectra of (η 5 -Cp*)Ir(phen)(SH)]PF 6 (1; A), (η 5 -Cp*)Ir(bpy)(SH)]PF 6 (2; B), (η 5 -Cp biph )Ir(phen)(SH)]PF 6 (3; C), (η 5 -Cp biph )Ir(bpy)(SH)]PF 6 (4; D) dissolved in DMSO-d 6. S8
9 Figure S5. ESI-MS of (η 5 -Cp*)Ir(phen)(SH)]PF 6 (1; A), (η 5 -Cp*)Ir(bpy)(SH)]PF 6 (2; B), (η 5 - Cp biph )Ir(phen)(SH)]PF 6 (3; C), (η 5 -Cp biph )Ir(bpy)(SH)]PF 6 (4; D) dissolved in methanol, recorded in the m/z range. Insets: comparison of the experimental (gray lines) and simulated (red triangles) isotopic distribution of the (η 5 -Cp x )Ir(N^N)(SH)] + species. S9
10 Intens. x10 4 +MS, min #( ) x C 22 H 24 Ir N 2 S, m/z Figure S6. Experimental (up) and simulated (down) high resolution MS of (η 5 - Cp*)Ir(phen)(SH)]PF 6 (1A) dissolved in methanol. S10
11 Figure S7. RP-HPLC chromatograms for (η 5 -Cp*)Ir(phen)(SH)]PF 6 (1; A), (η 5 - Cp*)Ir(bpy)(SH)]PF 6 (2; B), (η 5 -Cp biph )Ir(phen)(SH)]PF 6 (3; C) and (η 5 -Cp biph )Ir(bpy)(SH)]PF 6 (4; D) given together with ESI-MS of the individual HPLC peaks for 1. S11
12 Figure S8. ESI-MS for (η 5 -Cp*)Ir(phen)(SH)]PF 6 (1) dissolved in H 2 O/MeCN (top) and in H 2 O/MeCN with addition of 0.1% Htfa (bottom) S12
13 Figure S9. Part of the x-ray crystal structure showing both [(η 5 -Cp*)Ir(phen)(SH)]BPh 4 molecules in the asymmetric unit of 1` and disorder of the [(η 5 -Cp*)Ir(phen)(SH)] + cation containing the Ir2 atom. S13
14 Figure S10. π-π stacking in the x-ray crystal structure of 1 between two adjacent phen ligands with a centroid centroid distance of Å; symmetry code: i) 2-x, 2-y, 1-z. S14
15 Figure S11. 1 H NMR spectra recorded at different times at 293 K for 0.5 mm complexes (η 5 - Cp*)Ir(phen)(SH)]PF 6 (1; left) and (η 5 -Cp*)Ir(bpy)(SH)]PF 6 (2; right) dissolved in 20% MeOD/80% D 2 O. 4 mol equiv of NaCl were added after 48 h (orange rectangle). S15
16 Figure S12. ESI-MS spectra of (η 5 -Cp biph )Ir(phen)(SH)]PF 6 (3) mixed with reduced glutathione (GSH) in 20% MeOH/80% H 2 O. A - fresh solution; B - after 48 h of standing at ambient temperature. GSH - red squares, GSSG - blue squares, (η 5 -Cp biph )Ir(phen)(SH)] + peaks - green squares. S16
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