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
化学文摘社编号:
分子量:
419.41
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352202
EC Number:
253-753-4
MDL number:
产品名称
S-(4-硝基苄基)-6-硫肌苷, ≥98%, solid
InChI key
DYCJFJRCWPVDHY-LSCFUAHRSA-N
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
SMILES string
OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3c(SCc4ccc(cc4)[N+]([O-])=O)ncnc23
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
Quality Level
Gene Information
human ... ADORA1(134), ADORA2A(135), ADORA2B(136), ADORA3(140), SLC29A1(2030)
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Biochem/physiol Actions
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
General description
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。
存储类别
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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
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
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