Differential transmetallation of complexes of the anti-cancer thiosemicarbazone, Dp4e4mT: effects on anti-proliferative efficacy, redox activity, oxy-myoglobin and oxy-hemoglobin oxidation

Abstract

The differential transmetallation of Dp4e4mT complexes provides valuable insights into their biological mechanism of action, off-target effects, and their potential therapeutic applications.

Zinc(II) Complexes of SIRTi1/2 Analogues Transmetallating with Copper Ions and Inducing ROS Mediated Paraptosis

“…The compounds 5-fluoro salicylaldehyde and 5-nitro Salicylaldehyde were synthesized according to previously published literature. The solvents CDCl 3 and DMSO-d 6 were employed as solvents for conducting 1 H and 13 C nuclear magnetic resonance (NMR) experiments on JEOL 400 and 500 MHz spectrometers. The 1 H NMR chemical shifts were referenced by using the remaining hydrogen signal of the deuterated solutions.…”

“…The empirical 1:1 Zn(II) complexes were synthesized via the reaction of equimolar amounts of the ligands and anhydrous ZnCl 2 in methanol in the presence of triethylamine. All complexes were characterized by 1 H and 13 C NMR, IR, UV−vis, and ESI-MS, and their purity was assessed by HPLC and determined to be >95%. As anticipated, HL1− HL6 formed neutral dimeric 1:1 (Zinc(II)/ligand) complexes with ZnCl 2 upon deprotonation of the benzylic phenol scaffold in the presence of the base triethylamine (Scheme 1).…”

“…1 H NMR (500 MHz, CD 3 OD, δ ppm): 8.43 (s, 2H), 7.91−7.57 (m, 4H), 7.56−6.99 (m, 20H), 6.81 (s, 2H), 5.26 (s, 2H), 1.53 (d, 6H). 13 ZnL4. Followed the same procedure as above with ligand HL4 (0.1 mmol, 43.3 mg).…”

“…1 H NMR (500 MHz, CD 3 OD, δ ppm): 8.42 (s, 2H), 7.77 (s, 2H), 7.67 (s, 2H), 7.53−7.41 (m, 4H), 7.29 (dd, J = 20.9, 14.7 Hz, 14H), 7.19 (t, J = 7.3 Hz, 2H), 6.74 (s, 2H), 5.25 (d, J = 6.9 Hz, 2H), 1.53 (d, J = 6.9 Hz, 6H). 13 ZnL5. Followed the same procedure as above with ligand HL5 (0.1 mmol, 36.3 mg).…”

“…The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acsorginorgau.3c00052. Synthetic methods, characterization of the ligands and the complexes ( 1 H and 13 C NMR, IR, UV−vis, HPLC, single crystal X-ray diffraction, and protocols for biological assays (PDF)…”