maleimide reagents

19
Year 2004 2006 Unknown N/A 2005 N/A N/A 2011 N/A N/A 1995 N/A N/A 2001 N/A N/A 2006 N/A N/A 2011 N/A N/A 2005 N/A N/A 2003 N/A N/A 2004 N/A N/A Maleimide biotin (EZ- Link PEO maleimide biotin; ()-biotinyl-3- maleimidopropionamidyl- 3,6-dioxaoctanediamine, MB) sulfo-NHS-biotin (N- hydroxysulfosuccinimidob iotin) 525 Da Hydrophilic ER membrane permeable - microsomes 443 Da Negatively charged ER membrane permeable - microsomes

Upload: cnk91

Post on 12-Jan-2016

255 views

Category:

Documents


0 download

DESCRIPTION

Maleimide based reagents used in thiol chemistry reactivity used to study membrane topology and whole-cells and membrane systems.

TRANSCRIPT

Page 1: Maleimide Reagents

Year

2004

2006 Unknown N/A

2005 N/A N/A

2011 N/A N/A

1995 N/A N/A

2001 N/A N/A

2006 N/A N/A

2011 N/A N/A

2005 N/A N/A

2003 N/A N/A

2004 N/A N/A

Maleimide biotin (EZ-Link PEO maleimide biotin; ()-biotinyl-3-maleimidopropionamidyl-3,6-dioxaoctanediamine,MB)

sulfo-NHS-biotin (N-hydroxysulfosuccinimidobiotin)

525 Da Hydrophilic ER membrane permeable - microsomes

443 Da Negatively charged ER membrane permeable - microsomes

Page 2: Maleimide Reagents

2002 N/A N/A

2010 Cell membrane impermeable Cell membrane impermeable

2010 N/A N/A

1998 N/A N/A

2013 N/A N/A

2012 N/A N/A

1999 N/A N/A

2011 N/A N/A

2014 N/A N/A

1996

2004

Page 3: Maleimide Reagents

N/A

N/A N/A N/A

N/A N/A N/A N/A

N/A N/A N/A N/A

N/A N/A N/A

N/A N/A N/A

N/A N/A N/A

N/A N/A N/A N/A

N/A N/A N/A

N/A N/A N/A

N/A N/A N/A

EZ-Link sulfo-NHS-LC-biotin [sulfosuccinimidyl-6- (biotinamido) hexanoate]

N-(3-maleimidylpropionyl)biocytin

Maleimide-polyethyleneglycol (mPEG)

Sulfosuccinimidobiotin(SSB)

537 Da negatively charged ER membrane permbeable (selective modification) - whole cells

525 Da Hydrophilic ER membrane permeable - microsomes

5 kDA Hydrophilic ER membrane impermeable - whole cells

5 kDA Hydrophilic ER membrane impermeable - membrane vesicles

Cell membrane permeable

Cell membrane impermeable

Cell membrane permeable

ER membrane permeable - microsomes

Cell membrane permeable

ER membrane permeable - microsomes

Page 4: Maleimide Reagents

N/A N/A N/A

N/A N/A N/A N/A

N/A N/A N/A N/A

N/A N/A N/A N/A

N/A N/A N/A N/A

N/A N/A N/A

N/A N/A

N/A N/A N/A N/A

N/A N/A N/A N/A

Relatively membrane impermeable - proteoliposomes

Bacterial membrane permeable

Cell membrane impermeable

Cell membrane impermeable

Bacterial membrane permeable

Page 5: Maleimide Reagents

MTSEA MTSES

N/A N/A N/A N/A

N/A N/A

N/A N/A N/A

N/A N/A N/A

N/A N/A N/A N/A

N/A N/A N/A N/A

N/A N/A N/A

N/A N/A N/A

N/A N/A N/A N/A

N/A N/A N/A N/A

N/A N/A N/A N/A

Maleimide neutravidin (MN)

N-ethylmaleimide (NEM)

60 kDA ER membrane impermeable - membrane vesicles

ER membrane impermeable - membrane vesicles

Cell membrane permeableViral membrane permeable

Cell membrane permeable

Quncher (blocking agent)

Page 6: Maleimide Reagents

N/A N/A N/A N/A

N/A N/A N/A N/A

N/A N/A N/A

N/A N/A N/A N/A

N/A N/A N/A N/A

N/A N/A N/A N/A

N/A N/A N/A N/A

N/A N/A N/A N/A

N/A N/A N/A

ER membrane permeable - membrane vesicles

Membrane impermeable - blocking

Cell membrane permeable

Cell membrane impermeable

Cell membrane permeable

Page 7: Maleimide Reagents

N/A N/A N/A N/A

N/A N/A N/A N/A

N/A N/A N/A N/A

N/A N/A N/A N/A

N/A N/A N/A

N/A N/A N/A N/A

N/A N/A N/A N/A

N/A N/A N/A N/A

N/A N/A N/A N/A

N/A N/A N/A

N/A N/A N/A N/A

Stilbenedisulfonate maleimide (4-acetamido-4 -′maleimidylstilbene-2,2 -disulfonic acid′

PEG-mal,methoxypolyethylene glycol maleimide 5000;

Maleimide-PEO2-biotin (MPB)

Methyl-PEO12-maleimide (MPM)

