A matrix metalloproteinase inhibitor
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cis-ACCP

Item No. 10012583

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
P-[[[(1R,2S)-2-aminocyclohexyl]amino]carbonyl]-phosphonic acid
CAS Number
777075-44-2
Molecular Formula
C7H15N2O4P
Formula Weight
222.2
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
Water: 1 mg/ml
SMILES
N[C@H]1CCCC[C@H]1NC(P(O)(O)=O)=O
InChi Code
InChI=1S/C7H15N2O4P/c8-5-3-1-2-4-6(5)9-7(10)14(11,12)13/h5-6H,1-4,8H2,(H,9,10)(H2,11,12,13)/t5-,6+/m0/s1
InChi Key
XHCXISPZIHYKQD-NTSWFWBYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $32

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    5 mg

    $134

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    10 mg

    $238

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    50 mg

    $1,030

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    Cayman Chemical
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    Product Description

    Matrix metalloproteinases (MMPs) belong to a family of proteases that play a crucial role in tissue remodeling and repair by degrading extracellular matrix proteins, thus enabling cell migration.1 Overexpression of MMPs are linked to diseases such as cancer, arthritis, osteoporosis, and arteriosclerosis. 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).2 At 100 µM, cis-ACCP prevents 90% of tumor cell invasion across matrigel-coated membranes in vitro.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Nagase, H., and Woessner, J.F., Jr. Matrix metalloproteinases. The Journal of Biological Chemisty 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).