cis-ACCP CAS: 777075-44-2
MF: C7H15N2O4P
MW: 222.2
A reversible and competitive inhibitor of type IV collagen-specific MMP-2 and MMP-9.

cis-ACCP (CAS 777075-44-2)

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Alternate Names: cis-2-Aminocyclohexylcarbamoylphosphonic acid
Application: cis-ACCP is a reversible and competitive inhibitor of type IV collagen-specific MMP-2 and MMP-9
CAS Number: 777075-44-2
Purity: ≥95%
Molecular Weight: 222.2
Molecular Formula: C7H15N2O4P
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data (including water content).

cis-ACCP is a reversible and competitive inhibitor of type IV collagen-specific MMP-2 and MMP-9 with preference towards MMP-2 (IC50 = 4 and 20 μM, respectively). At 100 μM, cis-ACCP prevents 90% of tumor cell invasion across matrigel-coated membranes in vitro. Matrix metalloproteinases (MMPs) belong to a family of proteases that play a crucial role in tissue repair and remodeling by degrading extracellular matrix proteins, thus enabling cell migration. Overexpression of MMPs are linked to diseases such as arthritis, cancer, osteoporosis and arteriosclerosis.


References

1 Nagase, H., Woessner, J.F. Jr. Matrix metalloproteinases. J Biol Chem 274(31) 21491-21494 (1999). 2 Hoffman, A., Qadri, B., Frant, J., et al. Carbamoylphosphonate matrix metalloproteinase inhibitors 6: Cis-2-aminocyclohexylcarbamoylphosphonic acid, a novel orally active antimetastatic matrix metalloproteinase-2 selective inhibitor-synthesis and pharmacodynamic and pharmacokinetic analysis. J Med Chem 51 1406-1414 (2008).

Usage :
cis-ACCP is supplied as a crystalline solid. A stock solution may be made by dissolving the cis-ACCP in an organic solvent purged with an inert gas. cis-ACCP is soluble in ethanol to a concentration of approximately 0.15 mg/ml.

Further dilutions of the stock solution into aqueous buffers or isotonic saline should be made prior to performing biological experiments. Ensure that the residual amount of organic solvent is insignificant, since organic solvents may have physiological effects at low concentrations. Organic solvent-free aqueous solutions of cis-ACCP can be prepared by directly dissolving the crystalline compound in aqueous buffers. The solubility of cis-ACCP in PBS, pH 7.2, is approximately 0.3 mg/ml. We do not recommend storing the aqueous solution for more than one day.
Physical State :
Solid
Solubility :
Soluble in ethanol (~0.15 mg/ml), and PBS pH7.2 (~0.3 mg/ml).
Storage :
Store at -20° C
Density :
1.42 g/cm3 (Predicted)
Refractive Index :
n20D 1.54 (Predicted)
IC50 :
MMP-2: IC50 = 4 µM (human); MMP-9: IC50 = 20 µM (human)
pK Values :
pKa: 0.85 (Predicted), pKb: 9.71 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
PubChem CID :
44457233
MDL Number :
MFCD11976901
SMILES :
C1CC[[email protected]]([[email protected]](C1)N)NC(=O)P(=O)(O)O

Download SDS (MSDS)

Certificate of Analysis

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Is it cell-permeable or cell-impermeable?

Asked by: Jz28sail
Thank you for your question. Research suggests that sc-205252, cis-ACCP has poor cell membrane permeability (PMID: 18257543).
Answered by: Chemical Support 5
Date published: 2017-04-07
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