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203900

Sigma-Aldrich

Bufalin

A cardiotonic steroid isolated from toads of Bufo species that potently inhibits ouabain-sensitive Na+,K+-ATPase activity (IC₅₀ = 1.4 nM).

Synonym(s):

Bufalin, 5β, 20(22)-Bufadienolide-3β, 14-diol

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About This Item

Empirical Formula (Hill Notation):
C24H34O4
CAS Number:
465-21-4
Molecular Weight:
386.52
UNSPSC Code:
12352211
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

white to off-white

solubility

DMSO: 25 mg/mL
warm ethanol: 25 mg/mL

shipped in

ambient

storage temp.

−20°C

InChI

1S/C24H34O4/c1-22-10-7-17(25)13-16(22)4-5-20-19(22)8-11-23(2)18(9-12-24(20,23)27)15-3-6-21(26)28-14-15/h3,6,14,16-20,25,27H,4-5,7-13H2,1-2H3/t16-,17+,18-,19?,20?,22+,23-,24+/m1/s1

InChI key

QEEBRPGZBVVINN-ZXRSHIDQSA-N

General description

A cardiotonic steroid isolated from Bufo species toads that potently inhibits ouabain-sensitive Na+,K+-ATPase activity. Induces apoptosis in various human cell lines such as leukemia HL60 and U937 cells by altering the expression of apoptosis-related genes. Reported to stimulate the activities of p21 activated kinase (PAK) and c-Jun Kinase (JNK) in leukemic cell lines. Induces a transient increase in the expression of Tiam1 mRNA in U937 cell lines (~100 nM). Bufalin also down-regulates gene expression of the intracellular signaling protein 14-3-3 in rat lens, probably a consequence of Na+-K+-ATPase inhibitors. Reduces the level of topoisomerase II in human leukemia cells.
A cardiotonic steroid isolated from toads of Bufo species that potently inhibits ouabain-sensitive Na+,K+-ATPase activity (IC50 = 1.4 nM). Induces apoptosis in various human cell lines such as leukemia HL-60 and U937 cells by altering the expression of apoptosis-related genes. Reported to stimulate the activities of p21 activated kinase (PAK) and c-Jun Kinase (JNK) in leukemic cell lines. Induces a transient increase in the expression of Tiam1 mRNA in U937 cell lines (~100 nM). Bufalin also down-regulates gene expression of the intracellular signaling protein 14-3-3 in rat lens, probably a consequence of Na+,K+-ATPase inhibition. Reduces the level of topoisomerase II in human leukemia cells.

Biochem/physiol Actions

Cell permeable: no
Primary Target
Ouabain-sensitive Na+,K+-ATPase activity
Product does not compete with ATP.
Reversible: no
Target IC50: 1.4 nM against ouabain-sensitive Na+,K+-ATPase activity

Packaging

Packaged under inert gas

Warning

Toxicity: Highly Toxic (H)

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Other Notes

Due to the nature of the Hazardous Materials in this shipment, additional shipping charges may be applied to your order. Certain sizes may be exempt from the additional hazardous materials shipping charges. Please contact your local sales office for more information regarding these charges.
Kurosawa, M., et al. 2000. Am. J. Physiol.278, C500.
Kawazoe, N., et al. 1999. Oncogene 18, 2413.
McGowan, M.H., et al. 1999. J. Pharmacol. Exp. Ther. 289, 1559.
Watabe, M., et al. 1998. Oncogene 16, 779.
Hashimoto, S., et al. 1997. Leuk. Res. 21, 875.
Morris, J.F., et al. 1997. Comp. Biochem. Physiol. A Physiol. 118, 599.
Brownlee, A.A., et al. 1990. Clin. Sci.78, 169.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H300

Hazard Classifications

Acute Tox. 2 Oral

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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