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Dokumente

SML3656

Sigma-Aldrich

PAPTP trifluoroacetate

≥98% (HPLC)

Synonym(e):

(3-(4-(4-((7-Oxo-7H-furo[3,2-g]benzopyran-4-yl)oxy)butoxy)phenyl)propyl)triphenyl phosphonium trifluoroacetate, (3-(4-(4-(7-Oxo-7H-furo[3,2-g]chromen-4-yloxy)butoxy)phenyl)propyl)triphenylphosphonium trifluoroacetate

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About This Item

Empirische Formel (Hill-System):
C42H38O5P · xC2HF3O2
Molekulargewicht:
653.72 (free base basis)
UNSPSC-Code:
12352200
NACRES:
NA.21

Qualitätsniveau

100

Assay

≥98% (HPLC)

Form

powder

Lagerbedingungen

desiccated

Farbe

white to beige

Lagertemp.

-10 to -25°C

SMILES String

O=C1C=CC2=C(C3=C(C=C2O1)OC=C3)OCCCCOC4=CC=C(C=C4)CCC[P+](C5=CC=CC=C5)(C6=CC=CC=C6)C7=CC=CC=C7

Biochem./physiol. Wirkung

PAPTP is a PAP-1-derivatized Kv1.3-selective potassium channel blocker with a positively charged lipophilic propyl-triphenylphosphonium (TP) moiety that allows mitochondria-targeted PAPTP delivery. Mitochondria Kv1.3 inhibition induces oxygen species (ROS)-mediated cancer-selective killing both in cultures (by 28%/69%/95% post 24-hr 0/1/10 µM PAPTP treatment of primary B-CLL; 20%/24% normal B-cell death with 0/20 µM PAPTP) and in murine orthotopic models of melanoma and pancreatic ductal adenocarcinoma in vivo (5 µmol/kg q.o.d. via i.p.). PAPTP exhibits higher anti-cancer efficacy than PAP-1 both in vitro and in vivo, and and is less affected by ultidrug resistance (MDR).

Vorsicht

Hygroscopic

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Analysenzertifikate (COA)

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Sofia Parrasia et al.
Pharmaceuticals (Basel, Switzerland), 14(2) (2021-02-11)
A developing family of chemotherapeutics-derived from 5-(4-phenoxybutoxy)psoralen (PAP-1)-target mitochondrial potassium channel mtKv1.3 to selectively induce oxidative stress and death of diseased cells. The key to their effectiveness is the presence of a positively charged triphenylphosphonium group which drives their accumulation
Faye L Styles et al.
Cell death & disease, 12(4), 372-372 (2021-04-09)
Cellular energy metabolism is fundamental for all biological functions. Cellular proliferation requires extensive metabolic reprogramming and has a high energy demand. The Kv1.3 voltage-gated potassium channel drives cellular proliferation. Kv1.3 channels localise to mitochondria. Using high-resolution respirometry, we show Kv1.3
Roberto Costa et al.
Cell reports, 28(8), 1949-1960 (2019-08-23)
Wnt signaling affects fundamental development pathways and, if aberrantly activated, promotes the development of cancers. Wnt signaling is modulated by different factors, but whether the mitochondrial energetic state affects Wnt signaling is unknown. Here, we show that sublethal concentrations of
Luigi Leanza et al.
Cancer cell, 31(4), 516-531 (2017-04-12)
The potassium channel Kv1.3 is highly expressed in the mitochondria of various cancerous cells. Here we show that direct inhibition of Kv1.3 using two mitochondria-targeted inhibitors alters mitochondrial function and leads to reactive oxygen species (ROS)-mediated death of even chemoresistant
Elisa Venturini et al.
Neuro-Signals, 25(1), 26-38 (2017-09-05)
Glioblastoma (GBM) is one of the most aggressive cancers, counting for a high number of the newly diagnosed patients with central nervous system (CNS) cancers in the United States and Europe. Major features of GBM include aggressive and invasive growth
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