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Supporting Information of the Manuscript Synthesis, Antiproliferative Activity and DNA Binding Studies of Nucleoamino Acid-Conta

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Supporting Information of the Manuscript Synthesis, Antiproliferative Activity and DNA Binding Studies of Nucleoamino Acid-Conta Supporting Information of the manuscript Synthesis, antiproliferative activity and DNA binding studies of nucleoamino acid-containing Pt(II) complexes Claudia Riccardi,a§ Domenica Capasso,b§ Angela Coppola,a Chiara Platella,a Daniela Montesarchio,a Sonia Di Gaetano,c Giovanni N. Roviello,c Domenica Musumecia,c,* a Department of Chemical Sciences, University of Napoli Federico II, 80126, Napoli, Italy; b CESTEV, University of Naples Federico II, 80145 Naples, Italy; c CNR, Institute of Biostructure and Bioimaging, 80134 Napoli, Italy *Correspondence to: Domenica Musumeci, Department of Chemical Sciences, University of Napoli Federico II, Via Cintia, 21, I-80126 Napoli, Italy E-mail address: [email protected] Phone: +39-081-674143; § These authors contributed equally to this work Figure S1: DAP(T)-OH MS characterization. MALDI-TOF mass spectrum of 4 using α-cyano-4- hydroxycinnamic acid (CHCA) as matrix (up); ESI mass spectrum from LC-ESI-MS analysis of 4 dissolved in H2O/CH3CN (9:1, v/v), injected on a ZORBAX C18 column (1.8 μm, 50 x 4.6 mm) and eluted as follows: 5 min isocratic elution with 10% CH3CN in H2O (0.05 % TFA), then gradient to 95 % CH3CN in 10 min. TIC chromatogram of 4 is reported in the inset (tR = 3.7 min) (bottom). 1 13 Figure S2: H- (400 MHz) and C-NMR (100 MHz) spectra of DAP(T)-OH in D2O. 1 13 Figure S3: H- (500 MHz) and C-NMR (125 MHz) spectra of DAP(T)-OH in DMSO-d6. a) X10 7 +ESI TIC Scan Frag=175,0V 2 Pt complex recovered in CH3OH 1,8 1,6 t = 0 1,4 1,2 1 0,8 0,6 0,4 0,5 1 1,5 2,0 2,5 3 3,5 4 4,5 5 5,5 6 6,5 7 7,5 8 8,5 9 9,5 10 Counts vs. Acquisition Time (min) b) 7 X10 +ESI TIC Scan Frag=175,0V 2 Pt complex recovered in CH OH B 3 1,8 A A 1,6 t = 10 min 1,4 1,2 1 C 0,8 0,6 0,4 0,5 1 1,5 2 2,5 3 3,5 4 4,5 5 5,5 6 6,5 7 7,5 8 8,5 9 9,5 10 Counts vs. Acquisition Time (min) B C Figure S4: a),b) LC-ESI-MS analysis of the methanol-recovered Pt complex, dissolved in H2O/CH3CN (9:1, v/v), injected on a ZORBAX C18 column (1.8 μm, 50 x 4.6 mm) and eluted as follows: 3 min isocratic elution with 5 % CH3CN in H2O, then gradient to 50 % CH3CN in 10 min. a) Pt complex immediately injected (t = 0) after its dissolution (single peak at tR = 0.89 min); b) Pt complex injected 10 min after its dissolution (three peaks at tR = 0.81, 1.01, 1.50 min). a) 7 7 x10 x10 +ESI TIC 1,8 +ESI TIC 2,4 Scan Frag=175,0V Scan Frag=175,0V T1 1,6 T2 2 0,943 min 1,4 0,842 min 1,6 1,2 1,2 1 0,8 0,8 0,4 0,6 0 0,4 0,5 1 1,5 2 2,5 3 3,5 4 4,5 5 5,5 6 6,5 7 7,5 8 8,5 9 9,5 10 1 2 3 4 5 6 7 8 9 10 Counts vs. Acquisition Time (min) Counts vs. Acquisition Time (min) +ESI Scan +ESI Scan (0,842 min) (0,943 min) T1 T2 [DAP(T)-O ─ + Pt2+ ─ 2+ + DMSO + Cl ─] = M [DAP(T)-O + Pt + DMSO + Cl ─] = M Counts vs. Acquisition Time (min) Counts vs. Acquisition Time (min) b) Figure S5: a) LC-ESI-MS analysis of T1 (left) and T2 (right) complexes dissolved in H2O/CH3CN (9:1, v/v), injected on a ZORBAX C18 column (1.8 μm, 50 x 4.6 mm) and eluted as follows: 3 min isocratic elution with 10 % CH3CN in H2O, then gradient to 95 % CH3CN in 10 min (tR = 0.94 and 0.84 min, for T1 and T2, respectively); b) Comparison between theoretical and experimental mass isotope distribution of the peak at 579 m/z corresponding to the [M-H]+ species of the complex T1. 1 13 Figure S6: H- (400 MHz) and C-NMR (125 MHz) spectra of T1 in DMSO-d6. Enlargements of selected areas are also reported. 1 Figure S7: H-NMR spectrum (400 MHz) of T2 in DMSO-d6. 