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S0130

Streptozocin

Name: Streptozocin
Brand: SIGMA

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

Synonym(s):

STZ, Streptozotocine, N-(Methylnitrosocarbamoyl)-α-D-glucosamine, Streptozotocin

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About This Item

Empirical Formula (Hill Notation):

C₈H₁₅N₃O₇

CAS Number:

18883-66-4

Molecular Weight:

265.22

NACRES:

NA.77

PubChem Substance ID:

57654595

UNSPSC Code:

12352200

EC Number:

242-646-8

MDL number:

MFCD00006607

Beilstein/REAXYS Number:

2060675

Assay:

≥75% α-anomer basis, ≥98% (HPLC)

Form:

powder

Quality level:

200

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Properties

Product Name

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

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.