A lipophilic iron chelator
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Information provided in the product description is from published literature. Due to the nature of scientific experimentation, your results (e.g., selectivity and effective concentrations) or specific application for this product may differ. If you have questions about how this product fits your application, please contact our technical support staff.

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Pyridoxal isonicotinoyl hydrazone

Item No. 19357

Technical Information
Formal Name
4-pyridinecarboxylic acid, 2-[[3-hydroxy-5-(hydroxymethyl)-2-methyl-4-pyridinyl]methylene]hydrazide
CAS Number
737-86-0
Synonyms
  • NSC 77674
  • PIH
Molecular Formula
C14H14N4O3
Formula Weight
Purity
≥99%
A solid
DMF: 1 mg/mlDMSO: 5 mg/mlEthanol: 0.5 mg/ml
SMILES
CC1=NC=C(CO)C(/C=N/NC(C2=CC=NC=C2)=O)=C1O
InChi Code
InChI=1S/C14H14N4O3/c1-9-13(20)12(11(8-19)6-16-9)7-17-18-14(21)10-2-4-15-5-3-10/h2-7,19-20H,8H2,1H3,(H,18,21)/b17-7+
InChi Key
BQYIXOPJPLGCRZ-REZTVBANSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Pyridoxal isonicotinoyl hydrazine is a lipophilic, nontoxic, iron-chelating agent that shows high iron chelation efficacy both in vitro in cell culture models and in vivo in rats and mice.1,2 Because iron is a crucial component of metabolic pathways involved in DNA synthesis, cancerous cells have a high iron requirement due to rapid rates of proliferation. While pyridoxal isonicotinoyl hydrazine exhibits low anticancer activity, its analogs demonstrate antiproliferative effects in a range of tumor cells.3,4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ponka, P., Borova, J., Neuwirt, J., et alMobilization of iron from reticulocytes. Identification of pyridoxal isonicotinoyl hydrazone as a new iron chelating agent. FEBS Lett. 97(2), 317-321 (1979).

    2. Richardson, D.R., and Ponka, P. Pyridoxal isonicotinoyl hydrazone and its analogs: Potential orally effective iron-chelating agents for the treatment of iron overload disease. J. Lab. Clin. Med. 131(4), 306-315 (1998).

    3. Merlot, A.M., Pantarat, N., Lovejoy, D.B., et alMembrane transport and intracellular sequestration of novel thiosemicarbazone chelators for the treatment of cancer. Mol. Pharmacol. 78(4), 675-684 (2010).

    4. Richardson, D.R. Cytotoxic analogs of the iron(III) chelator pyridoxal isonicotinoyl hydrazone: Effects of complexation with copper(II), gallium(III), and iron (III) on their antiproliferative activities. Antimicrob. Agents Chemother. 41(9), 2061-2063 (1997).

    5. Gao, J., and Richardson, D.R. The potential of iron chelators of the pyridoxal isonicotinoyl hydrazone class as effective antiproliferative agents, IV: The mechanisms involved in inhibiting cell-cycle progression. Blood 98(3), 842-850 (2001).