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S0130

Sigma-Aldrich

Streptozocin

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

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Synonym(s):
STZ, Streptozotocine, N-(Methylnitrosocarbamoyl)-α-D-glucosamine, Streptozotocin
Empirical Formula (Hill Notation):
C8H15N3O7
CAS Number:
Molecular Weight:
265.22
Beilstein:
2060675
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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

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This Item
480743C884956218
Streptozocin ≥75% α-anomer basis, ≥98% (HPLC), powder

S0130

Streptozocin

α-Chloralose−HBC complex ≥92% α-anomer basis

C8849

α-Chloralose−HBC complex

Nystose analytical standard

56218

Nystose

Quality Level

200

Quality Level

100

Quality Level

100

Quality Level

100

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

-

storage temp.

2-8°C

color

white to light yellow

color

off-white

color

-

color

-

form

powder

form

solid

form

powder

form

-

mp

121 °C (dec.) (lit.)

mp

-

mp

-

mp

-

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

also commonly purchased with this product

Pictograms

FlameHealth hazard

Signal Word

Warning

Hazard Statements

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

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Review of the mechanism of cell death resulting from streptozotocin challenge in experimental animals, its practical use and potential risk to humans
Chinedum
Journal of diabetes and metabolic disorders, 12, 60-60 (2013)
Cordyceps militaris Treatment Preserves Renal Function in Type 2 Diabetic Nephropathy Mice
Sung-Hsun Yu
PLoS ONE (2016)
Streptozotocin
Abdollahi, M and Hosseini, A
Encyclopedia of Toxicology (2014)
Streptozotocin
Abdollahi, M and Hosseini, A
Encyclopedia of Toxicology (2014)
Acute stimulation of brain mu opioid receptors inhibits glucosestimulated
insulin secretion via sympathetic innervation
Eva Tuduri
Neuropharmacology, 110, 322-332 (2016)

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