905267
(6-Bromohexyl)triphenylphosphonium bromide
≥95%
Synonym(s):
Bromohexane TPP mitochondrial tag, Mitochondria-targeting probe building block, Phosphonium lipocation tag
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About This Item
Empirical Formula (Hill Notation):
C24H27Br2P
CAS Number:
Molecular Weight:
506.25
MDL number:
UNSPSC Code:
12352101
NACRES:
NA.22
assay
≥95%
form
solid
reaction suitability
reagent type: ligand
functional group
phosphine
storage temp.
2-8°C
SMILES string
BrCCCCCC[P+](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3.[Br]
InChI
1S/C24H27BrP.BrH/c25-20-12-1-2-13-21-26(22-14-6-3-7-15-22,23-16-8-4-9-17-23)24-18-10-5-11-19-24;/h3-11,14-19H,1-2,12-13,20-21H2;1H/q+1;/p-1
InChI key
RJXLPJGHUJHULP-UHFFFAOYSA-M
Application
Mitochondria perform several functions in the cell, and dysfunction has been implicated in various organ systems and disease states, including neurodegenerative disorders and cancers. The targeting of small molecules to the mitochondria can help to probe and better understand this relationship. This bromohexane triphenylphosphine (TPP) tag is conjugated to small molecules to localize them to the mitochondria in cells where the TPP cations facilitate both cellular uptake and accumulation in the mitochondria.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Yon Ju-Nam et al.
Organic & biomolecular chemistry, 4(23), 4345-4351 (2006-11-15)
We report the synthesis and structural characterisation of a new family of stable phosphonioalkylthiosulfate zwitterions, R3P+ (CH2)nS2O3- (R = Ph or Bu, n = 3,4,6, 8 or 10) which behave as cationic masked thiolate ligands with applications in the functionalisation
Marcel Culcasi et al.
Journal of medicinal chemistry, 56(6), 2487-2499 (2013-02-27)
A series of mitochondria targeted α-aminophosphonates combining a diethoxyphosphoryl group and an alkyl chain-connected triphenylphosphonium bromide tail were designed and synthesized, and their pH-sensitive (31)P NMR properties and biological activities in vitro and in vivo were evaluated. The results showed
Changwook Lee et al.
Journal of the American Chemical Society, 137(13), 4358-4367 (2015-03-19)
The mitochondrial pool of Hsp90 and its mitochondrial paralogue, TRAP1, suppresses cell death and reprograms energy metabolism in cancer cells; therefore, Hsp90 and TRAP1 have been suggested as target proteins for anticancer drug development. Here, we report that the actual