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Synthesis and Structure Determination of µ-Conotoxin PIIIA Isomers with Different Disulfide Connectivities

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Myochrysine solution structure and reactivity.

R C Elder¹, W B Jones, Z Zhao

¹Biomedical Chemistry Research Center Department of Chemistry and Biological Sciences University of Cincinnati Cincinnati OH 45221-0172 USA.

Metal-Based Drugs

|January 1, 1994

Summary

This summary is machine-generated.

The polymeric structure of Myochrysine (disodium gold(I)thiomalate) persists in dilute solutions, remaining oligomeric at patient-relevant concentrations. This gold-based drug reacts with cyanide and amino acids, with potential metabolites identified using capillary zone electrophoresis.

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Area of Science:

Inorganic Chemistry
Analytical Chemistry
Pharmacology

Background:

The solid-state structure of Myochrysine (disodium gold(I)thiomalate) is an open-chain polymer.
The relevance of this polymeric structure to dilute physiological concentrations was previously unknown.
Understanding Myochrysine's behavior in solution is crucial for its therapeutic application as an anti-arthritis drug.

Purpose of the Study:

To determine if the polymeric structure of Myochrysine persists in dilute aqueous solutions.
To investigate the reactivity of Myochrysine with cyanide and amino acids.
To evaluate capillary zone electrophoresis (CZE) as a tool for studying gold-based drugs.

Main Methods:

Extended X-ray absorption spectroscopy (EXAFS) was used to study Myochrysine structure at millimolar concentrations.
Capillary zone electrophoresis (CZE) was employed to analyze Myochrysine at micromolar concentrations and its reactions.
The reactivity with cyanide and subsequent reactions with amino acids (cysteine, N-acetylcysteine, glutathione) were investigated.

Main Results:

EXAFS confirmed the polymeric structure persists from molar down to millimolar concentrations.
CZE demonstrated that Myochrysine remains oligomeric at micromolar concentrations, relevant to in vivo levels.
Myochrysine reacts with cyanide, forming [Au(CN)2]-, which can be further displaced by amino acids to form potential active metabolites like [AuL2]-.

Conclusions:

The established polymeric structure of Myochrysine is maintained at physiologically relevant concentrations.
Capillary zone electrophoresis is a powerful and accessible technique for analyzing gold-based drugs and their metabolites.
Identified reaction products with cyanide and amino acids suggest potential metabolic pathways and active species in vivo.