Investigation of cobalt(III)-phenylalanine complexes for hypoxia-activated drug delivery.

Dalton Transactions : an International Journal of Inorganic Chemistry
Isabela Cristina Aguiar de SouzaMauricio Lanznaster

Abstract

Four cobalt(iii)-phenylalanine complexes, [Co(Phe)(py2en)](ClO4)2·H2O (1), [Co(Phe)(TPA)](ClO4)2·H2O (2), [Co(Phe)(py2enMe2)](ClO4)2·H2O (3) and [Co(bipy)2(Phe)](ClO4)2·H2O (4), were investigated as prototype models for hypoxia-activated delivery of melphalan - a phenylalanine derivative anticancer drug of the class of nitrogen mustards. Single crystal X-ray diffraction analysis provided the molecular structures of 1-4, as a single isomer/conformer. According with NMR and theoretical calculations, the solid-state structures of 2 and 4 are maintained in solutions. For complexes 1 and 3, though, a mixture of isomers was found in DMSO solutions: Λ-cisα(exo,exo) and Δ-cisβ1(exo,exo) for 1 (3 : 2 ratio), and Λ-cisα(exo,exo) and Δ-cisα(exo,exo) for 3 (5 : 1 ratio). Theoretical calculations point to a re-equilibration reaction of the solid-state Λ-cisβ1 isomer of 1 in solution. Electrochemical analysis revealed a correlation between the electron-donor capacity of the ancillary ligands and the redox potentials of the complexes. The potentials varied from +0.01 for 1 to +0.31 V vs. SHE for 4 in aqueous media and indicate that reduction should be achieved in biological media. The integrity of the complexes in pH 5.5 and 7.4 buffered solu...Continue Reading

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Citations

May 29, 2021·Inorganic Chemistry Frontiers·Marlene MathuberChristian R Kowol
Jul 3, 2021·Materials·Grzegorz ŚwiderskiWłodzimierz Lewandowski

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Methods Mentioned

BETA
X-ray
NMR

Software Mentioned

SHELXL
SQUEEZE
Crest
SHELXS
Orca
xTB
LibXC
GFN2
GaussView
Chemcraft

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