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N2255

S-(4-硝基苄基)-6-硫肌苷

Name: <I>S</I>-(4-硝基苄基)-6-硫肌苷
Brand: SIGMA

≥98%, solid

别名:

6-[(4-硝基苄基)硫代]-9-β-D-呋喃核糖基嘌呤, NBMPR, NBTI

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About This Item

经验公式（希尔记法）:

C₁₇H₁₇N₅O₆S

CAS号:

38048-32-7

分子量:

419.41

EC 号:

253-753-4

MDL编号:

MFCD00005745

UNSPSC代码:

12352202

PubChem化学物质编号:

24277723

NACRES:

NA.77

质量水平

100

检测方案

≥98%

形式

solid

颜色

white

mp

187-190 °C (lit.)

溶解性

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

储存温度

2-8°C

SMILES字符串

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

基因信息

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

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一般描述

S-（4-硝基苄基）-6-硫代肌苷（NBTI）属于S⁶取代的6-硫代嘌呤核苷家族，可调节动物体内的核苷转运机制。它能作为腺苷转运蛋白的一种配体。NBTI的结合位点位于脑毛细血管上。它可作为共价光亲和探针用于核苷转运。

生化/生理作用

中枢神经系统和血管平滑肌中平衡核苷转运蛋白（ENT），尤其是腺苷转运蛋白的抑制剂。

有效的腺苷摄取抑制剂

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

Eyeshields, Gloves, type N95 (US)

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

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

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)

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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