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Join us! · InformexUSA 2012 · New Orleans, Louisiana · February 14-17, 2012 · Booth 2514

1,4-DPCA

Cayman Chemical Item Number 71220

1,4-dihydrophenonthrolin-4-one-3-Carboxylic acid (CAS 331830-20-7)

1,4-DPCA (CAS 331830-20-7)

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Description

The pro-angiogenic factor HIF-1α is targeted for destruction in non-hypoxic environments by the hydroxylation of a specific proline residue, P564, by the oxygen-sensing enzyme HIF-α prolyl hydroxylase (HIF-PH).1 Inhibitors of prolyl 4-hydroxylase are potentially useful in controlling excess collagen deposition in pathological fibrosis. 1,4-DPCA is a competitive inhibitor of prolyl 4-hydroxylase in embryonic chick tendon cells and of collagen hydroxylation in human foreskin fibroblasts with an IC50 value of 3.6 and 2.4 µM, respectively.2 β-oxocarboxylic acids such as 1,4-DPCA have also been found to inhibit the asparaginyl-hydroxylase, factor inhibiting HIF (FIH), with an IC50 value of 60 µM.3

1 Jaakkola, P., Mole, D.R., Tian, Y., et al. Targeting of HIF-α to the von Hippel-Lindau ubiquitylation complex by O2-regulated prolyl hydroxylation. Science 292 468-472 (2001).

2 Franklin, T.J., Morris, W.P., Edwards, P.N., et al. Inhibition of prolyl 4-hydroxylase in vitro and in vivo by members of a novel series of phenanthrolinones. Biochem J 353 333-338 (2001).

3 Banerji, B., Conejo-Garcia, A., McNeill, L.A., et al. The inhibiton of factor inhibiting hypoxia-inducible factor (FIH) by β-oxocarboxylic acids. Chem Commun 5438-5440 (2005).

Synonyms
  • 1,4-dihydrophenonthrolin-4-one-3-Carboxylic acid
Formal Name 4,​4α-​dihydro-​4-​oxo-​1,​10-​phenanthroline-​3-​carboxylic acid
CAS Number 331830-20-7
Molecular Formula C13H8N2O3
Formula Weight 240.2
Formulation A crystalline solid
Purity ≥98%
λmax 216, 242, 261, 280, 317, 332,
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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O=C1C2=C(C3=NC=CC=C3C=C2)​N([H]​)​C=C1C(O)​=O

Background Reading

Jaakkola, P., Mole, D.R., Tian, Y., et al. Targeting of HIF-α to the von Hippel-Lindau ubiquitylation complex by O2-regulated prolyl hydroxylation. Science 292 468-472 (2001).

Banerji, B., Conejo-Garcia, A., McNeill, L.A., et al. The inhibiton of factor inhibiting hypoxia-inducible factor (FIH) by β-oxocarboxylic acids. Chem Commun 5438-5440 (2005).

Franklin, T.J., Morris, W.P., Edwards, P.N., et al. Inhibition of prolyl 4-hydroxylase in vitro and in vivo by members of a novel series of phenanthrolinones. Biochem J 353 333-338 (2001).

1,4-DPCA is available in the following screening library:

Size Price Quantity Subtotal
5 mg $16.00 $0.00
10 mg $30.00 $0.00
25 mg $72.00 $0.00
50 mg $128.00 $0.00
Bulk Contact
Cart Total $0.00

This product is available in custom sizes and/or larger quantities.

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Pricing updated 2012-02-11. Prices are subject to change without notice.

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Warning This product is not for human or veterinary use.

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