Menadione

For research use only.

Catalog No.S1949 Synonyms: Vitamin K3

4 publications

Menadione Chemical Structure

CAS No. 58-27-5

Menadione(Vitamin K3), a fat-soluble compound, is an inhibitor of Cdc25 phosphatase and mitochondrial DNA polymerase γ (pol γ), used as a nutritional supplement.

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Biological Activity

Description Menadione(Vitamin K3), a fat-soluble compound, is an inhibitor of Cdc25 phosphatase and mitochondrial DNA polymerase γ (pol γ), used as a nutritional supplement.
Targets
Cdc25 phosphatase [6] DNA polymerase γ [7]
In vitro

Menadione prevents mitochondrial Ca(2+) uptake in normal pancreatic acinar cells, which permits rapid spread of Ca(2+) throughout the cell. Menadione-induced mitochondrial depolarisation is due to induction of the permeability transition pore. [1] Menadione (nontoxic concentration) results in a brief activation of extracellular signal-regulated kinase (ERK) and c-Jun N-terminal kinase (JNK) in the RALA255-10G rat hepatocyte cell line. [2] Menadione is equipotent against multidrug-resistant and parental leukemia cell lines with IC50 values of 13.5 mM and 18 mM, respectively. Menadione inhibits the incorporation of radioactive thymidine, uridine and amino acids into DNA, RNA and protein, respectively, in three humancancer cell lines. [3] Menadione at 1-20 mM dose- and time-dependently inhibits cell proliferation of AR4-2J cells. Menadione (100 mM) causes rapid cell death. Menadione (100 mM) induces DNA smear in electrophoresis indicative of necrosis, while lower concentrations (10-20 mM) induces a DNA ladder indicative of apoptosis. Menadione at 1-20 mM induces wild-type P53, whereas the 100 mM menadione has a minor effect on wild-type P53. [4] Menadione treatment clearly affects the mitochondrial function of Jurkat T cells by inducing a collapse of the inner transmembrane potential (DeltaPsi(m)) and a decrease in inner membrane mass, which could be completely reversed by N-acetylcysteine. [5]

