2',3',5'-Tri-O-acetyladenosine

Names

[ Name ]:
2',3',5'-Tri-O-acetyladenosine

[Synonym ]:
MFCD00057001
Tri-O-acetyladenosine
2',3',5'-Tri-O-acetyladenosine
Adenosine, 2',3',5'-triacetate

Biological Activity

[Description]:

2’,3’,5’-Tri-O-acetyl adenosine is an adenosine analog. Adenosine analogs mostly act as smooth muscle vasodilators and have also been shown to inhibit cancer progression. Its popular products are adenosine phosphate, Acadesine (HY-13417), Clofarabine (HY-A0005), Fludarabine phosphate (HY-B0028) and Vidarabine (HY-B0277)[1].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Cell Cycle/DNA Damage >> Nucleoside Antimetabolite/Analog

[References]

[1]. Man S, et al. Potential and promising anticancer drugs from adenosine and its analogs. Drug Discov Today. 2021 Jun;26(6):1490-1500.

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
594.1±60.0 °C at 760 mmHg

[ Melting Point ]:
168-170ºC

[ Molecular Formula ]:
C₁₆H₁₉N₅O₇

[ Molecular Weight ]:
393.35

[ Flash Point ]:
313.1±32.9 °C

[ Exact Mass ]:
393.128448

[ PSA ]:
157.75000

[ LogP ]:
0.99

[ Vapour Pressure ]:
0.0±1.7 mmHg at 25°C

[ Index of Refraction ]:
1.680

[ Storage condition ]:
−20°C

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

Synthetic Route

Click to get detail synthetic route

Articles

Detection of proton-acceptor sites of hydrogen bonding in adenine X uracil base pairs by the use of 15N magnetic resonance.

Eur. J. Biochem. 117(3) , 553-8, (1981)

2',3',5'-Tri-O-acetyl[1,3,7,9,amino-15N]adenosine(ac3Ado) and its 8-2H and 8-bromo derivatives (ac3[8-2H]Ado and ac3br8Ado) were synthesized from 95% 15N-enriched adenosine which was obtained by micro...

An 15N NMR study of adenine-uracil base pair in a non-aqueous solvent.

Nucleic Acids Symp. Ser. (6) , s79-82, (1979)

[1,3,7,9,10-15N]-2',3',5'-Tri-O-acetyl adenosine (A) and its 8-D and 8-Br derivatives (AD and ABr) were prepared from 95% 15N enriched adenosine obtained from microbial fermentation. The chemical shif...