(-)-4-Bromotetramisole oxalate

Product Name(-)-4-Bromotetramisole oxalate
CAS62284-79-1
MFC13H13BrN2O4S
MW373.22
EINECS263-487-0
MOL File62284-79-1.mol

Chemical Properties

Melting point	192 °C (dec.) (lit.)
Flash point	87℃
storage temp.	2-8°C
solubility	Soluble in Water (up to 10 mg/ml)
form	liquid
color	White
optical activity	[α]25/D 104°, c = 0.5 in H2O
BRN	4944883
Stability	Stable for 1 year from date of purchase as supplied. Solutions in distilled water may be stored at -20°C for up to 3 months.
InChI	InChI=1/C11H11BrN2S.C2H2O4/c12-9-3-1-8(2-4-9)10-7-14-5-6-15-11(14)13-10;3-1(4)2(5)6/h1-4,10H,5-7H2;(H,3,4)(H,5,6)/t10-;/s3
InChIKey	ZULBIBHDIQCNIS-MEQOOBBNNA-N
SMILES	C(=O)(O)C(=O)O.BrC1C=CC([C@@H]2N=C3SCCN3C2)=CC=1 \|&1:11,r\|

Safety Information

Hazard Codes	Xn
Risk Statements	21/22-36/37/38-20/21/22
Safety Statements	24/25-36/37/39-26
WGK Germany	3
F	10
Storage Class	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Dermal Acute Tox. 4 Oral

MSDS

Provider	Language
ACROS	English
SigmaAldrich	English

Usage And Synthesis

Description

Four distinct human isoenzymes of alkaline phosphatase (AP) are known: intestinal (IAP), placental (PLAP), tissue non-specific (NSAP, also known as liver/bone/kidney AP), and germ cell AP (also known as placental-like AP, PLAP-like). L-p-Bromotetramisole is a cell-permeable inhibitor of all four human AP isoenzymes (K_is =18 and 56 μM for PLAP and NSAP, respectively). While PLAP is strongly inhibited by L-p-bromotetramisole, a second AP, possibly PLAP-like, shows only partial inhibition. L-p-Bromotetramisole has been shown to inhibit a tyrosine phosphatase from Drosophila and, as a result, is also used as a tyrosine phosphatase inhibitor.

Chemical Properties

white to light yellow crystal powde

Uses

L-p-Bromotetramisole Oxalate or (-)-p-Bromotetramisole Oxalate is a potent inhibitor of alkaline phosphatase.

Biochem/physiol Actions

(-)-p-Bromolevamisole oxalate inhibits L-isoforms of alkaline phosphatases.

target

alkaline phosphatase

References

[1] J S KOVACH D J S P A Svingen. Levamisole potentiation of fluorouracil antiproliferative activity mimicked by orthovanadate, an inhibitor of tyrosine phosphatase.[J]. JNCI Journal of the National Cancer Institute, 1992, 84 7: 515-519. DOI:10.1093/jnci/84.7.515
[2] J LUO. Role of protein phosphatases in the activation of CFTR (ABCC7) by genistein and bromotetramisole.[J]. American journal of physiology. Cell physiology, 2000, 279 1: C108-19. DOI:10.1152/ajpcell.2000.279.1.c108
[3] B M SCHER. The phosphatase inhibitors, orthovanadate and levamisole, inhibit induction of erythroid differentiation and abrogate the associated inhibition of glycolysis.[J]. International journal of oncology, 1998, 12 5: 987-996. DOI:10.3892/ijo.12.5.987

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