C6645

Cytosine β-D-arabinofuranoside hydrochloride

Name: Cytosine β-<SC>D</SC>-arabinofuranoside hydrochloride
Brand: SIGMA

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

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill) :

C₉H₁₃N₃O₅ · HCl

Numéro CAS:

69-74-9

Poids moléculaire :

279.68

NACRES:

NA.77

PubChem Substance ID:

24278329

UNSPSC Code:

12352202

EC Number:

200-713-9

MDL number:

MFCD00012839

Nom du produit

Cytosine β-D-arabinofuranoside hydrochloride, crystalline

InChI key

KCURWTAZOZXKSJ-JBMRGDGGSA-N

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

SMILES string

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

biological source

synthetic (inorganic)

assay

≥99% (HPLC)

form

crystalline

mp

197-198 °C (lit.)

solubility

water: 50 mg/mL, clear, colorless

storage temp.

2-8°C

Quality Level

200

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)

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Catégories apparentées

Chemistry & Biochemicals

Biochemicals

Nucleosides and Nucleotides

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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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

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)

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)

Regulation of cardiac gene expression by KLF15, a repressor of myocardin activity.

Joost J Leenders et al.

The Journal of biological chemistry, 285(35), 27449-27456 (2010-06-23)

Pathological forms of left ventricular hypertrophy (LVH) often progress to heart failure. Specific transcription factors have been identified that activate the gene program to induce pathological forms of LVH. It is likely that apart from activating transcriptional inducers of LVH

Phase III randomized study of rituximab/carmustine, etoposide, cytarabine, and melphalan (BEAM) compared with iodine-131 tositumomab/BEAM with autologous hematopoietic cell transplantation for relapsed diffuse large B-cell lymphoma: results from the BMT CTN 0401 trial.

Julie M Vose et al.

Journal of clinical oncology : official journal of the American Society of Clinical Oncology, 31(13), 1662-1668 (2013-03-13)

This clinical trial evaluated standard-dose radioimmunotherapy with a chemotherapy-based transplantation regimen followed by autologous hematopoietic cell transplantation versus rituximab with the same regimen in patients with relapsed diffuse large B-cell lymphoma (DLBCL). Patients with chemotherapy-sensitive persistent or relapsed DLBCL were

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Contenu apparenté

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