Cell Data
Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID
HT22 cells NF3TS2NHfW6ldHnvckBie3OjeR?= MWTO[ZVzd3C{b4TlZ5RqfmViYXP0bZZqfHliaX6gcY92e2ViSGSyNkBk\WyuczDhd5Nme3OnZDDhd{BxemW4ZX70bY9vKG[{b32g[4x2fGGvYYTlMYlv\HWlZXSgc5hq\GG2aY\lJINmdGxiZHXheIgh[nliTWTTJIF{e2G7LDDQSFUxRTBwN{m3JO69VQ>? MnPkNlM{Ojd2Nki=
HeLa cell NUHzdoJqS3m2b4TvfIlkcXS7IHHzd4F6 NVjCXplpS3m2b4TvfIlkcXS7IHHnZYlve3RiSHXMZUBk\WyuIHzpcoV{NCCHQ{WwQVMvPyEQvF2= MmDMNVU{Pjl2MEC=
PaCa2 cell NInGR2JRem:uaX\ldoF1cW:wIHHzd4F6 NFrxXJJCdnSrcILvcIln\XKjdHn2[UBi[3Srdnn0fUBi\2GrboP0JIh2dWGwIIDhcoNz\WG2aXOgZ4Fz[2mwb33hJG1q[SCSYVPhNkBk\WyuIHzpcoUh[nliY3;sc5JqdWW2cnnjJIF{e2G7LDDJR|UxRTZwMjFOwG0> NFTndoIyPjJzNkWwNC=>
HT-29 cells MVTDfZRwfG:6aXPpeJkh[XO|YYm= NEXJWW04OiCq MmXtR5l1d3SxeHnjbZR6KGGpYXnud5QhcHWvYX6gTHQuOjliY3XscJMh[XO|ZYPz[YQh[XNiZ4Lve5RpKGmwaHnibZRqd25iYX\0[ZIhPzJiaILzJIJ6KE2WUzDhd5NigSxiSVO1NF06NjZ7IN88US=> M3[xNlI{PzlzM{[3
DU145 cells M4XEeGN6fG:2b4jpZ4l1gSCjc4PhfS=> M3fzVlczKGh? M1XMeWN6fG:2b4jpZ4l1gSCjZ3HpcpN1KGi3bXHuJGRWOTR3IHPlcIx{KGG|c3Xzd4VlKGG|IHfyc5d1cCCrbnjpZol1cW:wIHHmeIVzKDd{IHjyd{BjgSCPVGOgZZN{[XluIFnDOVA:QS56NjFOwG0> MknLNlM4QTF|Nke=
MDA-MB-231 cells Mmq2R5l1d3SxeHnjbZR6KGG|c3H5 MWi3NkBp M3LybGN6fG:2b4jpZ4l1gSCjZ3HpcpN1KGi3bXHuJG1FSS2PQj2yN|Eh[2WubIOgZZN{\XO|ZXSgZZMh\3Kxd4ToJIlvcGmkaYTpc44h[W[2ZYKgO|IhcHK|IHL5JG1VWyCjc4PhfUwhUUN3ME2xNk43QCEQvF2= MkS3NlM4QTF|Nke=
human A2058 cells M13hdWN6fG:2b4jpZ4l1gSCjc4PhfS=> NILEOZZEgXSxdH;4bYNqfHliYXfhbY5{fCCqdX3hckBCOjB3ODDj[YxteyCjc4Pld5Nm\CCjczDpcohq[mm2aX;uJI9nKG[xcn3hfoFvKG[xcn3heIlwdiCjdDDkZZkhPSCkeTDt[YF{fXKrbnegZYJ{d3KkYX7j[UBifCB2M{Cgco0tKEmFNUC9NVMvPCEQvF2= MVyxPVk3QTRyMB?=
SAS cells M3fIb2N6fG:2b4jpZ4l1gSCjc4PhfS=> Mn3YOFghcA>? NV;WPWsxS3m2b4TvfIlkcXS7IHHnZYlve3RiaIXtZY4hW0GVIHPlcIx{KGG|c3Xzd4VlKGG|IILl[JVkfGmxbjDpckBk\WyuII\pZYJqdGm2eTDh[pRmeiB2ODDodpMh[nliTWTUJIF{e2G7LDDJR|UxRTF2IN88US=> NX3SfYtmOjR7MUO3NVI>
HaCaT cells MoPvSpVv[3Srb36gZZN{[Xl? M3LseVQ5KGh? NHSwOZJCdnSraInw[ZJxem:uaX\ldoF1cX[nIHHjeIl3cXS7IHHnZYlve3RiaIXtZY4hUGGFYWSgZ4VtdHNiYYPz[ZN{\WRiYYOgbY5pcWKrdHnvckBw\iClZXzsJIdzd3e2aDDh[pRmeiB2ODDodpMh[nlicHjhd4Uh[2:wdILhd5QhdWmlcn;zZ49xgSxiSVO1NF0yPS56IN88US=> M1:1RVI1QTZ2MkS2
HeLa cells MnTRR5l1d3SxeHnjbZR6KGG|c3H5 M3f3WVQ5KGh? NIDjU|NEgXSxdH;4bYNqfHliYXfhbY5{fCCqdX3hckBJ\UyjIHPlcIx{KGG|c3Xzd4VlKGG|IILl[JVkfGmxbjDpckBk\WyuII\pZYJqdGm2eTDh[pRmeiB2ODDodpMh[nliTWTUJIF{e2G7LDDJR|UxRTF6IN88US=> M4rBclI1QTF|N{Gy
CRL2796 cells NU\QOHpxS3m2b4TvfIlkcXS7IHHzd4F6 NF;WXFNEgXSxdH;4bYNqfHliYXfhbY5{fCCqdX3hckBEWkx{N{m2JINmdGy|IHHzd4V{e2WmIHHzJIlvcGmkaYTpc44hd2ZiZn;ycYF7[W5iZn;ycYF1cW:wIHH0JIRigSB2IHL5JI1m[XO3cnnu[{Bi[nOxcnLhcoNmKGG2IESzNEBvdSxiSVO1NF0zOSEQvF2= MVSxPVk3QTRyMB?=
HL60 cells MoPWSpVv[3Srb36gZZN{[Xl? NVLD[2JCPTBizszN NYDlfZBMUW6mdXP0bY9vKG:oIH7lZ5Jwe2m|IHnuJIlvfGGldDDoeY1idiCKTE[wJINmdGy|IHHzd4V{e2WmIHHzJIN6fG:|b3zpZ{BNTEhicnXs[YF{\SCjdDC1NEB2VQ>? MnPoNlU1PjJ{N{O=

... Click to View More Cell Line Experimental Data

Assay
Methods Test Index PMID
Western blot
p-JNK / JNK / p-c-Jun / c-Jun / p-ERK / ERK ; 

PubMed: 20578144     


Immunoblots of total protein from VEC and siAtg5 cells treated with 50 μM menadione for the times shown and probed for phospho-JNK (P-JNK), total JNK, phospho-c-Jun (P-c-Jun), total c-Jun, phospho-ERK1/2 (P-ERK1/2) and total ERK1/2.

Cyclin B1 / CDK1 / CDC25C ; 

PubMed: 28077999     


AGS cells were treated with indicated dose of menadione (0, 5, 10, 15 μM) for 24 h. A: The cell lysates were subjected to Westernblot for CyclinB1, CDK1, and CDC25C. 

c-Fos / HO-1 ; 

PubMed: 25414256     


Cells were exposed to 50 μm menadione for the indicated time and subjected to Northern blot analysis of c-Fos and Ho-1. GAPDH was used as a loading control. D and E, involvement of p53 in the regulation of ERK1/2 phosphorylation. 

20578144 28077999 25414256

Protocol

Solubility (25°C)

In vitro DMSO 34 mg/mL (197.46 mM)
Water Insoluble
Ethanol '34 mg/mL

* Please note that Selleck tests the solubility of all compounds in-house, and the actual solubility may differ slightly from published values. This is normal and is due to slight batch-to-batch variations.

Chemical Information

Molecular Weight 172.18
Formula

C11H8O2

CAS No. 58-27-5
Storage powder
in solvent
Synonyms Vitamin K3
Smiles CC1=CC(=O)C2=CC=CC=C2C1=O

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Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID