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C6645

Cytosine β-D-arabinofuranoside hydrochloride

Name: Cytosine &#946;-<SC>D</SC>-arabinofuranoside hydrochloride
Brand: SIGMA

≥99% (HPLC), synthetic (inorganic), crystalline

Synonyme(s) :

1-(β-D-Arabinofuranosyl)cytosine hydrochloride, Ara-C hydrochloride, Arabinocytidine hydrochloride, Arabinosylcytosine hydrochloride, Cytarabine hydrochloride, Cytosine arabinoside hydrochloride

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A propos de cet article

Formule empirique (notation de Hill) :

C₉H₁₃N₃O₅ · HCl

Numéro CAS:

69-74-9

Poids moléculaire :

279.68

NACRES:

NA.77

PubChem Substance ID:

24278329

EC Number:

200-713-9

MDL number:

MFCD00012839

UNSPSC Code:

12352208

Assay:

≥99% (HPLC)

Biological source:

synthetic (inorganic)

Form:

crystalline

Solubility:

water: 50 mg/mL, clear, colorless

Storage temp.:

2-8°C

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Propriétés

Nom du produit

Cytosine β-D-arabinofuranoside hydrochloride, crystalline

biological source

synthetic (inorganic)

Quality Level

200

assay

≥99% (HPLC)

form

crystalline

mp

197-198 °C (lit.)

solubility

water: 50 mg/mL, clear, colorless

storage temp.

2-8°C

SMILES string

Cl[H].NC1=NC(=O)N(C=C1)[C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O

InChI

1S/C9H13N3O5.ClH/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8;/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16);1H/t4-,6-,7+,8-;/m1./s1

InChI key

KCURWTAZOZXKSJ-JBMRGDGGSA-N

Gene Information

human ... POLA1(5422), POLA2(23649), POLD1(5424), POLD2(5425), POLD3(10714), POLD4(57804), POLE(5426), POLE2(5427), POLE3(54107), PRIM1(5557), PRIM2(5558)

Description

Application

Cytosine β-D-arabinofuranoside hydrochloride has been used in fetal bovine serum supplemented Dulbecco′s modified eagle medium (FBS-DMEM) and B27/neurobasal-A medium to inhibit the growth of glial cells. It has also been used to inhibit astrocyte proliferation in embryonic spinal cord neurons.

Biochem/physiol Actions

Ara-C is phosphorylated to Ara-CTP and is incorporatee into DNA. It inhibits DNA replication by forming cleavage complexes with topoisomerase I resulting in DNA fragmentation, and ultimately induces apoptosis via the PKC signaling pathway. Does not inhibit RNA synthesis. Anti-leukemia agent.

Other Notes

2024 CiteAb Award Winner for Supplier Succeeding in Parkinson′s Research

pictograms

GHS08,GHS07

signalword

Warning

hcodes

H317,H319,H341,H361

pcodes

P201 - P280 - P302 + P352 - P305 + P351 + P338 - P308 + P313

Hazard Classifications

Eye Irrit. 2 - Muta. 2 - Repr. 2 - Skin Sens. 1

Classe de stockage

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificats d'analyse (COA)

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Articles

DNA Damage and Repair

DNA damage and repair mechanism is vital for maintaining DNA integrity. Damage to cellular DNA is involved in mutagenesis, the development of cancer among others.

Contenu apparenté

Product Information Sheet - C6645

Reduced activity of AMP-activated protein kinase protects against genetic models of motor neuron disease

Lim MA, et al.

The Journal of Neuroscience, 32(3), 1123-1141 (2012)

Interleukin-8 blockade prevents activated endothelial cell mediated proliferation and chemoresistance of acute myeloid leukemia.

Vindhya Vijay et al.

Leukemia research, 84, 106180-106180 (2019-07-13)

One of the greatest challenges in treating acute myeloid leukemia (AML) is chemotherapy refractory disease. Previously, we demonstrated a novel mechanism whereby AML-induced endothelial cell (EC) activation leads to subsequent leukemia cell adherence, quiescence and chemoresistance, identifying activated ECs as

JNK plays a key role in tau hyperphosphorylation in Alzheimer's disease models

Ploia C, et al.

Journal of Alzheimer'S Disease, 26(2), 315-329 (2011)

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Numéro d'article de commerce international

Référence	GTIN
C6645-100MG	04061833511435
C6645-5G	04061833511466
C6645-1G	04061826744178
C6645-25MG	04061833511442
C6645-500MG	04061833511459