Alkyne-Bridged α-Conotoxin Vc1.1 Potently Reverses Mechanical Allodynia in Neuropathic Pain Models

Authors

Alessia Belgi, James V. Burnley, Christopher A. MacRaild, Sandeep Chhabra, Khaled A. Elnahriry, Samuel D. Robinson, Simon G. Gooding, Han-Shen Tae, Peter Bartels, Mahsa Sadeghi, Fei-Yue Zhao, Haifeng Wei, David Spanswick, David J. Adams, Ray S. Norton, Andrea. J. Robinson

Published Journal of Medicinal Chemistry
Graphical abstract  
Abstract

Several Conus-derived venom peptides are promising lead compounds for the management of neuropathic pain, with α-conotoxins being of particular interest. Modification of the interlocked disulfide framework of α-conotoxin Vc1.1 has been achieved using on-resin alkyne metathesis. Although introduction of a metabolically stable alkyne motif significantly disrupts backbone topography, the structural modification generates a potent and selective GABAB receptor agonist that inhibits Cav2.2 channels and exhibits dose-dependent reversal of mechanical allodynia in a behavioral rat model of neuropathic pain. The findings herein support the hypothesis that analgesia can be achieved via activation of GABABRs expressed in dorsal root ganglion (DRG) sensory neurons.

Citation

A. Belgi, J. V. Burnley, C. A. MacRaild, S. Chhabra, K. A. Elnahriry, S. D. Robinson, S. G. Gooding, H. S. Tae, P. Bartels, M. Sadeghi, F. Y. Zhao, H. Wei, D. Spanswick, D. J. Adams, R. S. Norton, A. J. Robinson, “Alkyne-Bridged α-Conotoxin Vc1.1 Potently Reverses Mechanical Allodynia in Neuropathic Pain Models”, J. Med. Chem., 2021, 64(6), 3233-3233.

Pdf  
Doi

https://doi.org/10.1021/acs.jmedchem.0c02151

Subjects

Hydrocarbons, Peptides and proteins, Organic polymers, Catalysts, Conformation

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