N2255
S-(4-硝基苄基)-6-硫肌苷
≥98%, Adenosine uptake inhibitor, 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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关于此项目
经验公式（希尔记法）:
C17H17N5O6S
CAS Number:
分子量:
419.41
EC 号:
MDL编号:
UNSPSC代码:
12352202
PubChem化学物质编号:
NACRES:
NA.77
Product Name
S-(4-硝基苄基)-6-硫肌苷, ≥98%, solid
质量水平
方案
≥98%
表单
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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相关类别
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
储存分类代码
11 - Combustible Solids
WGK
WGK 3
闪点(°F)
Not applicable
闪点(°C)
Not applicable
个人防护装备
Eyeshields, Gloves, type N95 (US)
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
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)
Daniela Maier-Begandt et al.
Science signaling, 14(672) (2021-03-04)
The endothelial cell barrier regulates the passage of fluid between the bloodstream and underlying tissues, and barrier function impairment exacerbates the severity of inflammatory insults. To understand how inflammation alters vessel permeability, we studied the effects of the proinflammatory cytokine
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