Multivalent fertilinbeta oligopeptides: the dependence of fertilization inhibition on length and density.

Chemistry & Biology
Keith A BaesslerN S Sampson

Abstract

The sperm protein fertilinbeta, a member of the ADAM family of proteins, is implicated in sperm-egg binding in all mammals studied to date. Multivalent inhibitors containing the three amino acid binding sequence of fertilinbeta, ECD, have been shown previously to be more effective inhibitors of fertilization than their monovalent counterparts. Here, we probed sperm-egg interactions with ruthenium-catalyzed ring-opening metathesis polymers that contained from 3 to 70 ECD pharmacophores in densities ranging from 10% to 100%. Evaluation of the polymer potencies, and synthesis of a triblock copolymer from two building blocks, revealed that two multivalent contacts are sufficient for maximal inhibition, and that the distance between ECD pharmacophores required is 7-9 monomers spanning 4-5 nm. We conclude that inhibition requires recruitment of two receptors on the egg surface into an inhibitory complex.

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Citations

Apr 3, 2009·ACS Chemical Biology·Keith A BaesslerNicole S Sampson
Jul 10, 2010·Journal of the American Chemical Society·Airong SongNicole S Sampson
Sep 1, 2007·Science·Kristi L Kiick
Feb 26, 2016·Accounts of Chemical Research·Kathlyn A Parker, Nicole S Sampson
Jun 20, 2006·Current Opinion in Structural Biology·Younjoo Lee, Nicole S Sampson
Nov 28, 2006·Advanced Drug Delivery Reviews·Monzur Ali, Steve Brocchini
Jul 17, 2007·Journal of Peptide Science : an Official Publication of the European Peptide Society·Oscar Vadas, Keith Rose
Feb 21, 2009·Chembiochem : a European Journal of Chemical Biology·Younjoo Lee, Nicole S Sampson
Jan 13, 2009·Macromolecules·Shuang LiuKristi L Kiick
Apr 6, 2006·Journal of the American Chemical Society·Jae Chul LeeNicole S Sampson

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