TPE-MI
Names
[ CAS No. ]:
1245606-71-6
[ Name ]:
TPE-MI
[Synonym ]:
1-[4-[2-(4-Methylphenyl)-1,2-diphenylethenyl]phenyl]-1H-pyrrole-2,5-dione
1-{4-[(E)-2-(4-Methylphenyl)-1,2-diphenylvinyl]phenyl}-1H-pyrrole-2,5-dione
TPE-Thiol
1H-Pyrrole-2,5-dione, 1-[4-[(E)-2-(4-methylphenyl)-1,2-diphenylethenyl]phenyl]-
Biological Activity
[Description]:
TPE-MI (Tetraphenylethene maleimide) is a thiol probe for measuring unfolded protein load and proteostasis in cells. TPE-MI can report imbalances in proteostasis in induced pluripotent stem cell models of Huntington disease, as well as cells transfected with mutant Huntington exon 1 before the formation of visible aggregates. TPE-MI also detects protein damage following dihydroartemisinin treatment of the malaria parasitesPlasmodium falciparum [1][2].
[Related Catalog]:
[In Vitro]
TPE-MI is inherently non-fluorescent until it is conjugated to a thiol via the maleimide. TPE-MI fluorescence is activated upon labelling free cysteine thiols, normally buried in the core of globular proteins that are exposed upon unfolding[1]. TPE-MI (50 µM; 0-60 min) exhibits a homogeneous cytoplasmic labelling pattern in live HeLa cells, with a lower level of labelling in the nucleus and apparent concentration in the region of the ER, which was anticipated as a major location for protein synthesis and folding[1]. At the high expression level, the mutant 97Q form of Httex1 was associated with an elevated TPE-MI fluorescence signal relative to a non-disease-causing 25Q form of Httex1[1]. TPE-MI consists of the aggregation-induced emission (AIE) fluorogen tetraphenylethane (TPE) and the thiol-reactive group maleimide (MI), thereby possessing both AIE phenomenon and selective thiol reactivity[2].
[References]
Chemical & Physical Properties
[ Density]:
1.2±0.1 g/cm3
[ Boiling Point ]:
565.7±29.0 °C at 760 mmHg
[ Molecular Formula ]:
C31H23NO2
[ Molecular Weight ]:
441.520
[ Flash Point ]:
228.0±16.6 °C
[ Exact Mass ]:
441.172882
[ LogP ]:
7.74
[ Vapour Pressure ]:
0.0±1.5 mmHg at 25°C
[ Index of Refraction ]:
1.665
Safety Information
[ RIDADR ]:
NONH for all modes of transport
Articles
Simple Biosensor with High Selectivity and Sensitivity: Thiol-Specific Biomolecular Probing and Intracellular Imaging by AIE Fluorogen on a TLC Plate through a Thiol–Ene Click Mechanism Yang Liu, Yong Yu, Jacky W. Y. Lam, Yuning Hong, Mahtab Faisal, et al
Chemistry 16(28) , 8433-8438, (2010)
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