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C6645

Sigma-Aldrich

Cytosine β-D-arabinofuranoside hydrochloride

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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About This Item

Formule empirique (notation de Hill):
C9H13N3O5 · HCl
Numéro CAS:
69-74-9
Poids moléculaire :
279.68
Numéro CE :
200-713-9
Numéro MDL:
MFCD00012839
Code UNSPSC :
12352202
ID de substance PubChem :
24278329
Nomenclature NACRES :
NA.77

Source biologique

synthetic (inorganic)

Pureté

≥99% (HPLC)

Forme

crystalline

Pf

197-198 °C (lit.)

Température de stockage

2-8°C

Chaîne SMILES 

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

Clé InChI

KCURWTAZOZXKSJ-JBMRGDGGSA-N

Informations sur le gène

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

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.

Actions biochimiques/physiologiques

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.

Autres remarques

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

Pictogrammes

Health hazardExclamation mark
GHS08,GHS07

Mention d'avertissement

Warning

Mentions de danger

H317,H319,H341,H361

Classification des risques

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

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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)
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)
Juan A Godoy et al.
Molecular neurobiology, 55(12), 8965-8977 (2018-04-06)
Mitochondria are widely recognized as fundamental organelles for cellular physiology and constitute the main energy source for different cellular processes. The location, morphology, and interactions of mitochondria with other organelles, such as the endoplasmic reticulum (ER), have emerged as critical
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
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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.

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