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.


Price and Availability

Size Price Shipping out time Quantity
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
Inquire bulk and customized quantity

Pricing updated 2020-09-30. Prices are subject to change without notice.

NBMPR is in stock.


Chemical Structure

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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


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


Technical Data

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


Additional Information

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.