Spectroscopic Characterization of Copper(II) Binding to the Immunosuppressive Drug Mycophenolic Acid

Jones, Christopher E.; Taylor, Paul J.; McEwan, Alastair G.; Hanson, Graeme R.

doi:10.1021/ja057651l

Cited by 11 publications

(6 citation statements)

References 43 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In addition, our electrospray mass spectrometry and DOSY 19 NMR data suggested that the mixed-ligand Cu(II) species are stable in the aqueous phase (see details in ESI), which ensures the validity of data measured in this work.…”

Section: Resultssupporting

confidence: 60%

Supramolecular Medicinal Chemistry: Mixed-Ligand Coordination Complexes

Moulton

2007

Mol. Pharmaceutics

View full text Add to dashboard Cite

We report on the supramolecular synthesis and characterization of examples from three series of mixed-ligand coordination complexes composed of copper(II), a drug, and an ancillary ligand (AL). Particularly, we demonstrate how the judicious choice of an ancillary ligand affords a large degree of control over the relative lipophilicity/hydrophilicity of the complex in relation to the uncomplexed drug molecule. Furthermore, we demonstrate several important factors to consider in the design of such complexes such as the additive-constitutive nature of the partition coefficient of the ancillary ligand and the relative size of the two types of ligands.

show abstract

Section: Resultssupporting

confidence: 60%

Supramolecular Medicinal Chemistry: Mixed-Ligand Coordination Complexes

Moulton

2007

Mol. Pharmaceutics

View full text Add to dashboard Cite

show abstract

“…2002). It is possible to observe coordination complexes by electrospray mass spectrometry, especially at low ionization energies (Jones et al. 2006), but we find no evidence for a stable copper‐bound product.…”

Section: Discussioncontrasting

confidence: 61%

Copper induced oxidation of serotonin: analysis of products and toxicity

Jones

Underwood

Coulson

et al. 2007

Journal of Neurochemistry

Self Cite

View full text Add to dashboard Cite

Serotonin is a major neurotransmitter that controls many functions, ranging from mood and behaviour through to sleep and motor functions. The non-enzymatic oxidation of serotonin is of significant importance as some oxidation products are considered to be neurotoxic. An interaction between copper and serotonin has been suggested by symptoms observed in a number of neurodegenerative diseases such as Wilson's and Prion diseases. Using PC12 cells as a model of neuronal cells, we show that the interaction between copper and serotonin is toxic to undifferentiated cells. The toxicity is largely due to reactive oxygen species as cell death is significantly reduced in the presence of the antioxidant mannitol.Differentiation of the PC12 cells also confers resistance to the oxidative process. In vitro oxidation of serotonin by copper results in the eventual formation of a coloured pigment, thought to be a melanin-like polymeric species. Using spectroscopic methods we provide evidence for the formation of a single intermediate product. This dimeric intermediate was identified and characterized as 5,5¢-dihydroxy-4,4¢-bitryptamine. These results indicate that copper structurally alters serotonin and this process may play a role in copper related neurodegenerative diseases.

show abstract

“…9 F01-1358A (2) was obtained as a white crystalline powder with a molecular formula C 20 H 26 O 6 (high resolution fast atom bombardment mass spectra (HRFABMS) m/z 363.1808, M+H + , calcd for 363.1808, D0.0 mmu error). The IR (KBr) spectrum suggested that 2 had a hydroxyl group (3423 cm À1 ), two carbonyl groups (1734 and 1705 cm À1 ) and an isolated alkenyl group (1622 cm À1 ).…”

mentioning

confidence: 99%