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Title: Log D versus HPLC derived hydrophobicity: The development of predictive tools to aid in the rational design of bioactive peptoids

Hydrophobicity has proven to be an extremely useful parameter in small molecule drug discovery programmes given that it can be used as a predictive tool to enable rational design. For larger molecules, including peptoids, where folding is possible, the situation is more complicated and the average hydrophobicity (as determined by RP-HPLC retention time) may not always provide an effective predictive tool for rational design. Herein, we report the first ever application of partitioning experiments to determine the log D values for a series of peptoids. By comparing log D and average hydrophobicities we highlight the potential advantage of employing the former as a predictive tool in the rational design of biologically active peptoids.
Authors:
 [1] ;  [1] ;  [1] ;  [2] ;  [1] ;  [1]
  1. Durham Univ., Durham (United Kingdom)
  2. Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
Publication Date:
Grant/Contract Number:
AC02-05CH11231
Type:
Published Article
Journal Name:
Biopolymers
Additional Journal Information:
Journal Volume: 108; Journal Issue: 4; Journal ID: ISSN 0006-3525
Publisher:
Wiley
Research Org:
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
Sponsoring Org:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
Country of Publication:
United States
Language:
English
Subject:
59 BASIC BIOLOGICAL SCIENCES; 60 APPLIED LIFE SCIENCES
OSTI Identifier:
1366313
Alternate Identifier(s):
OSTI ID: 1366314; OSTI ID: 1409436

Bolt, H. L., Williams, C. E. J., Brooks, R. V., Zuckermann, R. N., Cobb, S. L., and Bromley, E. H. C.. Log D versus HPLC derived hydrophobicity: The development of predictive tools to aid in the rational design of bioactive peptoids. United States: N. p., Web. doi:10.1002/bip.23014.
Bolt, H. L., Williams, C. E. J., Brooks, R. V., Zuckermann, R. N., Cobb, S. L., & Bromley, E. H. C.. Log D versus HPLC derived hydrophobicity: The development of predictive tools to aid in the rational design of bioactive peptoids. United States. doi:10.1002/bip.23014.
Bolt, H. L., Williams, C. E. J., Brooks, R. V., Zuckermann, R. N., Cobb, S. L., and Bromley, E. H. C.. 2017. "Log D versus HPLC derived hydrophobicity: The development of predictive tools to aid in the rational design of bioactive peptoids". United States. doi:10.1002/bip.23014.
@article{osti_1366313,
title = {Log D versus HPLC derived hydrophobicity: The development of predictive tools to aid in the rational design of bioactive peptoids},
author = {Bolt, H. L. and Williams, C. E. J. and Brooks, R. V. and Zuckermann, R. N. and Cobb, S. L. and Bromley, E. H. C.},
abstractNote = {Hydrophobicity has proven to be an extremely useful parameter in small molecule drug discovery programmes given that it can be used as a predictive tool to enable rational design. For larger molecules, including peptoids, where folding is possible, the situation is more complicated and the average hydrophobicity (as determined by RP-HPLC retention time) may not always provide an effective predictive tool for rational design. Herein, we report the first ever application of partitioning experiments to determine the log D values for a series of peptoids. By comparing log D and average hydrophobicities we highlight the potential advantage of employing the former as a predictive tool in the rational design of biologically active peptoids.},
doi = {10.1002/bip.23014},
journal = {Biopolymers},
number = 4,
volume = 108,
place = {United States},
year = {2017},
month = {1}
}

Works referenced in this record:

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journal, November 2000
  • Wender, P. A.; Mitchell, D. J.; Pattabiraman, K.
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Structural and Spectroscopic Studies of Peptoid Oligomers with α-Chiral Aliphatic Side Chains
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