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Merck
CN

N2255

S-(4-Nitrobenzyl)-6-thioinosine

≥98%, Adenosine uptake inhibitor, solid

Synonym(s):

6-[(4-Nitrobenzyl)thio]-9-β-D-ribofuranosylpurine, NBMPR, NBTI

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About This Item

Empirical Formula (Hill Notation):
C17H17N5O6S
CAS Number:
38048-32-7
Molecular Weight:
419.41
NACRES:
NA.77
PubChem Substance ID:
24277723
UNSPSC Code:
12352202
EC Number:
253-753-4
MDL number:
MFCD00005745

Key Documents

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Product Name

S-(4-Nitrobenzyl)-6-thioinosine, ≥98%, solid

InChI key

DYCJFJRCWPVDHY-LSCFUAHRSA-N

InChI

1S/C17H17N5O6S/c23-5-11-13(24)14(25)17(28-11)21-8-20-12-15(21)18-7-19-16(12)29-6-9-1-3-10(4-2-9)22(26)27/h1-4,7-8,11,13-14,17,23-25H,5-6H2/t11-,13-,14-,17-/m1/s1

SMILES string

OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3c(SCc4ccc(cc4)[N+]([O-])=O)ncnc23

assay

≥98%

form

solid

color

white

mp

187-190 °C (lit.)

solubility

0.1 M HCl: slightly soluble
0.1 M NaOH: slightly soluble
DMSO: soluble
H2O: insoluble

storage temp.

2-8°C

Quality Level

100

Gene Information

human ... ADORA1(134), ADORA2A(135), ADORA2B(136), ADORA3(140), SLC29A1(2030)

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Related Categories

Biochem/physiol Actions

Inhibitor of equilibrative nucleoside transporters (ENTs), particularly adenosine transporters, in central nervous system and vascular smooth muscle.
Potent adenosine uptake inhibitor

General description

S-(4-Nitrobenzyl)-6-thioinosine (NBTI) belongs to the family of S6-substituted 6-thiopurine nucleosides, which regulate nucleoside transport mechanisms in animals. It acts as a ligand of adenosine transporter. Binding sites for NBTI is located on brain capillaries. It functions as a covalent photoaffinity probe for nucleoside transport.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN6396
BCCL3153
BCCH8607
BCCF4866
BCCD1136

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Sebastián Alarcón et al.
Cells, 9(8) (2020-08-23)
Glioblastoma multiforme is one of the most malignant types of cancer. This is mainly due to a cell subpopulation with an extremely aggressive potential, called glioblastoma stem-like cells (GSCs). These cells produce high levels of extracellular adenosine which has been
Regulatory Function of Adenosine, 268(1), 14-18 (2012)
Sophie M Stief et al.
Leukemia, 34(1), 50-62 (2019-06-16)
Acute myeloid leukemia (AML) is an aggressive hematologic neoplasm resulting from the malignant transformation of myeloid progenitors. Despite intensive chemotherapy leading to initial treatment responses, relapse caused by intrinsic or acquired drug resistance represents a major challenge. Here, we report
A Tandon et al.
Journal of neurochemistry, 60(6), 2124-2133 (1993-06-01)
The present study was initiated to examine the effects of ATP on acetylcholine (ACh) synthesis. The exposure of superior cervical ganglia to ATP increased ACh stores by 25%, but this effect was also evident with ADP, AMP, and adenosine, but
Methods Used in Adenosine Research, 268(1), 14-18 (2013)
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