Effects of hydrophobic helix length and side chain chemistry on biomimicry in peptoid analogues of SP-C

Biochemistry
Nathan J BrownAnnelise E Barron

Abstract

The hydrophobic proteins of lung surfactant (LS), SP-B and SP-C, are critical constituents of an effective surfactant replacement therapy for the treatment of respiratory distress syndrome. Because of concerns and difficulties associated with animal-derived surfactants, recent investigations have focused on the creation of synthetic analogues of the LS proteins. However, creating an accurate mimic of SP-C that retains its biophysical surface activity is extraordinarily challenging given the lipopeptide's extreme hydrophobicity and propensity to misfold and aggregate. One successful approach that overcomes these difficulties is the use of poly-N-substituted glycines, or peptoids, to mimic SP-C. To develop a non-natural, bioactive mimic of SP-C and to investigate the effects of side chain chemistry and length of the helical hydrophobic region, we synthesized, purified, and performed in vitro testing of two classes of peptoid SP-C mimics: those having a rigid alpha-chiral aromatic helix and those having a biomimetic alpha-chiral aliphatic helix. The length of the two classes of mimics was also systematically altered. Circular dichroism spectroscopy gave evidence that all of the peptoid-based mimics studied here emulated SP-C's sec...Continue Reading

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Citations

Oct 7, 2008·Accounts of Chemical Research·Nathan J BrownAnnelise E Barron
May 21, 2010·Journal of the American Chemical Society·Michelle T DohmAnnelise E Barron
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Sep 6, 2011·Biophysical Journal·Nathan J BrownAnnelise E Barron
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