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C6645

Sigma-Aldrich

Cytosine β-D-arabinofuranoside hydrochloride

crystalline

Sinônimo(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

Fórmula empírica (Notação de Hill):
C9H13N3O5 · HCl
Número CAS:
69-74-9
Peso molecular:
279.68
Número CE:
200-713-9
Número MDL:
MFCD00012839
Código UNSPSC:
12352202
ID de substância PubChem:
24278329
NACRES:
NA.77

fonte biológica

synthetic (inorganic)

Ensaio

≥99% (HPLC)

Formulário

crystalline

pf

197-198 °C (lit.)

temperatura de armazenamento

2-8°C

cadeia de caracteres 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

chave InChI

KCURWTAZOZXKSJ-JBMRGDGGSA-N

Informações sobre genes

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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Aplicação

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.

Ações bioquímicas/fisiológicas

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.

Outras notas

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

Pictogramas

Health hazardExclamation mark
GHS08,GHS07

Palavra indicadora

Warning

Frases de perigo

H317,H319,H341,H361

Classificações de perigo

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

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Escolha uma das versões mais recentes:

Certificados de análise (COA)

Lot/Batch Number
SLCD6191
SLCD2059
SLBZ5371
SLBX3110
SLBQ8116V

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Reduced activity of AMP-activated protein kinase protects against genetic models of motor neuron disease
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The Journal of Neuroscience, 32(3), 1123-1141 (2012)
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Leukemia research, 84, 106180-106180 (2019-07-13)
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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
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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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