Adenine 9-beta-D-arabinofuranoside
| Code | Size | Price |
|---|
| CDX-A0279-G005 | 5 g | £157.00 |
Quantity:
| CDX-A0279-G025 | 25 g | £523.00 |
Quantity:
Prices exclude any Taxes / VAT
Overview
Regulatory Status: RUO
Shipping:
AMBIENT
Storage:
-20°C
Documents
Further Information
Alternate Names/Synonyms:
Adenine Arabinoside; Arabinosyladenine; 9-beta-D-Arabinofuranosyladenine; Ara-A; Vidarabine; NSC 247519; NSC 404241; Vira-A
Appearance:
White to off-white powder.
CAS:
5536-17-4
EClass:
32160000
Form (Short):
liquid
GHS Symbol:
GHS08
Handling Advice:
Protect from light and moisture.
Hazards:
H351-H360
InChi:
InChI=1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7+,10-/m1/s1
InChiKey:
OIRDTQYFTABQOQ-UHTZMRCNSA-N
Long Description:
Chemical. CAS: 5536-17-4. Formula: C10H13N5O4. MW: 267.24. Adenine 9-beta-D-arabinofuranoside is an analog of the nucleoside adenosine that has antiviral properties. It acts as a prodrug that, once phosphorylated by cellular enzymes, acts as both substrate and inhibitor of DNA polymerase. It has been shown to be effective against H. simplex, V. zoster and Epstein-Barr viruses. It is a potent inhibitor of AMP-activated protein kinase (AMPK) in liver, muscle and cardiac cells H9c2. It is also a neurotransmitter that acts as the preferred endogenous agonist at all adenosine receptor subtypes and showed anti-neoplastic activities. It has been shown to have inhibitory activity against SARS-CoV-2-ACE2 binding.
MDL:
MFCD00065471
Molecular Formula:
C10H13N5O4
Molecular Weight:
267.24
Package Type:
Vial
Precautions:
P281
Product Description:
Adenine 9-beta-D-arabinofuranoside is an analog of the nucleoside adenosine that has antiviral properties. It acts as a prodrug that, once phosphorylated by cellular enzymes, acts as both substrate and inhibitor of DNA polymerase. It has been shown to be effective against H. simplex, V. zoster and Epstein-Barr viruses. It is a potent inhibitor of AMP-activated protein kinase (AMPK) in liver, muscle and cardiac cells H9c2. It is also a neurotransmitter that acts as the preferred endogenous agonist at all adenosine receptor subtypes and showed anti-neoplastic activities. It has been shown to have inhibitory activity against SARS-CoV-2-ACE2 binding.
Purity:
>99% (HPLC)
Signal word:
Warning
SMILES:
NC1=NC=NC2=C1N=CN2[C@@H]3O[C@H](CO)[C@@H](O)[C@@H]3O
Solubility Chemicals:
Soluble in DMSO (20mg/ml) or DMF (5mg/ml). Slightly soluble in water (1mg/ml).
Transportation:
Non-hazardous
UNSPSC Category:
Biochemical Reagents
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 2 years after receipt when stored at -20°C.
References
(1) S. Yoshida, et al.; J. Biochem. 98, 433 (1985) | (2) W.B. Parker & Y. Cheng; Mol. Pharmacol. 31, 146 (1986) | (3) B. Bean; Clin. Microbiol. Rev. 5, 146 (1992) | (4) Y. Honma & N. Nitsu; Leuk. Lymphoma 399, 57 (2000) | (5) H. Kimura, et al.; J. Pediatr. Hematol. Oncol. 23, 294 (2001) | (6) A. Kishimoto, et al.; Mol. Biotechnol. 32, 17 (2006) | (7) M. Suzuki, et al.; Antiviral Res. 72, 157 (2006) | (8) K.A. Jacobson & Z.-G. Gao; Nat. Rev. Drug Discov. 5, 247 (2006) (Review) | (9) S. Holzer, et al.; ACS Chem. Biol. 14, 1904 (2019) | (10) M. Prajapat, et al.; J. Mol. Graph. Model 101, 107716 (2020)