Supplementary Information. DNA interaction of non-chelating tinidazole-based coordination compounds. Structural, redox and cytotoxic properties.
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1 Electronic Supplementry Mteril (ESI) for Dlton Trnsctions. This journl is The Royl Society of Chemistry 2018 Supplementry Informtion DNA interction of non-chelting tinidzole-bsed coordintion compounds. Structurl, redox nd cytotoxic properties. Rodrigo Cstro-Rmírez, Nytzé Ortiz-Pstrn, f An B. Cbllero, b,g Mtthew T. Zimmermn, c Brdley S. Stdelmn, c Andre A. E. Gertner, c Juli L. Brumghim, c Luís Korrodi-Gregório, d Ricrdo Pérez-Tomás, d Ptrick Gmez, b,e,g nd Norh Brb- Behrens,* Tble S1. Crystllogrphic dt nd structure refinement of compounds 3, 7, 9 nd 13 Compounds (3) (7) (9) (13) Chemicl formul C 16 H 26 N 8 O 14 S 2 Co C 16 H 21 N 6 O 8 S 2 C l 2 Cu C 16 H 26 N 8 O 14 S 2 Cu C 16 H 26 N 8 O 14 S 2 Zn F. W. (g mol -1 ) Spce group P2 1 /n P2 1 /c P2 1 /c P2 1 /n Crystl system Monoclinic Monoclinic Monoclinic Monoclinic (Å) (5) (11) b (Å) (8) (4) c (Å) (12) (11) ( ) ( ) (5) (10) ( ) V (Å 3 ) (16) (3) Z D cl (mg m -3 ) Indices (min) [-28,-8,-26 [-9,-24,-12 [-5,-14,-18 [-26,-8,-27 Indices (mx) [28,9,29 [8,36,18 [9,14,21 [25,8,25 Prmeters F(000) (mm -1 ) rnge ( ) dt collection Mesured reflections Independent reflections Reflections observed [I (I) R int R[F 2 2 (F 2 ) wr 2 (F 2 ) Goodness of fit (S) Δρ mx (e Å -3 ) Δρ min (e Å -3 ) Tble S2. Gel electrophoresis results for [Cu(tnz)(µ 2 -AcO) DNA dmge ssys with 50µM H 2 O 2. Supercoiled Nicked Dmge p Vlue 1: plsmid DNA (p) ± ± : p + H 2 O ± ± : p + Cu II + Ascorbic Acid + H 2 O ± ± : p + Compound + H 2 O ± ± ± ± ± ± 0.68 < ± ± ± 1.17 < ± ± ± 1.03 < ± ± ± 1.78 < Dt re reported s the verge of three trils with clculted stndrd devitions shown.
2 Tble S3. Gel electrophoresis results for Br 2 8 DNA dmge ssys with 50 µm H 2 O 2. Supercoiled Nicked Dmge p Vlue 1: plsmid DNA (p) ± ± : p + H 2 O ± ± : p + Cu II + Ascorbic Acid + H 2 O ± ± : p + Compound + H 2 O ± ± ± ± ± ± ± ± ± ± ± ± 3.15 < ± ± ± 2.54 < Dt re reported s the verge of three ssys with clculted stndrd devitions shown. Tble S4. Gel electrophoresis results for (NO 3 ) 2 9 DNA dmge ssys with 50 µm H 2 O 2. Supercoiled Nicked Dmge p Vlue 1: plsmid DNA (p) ± ± : p + H 2 O ± ± : p + Cu II + Ascorbic Acid + H 2 O ± ± : p + Compound + H 2 O ± ± ± ± ± ± ± ± ± ± ± ± 4.32 < ± ± ± 3.96 < Dt re reported s the verge of three ssys with clculted stndrd devitions shown.
