Synonym: NBMPR; NBTI; NSC 296962; NSC-296962; NSC296962; S-4-nitrophenylmethyl-6-thioinosine;

IUPAC/Chemical Name: (2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-((4-nitrobenzyl)thio)-9H-purin-9-yl)tetrahydrofuran-3,4-diol

InChi Key: DYCJFJRCWPVDHY-LSCFUAHRSA-N

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

SMILES Code: 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

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info: 1: Boleti H, Coe IR, Baldwin SA, Young JD, Cass CE. Molecular identification of the equilibrative NBMPR-sensitive (es) nucleoside transporter and demonstration of an equilibrative NBMPR-insensitive (ei) transport activity in human erythroleukemia (K562) cells. Neuropharmacology. 1997 Sep;36(9):1167-79. doi: 10.1016/s0028-3908(97)00136-6. PMID: 9364472. 2: Alanko L, Stenberg D, Porkka-Heiskanen T. Nitrobenzylthioinosine (NBMPR) binding and nucleoside transporter ENT1 mRNA expression after prolonged wakefulness and recovery sleep in the cortex and basal forebrain of rat. J Sleep Res. 2003 Dec;12(4):299-304. doi: 10.1046/j.0962-1105.2003.00372.x. PMID: 14633241. 3: Sundaram M, Yao SY, Ng AM, Cass CE, Baldwin SA, Young JD. Equilibrative nucleoside transporters: mapping regions of interaction for the substrate analogue nitrobenzylthioinosine (NBMPR) using rat chimeric proteins. Biochemistry. 2001 Jul 10;40(27):8146-51. doi: 10.1021/bi0101805. PMID: 11434784. 4: Karbanova S, Sorf A, Jiraskova L, Lalinska A, Ptackova Z, Staud F, Cerveny L. S-(4-Nitrobenzyl)-6-thioinosine (NBMPR) is Not a Selective Inhibitor of Equilibrative Nucleoside Transporters but Also Blocks Efflux Activity of Breast Cancer Resistance Protein. Pharm Res. 2020 Feb 21;37(3):58. doi: 10.1007/s11095-020-2782-5. PMID: 32086630. 5: Parkinson FE, Clanachan AS. Nitrobenzylthioinosine (NBMPR) binding sites in kidney. Proc West Pharmacol Soc. 1987;30:75-7. PMID: 3628321. 6: Thomas SA, Segal MB. Saturation kinetics, specificity and NBMPR sensitivity of thymidine entry into the central nervous system. Brain Res. 1997 Jun 20;760(1-2):59-67. doi: 10.1016/s0006-8993(97)00276-x. PMID: 9237518. 7: Yao SY, Ng AM, Muzyka WR, Griffiths M, Cass CE, Baldwin SA, Young JD. Molecular cloning and functional characterization of nitrobenzylthioinosine (NBMPR)-sensitive (es) and NBMPR-insensitive (ei) equilibrative nucleoside transporter proteins (rENT1 and rENT2) from rat tissues. J Biol Chem. 1997 Nov 7;272(45):28423-30. doi: 10.1074/jbc.272.45.28423. PMID: 9353301. 8: Handa M, Choi DS, Caldeiro RM, Messing RO, Gordon AS, Diamond I. Cloning of a novel isoform of the mouse NBMPR-sensitive equilibrative nucleoside transporter (ENT1) lacking a putative phosphorylation site. Gene. 2001 Jan 10;262(1-2):301-7. doi: 10.1016/s0378-1119(00)00555-2. PMID: 11179696. 9: Governo RJ, Deuchars J, Baldwin SA, King AE. Localization of the NBMPR- sensitive equilibrative nucleoside transporter, ENT1, in the rat dorsal root ganglion and lumbar spinal cord. Brain Res. 2005 Oct 19;1059(2):129-38. doi: 10.1016/j.brainres.2005.08.017. Epub 2005 Oct 14. PMID: 16226730. 10: Endres CJ, Sengupta DJ, Unadkat JD. Mutation of leucine-92 selectively reduces the apparent affinity of inosine, guanosine, NBMPR [S6-(4-nitrobenzyl)-mercaptopurine riboside] and dilazep for the human equilibrative nucleoside transporter, hENT1. Biochem J. 2004 May 15;380(Pt 1):131-7. doi: 10.1042/BJ20031880. PMID: 14759222; PMCID: PMC1224139. 