Literature DB >> 18950150

Influence of selective fluorination on the biological activity and proteolytic stability of glucagon-like peptide-1.

He Meng1, Subrahmanian Tarakkad Krishnaji, Martin Beinborn, Krishna Kumar.   

Abstract

The relative simplicity and high specificity of peptide therapeutics has fueled recent interest. However, peptide and protein drugs generally require injection and suffer from low metabolic stability. We report here the design, synthesis, and characterization of fluorinated analogues of the gut hormone peptide, GLP-1. Overall, fluorinated GLP-1 analogues displayed higher proteolytic stability with simultaneous retention of biological activity (efficacy). Fluorinated amino acids are useful for engineering peptide drug candidates and probing ligand-receptor interactions.

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Year:  2008        PMID： 18950150      PMCID： PMC2645917          DOI： 10.1021/jm8008579

Source DB:  PubMed          Journal:  J Med Chem        ISSN： 0022-2623            Impact factor:   7.446


  41 in total

1.  The positive charge of the imidazole side chain of histidine7 is crucial for GLP-1 action.

Authors:  A Hareter; E Hoffmann; H P Bode; B Göke; R Göke
Journal:  Endocr J       Date:  1997-10       Impact factor: 2.349

2.  Inhibition of dipeptidyl aminopeptidase IV (DP-IV) by Xaa-boroPro dipeptides and use of these inhibitors to examine the role of DP-IV in T-cell function.

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Journal:  Proc Natl Acad Sci U S A       Date:  1991-02-15       Impact factor: 11.205

3.  Exendin-4 is a high potency agonist and truncated exendin-(9-39)-amide an antagonist at the glucagon-like peptide 1-(7-36)-amide receptor of insulin-secreting beta-cells.

Authors:  R Göke; H C Fehmann; T Linn; H Schmidt; M Krause; J Eng; B Göke
Journal:  J Biol Chem       Date:  1993-09-15       Impact factor: 5.157

4.  Both subcutaneously and intravenously administered glucagon-like peptide I are rapidly degraded from the NH2-terminus in type II diabetic patients and in healthy subjects.

Authors:  C F Deacon; M A Nauck; M Toft-Nielsen; L Pridal; B Willms; J J Holst
Journal:  Diabetes       Date:  1995-09       Impact factor: 9.461

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Authors:  K Thornton; D G Gorenstein
Journal:  Biochemistry       Date:  1994-03-29       Impact factor: 3.162

6.  Cloning and functional expression of the human glucagon-like peptide-1 (GLP-1) receptor.

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Journal:  Endocrinology       Date:  1993-10       Impact factor: 4.736

7.  Novel dipeptidyl peptidase IV resistant analogues of glucagon-like peptide-1(7-36)amide have preserved biological activities in vitro conferring improved glucose-lowering action in vivo.

Authors:  B D Green; V A Gault; M H Mooney; N Irwin; C J Bailey; P Harriott; B Greer; P R Flatt; F P M O'Harte
Journal:  J Mol Endocrinol       Date:  2003-12       Impact factor: 5.098

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Authors:  W H Vine; K H Hsieh; G R Marshall
Journal:  J Med Chem       Date:  1981-09       Impact factor: 7.446

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Authors:  K Adelhorst; B B Hedegaard; L B Knudsen; O Kirk
Journal:  J Biol Chem       Date:  1994-03-04       Impact factor: 5.157

Review 10.  Prozac (fluoxetine, Lilly 110140), the first selective serotonin uptake inhibitor and an antidepressant drug: twenty years since its first publication.

Authors:  D T Wong; F P Bymaster; E A Engleman
Journal:  Life Sci       Date:  1995       Impact factor: 5.037
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  14 in total

Review 1.  Fluorine: a new element in protein design.

Authors:  Benjamin C Buer; E Neil G Marsh
Journal:  Protein Sci       Date:  2012-02-14       Impact factor: 6.725

2.  Impact of Substitution Registry on the Receptor-Activation Profiles of Backbone-Modified Glucagon-like Peptide-1 Analogues.

Authors:  Brian P Cary; Marlies V Hager; Samuel H Gellman
Journal:  Chembiochem       Date:  2019-09-20       Impact factor: 3.164

3.  Comparison of the structures and stabilities of coiled-coil proteins containing hexafluoroleucine and t-butylalanine provides insight into the stabilizing effects of highly fluorinated amino acid side-chains.

Authors:  Benjamin C Buer; Jennifer L Meagher; Jeanne A Stuckey; E Neil G Marsh
Journal:  Protein Sci       Date:  2012-10-01       Impact factor: 6.725

4.  O-GlcNAc Engineering of GPCR Peptide-Agonists Improves Their Stability and in Vivo Activity.

Authors:  Paul M Levine; Aaron T Balana; Emmanuel Sturchler; Cassandra Koole; Hiroshi Noda; Barbara Zarzycka; Eileen J Daley; Tin T Truong; Vsevolod Katritch; Thomas J Gardella; Denise Wootten; Patrick M Sexton; Patricia McDonald; Matthew R Pratt
Journal:  J Am Chem Soc       Date:  2019-08-28       Impact factor: 15.419

5.  A New Paradigm for Protein Design and Biological Self-Assembly.

Authors:  Gizem Akçay; Krishna Kumar
Journal:  J Fluor Chem       Date:  2009-12-01       Impact factor: 2.050

6.  Cross-strand interactions of fluorinated amino acids in β-hairpin constructs.

Authors:  Ginevra A Clark; James D Baleja; Krishna Kumar
Journal:  J Am Chem Soc       Date:  2012-10-18       Impact factor: 15.419

7.  Colocalization of the ganglioside G(M1) and cholesterol detected by secondary ion mass spectrometry.

Authors:  Mónica M Lozano; Zhao Liu; Eva Sunnick; Andreas Janshoff; Krishna Kumar; Steven G Boxer
Journal:  J Am Chem Soc       Date:  2013-04-03       Impact factor: 15.419

8.  Glucagon-like peptide-1 (GLP-1) analogs: recent advances, new possibilities, and therapeutic implications.

Authors:  Bikash Manandhar; Jung-Mo Ahn
Journal:  J Med Chem       Date:  2014-11-13       Impact factor: 7.446

9.  Position-dependent impact of hexafluoroleucine and trifluoroisoleucine on protease digestion.

Authors:  Susanne Huhmann; Anne-Katrin Stegemann; Kristin Folmert; Damian Klemczak; Johann Moschner; Michelle Kube; Beate Koksch
Journal:  Beilstein J Org Chem       Date:  2017-12-22       Impact factor: 2.883

10.  Ureidopeptide GLP-1 analogues with prolonged activity in vivo via signal bias and altered receptor trafficking.

Authors:  Juliette Fremaux; Claire Venin; Laura Mauran; Robert Zimmer; Florian Koensgen; Didier Rognan; Stavroula Bitsi; Maria A Lucey; Ben Jones; Alejandra Tomas; Gilles Guichard; Sébastien R Goudreau
Journal:  Chem Sci       Date:  2019-09-11       Impact factor: 9.825
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