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N2255

Sigma-Aldrich

S-(4-Nitrobenzyl)-6-thioinosine

≥98%, solid

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Synonym(s):
6-[(4-Nitrobenzyl)thio]-9-β-D-ribofuranosylpurine, NBMPR, NBTI
Empirical Formula (Hill Notation):
C17H17N5O6S
CAS Number:
Molecular Weight:
419.41
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

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

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1 of 4

This Item
I4125222801A4036
Inosine ≥99% (HPLC)

Sigma-Aldrich

I4125

Inosine

Adenosine suitable for cell culture, BioReagent

Sigma-Aldrich

A4036

Adenosine

form

solid

form

-

form

-

form

powder

mp

187-190 °C (lit.)

mp

222-226 °C (dec.) (lit.)

mp

32-34 °C (lit.)

mp

234-236 °C (lit.)

solubility

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

solubility

-

solubility

-

solubility

1 M NH4OH: 50 mg/mL, clear, colorless

storage temp.

2-8°C

storage temp.

-

storage temp.

2-8°C

storage temp.

2-8°C

Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

200

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 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

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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
Methods Used in Adenosine Research, 268(1), 14-18 (2013)
Regulatory Function of Adenosine, 268(1), 14-18 (2012)
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
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

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