Cell membrane impermeable

Cell membrane impermeable

Page 8: Maleimide Reagents

N/A N/A N/A N/A

N/A N/A N/A N/A

N/A N/A N/A N/A

N/A N/A N/A

N/A N/A N/A N/A

N/A N/A N/A N/A

N/A N/A N/A N/A

N/A N/A

N/A N/A N/A

Cell membrane impermeable

Membrane permeable

Membrane impermeable - blocking

Membrane impermeable - microsomes

Page 9: Maleimide Reagents

N/A N/A N/A N/A

N/A N/A N/A N/A

N/A N/A N/A N/A

N/A N/A N/A

N/A N/A N/A N/A

N/A N/A N/A

N/A N/A N/A N/A

N/A N/A N/A

N/A N/A N/A

N/A N/A N/A N/A

N/A N/A N/A

5,5'-dithio-bis-(2-nitrobenzoic acid) (DTNB)

[2-(trimethylammonium)ethyl]methanethiosulfonate bromide(MTSET)

4-acetamido-4¢-maleimidylstilbene-2,2¢-disulfonic acid (AMS)

Biotin-PEG2-maleimide

Viral membrane impermeable

Cell membrane impermeable

Bacterial outer membrane permeable, inner membrane impermeable

ER membrane impermeable (blocking)

ER membrane impermeable (blocking)

Page 10: Maleimide Reagents

N/A N/A N/A

N/A N/A N/A N/A

N/A N/A N/A N/A

N/A N/A N/A N/A

N/A N/A N/A N/A

N/A N/A N/A

N/A N/A N/A N/A

N/A N/A N/A N/A

N/A N/A N/A N/A

Membrane impermeable - proteoliposomes

Bacterial membrane impermeable (blocking)

Cell membrane impermeable

Bacterial membrane impermeable

Page 11: Maleimide Reagents

Biotin maleimide (BM) Protein

N/A N/A

N/A N/A DP1 and Rtn4c/NogoC

N/A N/A

N/A N/A

N/A N/A Human P Glycprotein

N/A N/A SUR1

N/A N/A N/A

N/A N/A SecY Channel

N/A N/A

N/A N/A HPC-1/syntaxin 1A

N/A N/A Human Insig-1

(methyl-PEG12)3-PEG4-maleimide (PEGmal).

Stearoyl-CoA desaturase (SCD)

Page 12: Maleimide Reagents

N/A N/A LacY

N/A N/A

Unknown N/A

N/A N/A Human P Glycprotein

N/A NBCe1 Protein

N/A N/A

N/A N/A

N/A N/A

N/A N/A DGAT2

Plasmalemmal dopamine transporter (DAT)

SA-I, type I signalanchor;SA-II, type II signal-anchor

Cell membrane permeable - whole cell

Polyisoprenyl-phosphate N-acetylaminosugar-1-phosphate transferase

Exofacial surface proteins

Cell surface glycoproteins

Page 13: Maleimide Reagents

Paper

The Endoplasmic Reticulum Membrane Is Permeable to Small Molecules

A Class of Membrane Proteins Shaping the Tubular Endoplasmic Reticulum

Distinct effects of N-ethylmaleimide on formyl peptide- and cyclopiazonic acid-induced Ca2+ signals through thiol modification in neutrophils

Membrane Topology of a Cysteine-less Mutant of Human P-glycoprotein

Transmembrane Topology of the Sulfonylurea Receptor SUR1

Membrane Topology of Mouse Stearoyl-CoA Desaturase 1*

Membrane Topology of Human Insig-1

Inactivation of hantaviruses by N-ethylmaleimidepreserves virion integrity

Topology of transmembrane proteins by scanning cysteineaccessibility mutagenesis methodology

Preserving the membrane barrier for smallmolecules during bacterial protein translocation

Identification of the Carboxyl-Terminal Membrane-AnchoringRegion of HPC-1/Syntaxin 1A with the Substituted-CysteineAccessibilityMethod and Monoclonal Antibodies

Page 14: Maleimide Reagents

Topology of polytopic membrane proteinsubdomains is dictated by membranephospholipid composition

Characterization of the highly conserved VFMGD motif in a bacterial polyisoprenyl-phosphate N-acetylaminosugar-1-phosphate transferase

Labile disulfide bonds are common at the leucocyte cell surface

On the Use of Thiol-modifying Agents to Determine Channel Topology

Membrane Topology of the H+-pyrophosphatase of Streptomyces coelicolor Determined by Cysteine-scanning Mutagenesis

Membrane Cholesterol Modulates the Outward FacingConformation of the Dopamine Transporter and AltersCocaine Binding*

Environmental Transition of Signal-Anchor Sequencesduring Membrane Insertion via the EndoplasmicReticulum Translocon

Molecular dissection of the human multidrugresistance P-glycoprotein

Topology of NBCe1 Protein Transmembrane Segment 1 andStructural Effect of Proximal Renal Tubular Acidosis (pRTA)S427L Mutation*

Redox Control of Exofacial Protein Thiols/Disulfides by ProteinDisulfide Isomeras

Characterization of the interaction of diacylglycerol acyltransferase-2with the endoplasmic reticulum and lipid droplets

Page 15: Maleimide Reagents

Distinct effects of N-ethylmaleimide on formyl peptide- and cyclopiazonic acid-induced Ca2+ signals through thiol modification in neutrophils

Page 16: Maleimide Reagents

Topology of polytopic membrane proteinsubdomains is dictated by membranephospholipid composition

Characterization of the highly conserved VFMGD motif in a bacterial polyisoprenyl-phosphate N-acetylaminosugar-1-phosphate transferase

Membrane Topology of the H+-pyrophosphatase of Streptomyces coelicolor Determined by Cysteine-scanning Mutagenesis