3 Tble S5. Gel electrophoresis results for CuSO 4 DNA dmge ssys without 50 µm H 2 O 2. Supercoiled Nicked Dmge p Vlue 1: plsmid DNA (p) ± ± : p + H 2 O ± ± : p + Cu II + Ascorbic Acid + H 2 O ± ± : p + Cu II + Ascorbic Acid ± 0 0 ± ± 0.27 < ± ± ± ± ± ± ± ± ± ± ± ± ± ± ± 0.86 < ± ± ± ± ± ± 2.50 < ± ± ± 0.27 < ± ± ± 0.51 < ± ± ± 0.64 < Dt re reported s the verge of three ssys with clculted stndrd devitions shown. Tble S6. Gel electrophoresis results for [Cu(tnz)(µ 2 -AcO) DNA dmge ssys without H 2 O 2. Supercoiled Nicked Dmge p Vlue 1: plsmid DNA (p) ± 0 0 ± 0 2: p + H 2 O ± 0 0 ± 0 3: p + Cu II + Ascorbic Acid + H 2 O ± ± : p + Compound + Ascorbic Acid ± 0 0 ± ± 0 < ± ± ± ± ± ± ± ± ± ± ± ± ± ± ± ± ± ± ± ± ± 1.01 < ± ± ± 2.78 < ± ± ± 1.21 < ± ± ± 0.56 < Dt re reported s the verge of three trils with clculted stndrd devitions shown.
4 Tble S7. Gel electrophoresis results for Br 2 8 DNA dmge ssys without H 2 O 2. Supercoiled Nicked Dmge p Vlue 1: plsmid DNA (p) ± ± 0 2: p + H 2 O ± ± 0 3: p + Cu II + Ascorbic Acid + H 2 O ± ± : p + Compound + Ascorbic Acid ± ± ± 0 < ± ± ± ± ± ± ± ± ± ± ± ± ± ± ± ± ± ± 2.24 < ± ± ± 1.10 < ± ± ± 3.57 < ± ± ± 2.54 < ± ± ± 0.09 < Dt re reported s the verge of three ssys with clculted stndrd devitions shown. Tble S8. Gel electrophoresis results for (NO 3 ) 2 9 DNA dmge ssys without H 2 O 2. Supercoiled Nicked Dmge p Vlue 1: plsmid DNA (p) ± 0 0 ± 0 2: p + H 2 O ± 0 0 ± 0 3: p + Cu II + Ascorbic Acid + H 2 O ± ± : p + Compound + Ascorbic Acid ± ± ± 0 < ± ± ± 0 < ± ± ± 0 < ± ± ± 0 < ± ± ± 0 < ± ± ± ± ± ± 0.14 < ± ± ± 1.81 < ± ± ± 0.25 < ± ± ± 0.42 < ± ± ± 1.82 < Dt re reported s the verge of three ssys with clculted stndrd devitions shown.
5 Tble S9. Gel electrophoresis results for CuSO 4 DNA dmge ssys without H 2 O 2. Supercoiled Nicked Dmge p Vlue 1: plsmid DNA (p) ± ± : p + H 2 O ± ± : p + Cu II + Ascorbic Acid + H 2 O ± ± : p + Cu II + Ascorbic Acid ± ± ± 0 < ± ± ± ± ± ± 0.57 < ± ± ± 1.45 < ± ± ± 3.87 < ± ± ± ± ± ± ± ± ± 2.71 < ± ± ± 0 < ± ± ± 0.24 < ± ± ± 0.68 < ± ± ± 0.06 < Fig. S1. ORTEP representtion for [Co(tnz) 2 (NO 3 ) 2 3, ellipsoids t 50 probbility.
6 Fig. S2. Suprmoleculr rrngement for [Zn(tnz) 2 (NO 3 ) DMSO (AcO) 2 2 Br 2 Cl 2 (NO 3 ) 2 (µ-cl)cl 2 wter (AcO) 2 2 Br 2 (NO 3 ) 2 Cl 2 (µ-cl)cl 2 Abs. 0.3 Abs Wvelength (nm) Wvelength (nm) 0.6 Acetonitrile (AcO) 2 2 Br 2 Cl 2 (NO 3 ) 2 (µ-cl)cl 2 Abs Wvelength (nm) Fig. S3. Electronic spectr for Cu II tnz complexes in DMSO, H 2 O nd cetonitrile (10-3 M).
