ChemicalBook Product Catalog Pharmaceutical intermediates Heterocyclic compound Pyridine compound Pyridine derivatives PYRIDINE-2,4-DICARBOXYLIC ACID MONOHYDRATE

PYRIDINE-2,4-DICARBOXYLIC ACID MONOHYDRATE

Product NamePYRIDINE-2,4-DICARBOXYLIC ACID MONOHYDRATE
CAS207671-42-9
MFC7H7NO5
MW185.13
EINECS629-130-1
MOL File207671-42-9.mol

Chemical Properties

Melting point	246-248 °C (dec.)(lit.)
storage temp.	Store at -20°C
solubility	DMSO: 1.4 mg/ml; PBS (pH 7.2): 0.2 mg/ml
form	A crystalline solid
BRN	131631
InChI	1S/C7H5NO4.H2O/c9-6(10)4-1-2-8-5(3-4)7(11)12;/h1-3H,(H,9,10)(H,11,12);1H2
InChIKey	PLNFTNOXJDBMSM-UHFFFAOYSA-N
SMILES	[H]O[H].OC(=O)c1ccnc(c1)C(O)=O

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	26
WGK Germany	3
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
SigmaAldrich	English
ALFA	English

Usage And Synthesis

Description

2,4-Pyridinedicarboxylic Acid (2,4-PDCA) is a compound that structurally mimics 2-oxoglutarate (2-OG, also known as α-ketoglutarate) and chelates zinc, thus affecting a range of enzymes. As a 2-OG mimic, it blocks the activity of 2-OG oxygenases, which include certain lysine demethylases and a variety of hydroxylases (e.g., prolyl, collagen, lysyl). 2,4-PDCA inhibits several Jumonji domain-containing lysine demethylases when used at low micromolar concentrations. Through its effects on hydroxylases, including prolyl hydroxlase 1 (IC₅₀ = 1.5 μM), 2,4-PDCA modulates hypoxia-inducible factor turnover, collagen synthesis, and plant cell wall formation. It can inhibit zinc-dependent enzymes, like metallo-β-lactamase. 2,4-PDCA also affects and is translocated by organic anion transporters.

References

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[2] M KRISTIAN KOSKI. The active site of an algal prolyl 4-hydroxylase has a large structural plasticity.[J]. The Journal of Biological Chemistry, 2007: 37112-37123. DOI: 10.1074/jbc.m706554200
[3] MUKRAM M. MACKEEN. Small-Molecule-Based Inhibition of Histone Demethylation in Cells Assessed by Quantitative Mass Spectrometry[J]. Journal of Proteome Research, 2010, 9 8: 4082-4092. DOI: 10.1021/pr100269b
[4] ULRIKE LEURS. Inhibitor scaffold for the histone lysine demethylase KDM4C (JMJD2C)[J]. Bioorganic & Medicinal Chemistry Letters, 2012, 22 18: Pages 5811-5813. DOI: 10.1016/j.bmcl.2012.07.091
[5] OLIVER N F KING. Quantitative high-throughput screening identifies 8-hydroxyquinolines as cell-active histone demethylase inhibitors.[J]. PLoS ONE, 2010: e15535. DOI: 10.1371/journal.pone.0015535
[6] LINE H. KRISTENSEN. Studies of H3K4me3 demethylation by KDM5B/Jarid1B/PLU1 reveals strong substrate recognition in vitro and identifies 2,4-pyridine-dicarboxylic acid as an in vitro and in cell inhibitor[J]. The FEBS journal, 2012, 279 11: 1905-1914. DOI: 10.1111/j.1742-4658.2012.08567.x
[7] SHOHEI HAMADA. Design, Synthesis, Enzyme-Inhibitory Activity, and Effect on Human Cancer Cells of a Novel Series of Jumonji Domain-Containing Protein 2 Histone Demethylase Inhibitors[J]. Journal of Medicinal Chemistry, 2010, 53 15: 5629-5638. DOI: 10.1021/jm1003655
[8] L E HORSFALL. Competitive inhibitors of the CphA metallo-beta-lactamase from Aeromonas hydrophila.[J]. Antimicrobial Agents and Chemotherapy, 2007: 2136-2142. DOI: 10.1128/aac.00866-06
[9] YOHANNES HAGOS. α-Ketoglutarate-related inhibitors of HIF prolyl hydroxylases are substrates of renal organic anion transporters 1 (OAT1) and 4 (OAT4).[J]. Pflugers Archiv: European journal of physiology, 2012, 464 4: 367-374. DOI: 10.1007/s00424-012-1140-9

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