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Literature DB >> 25313332

EPSA: A Novel Supercritical Fluid Chromatography Technique Enabling the Design of Permeable Cyclic Peptides.

Gilles H Goetz¹, Laurence Philippe¹, Michael J Shapiro¹.

Abstract

Most peptides are generally insufficiently permeable to be used as oral drugs. Designing peptides with improved permeability without reliable permeability monitoring is a challenge. We have developed a supercritical fluid chromatography technique for peptides, termed EPSA, which is shown here to enable improved permeability design. Through assessing the exposed polarity of a peptide, this technique can be used as a permeability surrogate.

Entities: Chemical Disease

Keywords: EPSA; cyclic peptides; intramolecular hydrogen bonding; permeability; polarity

Year: 2014 PMID： 25313332 PMCID： PMC4190640 DOI： 10.1021/ml500239m

Source DB: PubMed Journal: ACS Med Chem Lett ISSN： 1948-5875 Impact factor: 4.345

25 in total

1. ElogD(oct): a tool for lipophilicity determination in drug discovery. 2. Basic and neutral compounds.

Authors: F Lombardo; M Y Shalaeva; K A Tupper; F Gao
Journal: J Med Chem Date: 2001-07-19 Impact factor: 7.446

2. Intestinal permeability of cyclic peptides: common key backbone motifs identified.

Authors: Johannes G Beck; Jayanta Chatterjee; Burkhardt Laufer; Marelli Udaya Kiran; Andreas O Frank; Stefanie Neubauer; Oded Ovadia; Sarit Greenberg; Chaim Gilon; Amnon Hoffman; Horst Kessler
Journal: J Am Chem Soc Date: 2012-07-12 Impact factor: 15.419

3. Epithelial transport of drugs in cell culture. II: Effect of extracellular calcium concentration on the paracellular transport of drugs of different lipophilicities across monolayers of intestinal epithelial (Caco-2) cells.

Authors: P Artursson; C Magnusson
Journal: J Pharm Sci Date: 1990-07 Impact factor: 3.534

4. Caco-2 permeability of weakly basic drugs predicted with the double-sink PAMPA pKa(flux) method.

Authors: Alex Avdeef; Per Artursson; Sibylle Neuhoff; Lucia Lazorova; Johan Gråsjö; Staffan Tavelin
Journal: Eur J Pharm Sci Date: 2005-01-20 Impact factor: 4.384

5. Conformational flexibility, internal hydrogen bonding, and passive membrane permeability: successful in silico prediction of the relative permeabilities of cyclic peptides.

Authors: Taha Rezai; Jonathan E Bock; Mai V Zhou; Chakrapani Kalyanaraman; R Scott Lokey; Matthew P Jacobson
Journal: J Am Chem Soc Date: 2006-11-01 Impact factor: 15.419

6. Optimizing PK properties of cyclic peptides: the effect of side chain substitutions on permeability and clearance().

Authors: Arthur C Rand; Siegfried S F Leung; Heather Eng; Charles J Rotter; Raman Sharma; Amit S Kalgutkar; Yizhong Zhang; Manthena V Varma; Kathleen A Farley; Bhagyashree Khunte; Chris Limberakis; David A Price; Spiros Liras; Alan M Mathiowetz; Matthew P Jacobson; R Scott Lokey
Journal: Medchemcomm Date: 2012-10 Impact factor: 3.597

7. The effect of multiple N-methylation on intestinal permeability of cyclic hexapeptides.

Authors: Oded Ovadia; Sarit Greenberg; Jayanta Chatterjee; Burkhardt Laufer; Florian Opperer; Horst Kessler; Chaim Gilon; Amnon Hoffman
Journal: Mol Pharm Date: 2011-03-21 Impact factor: 4.939

Review 8. The rise of PAMPA.

Authors: Alex Avdeef
Journal: Expert Opin Drug Metab Toxicol Date: 2005-08 Impact factor: 4.481

9. N-methylation of peptides: a new perspective in medicinal chemistry.

Authors: Jayanta Chatterjee; Chaim Gilon; Amnon Hoffman; Horst Kessler
Journal: Acc Chem Res Date: 2008-07-18 Impact factor: 22.384

10. Epithelial transport of drugs in cell culture. I: A model for studying the passive diffusion of drugs over intestinal absorptive (Caco-2) cells.

Authors: P Artursson
Journal: J Pharm Sci Date: 1990-06 Impact factor: 3.534

22 in total

9. Steering New Drug Discovery Campaigns: Permeability, Solubility, and Physicochemical Properties in the bRo5 Chemical Space.

Authors: Giulia Caron; Jan Kihlberg; Gilles Goetz; Ekaterina Ratkova; Vasanthanathan Poongavanam; Giuseppe Ermondi
Journal: ACS Med Chem Lett Date: 2021-01-05 Impact factor: 4.345

Review 10. Improvement on Permeability of Cyclic Peptide/Peptidomimetic: Backbone N-Methylation as A Useful Tool.

Authors: Yang Li; Wang Li; Zhengshuang Xu
Journal: Mar Drugs Date: 2021-05-27 Impact factor: 5.118

EPSA: A Novel Supercritical Fluid Chromatography Technique Enabling the Design of Permeable Cyclic Peptides.

1. ElogD(oct): a tool for lipophilicity determination in drug discovery. 2. Basic and neutral compounds.

2. Intestinal permeability of cyclic peptides: common key backbone motifs identified.

3. Epithelial transport of drugs in cell culture. II: Effect of extracellular calcium concentration on the paracellular transport of drugs of different lipophilicities across monolayers of intestinal epithelial (Caco-2) cells.

4. Caco-2 permeability of weakly basic drugs predicted with the double-sink PAMPA pKa(flux) method.

5. Conformational flexibility, internal hydrogen bonding, and passive membrane permeability: successful in silico prediction of the relative permeabilities of cyclic peptides.

6. Optimizing PK properties of cyclic peptides: the effect of side chain substitutions on permeability and clearance().

7. The effect of multiple N-methylation on intestinal permeability of cyclic hexapeptides.

Review 8. The rise of PAMPA.

9. N-methylation of peptides: a new perspective in medicinal chemistry.

10. Epithelial transport of drugs in cell culture. I: A model for studying the passive diffusion of drugs over intestinal absorptive (Caco-2) cells.

1. Development of a Platform To Enable Efficient Permeability Evaluation of Novel Organo-Peptide Macrocycles.

2. Permeability of Cyclic Peptide Macrocycles and Cyclotides and Their Potential as Therapeutics.

3. ACS Medicinal Chemistry Letters: Technology Notes.

Review 4. Macrocycles as protein-protein interaction inhibitors.

5. Understanding Cell Penetration of Cyclic Peptides.

6. A Retrospective Look at the Impact of Binding Site Environment on the Optimization of TRPA1 Antagonists.

Review 7. High throughput methods to measure the propensity of compounds to form intramolecular hydrogen bonding.

Review 8. Emerging Methods and Design Principles for Cell-Penetrant Peptides.

9. Steering New Drug Discovery Campaigns: Permeability, Solubility, and Physicochemical Properties in the bRo5 Chemical Space.

Review 10. Improvement on Permeability of Cyclic Peptide/Peptidomimetic: Backbone N-Methylation as A Useful Tool.