Literature DB >> 16183278

Synthesis of desthio prenylcysteine analogs: sulfur is important for biological activity.

Brian S Henriksen1, Jessica L Anderson, Christine A Hrycyna, Richard A Gibbs.   

Abstract

N-Acetyl-S-farnesyl cysteine (AFC) is the minimal synthetic substrate for the enzyme Icmt, which methylates prenylated proteins. The desthio-AFC isostere 2 has been synthesized in racemic form. This analog was not an Icmt substrate, but instead a weak inhibitor with an IC50 of approximately 325 microM.

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Year:  2005        PMID： 16183278      PMCID： PMC3401638          DOI： 10.1016/j.bmcl.2005.07.075

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


  19 in total

Review 1.  Farnesyltransferase inhibitors: an overview of the results of preclinical and clinical investigations.

Authors:  Thomas B Brunner; Stephen M Hahn; Anjali K Gupta; Ruth J Muschel; W Gillies McKenna; Eric J Bernhard
Journal:  Cancer Res       Date:  2003-09-15       Impact factor: 12.701

2.  Crystallographic analysis of CaaX prenyltransferases complexed with substrates defines rules of protein substrate selectivity.

Authors:  T Scott Reid; Kimberly L Terry; Patrick J Casey; Lorena S Beese
Journal:  J Mol Biol       Date:  2004-10-15       Impact factor: 5.469

3.  Purification, functional reconstitution, and characterization of the Saccharomyces cerevisiae isoprenylcysteine carboxylmethyltransferase Ste14p.

Authors:  Jessica L Anderson; Hilary Frase; Susan Michaelis; Christine A Hrycyna
Journal:  J Biol Chem       Date:  2004-12-20       Impact factor: 5.157

Review 4.  Synthesis of prenylated peptides and peptide esters.

Authors:  F R Naider; J M Becker
Journal:  Biopolymers       Date:  1997       Impact factor: 2.505

5.  Geranylgeranyl switching regulates GDI-Rab GTPase recycling.

Authors:  Yu An; Ying Shao; Christelle Alory; Jeanne Matteson; Toshiaki Sakisaka; Wei Chen; Richard A Gibbs; Ian A Wilson; William E Balch
Journal:  Structure       Date:  2003-03       Impact factor: 5.006

6.  Farnesyl cysteine C-terminal methyltransferase activity is dependent upon the STE14 gene product in Saccharomyces cerevisiae.

Authors:  C A Hrycyna; S Clarke
Journal:  Mol Cell Biol       Date:  1990-10       Impact factor: 4.272

7.  Investigation of the nature of the methionine-pi interaction in beta-hairpin peptide model systems.

Authors:  Chad D Tatko; Marcey L Waters
Journal:  Protein Sci       Date:  2004-09       Impact factor: 6.725

8.  S-oxidative cleavage of farnesylcysteine and farnesylcysteine methyl ester by the flavin-containing monooxygenase.

Authors:  S B Park; W N Howald; J R Cashman
Journal:  Chem Res Toxicol       Date:  1994 Mar-Apr       Impact factor: 3.739

9.  Identifying the recognition unit for G protein methylation.

Authors:  E W Tan; D Pérez-Sala; F J Cañada; R R Rando
Journal:  J Biol Chem       Date:  1991-06-15       Impact factor: 5.157

10.  The Saccharomyces cerevisiae STE14 gene encodes a methyltransferase that mediates C-terminal methylation of a-factor and RAS proteins.

Authors:  C A Hrycyna; S K Sapperstein; S Clarke; S Michaelis
Journal:  EMBO J       Date:  1991-07       Impact factor: 11.598
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  6 in total

1.  Amide-modified prenylcysteine based Icmt inhibitors: Structure-activity relationships, kinetic analysis and cellular characterization.

Authors:  Jaimeen D Majmudar; Heather B Hodges-Loaiza; Kalub Hahne; James L Donelson; Jiao Song; Liza Shrestha; Marietta L Harrison; Christine A Hrycyna; Richard A Gibbs
Journal:  Bioorg Med Chem       Date:  2011-11-06       Impact factor: 3.641

2.  S-Farnesyl-Thiopropionic Acid (FTPA) Triazoles as Potent Inhibitors of Isoprenylcysteine Carboxyl Methyltransferase.

Authors:  Joel A Bergman; Kalub Hahne; Jiao Song; Christine A Hrycyna; Richard A Gibbs
Journal:  ACS Med Chem Lett       Date:  2011-11-28       Impact factor: 4.345

3.  Synthesis of Non-natural, Frame-Shifted Isoprenoid Diphosphate Analogues.

Authors:  Kayla J Temple; Elia N Wright; Carol A Fierke; Richard A Gibbs
Journal:  Org Lett       Date:  2016-11-14       Impact factor: 6.005

4.  Quantitative structure-activity relationship (QSAR) of indoloacetamides as inhibitors of human isoprenylcysteine carboxyl methyltransferase.

Authors:  Jo-Lene Leow; Rudi Baron; Patrick J Casey; Mei-Lin Go
Journal:  Bioorg Med Chem Lett       Date:  2006-11-15       Impact factor: 2.823

5.  Lipid and sulfur substituted prenylcysteine analogs as human Icmt inhibitors.

Authors:  Joel A Bergman; Kalub Hahne; Christine A Hrycyna; Richard A Gibbs
Journal:  Bioorg Med Chem Lett       Date:  2011-06-21       Impact factor: 2.823

Review 6.  Isoprenyl carboxyl methyltransferase inhibitors: a brief review including recent patents.

Authors:  Woo Seok Yang; Seung-Gu Yeo; Sungjae Yang; Kyung-Hee Kim; Byong Chul Yoo; Jae Youl Cho
Journal:  Amino Acids       Date:  2017-06-19       Impact factor: 3.520
  6 in total

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