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- Ἑρμοκράτης Κορνάρος
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1 Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2014 Supplementary Information A contribution to the rational design of Ru(CO) 3 Cl 2 L complexes for in vivo delivery of CO João D. Seixas, a,b Marino F. A. Santos, c Abhik Mukhopadhyay, c Ana C. Coelho, a, Patrícia M. Reis, a Luís F. Veiros, d Ana R. Marques, b Nuno Penacho, b Ana M. L. Gonçalves, b Maria J. Romão, c Gonçalo J. L. Bernardes,,b Teresa Santos-Silva*,c and Carlos C. Romão* a,b a Instituto de Tecnologia Química e Biológica-António Xavier da Universidade Nova de Lisboa, Av. da República, EAN, Oeiras, Portugal. b Alfama Ltd., Instituto de Biologia Experimental e Tecnológica, IBET, Av. da República, EAN, Oeiras, Portugal. c UCIBIO@REQUIMTE, Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa, Caparica, Portugal. d Centro de Química Estrutural, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, 1049 Lisboa, Portugal. Table of Contents Contents FTIR spectra CORM-2 in d6-dmso HPLC traces LC-(ESI)-MS data NO inhibition assay on RAW264.7 cells Atomic coordinates for all optimized molecules Page S2-S7 S9-S11 S12-S15 S16-S19 S20 S22-S27 S1
2 FTIR spectrum of RuCl 2 (CO) 2 (DMSO) 2 (4a + 4b) in KBr pellet S2
3 1017 cm -1 : SO FTIR spectrum of RuCl2(CO)3(L-(CH3SO(CH2)2CH(NH2)CO2H) (6a) in KBr pellet. FTIR spectrum of RuCl2(CO)3(D,L-(CH3SO(CH2)2CH(NH2)CO2H) (6b) in KBr pellet. S3
4 FTIR spectrum of RuCl2(CO)3(4-NC5H4(CH2)2SO3Na) (8) in KBr pellet S4
5 FTIR spectrum of RuCl2(CO)3(PTA) (9) in KBr pellet. FTIR spectrum of RuCl2(CO)3(DAPTA) (10) in KBr pellet. S5
6 FTIR spectrum of RuCl2(CO)3(CH3S(CH2)2CH(OH)CO2H) (11) in KBr pellet. % Transmittance FTIR spectrum of Ru(CO)3Cl2(CNCMe2CO2Me) (12) in KBr pellet. S6
7 FTIR spectrum of Ru(CO)3Cl2(CNCMeEtCO2Me) (13) in KBr pellet. % Transmittance FTIR spectrum of Ru(CO)3Cl2(CNC(CH2CH2)CO2Me) (14) in KBr pellet. S7
8 S8
9 Figure S1. Time evolution of 13C NMR spectrum of CORM-2 in d6-dmso, at room temperature, in the carbonyl region at t=0; t=1h; t=18h; t=25h; t=42h. Each spectrum was acquired over 29min, except t=1h that was acquired over 3h. At the time of dissolution 3 resonances are observed, two at δ and ppm from the tricarbonyl fac-rucl2(dmso)(co)3 (1) and one peak at δ ppm from RuCl2(DMSO)2(CO)2 (2a). After 1h three isomers of dicarbonyl species are observed and an unknown peak is observed at δ ppm. Later in time, after 18h, species 1 and 2a concentrations decreased and 2b isomer increased in solution. This tendency results in the formation of dicarbonyl isomers with the cis,trans,cis- RuCl2(DMSO)2(CO)2 as the main species after 42h. S9
10 Figure S2. Time evolution of 13C NMR spectrum of fac-rucl2(dmso)(co)3 (1) in d6- DMSO, showing the formation of RuCl2(DMSO)2(CO)2 (2). Each spectrum was acquired over 29 min, at room temperature, in the carbonyl region at t=0; t=6h; t=19h; t=25h; t=4 days. At the time of dissolution 1 has 2 resonances at δ and δ ppm in a 1:2 ratio, corresponding to the tricarbonyl compound and later while 4 new resonances from the dicarbonyl species 2 appeared at δ and ppm (2b; cis,cis,cis- RuCl2DMSO)2(CO)2) and ppm (2a; cis,trans,cis- RuCl2(DMSO)2(CO)2). The resonance at δ ppm cannot be clearly assigned to any species. After 19h the tricarbonyl compound 1 was already totally converted into dicarbonyl species 2. After 4 days in solution only the 2a and 2b isomers are present in solution and a new peak at δ ppm is observed, from a newly formed species. S10
