Antiplasmodial activity of targeted zinc(II)-dipicolylamine complexes

Rice, Douglas R.; Betancourt-Mendiola, Lourdes; Murillo-Solano, Claribel; Checkley, Lisa A.; Ferdig, Michael T.; Pizarro, J.C.; Smith, Bradley D.

doi:10.1016/j.bmc.2017.03.050

Cited by 12 publications

(2 citation statements)

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“…25 In particular, H-BPMP (i.e., BPMPOH), first reported in 1981 by Suzuki and co-workers, was utilized to generate a dicobalt(II)/O 2 adduct, 26 then structurally characterized as a peroxo-dicobalt(III) complex. 27 H-BPMP has elicited wide application to binuclear complexes of copper, 28 iron, 29 cobalt, 26,27,30 manganese, 31 zinc, 32 and heterobimetallic c o m p l e x e s .…”

Section: ■ Introductionmentioning

confidence: 99%

“…In particular, H-BPMP (i.e., BPMPOH), first reported in 1981 by Suzuki and co-workers, was utilized to generate a dicobalt(II)/O 2 adduct, then structurally characterized as a peroxo-dicobalt(III) complex . H-BPMP has elicited wide application to binuclear complexes of copper, iron, cobalt, ,, manganese, zinc, and heterobimetallic complexes . [Cu II 2 (BPMPO – )(OH)] 2+ and [Cu II 2 (BPMPO – )(OAc) 2 ] + , , with phenolate and hydroxide or acetate bridges, exhibit catecholase activity with O 2 present (catechols → quinones).…”

Section: Introductionmentioning

confidence: 99%

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Coordination Variations within Binuclear Copper Dioxygen-Derived (Hydro)Peroxo and Superoxo Species; Influences upon Thermodynamic and Electronic Properties

Hota,

Jose,

Panda

et al. 2024

J. Am. Chem. Soc.

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Copper ion is a versatile and ubiquitous facilitator of redox chemical and biochemical processes. These include the binding of molecular oxygen to copper(I) complexes where it undergoes stepwise reduction-protonation. A detailed understanding of thermodynamic relationships between such reduced/protonated states is key to elucidate the fundamentals of the chemical/ biochemical processes involved. The dicopper(I) complex [Cu I 2 (BPMPO − )] 1+ {BPMPOH = 2,6-bis{[(bis(2-pyridylmethyl)amino]methyl}-4-methylphenol)} undergoes cryogenic dioxygen addition; further manipulations in 2-methyltetrahydrofuran generate dicopper(II) peroxo [Cu II 2 (BPMPO − )(O 2 2− )] 1+ , hydroperoxo [Cu II 2 (BPMPO − )( − OOH)] 2+ , and superoxo [Cu II 2 (BPMPO − )(O 2 •− )] 2+ species, characterized by UV−vis, resonance Raman and electron paramagnetic resonance (EPR) spectroscopies, and cold spray ionization mass spectrometry. An unexpected EPR spectrum for [Cu II 2 (BPMPO − )(O 2 •− )] 2+ is explained by the analysis of its exchange-coupled three-spin frustrated system and DFT calculations. A redox equilibrium, [Cu II 2 (BPMPO − )(O 2 2− )] 1+ ⇄ [Cu II 2 (BPMPO − )(O 2 •− )] 2+ , is established utilizing Me 8 Fc + /Cr(η 6 -C 6 H 6 ) 2 , allowing for [Cu II 2 (BPMPO − )(O 2 •− )] 2+ /[Cu II 2 (BPMPO − )(O 2 2− )] 1+ reduction potential calculation, E°′ = −0.44 ± 0.01 V vs Fc +/0 , also confirmed by cryoelectrochemical measurements (E°′ = −0.40 ± 0.01 V). 2,6-Lutidinium triflate addition to [Cu II 2 (BPMPO − )-(O 2 2− )] 1+ produces [Cu II 2 (BPMPO − )( − OOH)] 2+ ; using a phosphazene base, an acid−base equilibrium was achieved, pK a = 22.3 ± 0.7 for [Cu II 2 (BPMPO − )( − OOH)] 2+ . The BDFE OO−H = 80.3 ± 1.2 kcal/mol, as calculated for [Cu II 2 (BPMPO − )( − OOH)] 2+ ; this is further substantiated by H atom abstraction from O−H substrates by [Cu II 2 (BPMPO − )(O 2 •− )] 2+ forming [Cu II 2 (BPMPO − )-( − OOH)] 2+ . In comparison to known analogues, the thermodynamic and spectroscopic properties of [Cu II 2 (BPMPO − )] O 2 -derived adducts can be accounted for based on chelate ring size variations built into the BPMPO − framework and the resulting enhanced Cu II -ion Lewis acidity.

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