3,4 Dichloroisocoumarin (CAS 51050-59-0)

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Synonym:	3,4-Dichloro-2-benzopyran-1-one
Application:	A granzyme, cathepsin G, and neutrolphil elastase inhibitor
CAS Number:	51050-59-0
Molecular Weight:	215.03
Molecular Formula:	C₉H₄Cl₂O₂

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Description

3,4 Dichloroisocoumarin is a potent, irreversible inhibitor of serine proteases which reacts with serine proteases to release an acylchloride moiety that can acylate another active site residue. 3,4 Dichloroisocoumarin inhibits granzymes A, B, and H, cathepsin G, neutrophil elastase, proteinase and blocks apoptotic internucleosomal DNA cleavage in thymocytes without the involvement of endonucleases. 3,4 Dichloroisocoumarin inhibits activation of neutral sphingomyelinase and daunorubicin-triggered apoptosis as well as apoptosis induced by camptothecin in HL-60 cells. 3,4 Dichloroisocoumarin inhibits migration of eosinophils through basement membrane components in vitro. 3,4 Dichloroisocoumarin does not affect thiol proteases and metalloproteases. 3,4 Dichloroisocoumarin does not exhibit any activity towards β-lactamases.

Usage

Effective concentration: 5-100 μM; t½ = 20 min at pH 7.5.

Technical Information

Appearance:	White lyophilized solid
Physical State:	Solid
Solubility:	Soluble in DMF (10 mM), DMSO (10 mM), and water (partly miscible).
Storage:	Store at 4° C
Boiling Point:	304.74 °C at 760 mmHg (Predicted)
Density:	1.54 g/cm³ (Predicted)
Refractive Index:	n²⁰_D 1.63 (Predicted)
IC50:	Leukocyte elastase: IC₅₀ = 100 nM (human); Lysosomal protective protein: IC₅₀ = 600 nM (human); Elastase 2A: IC₅₀ = 700 nM (rat)

Safety and Reference Information

Transport:	UN 2811, Class 6.1, Packing group III
WGK Germany:	3
PubChem CID:	1609
MDL Number:	MFCD00036960
Beilstein Registry:	6802625
SMILES:	ClC1=C(Cl)C2=CC=CC=C2C(=O)O1

For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.

References

1. Harper, J.W., et al. 1985. Biochemistry. 24: 183-1841. PMID: 3893537
2. Powers, J.C., et al. 1989. J. Cell Biochem. 39: 33-46. PMID: 2654146
3. Su, B., et al. 1994. Eur. J. Immunol. 24: 2073-2080. PMID: 8088328
4. Mansat, V., et al. 1997. FASEB J. 11: 695-702. PMID: 9240970
5. Shimizu,T., et al. 1997. Leukemia. 11: 1238-1244. PMID: 9264376
6. Okada, S., et al. 1997. Am. J. Respir. Cell Mol. Biol. 17: 519-528
. 7. Pham, C.T., et al. 1998. J. Biol. Chem. 273: 1629-1633. PMID: 9430705
8. Odake, S., et al. 1991. Biochemistry. 30: 2217-2227. PMID: 1998680
9. Edwards, K.M., et al. 1999. J.Biol. Chem. 274: 30468-30473. PMID: 10521426

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