Laboratory of Inorganic Chemistry, Faculty of Chemistry, Aristotle University of Thessaloniki, GR Thessaloniki, Greece. Supplementary material
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- Κόριννα Δαγκλής
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1 Quinolones and non-steroidal antiinflammatory drugs interacting with copper(ii), nickel(ii), cobalt(ii) and zinc(ii) : Structural features, biological evaluation and perspectives George Psomas* and Dimitris P. Kessissoglou* Laboratory of Inorganic Chemistry, Faculty of Chemistry, Aristotle University of Thessaloniki, GR Thessaloniki, Greece. Supplementary material * Corresponding authors: (G. Psomas): Tel.: ; Fax: ; gepsomas@chem.auth.gr (D.P. Kessissoglou): Tel.: ; Fax: ; kessisog@chem.auth.gr 1
2 Table S1. The DNA binding constants (K b ) and Stern-Volmer constants (K SV ) of EB-DNA fluorescence for Ni(II)-quinolone complexes. Compound K b (M -1 ) EB-DNA quenching % K SV(EB-DNA) (M -1 ) Hoxo 25d 3.02(±0.10) x not determined [Ni(oxo) 2 (H 2 O) 2 ] 25d 3.11(±0.11) x % 8.56(±0.37) x 10 5 [Ni(oxo) 2 (bipy)] 25d 1.43(±0.18) x % 1.20(±0.02) x 10 6 [Ni(oxo) 2 (phen)] 25d 2.12(±0.11) x % 8.99(±0.23) x 10 5 [Ni(oxo) 2 (bipyam)] 25f 1.41(±0.18) x % 8.91(±0.24) x 10 5 [Ni(oxo) 2 (py) 2 ] 25d 1.27(±0.06) x % 8.71(±0.53) x 10 5 Hflmq 25b 3.53(±0.45) x % 1.19(±0.06) x 10 6 [Ni(flmq) 2 (H 2 O) 2 ] 25b 6.75(±0.55) x % 6.60(±0.40) x 10 5 [Ni(flmq) 2 (py) 2 ] 25b 6.36(±0.40) x % 1.30(±0.08) x 10 5 [Ni(flmq) 2 (4bzpy) 2 ] 25b 6.81(±0.40) x % 1.54(±0.04) x 10 5 [Ni(flmq) 2 (bipy)] 25b 2.82(±0.09) x % 5.90(±0.45) x 10 5 [Ni(flmq) 2 (phen)] 25b 5.38(±0.20) x % 2.55(±0.08) x 10 4 [Ni(flmq) 2 (bipyam)] 25f 1.05(±0.17) x % 8.85(±0.38) x 10 5 Herx 25e 1.69(±0.04) x % 1.91(±0.07) x 10 5 [Ni(erx) 2 (H 2 O) 2 ] 25e 1.75(±0.40) x % 5.74(±0.20) x 10 5 [Ni(erx) 2 (py) 2 ] 25e 2.59(±0.48) x % 8.38(±0.23) x 10 5 [Ni(erx) 2 (bipy)] 25e 4.09(±0.53) x % 1.02(±0.09) x 10 6 [Ni(erx) 2 (phen)] 25e 1.63(±0.25) x % 1.03(±0.07) x 10 6 [Ni(erx) 2 (bipyam)] 25e 1.73(± 0.21) x % 1.78(±0.12) x 10 5 Hsf 25a 1.71(±0.02) x % 2.13(±0.09) x 10 6 [Ni(sf) 2 (H 2 O) 2 ] 25c 7.46(±0.17) x % 1.67(±0.10) x 10 6 [Ni(sf) 2 (py) 2 ] 25a 3.87(±0.14) x % 2.17(±0.16) x10 6 [Ni(sf) 2 (bipy)] 25c 7.75(±0.15) x % 2.31(±0.17) x 10 6 [Ni(sf) 2 (phen)] 25c 1.13(±0.18) x % 1.22(±0.07) x 10 6 [Ni(sf) 2 (bipyam)] 25f 2.23(±0.25) x % 8.70(±0.34) x
3 Table S2. The DNA binding constants (K b ) and Stern-Volmer constants (K SV ) of EB-DNA fluorescence for Cu(II)-quinolone complexes. Compound K b (M -1 ) % of EB-DNA quenching Ksv (M -1 ) Hnorf 26c 4.07x % 8.98x10 5 Hoflo 26c 3.91x % 4.68x10 5 [Cu(Hnorf)(phen)Cl]Cl 26c 1.83x % 4.74x10 5 [Cu(Hnorf) 2 ]Cl 2 6H 2 O 26c 4.08x % 3.69x10 5 [Cu(Hoflo) 2 ][(CuCl 2 ) 2 ] 26c 2.56x % 9.78x10 5 [Cu(Hnorf) 2 Cl 2 ] 2H 2 O 26c 1.97x % 7.63x10 5 Hflmq 3.53x % 1.19x10 6 [Cu(flmq) 2 (H 2 O) 2 ] 27g 8.39x % 5.50x10 5 [Cu(flmq)(bipyam)Cl] 27g 1.07x % 6.76x10 5 [Cu(flmq)(bipy)Cl] 27g 1.79x % 5.42x10 5 [Cu(flmq)(phen)Cl] 27g 2.39x % 4.32x10 5 [Cu(flmq) 2 (py) 2 ] 27g 8.12x % 5.42x10 5 3
4 Table S3. The DNA binding constants (K b ) and Stern-Volmer constants (K SV ) of EB-DNA fluorescence for Zn(II)-quinolone complexes. Complex K b ( Μ 1 ) Quenching % K SV (M -1 ) Hoxo 30c 3.02(±0.10) x nd a [Zn(oxo) 2 (H 2 O) 2 ] 30c 3.12(±0.05) x % 1.68(±0.01) x 10 5 [Zn(oxo)(bipy)Cl] 30c 5.91(±0.05) x % 1.77(±0.15) x 10 5 [Zn(oxo)(phen)Cl] 30a 1.17(±0.09) x % 3.66(±0.10) x 10 5 [Zn(oxo) 2 (bipy)] 30a 6.25(±0.15) x % 4.60(±0.19) x 10 5 [Zn(oxo) 2 (phen)] 30c 9.60(±0.02) x % 2.73(±0.13) x 10 5 [Zn(oxo) 2 (py) 2 ] 31e 1.16(±0.14) x % 3.68(±0.21) x 10 5 Hflmq 30b 3.53(±0.45) x % 1.19(±0.06) x 10 6 [Zn(flmq) 2 (H 2 O) 2 ] 30b 7.93(±0.23) x % 2.03(±0.06) x 10 5 [Zn(flmq)(bipy)Cl] 30b 2.04(±0.26) x % 1.04(±0.03) x 10 5 [Zn(flmq)(phen)Cl] 30a 1.22(±0.32) x % 0.59(±0.02) x 10 5 [Zn(flmq) 2 (bipy)] 30b 4.71(±0.22) x % 0.94(±0.05) x 10 5 [Zn(flmq) 2 (phen)] 30a 2.02 (±0.21) x % 1.54(±0.01) x 10 5 Herx 31e 1.69(±0.04) x % 1.91(±0.07) x 10 5 [Zn(erx) 2 (H 2 O) 