New luminescent polynuclear metal. complexes with anticancer properties: towards. structure activity relationships
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1 Supporting Information New luminescent polynuclear metal complexes with anticancer properties: towards structure activity relationships Margot Wenzel, a,d Andreia de Almeida, b Emilia Bigaeva, b Paul Kavanagh, c Michel Picquet, d Pierre Le Gendre, d Ewen Bodio,*,d and Angela Casini*,a,b a School of Chemistry, Cardiff University, Main Building, Park Place, CF10 3AT Cardiff, United Kingdom. b Dept. Pharmacokinetics, Toxicology and Targeting, Groningen Research Institute of Pharmacy, University of Groningen, Antonius Deusinglaan 1, 9713 AV Groningen, The Netherlands. c School of Chemistry, National University of Ireland Galway, University Road, Galway, Ireland. d Institut de Chimie Moléculaire de l Université de Bourgogne, UMR 6302 CNRS, Université de Bourgogne-Franche Comté, 9 avenue A. Savary, BP47870, Dijon, France. TABLE OF CONTENTS S-1) Stability of the complexes S-2) Photophysical properties S-3) Cyclic voltammogram of 1D 1
2 S-1) Stability of the complexes The stability of the luminescent bimetallic complexes 1A-PF 6-1D and 2A-2D has been monitored by UV-Visible spectroscopy using the same dilution conditions than the ones used for the cell viability testing, i.e. a dissolution of the complex in DMSO at a concentration of 10-2 M followed by a dilution in PBS to reach a final concentration of 10-4 M. Then, the absorbance of the solution has been measured between 300 and 800 nm at regular time intervals during 48 h at room temperature, allowing the monitoring of eventual processes such as degradation, hydrolysis or precipitation of the complex. Series I: 1A-PF 6 1B 1C 1D Figure S-1. UV-Visible spectra of 1A-PF 6-1D 2
3 Series II: 2A 2B 2C 2D Figure S-2. UV-Visible spectra of 2A-2D To study the stability of the non-luminescent moieties of the complexes, two monometallic complexes have been synthesized as analogs of the complexes in series 2 as recently described by us (8 and 9). 1 Scheme S-1. Synthesis of complexes 8 and 9 The complexes have been dissolved in DMSO-d 6 containing 2% of water and 31 P NMR spectra have been recorded at regular time intervals. 3
4 Time 8 Time 9 t=48 h t=48 h t=1 h t=24 h t=12 h t=6 h t=3 h t=1 h t=0 t=0 δ (ppm) δ (ppm) Figure S P NMR spectra of 8 and 9 over time S-2) Photophysical properties UV-Visible absorption spectra were recorded on a JASCO V630BIO spectrometer. The steady-state fluorescence emission spectra were obtained by using a JASCO FP8560 spectrofluorometer instrument. All fluorescence spectra were corrected for instrument response. The fluorescence quantum yields (Φ F ) were calculated from equation: φ F φ F R = n2 I F 0 2 n R IF R 0 (λ E,λ F )dλ F (λ E,λ F )dλ F 1 10 A R ( λ E ) 1 10 A ( λ E ) Φ F and Φ FR are the fluorescence quantum yields of the compound and the reference respectively. A(λ E ) and A R (λ E ) are the absorbance at the excitation wavelength (460 nm), and n is the refractive index of the medium. I F and I FR are fluorescent intensities of the compound and the reference respectively. Ru(bipyridyl) 3 (Φ F = 0.06 in degassed acetonitrile at 298 K) was used as standard. 2 In all Φ F determinations, correction for the solvent refractive index (η) was applied. 4
5 Table S-1. Photophysical data of the complexes in degassed and dried DMSO at 298 K. Complexes Solvent λ abs (nm) λ em (nm) ε (M -1.cm -1 ) Φ F (%) a B r (M -1.cm -1 ) b Δν (cm -1 ) 2 DMSO A DMSO < B DMSO < C DMSO < D DMSO PF 6 DMSO A-PF 6 DMSO B DMSO C DMSO D DMSO a Reference: Ru(bipy) 3 2+ (Φ F = 0.06 in degassed acetonitrile at 298 K, λ exc = 460 nm). b Brightness = ε.φ F. S-3) Cyclic voltammogram of 1D 5
6 Figure S-4. Cyclic voltammogram of 1D recorded in DMSO containing 0.1 M TBAP at a glassy carbon working electrode (3mm diameter). Scan rate 0.1 V/s. 1. Wenzel, M.; Bigaeva, E.; Richard, P.; Le Gendre, P.; Picquet, M.; Casini, A.; Bodio, E., Journal of Inorganic Biochemistry 2014, 141, Nakamaru, K., Bulletin of the Chemical Society of Japan 1982, 55,
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