Literature DB >> 23133740

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

Arthur C Rand1, 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.   

Abstract

A series of cyclic peptides were designed and prepared to investigate the physicochemical properties that affect oral bioavailabilty of this chemotype in rats. In particular, the ionization state of the peptide was examined by the incorporation of naturally occurring amino acid residues that are charged in differing regions of the gut. In addition, data was generated in a variety of in vitro assays and the usefulness of this data in predicting the subsequent oral bioavailability observed in the rat is discussed.

Entities:  

Year:  2012        PMID： 23133740      PMCID： PMC3488302          DOI： 10.1039/C2MD20203D

Source DB:  PubMed          Journal:  Medchemcomm        ISSN： 2040-2503            Impact factor:   3.597


  22 in total

1.  A hierarchical approach to all-atom protein loop prediction.

Authors:  Matthew P Jacobson; David L Pincus; Chaya S Rapp; Tyler J F Day; Barry Honig; David E Shaw; Richard A Friesner
Journal:  Proteins       Date:  2004-05-01

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.  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

Review 4.  High throughput ADME screening: practical considerations, impact on the portfolio and enabler of in silico ADME models.

Authors:  Cornelis E C A Hop; Mark J Cole; Ralph E Davidson; David B Duignan; James Federico; John S Janiszewski; Kelly Jenkins; Suzanne Krueger; Rebecca Lebowitz; Theodore E Liston; Walter Mitchell; Mark Snyder; Stefan J Steyn; John R Soglia; Christine Taylor; Matt D Troutman; John Umland; Michael West; Kevin M Whalen; Veronica Zelesky; Sabrina X Zhao
Journal:  Curr Drug Metab       Date:  2008-11       Impact factor: 3.731

5.  Molecular distributions in interphases: statistical mechanical theory combined with molecular dynamics simulation of a model lipid bilayer.

Authors:  T X Xiang; B D Anderson
Journal:  Biophys J       Date:  1994-03       Impact factor: 4.033

6.  Absorption enhancement, mechanistic and toxicity studies of medium chain fatty acids, cyclodextrins and bile salts as peroral absorption enhancers.

Authors:  Pradeep Sharma; Manthena V S Varma; Harmander P S Chawla; Ramesh Panchagnula
Journal:  Farmaco       Date:  2005-10-13

7.  The relationship between permeant size and permeability in lipid bilayer membranes.

Authors:  T X Xiang; B D Anderson
Journal:  J Membr Biol       Date:  1994-06       Impact factor: 1.843

8.  Solution structure of the luzopeptin-DNA complex.

Authors:  X L Zhang; D J Patel
Journal:  Biochemistry       Date:  1991-04-23       Impact factor: 3.162

9.  Crystal structure of human calcineurin complexed with cyclosporin A and human cyclophilin.

Authors:  Lei Jin; Stephen C Harrison
Journal:  Proc Natl Acad Sci U S A       Date:  2002-09-30       Impact factor: 11.205

10.  Phospholipid surface density determines the partitioning and permeability of acetic acid in DMPC:cholesterol bilayers.

Authors:  T X Xiang; B D Anderson
Journal:  J Membr Biol       Date:  1995-11       Impact factor: 1.843
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  22 in total

1.  Starting up and spinning out: The changing nature of partnerships between pharma and academia.

Authors:  Wudan Yan
Journal:  Nat Med       Date:  2015-09       Impact factor: 53.440

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

Authors:  Gilles H Goetz; Laurence Philippe; Michael J Shapiro
Journal:  ACS Med Chem Lett       Date:  2014-08-04       Impact factor: 4.345

Review 3.  Strategic approaches to optimizing peptide ADME properties.

Authors:  Li Di
Journal:  AAPS J       Date:  2014-11-04       Impact factor: 4.009

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

Authors:  Spiros Liras; Kim F Mcclure
Journal:  ACS Med Chem Lett       Date:  2019-06-14       Impact factor: 4.345

5.  Cyclic Penta- and Hexaleucine Peptides without N-Methylation Are Orally Absorbed.

Authors:  Timothy A Hill; Rink-Jan Lohman; Huy N Hoang; Daniel S Nielsen; Conor C G Scully; W Mei Kok; Ligong Liu; Andrew J Lucke; Martin J Stoermer; Christina I Schroeder; Stephanie Chaousis; Barbara Colless; Paul V Bernhardt; David J Edmonds; David A Griffith; Charles J Rotter; Roger B Ruggeri; David A Price; Spiros Liras; David J Craik; David P Fairlie
Journal:  ACS Med Chem Lett       Date:  2014-08-04       Impact factor: 4.345

6.  Quantifying the chameleonic properties of macrocycles and other high-molecular-weight drugs.

Authors:  Adrian Whitty; Mengqi Zhong; Lauren Viarengo; Dmitri Beglov; David R Hall; Sandor Vajda
Journal:  Drug Discov Today       Date:  2016-02-15       Impact factor: 7.851

7.  Beyond cyclosporine A: conformation-dependent passive membrane permeabilities of cyclic peptide natural products.

Authors:  Christopher L Ahlbach; Katrina W Lexa; Andrew T Bockus; Valerie Chen; Phillip Crews; Matthew P Jacobson; R Scott Lokey
Journal:  Future Med Chem       Date:  2015-06-12       Impact factor: 3.808

8.  Stereochemistry Balances Cell Permeability and Solubility in the Naturally Derived Phepropeptin Cyclic Peptides.

Authors:  Joshua Schwochert; Yongtong Lao; Cameron R Pye; Matthew R Naylor; Prashant V Desai; Isabel C Gonzalez Valcarcel; Jaclyn A Barrett; Geri Sawada; Maria-Jesus Blanco; R Scott Lokey
Journal:  ACS Med Chem Lett       Date:  2016-06-06       Impact factor: 4.345

Review 9.  Getting in shape: controlling peptide bioactivity and bioavailability using conformational constraints.

Authors:  Jonathan E Bock; Jason Gavenonis; Joshua A Kritzer
Journal:  ACS Chem Biol       Date:  2012-11-30       Impact factor: 5.100

Review 10.  Emerging Methods and Design Principles for Cell-Penetrant Peptides.

Authors:  Leila Peraro; Joshua A Kritzer
Journal:  Angew Chem Int Ed Engl       Date:  2018-08-17       Impact factor: 15.336
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