WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 565127
Description: SIH is a lipophilic cell-permeable iron chelator. It stimulates iron release from, and inhibits iron uptake by, SK-N-MC human neuroblastoma cells when used at a concentration of 25 µM. 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). It inhibits hydrogen peroxide-induced mitochondrial membrane depolarization in H9c2 rat cardiomyocytes (EC50 = 0.8 µM). SIH (1.0 mg/kg) completely prevents mortality in a rabbit model of cardiotoxicity induced by chronic administration of daunorubicin.
MedKoo Cat#: 565127
Chemical Formula: C13H11N3O2
Exact Mass: 241.0851
Molecular Weight: 241.25
Elemental Analysis: C, 64.72; H, 4.60; N, 17.42; O, 13.26
Synonym: Salizid; Nilazid; Nupasal; Salizide; Salicylaldehyde isonicotinoyl hydrazone; SIH1; SIH-1; SIH 1; Salinazid; Salicylaldehyde Isonicotinoyl Hydrazine; NSC 33760; NSC33760; NSC-33760;
IUPAC/Chemical Name: (E)-N'-(2-hydroxybenzylidene)isonicotinohydrazide
InChi Key: VBIZUNYMJSPHBH-OQLLNIDSSA-N
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)/b15-9+
SMILES Code: O=C(N/N=C/C1=CC=CC=C1O)C2=CC=NC=C2
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO
Shelf Life: >3 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
|Solvent||Max Conc. mg/mL||Max Conc. mM|
|DMF:PBS (pH 7.2) (1:3)||0.23||0.95|
The following data is based on the product molecular weight 241.25 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
|Concentration / Solvent Volume / Mass||1 mg||5 mg||10 mg|
|1 mM||1.15 mL||5.76 mL||11.51 mL|
|5 mM||0.23 mL||1.15 mL||2.3 mL|
|10 mM||0.12 mL||0.58 mL||1.15 mL|
|50 mM||0.02 mL||0.12 mL||0.23 mL|
1: Mittapalli S, Perumalla DS, Nanubolu JB, Nangia A. Thermomechanical effect in molecular crystals: the role of halogen-bonding interactions. IUCrJ. 2017 Oct 27;4(Pt 6):812-823. doi: 10.1107/S2052252517014658. PMID: 29123683; PMCID: PMC5668866.
2: Konijn AM, Glickstein H, Vaisman B, Meyron-Holtz EG, Slotki IN, Cabantchik ZI. The cellular labile iron pool and intracellular ferritin in K562 cells. Blood. 1999 Sep 15;94(6):2128-34. PMID: 10477743.
3: Tsafack A, Loyevsky M, Ponka P, Cabantchik ZI. Mode of action of iron (III) chelators as antimalarials. IV. Potentiation of desferal action by benzoyl and isonicotinoyl hydrazone derivatives. J Lab Clin Med. 1996 Jun;127(6):574-82. doi: 10.1016/s0022-2143(96)90148-1. PMID: 8648262.
4: Garrick LM, Gniecko K, Hoke JE, al-Nakeeb A, Ponka P, Garrick MD. Ferric- salicylaldehyde isonicotinoyl hydrazone, a synthetic iron chelate, alleviates defective iron utilization by reticulocytes of the Belgrade rat. J Cell Physiol. 1991 Mar;146(3):460-5. doi: 10.1002/jcp.1041460317. PMID: 2022700.
5: Evans AT, Croft SL, Peters W, Neal RA. Antileishmanial effects of clofazimine and other antimycobacterial agents. Ann Trop Med Parasitol. 1989 Oct;83(5):447-54. doi: 10.1080/00034983.1989.11812371. PMID: 2619361.
6: Ponka P, Schulman HM. Acquisition of iron from transferrin regulates reticulocyte heme synthesis. J Biol Chem. 1985 Nov 25;260(27):14717-21. PMID: 4055798.