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5.32606

5-Lipoxygenase Inhibitor, MK591

Name: 5-Lipoxygenase Inhibitor, MK591
Brand: MM

Synonym(s):

5-Lipoxygenase Inhibitor, MK591, FLAP Inhibitor, MK591, sodium 3-(3-(tert-butylthio)-1-(4-chlorobenzyl)-5-(quinolin-2-ylmethoxy)-1H-indol-2-yl]-2,2-dimethylpropanoate, L-686,708, MK-0591

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About This Item

Empirical Formula (Hill Notation):

C₃₄H₃₄ClN₂NaO₃S

CAS Number:

147030-01-1

Molecular Weight:

609.15

MDL number:

MFCD15143438

UNSPSC Code:

12352200

NACRES:

NA.77

Assay:

≥98% (HPLC)

Form:

solid

Storage condition:

OK to freeze, protect from light

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Properties

assay

≥98% (HPLC)

Quality Segment

100

form

solid

potency

3.1 nM IC₅₀

manufacturer/tradename

Calbiochem^®

storage condition

OK to freeze, protect from light

color

white

solubility

DMSO: 10 mg/mL

storage temp.

−20°C

SMILES string

[Na+].S(C(C)(C)C)c1c2c([n](c1CC(C)(C)C(=O)[O-])Cc5ccc(cc5)Cl)ccc(c2)OCc3nc4c(cc3)cccc4

InChI

1S/C34H35ClN2O3S.Na/c1-33(2,3)41-31-27-18-26(40-21-25-15-12-23-8-6-7-9-28(23)36-25)16-17-29(27)37(20-22-10-13-24(35)14-11-22)30(31)19-34(4,5)32(38)39;/h6-18H,19-21H2,1-5H3,(H,38,39);/q;+1/p-1

InChI key

YPURUCMVRRNPHJ-UHFFFAOYSA-M

Description

General description

A cell permeable, bioavailable, 2-indolealkanoic acid derived compound that acts as a highly potent and selective inhibitor of leukotriene biosynthesis (IC₅₀ = 3.1 nM in intact human polymorphonuclear leukocytes). Shown to inhibit 5-lipoxygenase (5-LOX) activity in LNCaP prostate cancer cells by high-affinity binding to 5-lipoxygenase activating protein (FLAP; IC₅₀ = 1.6 nM in a FLAP binding assay). Induces apoptosis in LNCaP cells without blocking PI 3 kinase-Akt or ERK activities. Also shown to induce rapid phosphorylation of c-Jun N-terminal Kinase (JNK) and indirectly block PKCε activity. Suppresses the deposition of Ab1-40 and Ab1-42 peptides in Tg2576 mice (~40 mg/kg/day in diet) with concomitant reduction in the levels of presenilin 1, nicastrin, APH-1 and Pen-2, but without affecting notch signaling. Exhibits desirable pharmacokinetic properties with tmax of 3.3 h and t1/2 = ~12 h.

MK591; MK0591; 5-LOX inhibitor, 5- Lipoxygenase inhibitor, FLAP

Biochem/physiol Actions

Cell permeable: yes

Primary Target
FLAP

Preparation Note

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

Other Notes

Chu, J., et al. 2012. J. Neuroinflamm.9, 127.
Sarveswaran, S., et al. 2011. Bioch. Biophy. Acta.1813, 2108.

Sarveswaran, S., et al. 2010. Cancer Lett.291, 167.
Uematsu, T., et al. 1995. Br. J. Clin. Pharm.40, 59.

Legal Information

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

Disclaimer

Toxicity: Standard Handling (A)

Storage Class

11 - Combustible Solids

WGK

WGK 3

Flash Point (°F)

Not applicable

Flash Point (°C)