2 ] 31f 9.32(±0.32) x % 2.33(±0.09) x 10 5 [Zn(erx)(bipy)Cl] 30a 1.74(±0.11) x % 3.88(±0.10) x 10 5 [Zn(erx)(phen)Cl] 30a 2.68(±0.20) x % 3.57(±0.11) x 10 5 [Zn(erx) 2 (bipy)] 31f 2.61(±0.20) x % 5.88(±0.19) x 10 5 [Zn(erx) 2 (phen)] 31f 8.03(±0.06) x % 4.31(±0.20) x 10 5 [Zn(erx) 2 (py) 2 ] 31e 3.35(±0.05) x % 3.40(±0.25) x 10 5 Hsf 31a 1.71(±0.02) x % 2.13(±0.09)x10 6 [Zn(sf) 2 (H 2 O) 2 ] 31a 1.11(±0.17) x % 1.29(±0.05)x10 6 [Zn(sf) 2 (bipy)] 31a 1.01(±0.06) x % 1.33(±0.03)x10 6 [Zn(sf) 2 (phen)] 31a 2.71(±0.22) x % 1.20(±0.04)x10 6 [Zn(sf) 2 (bipyam)] 31a 6.25(±0.09) x % 0.99(±0.03)x10 6 Hlevo 31a 4.36(±0.15) x % 1.11(±0.03)x10 6 [Zn(levo) 2 (H 2 O) 2 ] 31a 9.20(±0.20) x % 1.16(±0.05)x10 6 [Zn(levo) 2 (bipyam)] 31a 1.08(±0.07) x % 1.11(±0.03)x10 6 4
5 Table S4. The DNA binding constants (K b ) and Stern-Volmer constants (K SV ) of EB-DNA fluorescence for Co(II)-NSAID complexes. Complex K b (M -1 ) EB-DNA quenching K SV (M -1 ) Hmef 36a 1.05x % 1.58x10 5 [Co(mef) 2 (MeOH) 4 ] 36a 5.82x % 7.63x10 5 [Co(mef) 2 (py) 2 (MeOH) 2 ] 36a 4.59x % 1.09x10 6 [Co(mef) 2 (bipy)(meoh) 2 ] 36a 3.02x % 4.10x10 5 [Co(mef) 2 (phen)(meoh) 2 ] 36a 3.22x % 2.17x10 5 Ηnap 36c 2.67x % 1.47x10 5 [Co(nap) 2 (MeOH) 4 ] 36c 3.15x % 1.03x10 5 [Co(nap) 2 (py) 2 (H 2 O) 2 ] 36c 3.58x % 1.19x10 5 [Co(nap) 2 (bipy)(h 2 O) 2 ] 36c 2.76x % 2.24x10 5 [Co(nap) 2 (phen)(h 2 O) 2 ] 36c 2.29x % 7.17x10 4 Htolf 36b 5.00x % 1.15x10 6 [Co(tolf) 2 (MeOH) 4 ] 36b 1.14x % 1.14x10 6 [Co(tolf) 2 (bipy)(meoh) 2 ] 36b 4.18x % 1.26x10 6 [Co(tolf) 2 (phen)(meoh) 2 ] 36b 2.28x % 1.51x10 6 [Co(tolf) 2 (bipyam)] 36b 6.78x % 1.31x10 6 [Co(tolf) 2 (py) 2 (MeOH) 2 ] 36b 9.77x % 1.41x10 6 5
6 Table S5. The DNA binding constants (K b ) and Stern-Volmer constants (K SV ) of EB-DNA fluorescence for Cu(II)-NSAID complexes. Compound K b (M -1 ) EB-DNA quenching K SV (M -1 ) Hnap 38b 2.67x % 1.47x10 5 [Cu 2 (nap) 4 (H 2 O) 2 ] 38b 2.27x % 1.17x10 5 [Cu(nap) 2 (py) 2 (H 2 O)] 38b 8.97x % 1.88x10 4 [Cu(nap) 2 (bipy)] 38b 3.86x % 9.74x10 4 [Cu(nap) 2 (phen)] 38b 9.20x % 9.30x10 4 Na dicl 38b 3.16x % 2.47x10 5 [Cu 2 (dicl) 4 (H 2 O) 2 ] 38b 1.74x % 6.98x10 5 [Cu(dicl) 2 (py) 2 ] 38b 4.35x % 1.35x10 4 [Cu(dicl) 2 (phen)] 38b 1.81x % 4.82x10 5 Hmef 38a 1.05x % 1.58x10 5 [Cu 2 (mef) 4 (H 2 O) 2 ] 38a 7.59x % 1.99x10 5 [Cu(mef) 2 (bipy)] 38a 9.03x % 4.72x10 5 [Cu(mef) 2 (phen)] 38a 6.95x % 1.04x10 5 [Cu(mef) 2 (bipyam)] 38a 2.20x % 2.54x10 6 [Cu(mef) 2 (py) 2 (MeOH) 2 ] 38a 6.93x % 1.04x10 6 Hdifl 37b 3.08x % 8.59x10 5 [Cu 2 (difl) 4 (DMF) 2 ] 37b 3.10x % 9.03x10 5 [Cu(difl) 2 (py) 2 ] 37b 7.36x % 1.52x10 5 [Cu(difl) 2 (bipy)] 37b 2.97x % 4.61x10 5 [Cu(difl) 2 (phen)] 37b 5.61x % 6.20x10 5 [Cu(difl) 2 (bipyam)] 37b 8.05x % 7.26x10 4 6
7 Table S6. The albumins (BSA, HSA) quenching constants (k q ) and association binding constants (K) of Ni(II)-quinolone complexes. Compound k q(bsa) (M -1 s -1 ) K (BSA) (M -1 ) k q(hsa) (M -1 s -1 ) K (HSA) (M -1 ) Hoxo 25d 5.01x x x x10 5 [Ni(oxo) 2 (H 2 O) 2 ] 25d 2.48x x x x10 4 [Ni(oxo) 2 (bipy)] 25d 9.85x x x x10 4 [Ni(oxo) 2 (phen)] 25d 1.17x x x x10 4 [Ni(oxo) 2 (bipyam)] 25f 6.40x x x x10 4 [Ni(oxo) 2 (py) 2 ] 25d 6.86x x x x10 4 Hflmq 25b 8.26x x x x10 6 [Ni(flmq) 2 (H 2 O) 2 ] 25b 7.25x x x x10 6 [Ni(flmq) 2 (bipy)] 25b 1.24x x x x10 5 [Ni(flmq) 2 (phen)] 25b 1.68x x x x10 5 [Ni(flmq) 2 (bipyam)] 25f 4.41x x x x10 5 [Ni(flmq) 2 (py) 2 ] 25b 1.62x x x x10 5 [Ni(flmq) 2 (4bzpy) 2 ] 25b 1.84x x x x10 5 Herx 25e 4.40x x x x10 4 [Ni(erx) 2 (H 2 O) 2 ] 25e 7.98x x x x10 4 [Ni(erx) 2 (phen)] 25e 1.28x x x x10 4 [Ni(erx) 2 (bipy)] 25e 1.13x x x x10 4 [Ni(erx) 2 (bipyam)] 25f 1.28x x x x10 4 [Ni(erx) 2 (py) 2 ] 25e 7.71x x x x10 4 Hsf 25a 1.04x x x x10 4 [Ni(sf) 2 (H 2 O) 2 ] 25c 4.06x x x x10 4 [Ni(sf) 2 (phen)] 25c 4.77x x x x10 6 [Ni(sf) 2 (bipy)] 25c 2.25x x x x10 4 [Ni(sf) 2 (bipyam)] 25f 3.62x x x x10 4 [Ni(sf) 2 (py) 2 ] 25a 3.92x x x x10 5 7
8 Table S7. The albumins (BSA, HSA) quenching constants (k q ) and association binding constants (K) of Cu(II)-quinolone complexes. Compound k q(bsa) (M -1 s -1 ) K (BSA) (M -1 ) k q(hsa) (M -1 s -1 ) K (HSA) (M -1 ) Hnorf 26c 8.09x x x x10 5 Hoflo 26c 1.07x x x x10 4 [Cu(Hnorf)(phen)Cl]Cl 26c 1.92x x x x10 4 [Cu(Hnorf) 2 ]Cl 2 6H 2 O 26c 5.35x x x x10 4 [Cu(Hoflo) 2 ][(CuCl 2 ) 2 ] 26c 1.92x x x x10 4 [Cu(Hnorf) 2 Cl 2 ] 2H 2 O 26c 1.39x x x x10 4 Hflmq 27g 8.26x x x x10 6 [Cu(flmq) 2 (H 2 O) 2 ] 27g 1.35x x x x10 4 [Cu(flmq)(bipyam)Cl] 27g 8.04x x x x10 5 [Cu(flmq)(bipy)Cl] 27g 7.84x x x x10 5 [Cu(flmq)(phen)Cl] 27g 2.25x x x x10 5 [Cu(flmq) 2 (py) 2 ] 27g 7.85x x x x10 5 8
9 Table S8. The albumins (BSA, HSA) quenching constants (k q ) and association binding constants (K) of Zn(II)-quinolone complexes. Compound k q(bsa) (M -1 s -1 ) K (BSA) (M -1 ) k q(hsa) (M -1 s -1 ) K (HSA) (M -1 ) Hoxo 30c 5.01x x x x10 5 [Zn(oxo) 2 (H 2 O) 2 ] 30c 7.20x x x x10 4 [Zn(oxo)(bipy)Cl] 30c 3.35x x x x10 5 [Zn(oxo)(phen)Cl] 30a 8.96x x x x10 4 [Zn(oxo) 2 (bipy)] 30a 1.89x x x x10 5 [Zn(oxo) 2 (phen)] 30c 6.37x x x x10 4 Hflmq 30b 8.26x x x x10 6 [Zn(flmq) 2 (H 2 O) 2 ] 30b 1.07x x x x10 4 [Zn(flmq)(bipy)Cl] 30b 5.28x x x x10 4 [Zn(flmq)(phen)Cl] 30a 4.45x x x x10 4 [Zn(flmq) 2 (bipy)] 30b 1.68x x x x10 4 [Zn(flmq) 2 (phen)] 30a 4.45x x x x10 4 Herx 31e 4.48x x x x10 4 [Zn(erx) 2 (H 2 O) 2 ] 31f 6.98x x x x10 4 [Zn(erx)(bipy)Cl] 30a 5.08x x x x10 4 [Zn(erx)(phen)Cl] 30a 5.54x x x x10 5 [Zn(erx) 2 (bipy)] 31f 6.82x x x x10 4 [Zn(erx) 2 (phen)] 31f 6.29x x x x10 4 Hsf 31a 1.04x x x x10 4 [Zn(sf) 2 (H 2 O) 2 ] 31a 3.68x x x x10 5 [Zn(sf) 2 (bipy)] 31a 2.76x x x x10 4 [Zn(sf) 2 (phen)] 31a 5.19x x x x10 5 [Zn(sf) 2 (bipyam)] 31a 3.29x x x x10 4 Hlevo 31a 9.47x x x x10 5 [Zn(levo) 2 (H 2 O) 2 ] 31a 3.04x x x x10 5 [Zn(levo) 2 (bipyam)] 31a 3.98x x x x10 5 9
10 Table S9. The SA quenching and binding constants (k q and K) for the Co(II)-NSAID complexes. Compound k q(bsa) (M -1 s -1 ) K (BSA) (M -1 ) k q(hsa) (M -1 s -1 ) K (HSA) (M -1 ) Hmef 36a 2.78x x x x10 5 [Co(mef) 2 (MeOH) 4 ] 36a 2.11x x x x10 5 [Co(mef) 2 (bipy)(meoh) 2 ] 36a 2.86x x x x10 5 [Co(mef) 2 (phen)(meoh) 2 ] 36a 6.04x x x x10 5 [Co(mef) 2 (py) 2 (MeOH) 2 ] 36a 6.32x x x x10 5 Ηnap 36c 1.18x x x x10 4 [Co(nap) 2 (MeOH) 4 ] 36c 2.47x x x x10 4 [Co(nap) 2 (bipy)(h 2 O) 2 ] 36c 1.75x x x x10 4 [Co(nap) 2 (phen)(h 2 O) 2 ] 36c 2.09x x x x10 4 [Co(nap) 2 (py) 2 (H 2 O) 2 ] 36c 1.21x x x x10 4 Htolf 36b 2.18x x x x10 5 [Co(tolf) 2 (MeOH) 4 ] 36b 2.88x x x x10 5 [Co(tolf) 2 (bipy)(meoh) 2 ] 36b 8.60x x x x10 4 [Co(tolf) 2 (phen)(meoh) 2 ] 36b 3.02x x x x10 5 [Co(tolf) 2 (bipyam)] 36b 4.30x x x x10 4 [Co(tolf) 2 (py) 2 (MeOH) 2 ] 36b 2.74x x x x
11 Table S10. The SA quenching and binding constants (k q and K) for the Cu(II)-NSAID complexes. Compound k q(bsa) (M -1 s -1 ) K (BSA) (M -1 ) k q(hsa) (M -1 s -1 ) K (HSA) (M -1 ) Hnap 38b 1.18x x x x10 4 [Cu 2 (nap) 4 (H 2 O) 2 ] 38b 2.34x x x x10 4 [Cu(nap) 2 (py) 2 (H 2 O)] 38b 2.33x x x x10 3 [Cu(nap) 2 (bipy)] 38b 2.24x x x x10 4 [Cu(nap) 2 (phen)] 38b 2.94x x x x10 4 Na dicl 38b 8.11x x x x10 5 [Cu 2 (dicl) 4 (H 2 O) 2 ] 38b 1.90x x x x10 5 [Cu(dicl) 2 (py) 2 ] 38b 1.27x x x x10 5 [Cu(dicl) 2 (phen)] 38b 1.89x x x x10 5 Hmef 38a 2.78x x x x10 5 [Cu 2 (mef) 4 (H 2 O) 2 ] 38a 9.86x x x x10 5 [Cu(mef) 2 (py) 2 (MeOH) 2 ] 38a 1.31x x x x10 5 [Cu(mef) 2 (bipy)] 38a 3.76x x x x10 5 [Cu(mef) 2 (phen)] 38a 6.12x x x x10 5 [Cu(mef) 2 (bipyam)] 38a 2.88x x x x10 5 Hdifl 37b 1.53x x x x10 5 [Cu 2 (difl) 4 (DMF) 2 ] 37b 3.09x x x x10 5 [Cu(difl) 2 (py) 2 ] 37b 6.16x x x x10 5 [Cu(difl) 2 (bipy)] 37b 5.95x x x x10 5 [Cu(difl) 2 (phen)] 37b 8.87x x x x10 5 [Cu(difl) 2 (bipyam)] 37b 1.49x x x x
12 Table S11. The SA quenching and binding constants (k q and K) for the Htolf and its complexes. Compound k q(bsa) (M -1 s -1 ) K (BSA) (M -1 ) k q(hsa) (M -1 s -1 ) K (HSA) (M -1 ) Htolf 35a 2.18x x x x10 5 [Zn 3 (tolf) 6 (CH 3 OH) 2 ] 35a 1.87x x x x10 5 [Zn(tolf)(phen)Cl] 35a 9.99x x x x10 5 [Zn(tolf)(bipy)Cl] 35a 1.15x x x x10 5 [Ζn(tolf) 2 (phen)] 35a 1.00x x x x10 5 [Zn(tolf) 2 (bipy)] 35a 3.67x x x x
