Tris(2-carboxyethyl)phosphine Hydrochloride

Names

[ Name ]:
Tris(2-carboxyethyl)phosphine Hydrochloride

[Synonym ]:
Propanoic acid, 3,3',3''-phosphinidynetris-, hydrochloride (1:1)
3-[bis(2-carboxyethyl)phosphanyl]propanoic acid,hydrochloride
3,3',3''-Phosphinetriyltripropanoic acid hydrochloride (1:1)
Tris(2-carboxyethyl)phosphine Hydrochloride
3,3',3''-Phosphinetriyltripropanoic acid hydrochloride
MFCD00145469

Biological Activity

[Description]:

TCEP hydrochloride (Tris(2-carboxyethyl)phosphine hydrochloride) is a non-thiol reducing agent that is more stable and produces a faster S-S reductive reaction than other chemical reductants. TCEP hydrochloride is a trialkylphosphine, selectively reduces protein disuldes without altering the properties or interacting with thiol-directed agents in the reaction mixture. TCEP hydrochloride is also a commonly used reducing agent in the DNA/AuNP chemistry[1][2][3][4].

[Related Catalog]:

Research Areas >> Others

Signaling Pathways >> Others >> Others

[In Vitro]

TCEP hydrochloride has been introduced which oers the prospect of serving as an alternative to the more commonly employed DTT in the NF-κB-DNA binding reactions in vitro, using recombinant p50 protein and a 32P-labelled κB oligonucleotide. DTT promotes NF-κB-DNA binding in concentrations from 0.25 to 2.6 mM in binding reactions. However, in the presence of 0.25 mM DTT, inhibition of NF-κB binding is seen only at Hg2+ concentrations greater than 100 μM and results are highly variable. In contrast, TCEP hydrochloride promotes NF-κB-DNA binding in a dose-related manner in concentrations from 0.25 to 6 mM. In the presence of even 6 mM TCEP hydrochloride, Hg2+ prevents NF-κB-DNA binding at concentrations as low as 20 μM in binding reactions[1]. The human lactoferrin (hLF) peptide is dissolved in phosphate buffer to a concentration of 0.1 mm. Reduction of the disulfide bonds is obtained by adding a 30-fold molar excess of TCEP hydrochloride with subsequent incubation for 2 h at 37 ℃[2].

[References]

[1]. Dieguez-Acuña FJ, et al. Inhibition of NF-kappaB-DNA binding by mercuric ion: utility of the non-thiol reductant, tris(2-carboxyethyl)phosphine hydrochloride (TCEP), on detection of impaired NF-kappaB-DNA binding by thiol-directed agents. Toxicol In Vitro. 2000 Feb;14(1):7-16.

[2]. Duchardt F, et al. A cell-penetrating peptide derived from human lactoferrin with conformation-dependent uptake efficiency. J Biol Chem. 2009 Dec 25;284(52):36099-108.

[3]. Sequeira MA, et al. Modulating amyloid fibrillation in a minimalist model peptide by intermolecular disulfide chemical reduction. Phys Chem Chem Phys. 2019 Jun 5;21(22):11916-11923.

[4]. Wu R, et al. Effects of Small Molecules on DNA Adsorption by Gold Nanoparticles and a Case Study of Tris(2-carboxyethyl)phosphine (TCEP). Langmuir. 2019 Oct 15;35(41):13461-13468.

Chemical & Physical Properties

[ Density]:
1.041 g/mL at 25 °C

[ Boiling Point ]:
519.4ºC at 760 mmHg

[ Melting Point ]:
177 °C

[ Molecular Formula ]:
C₉H₁₆ClO₆P

[ Molecular Weight ]:
286.647

[ Flash Point ]:
267.9ºC

[ Exact Mass ]:
286.037292

[ PSA ]:
125.49000

[ LogP ]:
1.69440

[ Appearance of Characters ]:
powder | white

[ Index of Refraction ]:
n20/D 1.367

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
H2O: 50 mg/mL

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS05

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H314

[ Precautionary Statements ]:
P280-P305 + P351 + P338-P310

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ Hazard Codes ]:
Xi:Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S37/39-S36/37/39-S27

[ RIDADR ]:
UN 3261 8/PG 2

[ WGK Germany ]:
2

[ Packaging Group ]:
III

[ Hazard Class ]:
8.0

[ HS Code ]:
2915900090

Customs

[ HS Code ]: 2915900090

[ Summary ]:
2915900090 other saturated acyclic monocarboxylic acids and their anhydrides, halides, peroxides and peroxyacids; their halogenated, sulphonated, nitrated or nitrosated derivatives VAT:17.0% Tax rebate rate:9.0% Supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward) MFN tariff:5.5% General tariff:30.0%

Articles

Injectable Peptide Decorated Functional Nanofibrous Hollow Microspheres to Direct Stem Cell Differentiation and Tissue Regeneration.

Adv. Funct. Mater. 25(3) , 350-360, (2015)

Injectable microspheres are attractive stem cell carriers for minimally invasive procedures. For tissue regeneration, the microspheres need to present the critical cues to properly direct stem cell di...

Chitosan functionalisation of gold nanoparticles encourages particle uptake and induces cytotoxicity and pro-inflammatory conditions in phagocytic cells, as well as enhancing particle interactions with serum components.

J. Nanobiotechnology 13 , 84, (2015)

Gold nanoparticles (AuNPs) are a popular choice for use in medical and biomedical research applications. With suitable functionalisation AuNPs can be applied in drug delivery systems, or can aid in di...

Diatomite biosilica nanocarriers for siRNA transport inside cancer cells.

Biochim. Biophys. Acta 1840(12) , 3393-403, (2014)

Diatomite is a natural porous biomaterial of sedimentary origin, formed by fragments of diatom siliceous skeletons, called "frustules". Due to large availability in many areas of the world, chemical s...