Literature DB >> 26709869

Synthetic isoprenoid analogues for the study of prenylated proteins: Fluorescent imaging and proteomic applications.

Yen-Chih Wang1, Mark D Distefano2.   

Abstract

Protein prenylation is a posttranslational modification catalyzed by prenyltransferases involving the attachment of farnesyl or n class="Chemical">geranylgeranyl groups to residues near the C-termini of proteins. This irreversible covalent modification is important for membrane localization and proper signal transduction. Here, the use of isoprenoid analogues for studying prenylated proteins is reviewed. First, experiments with analogues containing small fluorophores that are alternative substrates for prenyltransferases are described. Those analogues have been useful for quantifying binding affinity and for the production of fluorescently labeled proteins. Next, the use of analogues that incorporate biotin, bioorthogonal groups or antigenic moieties is described. Such probes have been particularly useful for identifying proteins that are naturally prenylated within mammalian cells. Overall, the use of isoprenoid analogues has contributed significantly to the understanding of protein prenlation.
Copyright © 2015 Elsevier Inc. All rights reserved.

Entities:  

Keywords:  Bioorthogonal labeling; Farnesylation; Fluorescent isoprenoids; Geranylgeranylation; Prenylomics; Protein prenylation; Proteomics

Mesh:

Substances:

Year:  2015        PMID: 26709869      PMCID: PMC4731301          DOI: 10.1016/j.bioorg.2015.12.003

Source DB:  PubMed          Journal:  Bioorg Chem        ISSN: 0045-2068            Impact factor:   5.275


  65 in total

Review 1.  Protein isoprenylation in plants.

Authors:  S K Randall; D N Crowell
Journal:  Crit Rev Biochem Mol Biol       Date:  1999       Impact factor: 8.250

2.  RhoB prenylation is driven by the three carboxyl-terminal amino acids of the protein: evidenced in vivo by an anti-farnesyl cysteine antibody.

Authors:  R Baron; E Fourcade; I Lajoie-Mazenc; C Allal; B Couderc; R Barbaras; G Favre; J C Faye; A Pradines
Journal:  Proc Natl Acad Sci U S A       Date:  2000-10-10       Impact factor: 11.205

3.  A new class of type I protein geranylgeranyltransferase (GGTase I) inhibitor.

Authors:  Satoshi Sunami; Mitsuru Ohkubo; Takeshi Sagara; Jun Ono; Shuichi Asahi; Seita Koito; Hajime Morishima
Journal:  Bioorg Med Chem Lett       Date:  2002-02-25       Impact factor: 2.823

Review 4.  Enzymology and biology of CaaX protein prenylation.

Authors:  H W Fu; P J Casey
Journal:  Recent Prog Horm Res       Date:  1999

Review 5.  Non-peptidic prenyltransferase inhibitors: diverse structural classes and surprising anti-cancer mechanisms.

Authors:  R A Gibbs; T J Zahn; J S Sebolt-Leopold
Journal:  Curr Med Chem       Date:  2001-10       Impact factor: 4.530

6.  The basis for K-Ras4B binding specificity to protein farnesyltransferase revealed by 2 A resolution ternary complex structures.

Authors:  S B Long; P J Casey; L S Beese
Journal:  Structure       Date:  2000-02-15       Impact factor: 5.006

7.  Cell surface engineering by a modified Staudinger reaction.

Authors:  E Saxon; C R Bertozzi
Journal:  Science       Date:  2000-03-17       Impact factor: 47.728

8.  Phosphoisoprenoid binding specificity of geranylgeranyltransferase type II.

Authors:  N H Thomä; A Iakovenko; D Owen; A S Scheidig; H Waldmann; R S Goody; K Alexandrov
Journal:  Biochemistry       Date:  2000-10-03       Impact factor: 3.162

9.  Didehydrogeranylgeranyl (Delta Delta GG): a fluorescent probe for protein prenylation.

Authors:  Xiao-hui Liu; Glenn D Prestwich
Journal:  J Am Chem Soc       Date:  2002-01-09       Impact factor: 15.419

10.  Photoaffinity analogues of farnesyl pyrophosphate transferable by protein farnesyl transferase.

Authors:  Kareem A H Chehade; Katarzyna Kiegiel; Richard J Isaacs; Jennifer S Pickett; Katherine E Bowers; Carol A Fierke; Douglas A Andres; H Peter Spielmann
Journal:  J Am Chem Soc       Date:  2002-07-17       Impact factor: 15.419

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  7 in total

1.  Chemical Proteomic Profiling of the Interacting Proteins of Isoprenoid Pyrophosphates.

Authors:  Rong Cai; Xuejiao Dong; Kailin Yu; Xiaomei He; Xiaochuan Liu; Yinsheng Wang
Journal:  Anal Chem       Date:  2020-05-27       Impact factor: 6.986

2.  Metabolic Labeling of Prenylated Proteins Using Alkyne-Modified Isoprenoid Analogues.

Authors:  Kiall F Suazo; Alexander K Hurben; Kevin Liu; Feng Xu; Pa Thao; Ch Sudheer; Ling Li; Mark D Distefano
Journal:  Curr Protoc Chem Biol       Date:  2018-07-30

3.  Protein Farnesyltransferase Catalyzes Unanticipated Farnesylation and Geranylgeranylation of Shortened Target Sequences.

Authors:  Sudhat Ashok; Emily R Hildebrandt; Colby S Ruiz; Daniel S Hardgrove; David W Coreno; Walter K Schmidt; James L Hougland
Journal:  Biochemistry       Date:  2020-03-10       Impact factor: 3.162

4.  Combining Isoprenoid Probes with Antibody Markers for Mass Cytometric Analysis of Prenylation in Single Cells.

Authors:  Zoë A Maxwell; Kiall F Suazo; Heather M G Brown; Mark D Distefano; Edgar A Arriaga
Journal:  Anal Chem       Date:  2022-08-11       Impact factor: 8.008

Review 5.  A Not-So-Ancient Grease History: Click Chemistry and Protein Lipid Modifications.

Authors:  Kiall F Suazo; Keun-Young Park; Mark D Distefano
Journal:  Chem Rev       Date:  2021-04-06       Impact factor: 72.087

6.  Protein Isoprenylation in Yeast Targets COOH-Terminal Sequences Not Adhering to the CaaX Consensus.

Authors:  Brittany M Berger; June H Kim; Emily R Hildebrandt; Ian C Davis; Michael C Morgan; James L Hougland; Walter K Schmidt
Journal:  Genetics       Date:  2018-09-26       Impact factor: 4.562

7.  Metabolic labeling with an alkyne probe reveals similarities and differences in the prenylomes of several brain-derived cell lines and primary cells.

Authors:  Kiall F Suazo; Angela Jeong; Mina Ahmadi; Caroline Brown; Wenhui Qu; Ling Li; Mark D Distefano
Journal:  Sci Rep       Date:  2021-02-23       Impact factor: 4.379

  7 in total

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