13 Table S12. Minimum inhibitory concentration (MIC, in μg ml -1 ) of diverse metal-quinolone complexes Compound E. coli P. aeruginosa S. aureus Ηoxo 37f [Cu(oxo) 2 (H 2 O)] 37f [UO 2 (oxo) 2 ] 44a [MoO 2 (oxo) 2 ] 44a ΗPPA 44b [VO(PPA) 2 (H 2 O)] 44b [Mn(PPA) 2 (H 2 O) 2 ] 44b [Fe(PPA) 3 ] 44b [Co(PPA) 2 (H 2 O) 2 ] 44b [Ni(PPA) 2 (H 2 O) 2 ] 44b [Cu(PPA) 2 (H 2 O)] 44c [Zn(PPA) 2 (H 2 O) 2 ] 44b [MoO 2 (PPA) 2 ] 44b [Cd(PPA) 2 (H 2 O) 2 ] 44b [UO 2 (PPA) 2 ] 44b Ηpr-norf 44d [VO(pr-norf) 2 (H 2 O)] 44d [Mn(pr-norf) 2 (H 2 O) 2 ] 44d [Fe(pr-norf) 3 ] 44d [Co(pr-norf) 2 (H 2 O) 2 ] 44d [Ni(pr-norf) 2 (H 2 O) 2 ] 44d [Cu(pr norf) 2 (H 2 O)] 44c [Zn(pr-norf) 2 (H 2 O) 2 ] 44d [MoO 2 (pr-norf) 2 ] 44d [Cd(pr-norf) 2 (H 2 O) 2 ] 44d [UO 2 (pr-norf) 2 ] 44d Ηerx 27e [VO(erx) 2 (H 2 O)] 44e [Mn(erx) 2 (H 2 O) 2 ] 44f [Fe(erx) 3 ] 44f
14 [Co(erx) 2 (H 2 O) 2 ] 44f [Ni(erx) 2 (H 2 O) 2 ] 44f [Cu(erx) 2 (H 2 O)] 27e [Zn(erx) 2 (H 2 O) 2 ] 44f [Cd(erx) 2 (H 2 O) 2 ] 44f [UO 2 (erx) 2 ] 44f [MoO 2 (erx) 2 ] 44g Ηsf 26a [VO(sf) 2 (H 2 O)] 44h [Mn(sf) 2 (H 2 O) 2 ] 44h [Fe(sf) 3 ] 44h [Co(sf) 2 (H 2 O) 2 ] 44i [Ni(sf) 2 (H 2 O) 2 ] 25c [Cu(sf) 2 ] 26a [UO 2 (sf) 2 ] 44h [MoO 2 (sf) 2 ] 44g
15 Table S13. Minimum inhibitory concentration (MIC, in μg ml -1 ) of diverse copper(ii)-quinolone complexes. Compound E. coli P. aeruginosa S. aureus Hoxo 27f [Cu(oxo) 2 (H 2 O)] 27f [Cu(oxo)(bipy)Cl] 27f [Cu(oxo)(phen)Cl] 27f [Cu(oxo)(bipyam)Cl] 27f HPPA 44c [Cu(PPA) 2 (H 2 O)] 44c [Cu(PPA)(bipy)Cl] 44c [Cu(PPA)(phen)Cl] 44c [Cu(PPA)(bipyam)Cl] 44c Herx 27e [Cu(erx) 2 (H 2 O)] 27e [Cu(erx)(bipy)(H 2 O)]Cl 27e [Cu(erx)(phen)Cl] 27e Hpr-norf 27a [Cu(pr norf) 2 (H 2 O)] 44c [Cu(pr norf)(bipy)cl] 27a [Cu(pr norf)(phen)cl] 45a [Cu(pr norf)(bipyam)cl] 44c Hsf 26a [Cu(sf) 2 ] 26a [Cu(sf)(bipy)Cl] 45b [Cu(sf)(phen)Cl] 45b [Cu(sf)(bipyam)Cl] 45b