11 Figure S3. Time evolution of 1 H NMR spectrum of CORM-2 in d 6 -DMSO, showing the changes in the water chemical shift from δ 4.24 ppm (t=0) to δ 4.26 ppm (t=3h); δ 4.16 ppm (t=7h) and 3.96 ppm (t=24h). S11
12 Figure S4: HPLC traces of CORM-2 (ALF420). Initial concentration 1 mg/ml in Me2CO. Column: Nucleosil C18 5µm 150mmx4,6mm Supelco (Z226173). Elution gradient 10%MeOH/H2O 1ml/min. Top: Initial chromatogram (t = 0). Bottom: Chromatogram at t = 60 min. Right table: AUC along time for the three earlier peaks. S12
13 3 1 3 ALF450 5 tim e (m in) 1 RT= 5.55 % m ax 2 RT= RT= Figure S5. HPLC traces of (5). Initial concentration 1 mg/ml in Me2CO. Column: Nucleosil C18 5µm 150mmx4,6mm Supelco (Z226173). Elution gradient 10%MeOH/H2O 1mL/min. Top: Initial chromatogram (t = 0). Bottom: Chromatogram at t = 60 min. Right table: relative values of AUC in % of maximum area along time. S13
14 Figure S6. HPLC traces of 4. Initial concentration: 1 mg/ml in 10%DMSO/H2O. Column: Nucleosil C18 5µm 150mmx4,6mm Supelco (Z226173). Elution gradient 10%MeOH/H2O 1mL/min. 2 acetone A LF452 3 Peak - A U C (2 3 6 n m ) tim e (m in) RT= 2.58 RT= 2.96 RT= 3.49 RT= Figure S7. HPLC traces of 3. Initial concentration: 1 mg/ml in 10%DMSO/H2O. Column: Nucleosil C18 5µm 150mmx4,6mm Supelco (Z226173). Elution gradient 10%MeOH/H2O 1mL/min S14
15 2 1 6b A LF tim e (m in ) P e a k - A U C (2 3 6 n m ) 1 2 RT= 2.97 RT= Figure S8. HPLC traces of (6b). Initial concentration: 1 mg/ml in 10%DMSO/H2O. Column: Nucleosil C18 5µm 150mmx4,6mm Supelco (Z226173). Elution gradient 10%MeOH/H2O 1mL/ min Figure S9. HPLC traces of 10. Initial concentration: 1 mg/ml in 10%DMSO/H2O. Column: Nucleosil C18 5µm 150mmx4,6mm Supelco (Z226173). Elution gradient 10%MeOH/H2O 1mL/min S15
16 Figure S10. Mass spectrum in positive ion mode of the fraction corresponding to the HPLC peak of (3) with Retention Time min. S16
17 Figure S11. Mass spectrum in positive ion mode of the fraction corresponding to the HPLC peak of 6b with Retention Time min. S17
18 Figure S12. Mass spectrum in negative ion mode of the fraction corresponding to the HPLC peak of 6b with Retention Time min. Figure S13. Mass spectrum in negative ion mode of the fraction corresponding to the HPLC peak of 6b with Retention Time min. S18
19 Figure S13. Mass spectrum in negative ion mode of the fraction corresponding to the HPLC peak of 6b with Retention Time min. S19
20 LPS CORM-2 6b LPS Figure S14. Inhibition of NO induced by LPS in RAW264.7 macrophages upon treatment with different doses of [Ru II CO)3] based CORMs. S20
21
22 Atomic coordinates for all the optimized molecules fac-[rucl 2 (CO) 3 (Me 2 SO)] Ru Cl S O C H Cl O C H O C H O C H C H H fac-[rucl 2 (CO) 3 (Me 2 SO)] Ru C S Cl O H C Cl O H C O H C O H C H H A Ru C O H H N O O C H N O H C C C C H C H H Cl H H Cl S22
23 O TS AB Ru C O H H N O O C H N O H C C C C H C H H Cl H H Cl O B Ru C O H H N O O C H N O H C C C C H C H H Cl H H Cl O C Ru H N O O C H H N O S23
24 H C C C C C H O C H H Cl H H Cl O TS CD Ru H N O O C H H N O H C C C C C H O C H H Cl H H Cl O D Ru H N O O C H H N O H C C C C C H O C H H Cl H H S24
25 Cl O TS DE Ru H N O O C H H N O H C C C C C H O C H H Cl H H Cl O E Ru H N O O C H H N O H C C C C C H O C H H Cl H H Cl O F Ru N C N O H C H C S25
26 C H C C H O O H H O H H O H H H H G Ru N C N O H C H C C H O C H H C H H O H H O O H H H H Ru N O N H H C H C C H C C H O O H H C H H O H S26
27 H O H I Ru N C N O H C H C C H O C H H O H H H O H H O H H H H J Ru N O N H H C H C C H O C H H C H H H O H H O O H H H S27
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