NBTGR

• CAT Number: M053621
• CAS Number: 13153-27-0
• Molecular Formula: C17H18N6O6S
• Molecular Weight: 434.43
• Purity: ≥95%
• Synonyms: (2R,3R,4S,5R)-2-[2-amino-6-[(4-nitrophenyl)methylsulfanyl]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• InChI: InChI=1S/C17H18N6O6S/c18-17-20-14-11(19-7-22(14)16-13(26)12(25)10(5-24)29-16)15(21-17)30-6-8-1-3-9(4-2-8)23(27)28/h1-4,7,10,12-13,16,24-26H,5-6H2,(H2,18,20,21)/t10-,12-,13-,16-/m1/s1
• InChIKey: BRSNNJIJEZWSBU-XNIJJKJLSA-N
• SMILES: C1=CC(=CC=C1CSC2=NC(=NC3=C2N=CN3C4C(C(C(O4)CO)O)O)N)[N+](=O)[O-]

NBTGR (p-Nitrobenzylthioguanosine) is a potent inhibitor of nucleoside transport; inhibits adenosine uptake with a Ki of 70 nM.
A group of purine ribonucleosides with alkarylmercapto substituents at the purine 6-position are potent inhibitors of several aspects of nucleoside metabolism that involved the transfer of ribosyl groups. NBTGR is one of the compounds that inhibits nucleoside transport by human erythrocytes; initial rates of uridine uptake are reduced to zero upon exposure of cells to 1 μM NBTGR. The inhibitor is firmly bound because repeated washing cannot restore uridine transport capability to NBTGR-treated cells. NBTGR inhibits the influx of uridine, inosine, and cytidine, without inhibiting the uptake of the corresponding bases, or that of D-glucose or L-leucine. Uridine antagonizes the NBTGR inhibition of uidine transport in a concentration-dependent manner. NBTGR and related compounds appear to interact with the mechanism for the facilitated transport of nucleosides[2].

Reference

[1]. Turnheim K, et al. Inhibition of adenosine uptake in human erythrocytes by adenosine-5′-carboxamides, xylosyladenine, dipyridamole, hexobendine, and p-nitrobenzylthioguanosine. Biochem Pharmacol. 1978;27(18):2191-7.
 [Content Brief]

[2]. Parterson A, et al. Nucleoside Transport II Inhibition by p-Nitrobeazylthiogoanosine and Related Compounds. Can. J. Biochem. 49,271-274 (1971)