11: Crawford CR, Patel DH, Naeve C, Belt JA. Cloning of the human equilibrative, nitrobenzylmercaptopurine riboside (NBMPR)-insensitive nucleoside transporter ei by functional expression in a transport-deficient cell line. J Biol Chem. 1998 Feb 27;273(9):5288-93. doi: 10.1074/jbc.273.9.5288. PMID: 9478986. 12: Sundaram M, Yao SY, Ingram JC, Berry ZA, Abidi F, Cass CE, Baldwin SA, Young JD. Topology of a human equilibrative, nitrobenzylthioinosine (NBMPR)-sensitive nucleoside transporter (hENT1) implicated in the cellular uptake of adenosine and anti-cancer drugs. J Biol Chem. 2001 Nov 30;276(48):45270-5. doi: 10.1074/jbc.M107169200. Epub 2001 Oct 2. PMID: 11584005. 13: Yao SY, Ng AM, Sundaram M, Cass CE, Baldwin SA, Young JD. Transport of antiviral 3'-deoxy-nucleoside drugs by recombinant human and rat equilibrative, nitrobenzylthioinosine (NBMPR)-insensitive (ENT2) nucleoside transporter proteins produced in Xenopus oocytes. Mol Membr Biol. 2001 Apr-Jun;18(2):161-7. doi: 10.1080/09687680110048318. PMID: 11463208. 14: Wiebe LI, Knaus EE. Drug-induced perturbations in the in vivo distribution of oncological radiotracers--I. 5-Fluoro-6-3H-2'-deoxyuridine influenced by nitrobenzylthioinosine 5'-phosphate (NBMPR-P). Int J Rad Appl Instrum B. 1986;13(3):257-9. doi: 10.1016/0883-2897(86)90105-4. PMID: 2945804. 15: Zhu Z, Furr J, Buolamwini JK. Synthesis and flow cytometric evaluation of novel 1,2,3,4-tetrahydroisoquinoline conformationally constrained analogues of nitrobenzylmercaptopurine riboside (NBMPR) designed for probing its conformation when bound to the es nucleoside transporter. J Med Chem. 2003 Feb 27;46(5):831-7. doi: 10.1021/jm020405p. PMID: 12593662. 16: Abd-Elfattah AS, Wechsler AS. Separation between ischemic and reperfusion injury by site specific entrapment of endogenous adenosine and inosine using NBMPR and EHNA. J Card Surg. 1994 May;9(3 Suppl):387-96. doi: 10.1111/jocs.1994.9.3s.387. PMID: 8069025. 17: Zhu Z, Buolamwini JK. Constrained NBMPR analogue synthesis, pharmacophore mapping and 3D-QSAR modeling of equilibrative nucleoside transporter 1 (ENT1) inhibitory activity. Bioorg Med Chem. 2008 Apr 1;16(7):3848-65. doi: 10.1016/j.bmc.2008.01.044. Epub 2008 Jan 30. PMID: 18289860; PMCID: PMC2772873. 18: Yao SY, Sundaram M, Chomey EG, Cass CE, Baldwin SA, Young JD. Identification of Cys140 in helix 4 as an exofacial cysteine residue within the substrate- translocation channel of rat equilibrative nitrobenzylthioinosine (NBMPR)-insensitive nucleoside transporter rENT2. Biochem J. 2001 Jan 15;353(Pt 2):387-93. doi: 10.1042/0264-6021:3530387. PMID: 11139404; PMCID: PMC1221582. 19: Gupte A, Buolamwini JK. CoMFA and CoMSIA 3D-QSAR studies on S(6)-(4-nitrobenzyl)mercaptopurine riboside (NBMPR) analogs as inhibitors of human equilibrative nucleoside transporter 1 (hENT1). Bioorg Med Chem Lett. 2009 Jan 15;19(2):314-8. doi: 10.1016/j.bmcl.2008.11.092. Epub 2008 Nov 27. PMID: 19091561. 20: Wiebe LI, Knaus EE, Gati WP, Iwashina T, McQueen L. Drug-induced perturbations in the in vivo distribution of oncological radiotracers--II. 5-[125I]iodo-2'-deoxyuridine influenced by nitrobenzylthioinosine-5'-phosphate (NBMPR-P) and acyclothymidine (ACT). Int J Rad Appl Instrum A. 1990;41(2):159-62. doi: 10.1016/0883-2889(90)90101-l. PMID: 2158945.