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Merck

D141

Sigma-Aldrich

Digitonin

Used as non-ionic detergent

Synonim(y):

Digitin

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About This Item

Wzór empiryczny (zapis Hilla):
C56H92O29
Numer CAS:
Masa cząsteczkowa:
1229.31
Beilstein:
78654
Numer WE:
Numer MDL:
Kod UNSPSC:
12161900
Identyfikator substancji w PubChem:
NACRES:
NA.25

pochodzenie biologiczne

plant seeds (Digitalis purpurea)

Poziom jakości

Formularz

powder

aktywność optyczna

[α]20/D −54°, c = 2.8 in methanol(lit.)

masa cząsteczkowa

micellar avg mol wt 70,000

liczba agregacji

60

zanieczyszczenia

<6.0% water

CMC

<0.5 mM (20-25°C)
<0.5 mM (20-25°C)

mp

230-240 °C (dec.) (lit.)

rozpuszczalność

H2O: ~5 % (w/v) (solubilized by heating to 95 °C - 98 °C and then cooling to room temp.)

ciąg SMILES

C[C@@]12[C@]([C@@H]3C)([H])[C@](O[C@]34CC[C@@H](C)CO4)([H])[C@@H](O)[C@@]1([H])[C@@](CC[C@]5([H])[C@@]6(C[C@@H](O)[C@H](O[C@]([C@@H]([C@@H](O)[C@H]7O[C@@](O[C@H](CO)[C@@H](O)[C@@H]8O[C@@](OC[C@@H](O)[C@@H]9O)([H])[C@@H]9O)([H])[C@@H]8O[C@@](O[C@H](CO)[C@H

InChI

1S/C56H92O29/c1-19-7-10-56(75-17-19)20(2)31-45(85-56)37(67)32-22-6-5-21-11-26(24(61)12-55(21,4)23(22)8-9-54(31,32)3)76-50-42(72)39(69)44(30(16-60)80-50)81-53-48(47(36(66)29(15-59)79-53)83-49-40(70)33(63)25(62)18-74-49)84-52-43(73)46(35(65)28(14-58)78-52)82-51-41(71)38(68)34(64)27(13-57)77-51/h19-53,57-73H,5-18H2,1-4H3/t19-,20+,21+,22-,23+,24-,25-,26-,27-,28-,29-,30-,31+,32-,33+,34-,35+,36-,37+,38+,39-,40-,41-,42-,43-,44+,45-,46+,47+,48-,49+,50-,51+,52+,53+,54-,55+,56-/m1/s1

Klucz InChI

UVYVLBIGDKGWPX-KUAJCENISA-N

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Opis ogólny

Digitonin, a steroidal saponin extracted from the purple foxglove plant (Digitalis purpurea), stands as a versatile non-ionic detergent crucial for cell biology and biochemical research. Its unique attributes position it as a valuable asset in the exploration of cellular membranes, membrane proteins, and intracellular components. Digitonin′s key properties and applications include its ability to solubilize membrane-bound proteins effectively while preserving their native conformation, making it an ideal tool for studying membrane protein interactions and activities.

Moreover, Digitonin selectively permeabilizes the cholesterol-rich plasma membrane, leaving organelle membranes intact. This feature facilitates the extraction and purification of specific organelles, contributing to the study of their functions and roles in cellular processes. The detergent′s capability to permeabilize diverse cell types allows the study of intracellular components and processes by introducing molecules, antibodies, or enzymes into cells. Additionally, Digitonin finds application in immunocytochemistry experiments, enabling the labeling and detection of intracellular proteins and structures.

Zastosowanie

Digitonin has been used along with permeabilization buffer for cyclic guanosine monophosphate-adenosine monophosphate (cyclic GMP-AMP) stimulation in cells.
Digitonin has been used in a study to assess a procedure for isolating mitochondria from ascites tumor cells. It has also been used in a study to investigate its effect on the cytotoxicity of plant secondary metabolites in cancer cells.

Działania biochem./fizjol.

Digitonin plays a key role in permeabilizing cell membranes. It is capable of lysing eukaryotic cells but not bacterial membranes. It is also used to solubilize membrane components. It helps to create pores by interacting specifically with cholesterol in the membrane. It is preferred in biotechnology due to its mild detergency. This membrane-active compound act with doxorubicin against multi-drug resistant cancer cells.

Cechy i korzyści

Highly versatile compound for your cell biology and biochemical research

Jakość

Preparation is free of water-insoluble constituents.

Inne uwagi

For additional information on our range of Biochemicals, please complete this form.
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Piktogramy

Skull and crossbonesHealth hazard

Hasło ostrzegawcze

Danger

Zwroty wskazujące rodzaj zagrożenia

Zwroty wskazujące środki ostrożności

Klasyfikacja zagrożeń

Acute Tox. 3 Oral - STOT RE 2

Kod klasy składowania

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Klasa zagrożenia wodnego (WGK)

WGK 3

Temperatura zapłonu (°F)

Not applicable

Temperatura zapłonu (°C)

Not applicable

Środki ochrony indywidualnej

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges


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R W Moreadith et al.
Analytical biochemistry, 137(2), 360-367 (1984-03-01)
A new, improved procedure for isolating mitochondria from ascites tumor cells is described. The unique feature of this technique is the use of digitonin to make the cells susceptible to disruption by Teflon pestle/glass vessel homogenization. The yield and respiratory
Dominic S Alonzi et al.
Cellular and molecular life sciences : CMLS, 70(15), 2799-2814 (2013-03-19)
Endoplasmic reticulum-associated degradation (ERAD) is a key cellular process whereby misfolded proteins are removed from the endoplasmic reticulum (ER) for subsequent degradation by the ubiquitin/proteasome system. In the present work, analysis of the released, free oligosaccharides (FOS) derived from all
Wattamon Srisakuldee et al.
Cardiovascular research, 103(1), 72-80 (2014-03-22)
Fibroblast growth factor 2 (FGF-2) protects the heart from ischaemia- and reperfusion-induced cell death by a mechanism linked to protein kinase C (PKC)ε-mediated connexin 43 (Cx43) phosphorylation. Cx43 localizes predominantly to gap junctions, but has also been detected at subsarcolemmal
Akira Hashimoto et al.
Carbohydrate research, 346(17), 2760-2768 (2011-11-11)
This study reinvestigated the synthesis of cellulose in vitro with a well-known cellulose-producing bacterium, Gluconacetobacter xylinus. Alkylmaltoside detergents, which are more frequently used in recent structural biological researches, are uniquely used in this study to solubilize cellulose-synthesizing activity from the
Xianying A Cui et al.
Journal of visualized experiments : JoVE, (70)(70), e50066-e50066 (2012-12-29)
In eukaryotes, most of the messenger RNAs (mRNAs) that encode secreted and membrane proteins are localized to the surface of the endoplasmic reticulum (ER). However, the visualization of these mRNAs can be challenging. This is especially true when only a

Protokoły

This page shows how to solubilize membrane proteins with products from GE Healthcare.

Na tej stronie przedstawiono sposób solubilizacji białek błonowych za pomocą produktów firmy Cytiva.

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