Pyridoxal isonicotinoyl hydrazone

Pyridoxal isonicotinoyl hydrazone is an orally active and lipophilic iron-specific chelator that acts as a non-competitive inhibitor of ferrochelatase (FECH) by binding iron ions. Pyridoxal isonicotinoyl hydrazone disrupts heme biosynthesis, leading to reduced FECH stability and increased protoporphyrin IX (PPIX) accumulation. Pyridoxal isonicotinoyl hydrazone is promising for research of iron-overload diseases (e.g., β-thalassemia) [1][2][3][4][5][6].

Product Specifications

CAS Number

[737-86-0]

UNSPSC

12352005

Hazard Statement

H302, H315, H319, H335

Target

Biochemical Assay Reagents; Ferrochelatase

Type

Reference compound

Related Pathways

Metabolic Enzyme/Protease; Others

Applications

Cancer-programmed cell death

Field of Research

Cardiovascular Disease

Assay Protocol

https://www.medchemexpress.com/pyridoxal-isonicotinoyl-hydrazone.html

Purity

99.96

Solubility

DMSO : 7 mg/mL (ultrasonic; heat to 60°C)

Smiles

CC1=NC=C(C(/C=N/NC(C2=CC=NC=C2)=O)=C1O)CO

Molecular Formula

C14H14N4O3

Molecular Weight

286.29

Precautions

H302, H315, H319, H335

References & Citations

[1]Hermes-Lima M, et al. The iron chelator pyridoxal isonicotinoyl hydrazone (PIH) and its analogues prevent damage to 2-deoxyribose mediated by ferric iron plus ascorbate. Biochim Biophys Acta. 2000 Oct 18;1523 (2-3) :154-60.|[2]Landschulz W, et al. A lipophilic iron chelator can replace transferrin as a stimulator of cell proliferation and differentiation. J Cell Biol. 1984 Feb;98 (2) :596-601.|[3]Brewer CT, et al. The Isoniazid Metabolites Hydrazine and Pyridoxal Isonicotinoyl Hydrazone Modulate Heme Biosynthesis. Toxicol Sci. 2019 Mar 1;168 (1) :209-224.|[4]Sookvanichsilp N, et al. Toxicological study of pyridoxal isonicotinoyl hydrazone: acute and subchronic toxicity. Drug Chem Toxicol. 1991;14 (4) :395-403.|[5]Buss JL, et al. Oxidative stress mediates toxicity of pyridoxal isonicotinoyl hydrazone analogs. Arch Biochem Biophys. 2004 Jan 1;421 (1) :1-9.|[6]Zhang H, et al. Pyridoxal Isonicotinoyl Hydrazone Improves Neurological Recovery by Attenuating Ferroptosis and Inflammation in Cerebral Hemorrhagic Mice. Biomed Res Int. 2021 Sep 8;2021:9916328.