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SML0628

Sigma-Aldrich

8-Aminoadenosine

≥98% (HPLC)

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Synonym(s):
6,8-Diamino-9-β-D-ribofuranosyl-9H-purine, 8-Amino Adenosine, 8-Amino-Adenosine, 8-NH2-Ado, NSC 90394
Empirical Formula (Hill Notation):
C10H14N6O4
CAS Number:
Molecular Weight:
282.26
NACRES:
NA.77

Quality Level

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

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This Item
D8668D7400SML1852
Sigma-Aldrich

SML0628

8-Aminoadenosine

2′-Deoxyadenosine monohydrate powder, BioReagent, suitable for cell culture

D8668

2′-Deoxyadenosine monohydrate

2′-Deoxyadenosine monohydrate ≥99%

D7400

2′-Deoxyadenosine monohydrate

8-Aminoguanosine ≥98% (HPLC)

SML1852

8-Aminoguanosine

assay

≥98% (HPLC)

assay

≥99% (HPLC)

assay

≥99%

assay

≥98% (HPLC)

Quality Level

100

Quality Level

200

Quality Level

-

Quality Level

100

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

solubility

H2O: 2 mg/mL, clear (warmed)

solubility

H2O: soluble 25 mg/mL, clear to slightly hazy, colorless to faintly yellow

solubility

water: 25 mg/mL, clear to slightly hazy, colorless to faintly yellow

solubility

DMSO: 1 mg/mL, clear (warmed)

color

white to beige

color

-

color

-

color

white to brown

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

signalword

Danger

hcodes

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
Non-tyrosine kinase inhibitor-targeting of BCR-ABL expressing cells.
Olga Frankfurt et al.
Leukemia & lymphoma, 53(10), 1857-1858 (2012-05-10)
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
Rathi N Pillai et al.
Leukemia & lymphoma, 53(10), 2024-2032 (2012-03-28)
Survival of chronic myelogenous leukemia (CML) cells is dependent on BCR-ABL kinase, the activity of which is contingent on the level of BCR-ABL protein and the availability of adenosine triphosphate (ATP). We hypothesized that 8-amino-adenosine (8-amino-Ado)-mediated reduction in cellular ATP
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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