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Merck
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Key Documents

SML0628

Sigma-Aldrich

8-Aminoadenosine

≥98% (HPLC)

Sinónimos:

6,8-Diamino-9-β-D-ribofuranosyl-9H-purine, 8-Amino Adenosine, 8-Amino-Adenosine, 8-NH2-Ado, NSC 90394

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About This Item

Fórmula empírica (notación de Hill):
C10H14N6O4
Número de CAS:
3868-33-5
Peso molecular:
282.26
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

H2O: 2 mg/mL, clear (warmed)

storage temp.

−20°C

InChI

1S/C10H14N6O4/c11-7-4-8(14-2-13-7)16(10(12)15-4)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H2,12,15)(H2,11,13,14)

InChI key

DVGWFQILDUEEGX-UHFFFAOYSA-N

Biochem/physiol Actions

8-Aminoadenosine, a ribose nucleoside, reduces cellular ATP levels and inhibits mRNA synthesis. 8-Aminoadenosine also inhibits transcription and polyadenylation. 8-Aminoadenosine potently inhibits varies breast cancer cell lines proliferation and activates cell death independent of p53. 8-NH2-Ado is highly cytotoxic to other cancer cell lines.

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Jennifer Ann Frey et al.
Molecular cancer therapeutics, 9(1), 236-245 (2010-01-08)
Roscovitine and flavopiridol suppress cyclin-dependent kinase 7 (CDK7) and CDK9 activity resulting in transcription inhibition, thus providing an alternative mechanism to traditional genotoxic chemotherapy. These agents have been effective in slow or nonreplicative cell types. 8-Amino-adenosine is a transcription inhibitor
K B Roy et al.
Biochemistry, 21(1), 57-62 (1982-01-05)
Equilibrium binding isotherms have been measured as a function of temperature for the interaction of 2- and 8-aminoadenosine with poly(U) by continuous, constant-volume ultrafiltration. An analytical method is described for determining the entire isotherm in a single experiment on a
Non-tyrosine kinase inhibitor-targeting of BCR-ABL expressing cells.
Olga Frankfurt et al.
Leukemia & lymphoma, 53(10), 1857-1858 (2012-05-10)
Kulsoom Ghias et al.
Molecular cancer therapeutics, 4(4), 569-577 (2005-04-14)
Multiple myeloma is a slowly proliferating B-cell malignancy that accumulates apoptosis-resistant and replication-quiescent cell populations, posing a challenge for current chemotherapeutics that target rapidly replicating cells. Multiple myeloma remains an incurable disease in need of new therapeutic approaches. The purine
Kumudha Balakrishnan et al.
Clinical cancer research : an official journal of the American Association for Cancer Research, 11(18), 6745-6752 (2005-09-17)
To determine if RNA-directed nucleoside analogue, 8-NH(2)-adenosine, induces cell death and if that is accompanied with transcription inhibition of the key survival factors of chronic lymphocytic leukemia (CLL) cells. Primary lymphocytes from CLL patients were incubated with 10 micromol/L 8-NH(2)-adenosine
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