7 Fig. S4. Cyclic voltmmogrms vs. NHE for A) [Co(tnz) 2 Br 2 2, B) [Co(tnz) 2 Cl 2 1, nd C) [Co(tnz) 2 (NO 3 ) 2 3. Smples re 1 in cetonitrile with 100 TBAPF 6 s the supporting electrolyte. Fig. S5. Cyclic voltmmogrms vs. NHE for A) [Ni(tnz) 2 Br 2 4 nd B) [Ni(tnz) 2 (NO 3 ) 2 5. Smples re 1 in cetonitrile with 100 TBAPF 6 s the supporting electrolyte.
8 Fig. S6. Cyclic voltmmogrms vs. NHE for A) [Zn(tnz) 2 Br 2 12, B) [Zn(tnz) 2 Cl 2 11, nd C) [Zn(tnz) 2 (NO 3 ) Smples re 1 in cetonitrile with 100 TBAPF 6 s the supporting electrolyte.
9 A B C D E Fig. S7. Cyclic voltmmogrms vs. NHE for A) [Cu(tnz)(µ-OAc) 2 2, B) (µ-cl)cl 2, C) Br 2, D) Cl 2, nd E) (NO 3 ) 2. 1 in cetonitrile with 100 TBAPF 6 s supporting electrolyte.
10 Percent DNA dmge A EC 50 = 1.04 ± 0.01 µm EC 50 = 3.33 ± 0.01 µm Percent DNA Dmge B log [Cu 2 (tnz) 4 (µ 2 -OAc) 4 (µm) log [Cu(tnz)2Br2 ( M) Percent DNA dmge EC 50 = 1.87 ± 0.01 µm C log [Cu(tnz)2(NO3)2 ( M) Fig. S8. Dose-response curves for DNA dmge by ddition of 50 µm H 2 O 2 : A) [Cu(tnz)(µ 2 -AcO 2 ) 2 10, B) Br 2 8, nd C) (NO 3 ) 2 9.
11 Fig. S9. Dose-response curves for DNA dmge with scorbic cid nd without the ddition of H 2 O 2 : A) [Cu(tnz)(µ 2 - AcO 2 ) 2 10, B) Br 2 8, C) (NO 3 ) 2 9 nd D) CuSO 4 Tble S10. Cell-vibility percentge for copper(ii) tnz complexes ginst different cell lines. A549 SKOV-3 A375 MCF-7 SW tinidzole (µ-cl)cl [Cu(tnz)(µ-AcO) Br Cl (NO 3 ) Cell vibility ws determined twice for ech compound.
12 Tble S11. Inhibitory concentrtions for copper(ii) tnz complexes ginst different cell lines t 24h nd selectivity index (MCF-7 vs MCF-10A) MCF-7 SW620 MCF-10A Selectivity index Compound Nme IC Averge SD Averge SD Averge SD (IC 50 MCF-7/IC 50 MCF-10A) IC 75 >100 n.. >100 n.. >100 n.. Tinidzol IC 50 >100 n.. >100 n.. >100 n.. n.d IC 25 >100 n.. >100 n.. >100 n.. Br 2 IC IC IC (u-cl)cl 2 IC IC IC Cl 2 (NO 3 ) 2 IC >100 n IC >100 n IC >100 n IC >100 n.. IC IC [Cu(tnz)(μ-AcO) 2 2 IC IC IC Absorbnce Wvelength (nm) [DNA/(ɛ-ɛf) M2 cm 1.2E-9 1E-9 8E-10 6E-10 4E-10 2E E+00 1E-05 2E-05 3E-05 4E-05 [DNA M Fig. S10. Absorption spectr for (µ-cl)cl 2 7 (25 M in sodium ccodylte 1 20 of NCl 2 buffer, ph = 7.25; ct-dna: 0-25 M). Liner [DNA/ε-εf vs [DNA plot for the determintion of the intrinsic binding constnt K b. The rrow shows n increse in ct-[dna.
13 Intensity (. u.) wvelength (nm) I0/I [complex 0E+00 1E-05 2E-05 3E-05 4E-05 5E-05 6E-05 Fig. S11. Emission spectr for EB-DNA upon incresing concentrtion of (µ-cl)cl 2 7 (1-50 M). λ ex = 514 nm y λ em = 607 nm. Linel I 0 /I vs [complex plot for the determintion of the Stern-Volmer K sv. The rrow shows n increse of [complex.
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