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Alkyl and aromatic isocyanide binding to haem complexes.

M J Patel¹, R J Kassner

¹Department of Chemistry, University of Illinois, Chicago 60680.

The Biochemical Journal

|September 15, 1989

Summary

This study re-evaluates isocyanide binding to imidazole-haem complexes, finding no electronic effect for DIMPI binding. Hydrophobic effects alone do not explain the high binding affinity observed in myoglobin.

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Area of Science:

Biochemistry
Chemical Kinetics
Molecular Biophysics

Background:

Previous research suggested electronic effects influenced myoglobin's high affinity for 2,6-dimethylphenyl isocyanide (DIMPI) compared to ethyl isocyanide (EIC).
Understanding ligand binding mechanisms is crucial for protein function and drug design.

Purpose of the Study:

To determine equilibrium constants for various isocyanides binding to an imidazole-haem complex in different environments.
To re-evaluate the binding affinity of DIMPI to myoglobin and analyze the underlying factors, challenging previous electronic effect explanations.

Main Methods:

Determination of equilibrium binding constants for ethyl isocyanide (EIC), n-butyl isocyanide (BIC), p-toluenesulphonylmethyl isocyanide (TMIC), and 2,6-dimethylphenyl isocyanide (DIMPI).
Studies conducted in toluene and aqueous detergent micelle solutions using an imidazole-haem complex.
Re-measurement of the equilibrium binding constant for DIMPI to myoglobin and analysis of standard free energy of binding.

Main Results:

Binding constants for EIC, BIC, and DIMPI to the imidazole-haem complex in toluene showed similarity, contradicting earlier electronic effect hypotheses.
The measured hydrophobic effect (KDIMPI/KEIC = 11) was insufficient to explain the previously reported high binding constant of DIMPI to myoglobin.
New measurements of DIMPI-myoglobin binding constants and free energy analysis were performed based on these model system findings.

Conclusions:

The binding of DIMPI to the imidazole-haem model system is not significantly influenced by electronic effects, contrary to prior interpretations.
Hydrophobic interactions alone cannot account for the observed high affinity of DIMPI to myoglobin.
This study necessitates a re-evaluation of the factors governing DIMPI binding to myoglobin, suggesting alternative or combined mechanisms.

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