S0130

Streptozocin

≥75% α-anomer basis, ≥98% (HPLC), powder

• Synonym(s): STZ, Streptozotocine, N-(Methylnitrosocarbamoyl)-α-D-glucosamine, Streptozotocin
• Empirical Formula (Hill Notation): C₈H₁₅N₃O₇
• CAS Number: 18883-66-4
• Molecular Weight: 265.22
• Beilstein: 2060675
• EC Number: 242-646-8
• MDL number: MFCD00006607
• UNSPSC Code: 12352200
• PubChem Substance ID: 57654595
• NACRES: NA.77

Properties

• Quality Level: 200
• Assay: ≥75% α-anomer basis; ≥98% (HPLC)
• form: powder
• color: white to light yellow
• mp: 121 °C (dec.) (lit.)
• antibiotic activity spectrum: neoplastics
• Mode of action: DNA synthesis | interferes
• storage temp.: −20°C
• SMILES string: CN(N=O)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O
• InChI: 1S/C8H15N3O7/c1-11(10-17)8(16)9-4-6(14)5(13)3(2-12)18-7(4)15/h3-7,12-15H,2H2,1H3,(H,9,16)/t3-,4-,5-,6-,7+/m1/s1
• InChI key: ZSJLQEPLLKMAKR-GKHCUFPYSA-N

Description

General description

Streptozocin (STZ) is an antineoplastic antibiotic. This N-nitroso-containing compound acts as a nitric oxide donor in pancreatic islets. It is a methylnitrosourea attached to a single molecule of glucosamine and has a high affinity for the cell surface glucose transporter glucose transporter type 2 (GLUT2), which is highly expressed on beta cells of the islets of Langerhans. Streptozotocin cannot pass through the blood-brain barrier, but its metabolites are usually seen in the cerebrospinal fluid.

In cell culture medium, it has been shown to have a biological half-life of approximately 19 minutes. It is a strong methylating agent that interacts with DNA in vitro to produce methylated purines. It can impact glucose metabolism because STZ is particularly toxic to the insulin-producing beta cells of the pancreas in mammals and is also an effective antibiotic against Gram-negative bacteria. It inhibits the synthesis of DNA in microorganisms and mammalian cells by alkylation and cross-linking the strands of DNA and affects all stages of the mammalian cell cycle. STZ is considered mutagenic, carcinogenic, and possibly teratogenic in humans. It is cytotoxic to the neuroendocrine tumor cell lines that express the GLUT2 glucose transporter.

Application

Streptozocin or streptozotocin is used to induce type 1 diabetes for medical research.

Biochem/physiol Actions

An N-nitroso-containing compound that acts as a nitric oxide donor in pancreatic islets; induces death of insulin-secreting cells, producing an animal model of diabetes. Potent DNA methylating agent that induces chromosomal breakage. Cytotoxic to neuroendocrine tumor cell lines that express the GLUT2 glucose transporter.

Other Notes

Mixed anomers

Safety Information

• Pictograms: GHS02,GHS08
• Signal Word: Warning
• Hazard Statements: H228 - H341 - H351
• Precautionary Statements: P202 - P210 - P240 - P241 - P280 - P308 + P313
• Hazard Classifications: Carc. 2 - Flam. Sol. 2 - Muta. 2
• Storage Class Code: 4.1B - Flammable solid hazardous materials
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves