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N2255

Sigma-Aldrich

S-(4-Nitrobenzyl)-6-thioinosine

≥98%, 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
EC Number:
253-753-4
MDL number:
MFCD00005745
UNSPSC Code:
12352202
PubChem Substance ID:
24277723
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

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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