16 Table S14. Interaction % with DPPH (RA%), superoxide radical scavenging activity (ABTS%) and competition % with DMSO for hydroxyl radical (. OH%) of 0.1 mm solution and in vitro inhibition of soybean lipoxygenase (LOX) (IC 50, μm)of the quinolones and their Ni(II) complexes. Compound (RA%) ABTS%. OH% LOX (IC 50, μm) Hoxo 25f [Ni(oxo) 2 (H 2 O) 2 ] 25f [Ni(oxo) 2 (py) 2 ] 25f [Ni(oxo) 2 (4bzpy) 2 ] 25f [Ni(oxo) 2 (bipy)] 25f [Ni(oxo) 2 (phen)] 25f [Ni(oxo) 2 (bipyam)] 25f Hflmq 25f [Ni(flmq) 2 (H 2 O) 2 ] 25f [Ni(flmq) 2 (py) 2 ] 25f [Ni(flmq) 2 (4bzpy) 2 ] 25f [Ni(flmq) 2 (bipy)] 25f [Ni(flmq) 2 (phen)] 25f [Ni(flmq) 2 (bipyam)] 25f Herx 25f [Ni(erx) 2 (H 2 O) 2 ] 25f [Ni(erx) 2 (py) 2 ] 25f [Ni(erx) 2 (4bzpy) 2 ] 25f [Ni(erx) 2 (bipy)] 25f [Ni(erx) 2 (phen)] 25f [Ni(erx) 2 (bipyam)] 25f Hsf 25f [Ni(sf) 2 (H 2 O) 2 ] 25f [Ni(sf) 2 (py) 2 ] 25f [Ni(sf) 2 (4bzpy) 2 ] 25f [Ni(sf) 2 (bipy)] 25f [Ni(sf) 2 (phen)] 25f [Ni(sf) 2 (bipyam)] 25f NDGA 25f BHT 25f Trolox 25f Caffeic acid 25f
17 Table S15. Interaction % with DPPH (RA%), superoxide radical scavenging activity (ABTS%) and competition % with DMSO for hydroxyl radical (. OH%) of 0.1 mm solution of the NSAIDs and their Co(II) complexes. Compound RA% ABTS% OH% Hmef 36a [Co(mef) 2 (MeOH) 4 ] 36a [Co(mef) 2 (py) 2 (MeOH) 2 ] 36a [Co(mef) 2 (bipy)(meoh) 2 ] 36a [Co(mef) 2 (phen)(meoh) 2 ] 36a Ηnap 36c [Co(nap) 2 (MeOH) 4 ] 36c [Co(nap) 2 (py) 2 (H 2 O) 2 ] 36c [Co(nap) 2 (bipy)(h 2 O) 2 ] 36c [Co(nap) 2 (phen)(h 2 O) 2 ] 36c NDGA 36a BHT 36a Trolox 36a
18 Table S16. Interaction % with DPPH (RA%), superoxide radical scavenging activity (ABTS%), competition % with DMSO for hydroxyl radical (. OH%) of 0.1 mm solution of the NSAIDs and their Cu(II) complexes. In vitro inhibition of soybean lipoxygenase (LOX) (IC 50, μm). Compound RA% ABTS% OH% LOX IC 50 (μm) Hmef 38a [Cu 2 (mef) 4 (H 2 O) 2 ] 38a [Cu(mef) 2 (py) 2 (MeOH) 2 ] 38a [Cu(mef) 2 (bipy)] 38a [Cu(mef) 2 (phen)] 38a [Cu(mef) 2 (bipyam)] 38a Ηnap 36c c [Cu(nap) 2 (H 2 O)] [Cu(nap) 2 (py) 2 (H 2 O)] 36c [Cu(nap) 2 (bipy)] H 2 O 36c [Cu(nap) 2 (phen)] H 2 O 36c NDGA 38a 82.6 BHT 38a 60 Trolox 38a Caffeic acid 38a
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