PMID: 9443343Jan 27, 1998Paper

Octanol-water partition of nonzwitterionic peptides: predictive power of a molecular size-based model

Proteins
P Buchwald, N Bodor

Abstract

A remarkably simple, molecular size-based model developed to predict octanol-water partition coefficients for organic compounds is tested on a set of 188 neutral peptides with available experimental partition data. Despite using only two parameters, it gives a promising correlation (r2 = 0.914; sigma = 0.455, F = 1978.0), and predictions are in a realistic range even for larger peptides (cyclosporin, melanotan, sandostatin) where common, overparametrized fragment methods become quite unreliable. Ion-pair partitioning and the extraction constant formalism is briefly reviewed to describe the sigmoidal lipophilicity profile of ionizable, nonzwitterionic peptides. It seems possible to extend the present model to estimate apparent partition coefficients measured around neutral pH and physiological conditions for monoionic peptides; however, as no standard conditions are yet defined and only relatively small number of experimental data are available, the situation here is more complex.

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Citations

Oct 16, 1999·Journal of Controlled Release : Official Journal of the Controlled Release Society·N Bodor
Feb 18, 2005·NeuroRx : the Journal of the American Society for Experimental NeuroTherapeutics·Richard D Egleton, Thomas P Davis
Feb 5, 2013·Proceedings of the National Academy of Sciences of the United States of America·Sehan LeeKyoung Tai No
Feb 14, 2009·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Katalin Prokai-Tatrai, Laszlo Prokai
Jul 1, 2007·Expert Opinion on Drug Discovery·Peter Buchwald
Oct 4, 2005·Journal of Pharmaceutical Sciences·Peter Buchwald
Apr 28, 2009·Progress in Neurobiology·Ivona BrasnjevicUNKNOWN European NanoBioPharmaceutics Research Initiative
Nov 18, 2006·Applied Radiation and Isotopes : Including Data, Instrumentation and Methods for Use in Agriculture, Industry and Medicine·T ErtayH Durak
Feb 23, 2007·Chemical Biology & Drug Design·John J LoweryRobin Polt
May 19, 2011·Environmental Toxicology and Chemistry·Rikke Gleerup OvesenHans Christian Bruun Hansen
Apr 1, 2005·Applied Radiation and Isotopes : Including Data, Instrumentation and Methods for Use in Agriculture, Industry and Medicine·T ErtayH Durak
Jul 27, 1999·Current Opinion in Chemical Biology·D A Smith, H van de Waterbeemd
Jan 5, 2002·Journal of Receptor and Signal Transduction Research·N Bodor, P Buchwald
Jun 14, 2005·British Journal of Pharmacology·Joost BartN Harry Hendrikse
Aug 24, 2001·The Journal of Pharmacy and Pharmacology·P Buchwald, N Bodor
Dec 23, 1999·Medicinal Research Reviews·N Bodor, P Buchwald
Jun 3, 2004·Clinical Cancer Research : an Official Journal of the American Association for Cancer Research·Margret SchotteliusHans-Jürgen Wester
Aug 30, 2008·Biomacromolecules·Harald Nuhn, Harm-Anton Klok
May 31, 2008·Bioconjugate Chemistry·Margret SchotteliusHans-Jürgen Wester
May 31, 2021·The Science of the Total Environment·Anne Sofie Bruun RasmussenSteffen Foss Hansen
Oct 7, 2017·The Journal of Physical Chemistry. B·Chenyu Wei, Andrew Pohorille
Feb 12, 2019·The Journal of Physical Chemistry Letters·William J ZamoraF Javier Luque

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