A nucleoside transport inhibitor
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S-(4-Nitrobenzyl)-6-thioinosine

Item No. 16403

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
6-S-[(4-nitrophenyl)methyl]-6-thio-inosine
CAS Number
38048-32-7
Synonyms
  • NBMPR
  • NBTI
  • NSC 296962
Molecular Formula
C17H17N5O6S
Formula Weight
419.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 15 mg/mlDMF:PBS(pH 7.2)(1:1): 0.5 mg/mlDMSO: 10 mg/ml
λmax
284 nm
SMILES
O[C@H]1[C@@H](O)[C@H](N2C=NC3=C2N=CN=C3SCC4=CC=C([N+]([O-])=O)C=C4)O[C@@H]1CO
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    25 mg

    $63

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    50 mg

    $86

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    100 mg

    $158

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    Product Description

    S-(4-Nitrobenzyl)-6-thioinosine is a nucleoside analog that competitively inhibits the equilibrative nucleoside transporter 1 (Kd = 0.1-1.0 nM; IC50s = 4.6 and 3.6 nM in rat and human, respectively).1,2 It blocks adenosine flux across the plasma membrane, thereby potentiating the interaction of extracellular adenosine with purinoreceptors, which can affect cardiac signaling associated with adenosine.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Aronow, B., Allen, K., Patrick, J., et al. Altered nucleoside transporters in mammalian cells selected for resistance to the physiological effects of inhibitors of nucleoside transport. The Journal of Biological Chemisty 260(10), 6226-6233 (1985).

    2. Yao, S.Y.M., Ng, A.M.L., Muzyka, W.R., et al. Molecular cloning and functional characterization of nitrobenzylthioinosine (NBMPR)-sensitive (es) and NBMPR-insensitive (ei) equilibrative nucleoside transporter proteins (rENT1 and rENT2) from rat tissues. The Journal of Biological Chemisty 272(45), 28423-28430 (1997).