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Merck
CN

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:
83152-22-1
Molecular Weight:
506.25
MDL number:
MFCD32197454
UNSPSC Code:
12352101
NACRES:
NA.22

Key Documents

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Product Name

(6-Bromohexyl)triphenylphosphonium bromide, ≥95%

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

assay

≥95%

form

solid

reaction suitability

reagent type: ligand

functional group

phosphine

storage temp.

2-8°C

Related Categories

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.

Other Notes

Targeting lipophilic cations to mitochondria

Photoswitchable polyfluorophores based on perylenemonoimide-dithienylethene conjugates as super-resolution MitoTrackers

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCK5289

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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
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
Friedrich Kreyenschmidt et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 24(5), 1168-1177 (2017-11-08)
The combination of CoCl2 and 1,3-dienes is known to catalyze challenging alkyl-alkyl cross-coupling reactions between Grignard reagents and alkyl halides, but the mechanism of these valuable transformations remains speculative. Herein, electrospray-ionization mass spectrometry is used to identify and characterize the
Wen Zhang et al.
Analytical chemistry, 89(12), 6840-6845 (2017-05-16)
Mitochondrial morphology regulated by fusion and fission processes determines mitochondrial function and cell fate. Some studies showed hyperfused mitochondria could induce apoptosis in cancer cells, but the relevant molecular mechanisms remain elusive. Superoxide (O2•-) and pH play vital roles in
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
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