An iron chelator
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SIH

Item No. 33314

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-[(2-hydroxyphenyl)methylene]hydrazide 4-pyridinecarboxylic acid
CAS Number
495-84-1
Synonyms
  • NSC 33760
  • Salicylaldehyde Isonicotinoyl Hydrazine
  • Salinazid
Molecular Formula
C13H11N3O2
Formula Weight
241.2
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMF:PBS (pH 7.2) (1:3): 0.23 mg/mlDMSO: 5 mg/ml
λmax
215, 290, 335 nm
SMILES
O=C(C1=CC=NC=C1)NN=CC2=C(O)C=CC=C2
InChi Code
InChI=1S/C13H11N3O2/c17-12-4-2-1-3-11(12)9-15-16-13(18)10-5-7-14-8-6-10/h1-9,17H,(H,16,18)
InChi Key
VBIZUNYMJSPHBH-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    50 mg

    $81

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    100 mg

    $152

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    250 mg

    $357

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    500 mg

    $633

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    Product Description

    SIH is a lipophilic cell-permeable iron chelator.1,2 It stimulates iron release from, and inhibits iron uptake by, SK-N-MC human neuroblastoma cells when used at a concentration of 25 µM.3 SIH inhibits cumene hydroperoxide-induced membrane lipid peroxidation but not ABAP-induced formation of cytosolic peroxyl radicals in HepG2 human hepatocellular carcinoma cells (IC50s = 0.833 and >4,000 µM, respectively).1 It inhibits hydrogen peroxide-induced mitochondrial membrane depolarization in H9c2 rat cardiomyocytes (EC50 = 0.8 µM).2 SIH (1.0 mg/kg) completely prevents mortality in a rabbit model of cardiotoxicity induced by chronic administration of daunorubicin (Item No. 14159).4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hofer, T., Jørgensen, T.Ø., and Olsen, R.L. Comparison of food antioxidants and iron chelators in two cellular free radical assays: Strong protection by luteolin. J. Agric. Food Chem. 62(33), 8402-8410 (2014).

    2. Šimůnek, T., Boer, C., Bouwman, R.A., et al. SIH—a novel lipophilic iron chelator—protects H9c2 cardiomyoblasts from oxidative stress-induced mitochondrial injury and cell death. J. Mol. Cell. Cardiol. 39(2), 345-354 (2005).

    3. Wu, Z., Palanimuthu, D., Braidy, N., et al. Novel multifunctional iron chelators of the aroyl nicotinoyl hydrazone class that markedly enhance cellular NAD+ /NADH ratios. Br. J. Pharmacol. 177(9), 1967-1987 (2019).

    4. Štĕrba, M., Popelová, O., Šimůnek, T., et al. Iron chelation-afforded cardioprotection against chronic anthracycline cardiotoxicity: A study of salicylaldehyde isonicotinoyl hydrazone (SIH). Toxicology 235(3), 150-166 (2007).