13 Figure S8: C-NMR (100 MHz) spectrum of T2 in DMSO-d6. Table S1: Direct 1H 13C correlations based on the observed cross peaks in the bidimensional HSQC spectra of DAP(T)-OH, T1 and T2. Table S2: 1H 1H correlations based on the observed cross peaks in the bidimensional COSY spectra of DAP(T)-OH, T1 and T2. Table S3: Long range 1H 13C correlations based on the observed cross peaks in the bidimensional HMBC spectra of T1 and T2. Table S4: 1H 1H correlations based on the observed cross peaks in the bidimensional NOESY spectra of T1 and T2 (the red arrow indicates the correlation useful to discriminate the relative position of the DMSO and chloride ligands in T2). Figure S9: Enlargement of the NOESY spectrum (400 MHz) of T2 in DMSO-d6. Figure S10: Energy-minimized three dimensional structure of T1 {isomeric SMILES CC1C(=O)N([H])C(=O)N(CC(N([H])CC2C(=O)O[Pt+2](Cl)(S(=O)(C)C)N2([H])[H])=O)C=1}: 3D structure images (random low energy conformers) realized by MOLVIEW (http://molview.org). Light blue dashed arrows highlighted the spatial proximity of the corresponding protons, as also experimentally evidenced in the NOESY spectra (Table S4). Figure S11: Energy-minimized three dimensional structure of T2 (up) {isomeric SMILES CC1=CN(CC(=O)N(CC2N([H])([H])[Pt+2](Cl)(S(C)(C)=O)OC2=O)[H])C(=O)N([H])C1=O}: 3D structure images (random low energy conformers) realized by MOLVIEW (http://molview.org). Light blue dashed arrows highlighted the spatial proximity of the corresponding protons, as also experimentally evidenced in the NOESY spectra (see Table S4). Final structures of T1 and T2 and hypothesized ones for their initially-formed precursors, the methanol- and water-recovered Pt complexes (bottom). 1 1 DAP(T)-OH in PBS 1x 268 80 µM t = 0 0.5 h Abs 1 h Abs 2 h 0 0.3 240 260 280 300 320 240 250 260 270 280 290 Wavelength [nm] Wavelength [nm] Figure S12: UV-vis spectra of DAP(T)-OH in PBS monitored over time (for clarity, only the overlapped spectra of the first 2 h monitoring were shown). Figure S13: a,b) UV-vis spectra of T1 in PBS at 80 μM concentration recorded over time, up to 48 h. c) Overlapped UV-vis spectra of T1 immediately after its dissolution in PBS and after 48 h (black and red lines, respectively). Figure S14: a,b) UV-vis spectra of T2 in PBS at 80 μM concentration recorded over time, up to 48 h. c) Overlapped UV-vis spectra of T2 immediately after its dissolution in PBS and after 48 h (black and red lines, respectively). 1H-NMR of T2 in DMSO-d + 10% D O at 48 h a) 6 2 Pt) - CH3-5 5 A d H2O - (DMSO 3 CH DMSO 3 Free DMSO 6 E NH-C NH2-Pt (G1, G2) D1 D2 1 Figure S15: H-NMR spectra (400 MHz) of T2 a) in DMSO-d6, 48 h after the addition of 10% D2O and b) 96 h after its dissolution in D2O. 100 80 signal 60 40 20 0 % free DMSO DMSO NMR % free 0 10 20 30 40 50 60 70 80 90 100 110 Time (h) 1 Figure S16: H-NMR-time course experiments on T1 and T2 dissolved in D2O. The % of the free DMSO NMR signal, compared to that of CH3-5, was reported as a function of the time (h) after platinum complexes dissolution. Figure S17: Comparison of HeLa, WM266, MCF-7 and HDF cell viability incubated with CDDP or T2 at 25 μM concentration at 37 °C for 48 h. Cell viability was measured by using the MTT assay. The results are presented as the percentage of living cells with respect to the control (vehicle-treated cells) and are expressed as means ± SE of at least three independent experiments performed in triplicate. a) b) 8 4 4 ] ] 2 0 mdeg mdeg -4 CD[ 0 CD[ ds27 duplex ODN1 ss -8 -2 240 260 280 300 320 240 260 280 300 320 c) 10 d) 8 ] ] 5 4 mdeg mdeg 0 CD[ CD[ 0 dsGG duplex -5 tel26 G4 240 260 280 300 320 240 260 280 300 320 Wavelength [nm] Wavelength [nm] Figure S18: CD spectra of (a) the single strand ODN1, (b) the hairpin duplex ds27, (c) the hairpin duplex dsGG, and (d) the G-quadruplex tel26. All the sequences were analysed at a 2 μM concentration in 100 mM KCl, 7 mM Na2HPO4/NaH2PO4, pH = 7.2, 20 °C (optical path = 1 cm). a) b) 9 0.4 T1 5 ] T2 ] 0.2 0 0 mdeg mdeg T1 ds27 -5 T2 dsGG CD[ -0.2 CD[ ODN1 tel26 -0.4 -11 240 260 280 300 320 240 260 280 300 320 Wavelength [nm] Wavelength [nm] Figure S19: Overlapped CD spectra of T1 and T2 at 20 μM concentration in 100 mM KCl, 7 mM Na2HPO4/NaH2PO4, pH = 7.2, at 20 °C, (a) alone or (b) in comparison with the indicated DNA systems, each at 2 μM concentration (optical path = 1 cm).
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