1,4-DPCA

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)

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%

λ_max

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).

Size

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