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N2255

S-(4-Nitrobenzyl)-6-thioinosine

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

≥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:

38048-32-7

Molecular Weight:

419.41

EC Number:

253-753-4

MDL number:

MFCD00005745

PubChem Substance ID:

24277723

NACRES:

NA.77

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)

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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.

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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Improved syntheses of 5'-S-(2-aminoethyl)-6-N-(4-nitrobenzyl)-5'-thioadenosine (SAENTA), analogues, and fluorescent probe conjugates: analysis of cell-surface human equilibrative nucleoside transporter 1 (hENT1) levels for prediction of the antitumor efficacy of gemcitabine.

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

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)

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

Increased acetylcholine content induced by adenosine in a sympathetic ganglion and its subsequent mobilization by electrical stimulation.

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

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

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