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SML0628

Sigma-Aldrich

8-Aminoadenosine

≥98% (HPLC)

Synonym(s):

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

Empirical Formula (Hill Notation):
C10H14N6O4
CAS Number:
3868-33-5
Molecular Weight:
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

Related Categories

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

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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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
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
Nancy L Krett et al.
Molecular cancer therapeutics, 3(11), 1411-1420 (2004-11-16)
Multiple myeloma (MM) is a malignancy of clonal B-cells that accounts for 10% of all hematologic malignancies. We have shown previously that a novel purine analogue, 8-chloro-adenosine, has significant activity for MM in preclinical studies. Using MM cell lines, we
Krishna N Ganesh et al.
Nucleic acids symposium series (2004), (51)(51), 17-18 (2007-11-22)
We herein describe the introduction of gem-dimethyl substitution into the aminoethylglycyl backbone of PNA to impart steric constraint and pre-organise PNA for selective recognition of nucleic acids. Introduction of cyanuric acid and 8-aminoadenine as pyrimidine and purine analogs that can
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
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