Literature DB >> 17279799

Design, synthesis, and validation of a branched flexible linker for bioactive peptides.

Martina E Bowen1, Yasunari Monguchi, Rajesh Sankaranarayanan, Josef Vagner, Lucinda J Begay, Liping Xu, Bhumasamudram Jagadish, Victor J Hruby, Robert J Gillies, Eugene A Mash.   

Abstract

A branched flexible linker that incorporates a fluorescent dansyl moiety was synthesized and used to connect two high affinity NDP-alpha-MSH ligands or two low affinity MSH(4) ligands. The linker was incorporated into the conjugate by solid-phase synthesis. In vitro biological evaluations showed that potency of binding to the human melanocortin 4 receptor was not diminished for linker-ligand combinations relative to the corresponding ligand alone.

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Year:  2007        PMID： 17279799      PMCID： PMC3538035          DOI： 10.1021/jo062276g

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  26 in total

1.  Multimeric cyclic RGD peptides as potential tools for tumor targeting: solid-phase peptide synthesis and chemoselective oxime ligation.

Authors:  Georgette Thumshirn; Ulrich Hersel; Simon L Goodman; Horst Kessler
Journal:  Chemistry       Date:  2003-06-16       Impact factor: 5.236

2.  Synthesis of rigid multivalent scaffolds based on adamantane.

Authors:  Wolfgang Maison; John V Frangioni; Nadine Pannier
Journal:  Org Lett       Date:  2004-11-25       Impact factor: 6.005

Review 3.  Hitting multiple targets with multimeric ligands.

Authors:  Heather L Handl; Josef Vagner; Haiyong Han; Eugene Mash; Victor J Hruby; Robert J Gillies
Journal:  Expert Opin Ther Targets       Date:  2004-12       Impact factor: 6.902

4.  Reductive and catalytic monoalkylation of primary amines using nitriles as an alkylating reagent.

Authors:  Hironao Sajiki; Takashi Ikawa; Kosaku Hirota
Journal:  Org Lett       Date:  2004-12-23       Impact factor: 6.005

5.  Non-natural glycosphingolipids and structurally simpler analogues bind HIV-1 recombinant Gp120.

Authors:  Katherine D McReynolds; Abhijit Bhat; John C Conboy; S Scott Saavedra; Jacquelyn Gervay-Hague
Journal:  Bioorg Med Chem       Date:  2002-03       Impact factor: 3.641

6.  Expression-driven reverse engineering of targeted imaging and therapeutic agents.

Authors:  Robert J Gillies; Victor J Hruby
Journal:  Expert Opin Ther Targets       Date:  2003-04       Impact factor: 6.902

7.  Calcium-dependent prolonged effects on melanophores of [4-norleucine, 7-D-phenylalanine]-alpha-melanotropin.

Authors:  M E Hadley; B Anderson; C B Heward; T K Sawyer; V J Hruby
Journal:  Science       Date:  1981-08-28       Impact factor: 47.728

8.  Lanthanide-based time-resolved fluorescence of in cyto ligand-receptor interactions.

Authors:  Heather L Handl; Josef Vagner; Henry I Yamamura; Victor J Hruby; Robert J Gillies
Journal:  Anal Biochem       Date:  2004-07-15       Impact factor: 3.365

9.  4-Norleucine, 7-D-phenylalanine-alpha-melanocyte-stimulating hormone: a highly potent alpha-melanotropin with ultralong biological activity.

Authors:  T K Sawyer; P J Sanfilippo; V J Hruby; M H Engel; C B Heward; J B Burnett; M E Hadley
Journal:  Proc Natl Acad Sci U S A       Date:  1980-10       Impact factor: 11.205

10.  Lipopeptides incorporated into supported phospholipid monolayers have high specific activity at low incorporation levels.

Authors:  Tor W Jensen; Bi-Huang Hu; Shara M Delatore; Ana Sofia Garcia; Phillip B Messersmith; William M Miller
Journal:  J Am Chem Soc       Date:  2004-11-24       Impact factor: 15.419
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  12 in total

1.  A sucrose-derived scaffold for multimerization of bioactive peptides.

Authors:  Venkataramanarao Rao; Ramesh Alleti; Liping Xu; Narges K Tafreshi; David L Morse; Robert J Gillies; Eugene A Mash
Journal:  Bioorg Med Chem       Date:  2011-08-27       Impact factor: 3.641

2.  Design, synthesis, and evaluation of 1,4,7,10-tetraazacyclododecane-1,4,7-triacetic acid derived, redox-sensitive contrast agents for magnetic resonance imaging.

Authors:  Natarajan Raghunand; Gerald P Guntle; Vijay Gokhale; Gary S Nichol; Eugene A Mash; Bhumasamudram Jagadish
Journal:  J Med Chem       Date:  2010-09-23       Impact factor: 7.446

3.  Heterobivalent ligands crosslink multiple cell-surface receptors: the human melanocortin-4 and delta-opioid receptors.

Authors:  Josef Vagner; Liping Xu; Heather L Handl; Jatinder S Josan; David L Morse; Eugene A Mash; Robert J Gillies; Victor J Hruby
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

Review 4.  Bench-top to clinical therapies: A review of melanocortin ligands from 1954 to 2016.

Authors:  Mark D Ericson; Cody J Lensing; Katlyn A Fleming; Katherine N Schlasner; Skye R Doering; Carrie Haskell-Luevano
Journal:  Biochim Biophys Acta Mol Basis Dis       Date:  2017-03-29       Impact factor: 5.187

5.  Synthesis and bioactivity of MSH4 oligomers prepared by an A2 + B2 strategy.

Authors:  Dilani Chathurika Dehigaspitiya; Suryakiran Navath; Craig S Weber; Ronald M Lynch; Eugene A Mash
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

6.  Developing a Biased Unmatched Bivalent Ligand (BUmBL) Design Strategy to Target the GPCR Homodimer Allosteric Signaling (cAMP over β-Arrestin 2 Recruitment) Within the Melanocortin Receptors.

Authors:  Cody J Lensing; Katie T Freeman; Sathya M Schnell; Robert C Speth; Adam T Zarth; Carrie Haskell-Luevano
Journal:  J Med Chem       Date:  2018-05-09       Impact factor: 7.446

7.  A solanesol-derived scaffold for multimerization of bioactive peptides.

Authors:  Ramesh Alleti; Venkataramanarao Rao; Liping Xu; Robert J Gillies; Eugene A Mash
Journal:  J Org Chem       Date:  2010-09-03       Impact factor: 4.354

8.  A Direct in Vivo Comparison of the Melanocortin Monovalent Agonist Ac-His-DPhe-Arg-Trp-NH2 versus the Bivalent Agonist Ac-His-DPhe-Arg-Trp-PEDG20-His-DPhe-Arg-Trp-NH2: A Bivalent Advantage.

Authors:  Cody J Lensing; Danielle N Adank; Stacey L Wilber; Katie T Freeman; Sathya M Schnell; Robert C Speth; Adam T Zarth; Carrie Haskell-Luevano
Journal:  ACS Chem Neurosci       Date:  2017-02-16       Impact factor: 4.418

9.  An in Vitro and in Vivo Investigation of Bivalent Ligands That Display Preferential Binding and Functional Activity for Different Melanocortin Receptor Homodimers.

Authors:  Cody J Lensing; Katie T Freeman; Sathya M Schnell; Danielle N Adank; Robert C Speth; Carrie Haskell-Luevano
Journal:  J Med Chem       Date:  2016-03-29       Impact factor: 7.446

10.  Synthesis of oligo(ethylene glycol) substituted phosphatidylcholines: secretory PLA2-targeted precursors of NSAID prodrugs.

Authors:  Renato Rosseto; Joseph Hajdu
Journal:  Chem Phys Lipids       Date:  2010-01       Impact factor: 3.329
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