NBMPR


Catalog No. size PriceQuantity
M7080-2 2mg solid $100
M7080-10 10mg solid $396

Description

Cas:38048-32-7

Product Information

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 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

 

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

 

 

References

 

  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.

 

  1. 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.

 

  1. 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.

 

  1. 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.

 

  1. Parkinson FE, Clanachan AS. Nitrobenzylthioinosine (NBMPR) binding sites in kidney. Proc West Pharmacol Soc. 1987;30:75-7. PMID: 3628321.

 

  1. 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.

 

Products are for research use only. Not for human use.

 

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