S0130

Streptozocin

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

• Szinonimák: STZ, Streptozotocine, N-(Methylnitrosocarbamoyl)-α-D-glucosamine, Streptozotocin
• Tapasztalati képlet (Hill-képlet): C₈H₁₅N₃O₇
• CAS-szám: 18883-66-4
• Molekulatömeg: 265.22
• Beilstein: 2060675
• EC-szám: 242-646-8
• MDL-szám: MFCD00006607
• UNSPSC kód: 12352200
• PubChem Substance ID: 57654595
• NACRES: NA.77

Tulajdonságok

• product name: Streptozocin, ≥75% α-anomer basis, ≥98% (HPLC), powder
• Minőségi szint: 200
• Teszt: ≥75% α-anomer basis; ≥98% (HPLC)
• form: powder
• szín: white to light yellow
• mp: 121 °C (dec.) (lit.)
• antibiotikus hatásspektrum: neoplastics
• Hatásmechanizmus: DNA synthesis | interferes
• tárolási hőmérséklet: −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
• Nemzetközi kémiai azonosító kulcs: ZSJLQEPLLKMAKR-GKHCUFPYSA-N

Leírás

Általános leírás

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.

Alkalmazás

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

Biokémiai/fiziológiai hatások

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.

Egyéb megjegyzések

Mixed anomers

Biztonsági adatok

• Piktogramok: GHS02,GHS08
• Figyelmeztetés: Warning
• Figyelmeztető mondatok: H228,H341,H351
• Óvintézkedésre vonatkozó mondatok: P202 - P210 - P240 - P241 - P280 - P308 + P313
• Veszélyességi osztályok: Carc. 2 - Flam. Sol. 2 - Muta. 2
• Tárolási osztály kódja: 4.1B - Flammable solid hazardous materials
• WGK: WGK 3
• Lobbanási pont (F): Not applicable
• Lobbanási pont (C): Not applicable
• Egyéni védőeszköz: Eyeshields, Gloves, type P3 (EN 143) respirator cartridges