Literature DB >> 19635667

Semi-rigid tripeptide agonists of melanocortin receptors.

Andrew R Ruwe1, Leonid Koikov, Zalfa Abdel-Malek, Carrie Haskell-Luevano, Marvin L Dirain, Federico Portillo, Zhimin Xiang, Matt Wortman, James J Knittel.   

Abstract

A series of 30 RCO-HfR-NH(2) derivatives show preference for the mouse MC1R vs MC3-5Rs. trans-4-HOC(6)H(4)CH=CHCO-HfR-NH(2) (13) [EC(50) (nM): MC1R 83, MC3R 20500, MC4R 18130 and MC5R 935; ratio 1:246:217:11] is 11 times more potent than the lead compound LK-394 Ph(CH(2))(3)CO-HfR-NH(2) (2) and only 11 times less potent than the native tridecapeptide alpha-MSH at mMC1R. Differences in conformations of 2 and 13 are discussed.

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Year:  2009        PMID： 19635667      PMCID： PMC2758050          DOI： 10.1016/j.bmcl.2009.07.025

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  25 in total

Review 1.  Melanocortin receptors: their functions and regulation by physiological agonists and antagonists.

Authors:  Z A Abdel-Malek
Journal:  Cell Mol Life Sci       Date:  2001-03       Impact factor: 9.261

Review 2.  Melanocortin ligands: 30 years of structure-activity relationship (SAR) studies.

Authors:  Jerry Ryan Holder; Carrie Haskell-Luevano
Journal:  Med Res Rev       Date:  2004-05       Impact factor: 12.944

3.  alpha-Melanotropin: the minimal active sequence in the frog skin bioassay.

Authors:  V J Hruby; B C Wilkes; M E Hadley; F Al-Obeidi; T K Sawyer; D J Staples; A E de Vaux; O Dym; A M Castrucci; M F Hintz
Journal:  J Med Chem       Date:  1987-11       Impact factor: 7.446

4.  Structure-activity relationships of the melanocortin tetrapeptide Ac-His-D-Phe-Arg-Trp-NH2 at the mouse melanocortin receptors. 4. Modifications at the Trp position.

Authors:  Jerry Ryan Holder; Zhimin Xiang; Rayna M Bauzo; Carrie Haskell-Luevano
Journal:  J Med Chem       Date:  2002-12-19       Impact factor: 7.446

5.  Compounds that activate the mouse melanocortin-1 receptor identified by screening a small molecule library based upon the beta-turn.

Authors:  C Haskell-Luevano; A Rosenquist; A Souers; K C Khong; J A Ellman; R D Cone
Journal:  J Med Chem       Date:  1999-10-21       Impact factor: 7.446

6.  Characterization of melanocortin NDP-MSH agonist peptide fragments at the mouse central and peripheral melanocortin receptors.

Authors:  C Haskell-Luevano; J R Holder; E K Monck; R M Bauzo
Journal:  J Med Chem       Date:  2001-06-21       Impact factor: 7.446

7.  Molecular determinants of melanocortin 4 receptor ligand binding and MC4/MC3 receptor selectivity.

Authors:  Sarah A Nickolls; Mary I Cismowski; Xiaochuan Wang; Meira Wolff; Paul J Conlon; Richard A Maki
Journal:  J Pharmacol Exp Ther       Date:  2003-03       Impact factor: 4.030

8.  Sub-nanomolar hMC1R agonists by end-capping of the melanocortin tetrapeptide His-D-Phe-Arg-Trp-NH(2).

Authors:  L N Koikov; F H Ebetino; M G Solinsky; D Cross-Doersen; J J Knittel
Journal:  Bioorg Med Chem Lett       Date:  2003-08-18       Impact factor: 2.823

9.  Synthesis and biological evaluation of alpha-MSH analogues substituted with alanine.

Authors:  U G Sahm; G W Olivier; S K Branch; S H Moss; C W Pouton
Journal:  Peptides       Date:  1994       Impact factor: 3.750

10.  The melanocortin (MC3) receptor from rat hypothalamus: photoaffinity labelling and binding of alanine-substituted alpha-MSH analogues.

Authors:  U G Sahm; M A Qarawi; G W Olivier; A R Ahmed; S K Branch; S H Moss; C W Pouton
Journal:  FEBS Lett       Date:  1994-08-15       Impact factor: 4.124
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  3 in total

Review 1.  Paracrine regulation of melanocyte genomic stability: a focus on nucleotide excision repair.

Authors:  Stuart Gordon Jarrett; Katharine Marie Carter; John August D'Orazio
Journal:  Pigment Cell Melanoma Res       Date:  2017-04-20       Impact factor: 4.693

Review 2.  Pharmacologic manipulation of skin pigmentation.

Authors:  Gabriel H Kindl; John A D'Orazio
Journal:  Pigment Cell Melanoma Res       Date:  2021-03-12       Impact factor: 4.159

Review 3.  UV radiation and the skin.

Authors:  John D'Orazio; Stuart Jarrett; Alexandra Amaro-Ortiz; Timothy Scott
Journal:  Int J Mol Sci       Date:  2013-06-07       Impact factor: 5.923
  3 in total

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