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Sigma-Aldrich

N6-Benzyladenosine

≥99.0%

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About This Item

Empirical Formula (Hill Notation):
C17H19N5O4
CAS Number:
4294-16-0
Molecular Weight:
357.36
Beilstein:
56815
EC Number:
224-298-9
MDL number:
MFCD00005740
UNSPSC Code:
12352200
PubChem Substance ID:
57647065

Quality Level

100

Assay

≥99.0%

form

powder

mp

184-186 °C

storage temp.

2-8°C

SMILES string

OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3c(NCc4ccccc4)ncnc23

InChI

1S/C17H19N5O4/c23-7-11-13(24)14(25)17(26-11)22-9-21-12-15(19-8-20-16(12)22)18-6-10-4-2-1-3-5-10/h1-5,8-9,11,13-14,17,23-25H,6-7H2,(H,18,19,20)/t11-,13-,14-,17-/m1/s1

InChI key

MRPKNNSABYPGBF-LSCFUAHRSA-N

Gene Information

human ... ADORA3(140)
rat ... Adora1(29290) , Adora2a(25369) , Adora3(25370)

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Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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R G Luiten et al.
Nucleic acids research, 11(22), 8073-8085 (1983-11-25)
From in vitro protein synthesis studies and nucleotide sequence analysis it has been deduced that, unlike the major coat proteins of the hitherto studied filamentous bacterial viruses Ff (M13, fd and f1), IKe and Pf1, the major coat protein of
P Mlejnek
Journal of cellular biochemistry, 83(4), 678-689 (2001-12-18)
As an extension of our recently published work (Mlejnek and Kuglík [2000] J. Cell. Biochem. 77:6-17), the role of caspases in N(6)-benzylaminopurine riboside (BAPR)-induced apotosis in HL-60 cells was evaluated in this study. Here, BAPR-induced apoptosis was accompanied by activation
Karel Dolezal et al.
Bioorganic & medicinal chemistry, 15(11), 3737-3747 (2007-04-10)
Cytokinin activity of forty-eight 6-benzyladenosine derivatives at both the receptor and cellular levels as well as their anticancer properties were compared in various in vitro assays. The compounds were prepared by the condensation of 6-chloropurine riboside with corresponding substituted benzylamines
B C Froehler et al.
Nucleic acids research, 11(22), 8031-8036 (1983-11-25)
Sterically hindered N6-dialkylformamidine protected deoxyadenosine is more stable to acidic depurination than N6-benzoyldeoxyadenosine and is potentially a valuable protecting group in the synthesis of deoxyoligonucleotides.
Petr Dolezel et al.
Toxicology in vitro : an international journal published in association with BIBRA, 24(8), 2079-2083 (2010-07-20)
Cytotoxicity of two halogen derivatives of N⁶-benzyladenosine (BAPR), N⁶-(3-iodobenzyl)-adenosine (I-BAPR) and 2-chloro-N⁶-(3-iodobenzyl)-adenosine (Cl-I-BAPR), was tested in human leukemia U937 cell line. Our results revealed that their cytotoxicity was surprisingly low. I-BAPR and also Cl-I-BAPR induced cell death with morphological and
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