NBMPR
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MedKoo CAT#: 555827

CAS#: 38048-32-7

Description: NBMPR, also known as S-4-nitrophenylmethyl-6-thioinosine, is a nucleoside analog that competitively inhibits the equilibrative nucleoside transporter 1. NBMPR is routinely used at concentrations of 0.10 μM and 0.10 mM to specifically inhibit transport of nucleosides mediated by equilibrative nucleoside transporters 1 (ENT1) and 2 (ENT2), respectively. NBMPR at a concentration of 0.10 mM abolishes ABCG2 activity.

Chemical Structure

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NBMPR
CAS# 38048-32-7
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 555827
Name: NBMPR
CAS#: 38048-32-7
Chemical Formula: C17H17N5O6S
Exact Mass: 419.09
Molecular Weight: 419.412
Elemental Analysis: C, 48.68; H, 4.09; N, 16.70; O, 22.89; S, 7.64

Price and Availability

Size Price Availability Quantity
10mg USD -2 2 Weeks
25mg USD -2 2 Weeks
50mg USD -2 2 Weeks
5g USD -2 2 Weeks
100mg USD 750 2 Weeks
200mg USD 1250 2 Weeks
500mg USD 1650 2 Weeks
1g USD 2650 2 Weeks
2g USD 4650 2 Weeks
Bulk inquiry

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.

Product Data:
Product Data
Instruction:
View handling instruction
Biological target: Nitrobenzylthioinosine is an ENT1 transporter inhibitor that binds to ENT1 transporter with high affinity.
In vitro activity: A [3H] gemcitabine cellular uptake assay was performed to examine the inhibition of hENT1 by nitrobenzylmercaptoprine ribonucleoside (NBMPR). In the PSN1 cells, [3H] gemcitabine uptake via hENT1 was significantly inhibited by NBMPR, and 5-FU sensitivity was significantly increased when the cells were pretreated with NBMPR. Reference: Anticancer Res. 2007 Jul-Aug;27(4B):2241-9. https://pubmed.ncbi.nlm.nih.gov/17695509/
In vivo activity: To test whether NBTI (NBPMR) mimics adenosine effecting on eEPSCs mediated by adenosine A1 receptor, this study investigated the role of adenosine and adenosine A1 receptor antagonist DPCPX in the process of NBTI regulating eEPSCs. At 24 h after pilocarpine induced rat seizures, preparation of hippocampal slices, selecting the pyramidal neurons of hippocampus CA1 region, the eEPSCs amplitudes were recorded by the whole-cell patch clamp, and they were stable during the whole recording process, which was consistent with previous study. Compared to the eEPSCs amplitude of control epilepsy group (1.44±0.05), bath application of NBTI (100 nM) significantly reduced eEPSCs amplitude at 10 min (0.67±0.06) and 30 min (0.63±0.08), while application of A1 receptor inhibitor DPCPX (10 μM) partially reversed this effect (0.87±0.08, Figure 3A and 3B, n = 5). In addition, inhibition of eEPSCs amplitude by adenosine was mimicked by NBTI (100 nM), and the reduced eEPSCs amplitude by adenosine (50M, 0.45±0.06) were further inhibited by NBTI (100 nM, 0.17±0.04, Figure 4A and 4B, n = 5). Reference: Oncotarget. 2017 May 30;8(22):35573-35582. https://pubmed.ncbi.nlm.nih.gov/28415676/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 15.0 35.76
DMF:PBS (pH 7.2) (1:1) 0.5 1.19
DMSO 46.5 110.83

Preparing Stock Solutions

The following data is based on the product molecular weight 419.41 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Tsujie M, Nakamori S, Nakahira S, Takahashi Y, Hayashi N, Okami J, Nagano H, Dono K, Umeshita K, Sakon M, Monden M. Human equilibrative nucleoside transporter 1, as a predictor of 5-fluorouracil resistance in human pancreatic cancer. Anticancer Res. 2007 Jul-Aug;27(4B):2241-9. PMID: 17695509. 2. Lin W, Buolamwini JK. Synthesis, flow cytometric evaluation, and identification of highly potent dipyridamole analogues as equilibrative nucleoside transporter 1 inhibitors. J Med Chem. 2007 Aug 9;50(16):3906-20. doi: 10.1021/jm070311l. Epub 2007 Jul 18. PMID: 17636949; PMCID: PMC2536492. 3. Huang H, Wang J, Zhang J, Luo Z, Li D, Qiu X, Peng Y, Xu Z, Xu P, Xu Z. Nitrobenzylthioinosine mimics adenosine to attenuate the epileptiform discharge of hippocampal neurons from epileptic rats. Oncotarget. 2017 May 30;8(22):35573-35582. doi: 10.18632/oncotarget.16012. PMID: 28415676; PMCID: PMC5482599. 4. Parkinson FE, Zhang YW, Shepel PN, Greenway SC, Peeling J, Geiger JD. Effects of nitrobenzylthioinosine on neuronal injury, adenosine levels, and adenosine receptor activity in rat forebrain ischemia. J Neurochem. 2000 Aug;75(2):795-802. doi: 10.1046/j.1471-4159.2000.0750795.x. PMID: 10899957.
In vitro protocol: 1. Tsujie M, Nakamori S, Nakahira S, Takahashi Y, Hayashi N, Okami J, Nagano H, Dono K, Umeshita K, Sakon M, Monden M. Human equilibrative nucleoside transporter 1, as a predictor of 5-fluorouracil resistance in human pancreatic cancer. Anticancer Res. 2007 Jul-Aug;27(4B):2241-9. PMID: 17695509. 2. Lin W, Buolamwini JK. Synthesis, flow cytometric evaluation, and identification of highly potent dipyridamole analogues as equilibrative nucleoside transporter 1 inhibitors. J Med Chem. 2007 Aug 9;50(16):3906-20. doi: 10.1021/jm070311l. Epub 2007 Jul 18. PMID: 17636949; PMCID: PMC2536492.
In vivo protocol: 1. Huang H, Wang J, Zhang J, Luo Z, Li D, Qiu X, Peng Y, Xu Z, Xu P, Xu Z. Nitrobenzylthioinosine mimics adenosine to attenuate the epileptiform discharge of hippocampal neurons from epileptic rats. Oncotarget. 2017 May 30;8(22):35573-35582. doi: 10.18632/oncotarget.16012. PMID: 28415676; PMCID: PMC5482599. 2. Parkinson FE, Zhang YW, Shepel PN, Greenway SC, Peeling J, Geiger JD. Effects of nitrobenzylthioinosine on neuronal injury, adenosine levels, and adenosine receptor activity in rat forebrain ischemia. J Neurochem. 2000 Aug;75(2):795-802. doi: 10.1046/j.1471-4159.2000.0750795.x. PMID: 10899957.

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