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N2255

S-(4-Nitrobenzyl)-6-thioinosine

Name: <I>S</I>-(4-Nitrobenzyl)-6-thioinosine
Brand: SIGMA

≥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

Assay:

≥98%

Form:

solid

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Product Name

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

Quality Level

100

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

SMILES string

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

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

InChI key

DYCJFJRCWPVDHY-LSCFUAHRSA-N

Gene Information

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

Related Categories

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

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.

Biochem/physiol Actions

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

Potent adenosine uptake inhibitor

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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Decreased Equilibrative Nucleoside Transporter 1 (ENT1) Activity Contributes to the High Extracellular Adenosine Levels in Mesenchymal Glioblastoma Stem-Like Cells.

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

Methods Used in Adenosine Research, 268(1), 14-18 (2013)

Regulatory Function of Adenosine, 268(1), 14-18 (2012)

Loss of KDM6A confers drug resistance in acute myeloid leukemia.

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

Biodistribution and uptake of 3'-deoxy-3'-fluorothymidine in ENT1-knockout mice and in an ENT1-knockdown tumor model.

Robert J Paproski et al.

Journal of nuclear medicine : official publication, Society of Nuclear Medicine, 51(9), 1447-1455 (2010-08-20)

(18)F-3'-Deoxy-3'-fluorothymidine ((18)F-FLT) is a PET tracer that accumulates in proliferating tissues. The current study was undertaken to determine whether equilibrative nucleoside transporter 1 (ENT1) is important for (18)F-FLT uptake in normal tissues and tumors. ENT1-knockout (ENT1(-/-)) mice were generated and

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Global Trade Item Number

SKU	GTIN
N2255-25MG	04061833273142
N2255-100MG	04061833273128
N2255-250MG	04061833273135

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