N2255

Sigma-Aldrich

S-(4-Nitrobenzyl)-6-thioinosine

≥98%, solid

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

Quality Level

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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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.

Packaging

25 mg in glass bottle
100, 250 mg in poly bottle

Biochem/physiol Actions

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

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

storage_class_code

13 - Non Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

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...
Blood-brain barrier transport and brain metabolism of adenosine and adenosine analogs.
Pardridge WM, et al.
Journal of Pharmacology and Experimental Therapeutics, 268(1), 14-18 (1994)
Morris J Robins et al.
Journal of medicinal chemistry, 53(16), 6040-6053 (2010-08-20)
5'-S-(2-aminoethyl)-6-N-(4-nitrobenzyl)-5'-thioadenosine (SAENTA), 5'-S-(2-acetamidoethyl)-6-N-[(4-substituted)benzyl]-5'-thioadenosine analogues, 5'-S-[2-(6-aminohexanamido)]ethyl-6-N-(4-nitrobenzyl)-5'-thioadenosine (SAHENTA), and related compounds were synthesized by S(N)Ar displacement of fluoride from 6-fluoropurine intermediates with 4-(substituted)benzylamines. Conjugation of the pendant amino groups of SAENTA and SAHENTA with fluorescein-5-yl isothiocyanate (FITC) gave fluorescent probes that bound...
Methods Used in Adenosine Research, 268(1), 14-18 (2013)

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