Literature DB >> 16777414

Amide-substituted farnesylcysteine analogs as inhibitors of human isoprenylcysteine carboxyl methyltransferase.

James L Donelson1, Heather B Hodges, Daniel D Macdougall, Brian S Henriksen, Christine A Hrycyna, Richard A Gibbs.   

Abstract

N-Acetyl-S-farnesyl-L-cysteine (AFC) is the minimal substrate for the enzyme isoprenylcysteine carboxyl methyltransferase (Icmt). A series of amide-modified farnesylcysteine analogs were synthesized and screened against human Icmt. From a 23-membered library of compounds, six inhibitors were identified and evaluated further. The adamantyl derivative 7c was the most potent inhibitor with an IC(50) of 12.4 microM.

Entities:  

Mesh：

Substances：

Year:  2006        PMID： 16777414      PMCID： PMC3401632          DOI： 10.1016/j.bmcl.2006.05.029

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


  18 in total

1.  Dual protein farnesyltransferase-geranylgeranyltransferase-I inhibitors as potential cancer chemotherapeutic agents.

Authors:  S Jane deSolms; Terrence M Ciccarone; Suzanne C MacTough; Anthony W Shaw; Carolyn A Buser; Michelle Ellis-Hutchings; Christine Fernandes; Kelly A Hamilton; Hans E Huber; Nancy E Kohl; Robert B Lobell; Ronald G Robinson; Nancy N Tsou; Eileen S Walsh; Samuel L Graham; Lorena S Beese; Jeffrey S Taylor
Journal:  J Med Chem       Date:  2003-07-03       Impact factor: 7.446

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.  Postprenylation CAAX processing is required for proper localization of Ras but not Rho GTPases.

Authors:  David Michaelson; Wasif Ali; Vi K Chiu; Martin Bergo; Joseph Silletti; Latasha Wright; Stephen G Young; Mark Philips
Journal:  Mol Biol Cell       Date:  2005-01-19       Impact factor: 4.138

4.  The isoprenoid substrate specificity of isoprenylcysteine carboxylmethyltransferase: development of novel inhibitors.

Authors:  Jessica L Anderson; Brian S Henriksen; Richard A Gibbs; Christine A Hrycyna
Journal:  J Biol Chem       Date:  2005-06-09       Impact factor: 5.157

5.  Direct demonstration of geranylgeranylation and farnesylation of Ki-Ras in vivo.

Authors:  C A Rowell; J J Kowalczyk; M D Lewis; A M Garcia
Journal:  J Biol Chem       Date:  1997-05-30       Impact factor: 5.157

6.  Yeast STE14 methyltransferase, expressed as TrpE-STE14 fusion protein in Escherichia coli, for in vitro carboxylmethylation of prenylated polypeptides.

Authors:  C A Hrycyna; S J Wait; P S Backlund; S Michaelis
Journal:  Methods Enzymol       Date:  1995       Impact factor: 1.600

7.  Farnesylcysteine analogs to probe role of prenylated protein methyltransferase.

Authors:  Y T Ma; B A Gilbert; R R Rando
Journal:  Methods Enzymol       Date:  1995       Impact factor: 1.600

Review 8.  Post-prenylation-processing enzymes as new targets in oncogenesis.

Authors:  Ann M Winter-Vann; Patrick J Casey
Journal:  Nat Rev Cancer       Date:  2005-05       Impact factor: 60.716

9.  A Phase I trial of the farnesyl transferase inhibitor SCH66336: evidence for biological and clinical activity.

Authors:  A A Adjei; C Erlichman; J N Davis; D L Cutler; J A Sloan; R S Marks; L J Hanson; P A Svingen; P Atherton; W R Bishop; P Kirschmeier; S H Kaufmann
Journal:  Cancer Res       Date:  2000-04-01       Impact factor: 12.701

10.  Farnesyl derivatives of rigid carboxylic acids-inhibitors of ras-dependent cell growth.

Authors:  D Marciano; G Ben-Baruch; M Marom; Y Egozi; R Haklai; Y Kloog
Journal:  J Med Chem       Date:  1995-04-14       Impact factor: 7.446
View more
  12 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.  High-throughput screening for inhibitors of Mycobacterium tuberculosis H37Rv.

Authors:  Subramaniam Ananthan; Ellen R Faaleolea; Robert C Goldman; Judith V Hobrath; Cecil D Kwong; Barbara E Laughon; Joseph A Maddry; Alka Mehta; Lynn Rasmussen; Robert C Reynolds; John A Secrist; Nice Shindo; Dustin N Showe; Melinda I Sosa; William J Suling; E Lucile White
Journal:  Tuberculosis (Edinb)       Date:  2009-09-15       Impact factor: 3.131

Review 3.  Small change, big effect: Taking RAS by the tail through suppression of post-prenylation carboxylmethylation.

Authors:  Hiu Yeung Lau; Mei Wang
Journal:  Small GTPases       Date:  2018-01-25

4.  Probing the isoprenylcysteine carboxyl methyltransferase (Icmt) binding pocket: sulfonamide modified farnesyl cysteine (SMFC) analogs as Icmt inhibitors.

Authors:  Jaimeen D Majmudar; Kalub Hahne; Christine A Hrycyna; Richard A Gibbs
Journal:  Bioorg Med Chem Lett       Date:  2011-01-22       Impact factor: 2.823

5.  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

6.  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

7.  Solid-phase synthesis of prenylcysteine analogs.

Authors:  James L Donelson; Heather B Hodges-Loaiza; Brian S Henriksen; Christine A Hrycyna; Richard A Gibbs
Journal:  J Org Chem       Date:  2009-04-17       Impact factor: 4.354

Review 8.  Protein prenylation: unique fats make their mark on biology.

Authors:  Mei Wang; Patrick J Casey
Journal:  Nat Rev Mol Cell Biol       Date:  2016-01-21       Impact factor: 94.444

9.  Inactivating Icmt ameliorates K-RAS-induced myeloproliferative disease.

Authors:  Annika M Wahlstrom; Briony A Cutts; Meng Liu; Annika Lindskog; Christin Karlsson; Anna-Karin M Sjogren; Karin M E Andersson; Stephen G Young; Martin O Bergo
Journal:  Blood       Date:  2008-05-23       Impact factor: 22.113

Review 10.  Isoprenoids and protein prenylation: implications in the pathogenesis and therapeutic intervention of Alzheimer's disease.

Authors:  Angela Jeong; Kiall Francis Suazo; W Gibson Wood; Mark D Distefano; Ling Li
Journal:  Crit Rev Biochem Mol Biol       Date:  2018-06       Impact factor: 8.250
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.