Pimonidazole

• CAT Number: I008768
• CAS Number: 70132-50-2
• Molecular Formula: C11H18N4O3
• Molecular Weight: 254.29
• Purity: ≥95%
• Synonyms: PD 126675; Ro 038799; PD126675; Ro038799; PD-126675; Ro-038799; Pimonidazole; NSC 380540.;1-(2-nitro-1H-imidazol-1-yl)-3-(piperidin-1-yl)propan-2-ol
• Solubility: Soluble in DMSO
• Storage: -20°C
• IUPAC Name: 1-(2-nitroimidazol-1-yl)-3-piperidin-1-ylpropan-2-ol
• InChI: InChI=1S/C11H18N4O3/c16-10(8-13-5-2-1-3-6-13)9-14-7-4-12-11(14)15(17)18/h4,7,10,16H,1-3,5-6,8-9H2
• InChIKey: WVWOOAYQYLJEFD-UHFFFAOYSA-N
• SMILES: C1CCN(CC1)CC(CN2C=CN=C2[N+](=O)[O-])O

Pimonidazole (Cat.No:I008768), also known as Ro 03-8799 and PD 126675, is a nitroimidazole drug with hypoxic selectivity and radiosensitizing property. Pimonidazole is reduced in hypoxic environments as in tumor cells, thereby it can be used as an hypoxia marker. In hypoxic cells, reduced pimonidazole binds to -SH-containing molecules such as glutathione and proteins, and the resulting complexes accumulated in tissues, thereby sensitizing cells to be more susceptible for radiation treatment.

Reference

1:Imaging Mass Spectrometry Revealed the Accumulation Characteristics of the 2-Nitroimidazole-Based Agent /Pimonidazole/ in Hypoxia. Masaki Y, Shimizu Y, Yoshioka T, Feng F, Zhao S, Higashino K, Numata Y, Kuge Y.PLoS One. 2016 Aug 31;11(8):e0161639. doi: 10.1371/journal.pone.0161639. eCollection 2016. PMID: 27580239 Free PMC Article2:Correlation of FMISO simulations with pimonidazole-stained tumor xenografts: A question of O2 consumption? Wack LJ, Mönnich D, Yaromina A, Zips D, Baumann M, Thorwarth D.Med Phys. 2016 Jul;43(7):4113. doi: 10.1118/1.4951728. PMID: 27370131 3:Mass Spectrometry Imaging of the Hypoxia Marker Pimonidazole in a Breast Tumor Model. Mascini NE, Cheng M, Jiang L, Rizwan A, Podmore H, Bhandari DR, Römpp A, Glunde K, Heeren RM.Anal Chem. 2016 Mar 15;88(6):3107-14. doi: 10.1021/acs.analchem.5b04032. Epub 2016 Feb 29. PMID: 26891127 4:Analysis of the intra- and intertumoral heterogeneity of hypoxia in pancreatic cancer patients receiving the nitroimidazole tracer pimonidazole. Dhani NC, Serra S, Pintilie M, Schwock J, Xu J, Gallinger S, Hill RP, Hedley DW.Br J Cancer. 2015 Sep 15;113(6):864-71. doi: 10.1038/bjc.2015.284. Epub 2015 Sep 1. PMID: 26325106 Free PMC Article5:The tumour hypoxia marker pimonidazole reflects a transcriptional programme associated with aggressive prostate cancer. Ragnum HB, Vlatkovic L, Lie AK, Axcrona K, Julin CH, Frikstad KM, Hole KH, Seierstad T, Lyng H.Br J Cancer. 2015 Jan 20;112(2):382-90. doi: 10.1038/bjc.2014.604. Epub 2014 Dec 2. PMID: 25461803 Free PMC Article6:Hypoxia Studies with Pimonidazole in vivo. Aguilera KY, Brekken RA.Bio Protoc. 2014 Oct 5;4(19). pii: e1254. PMID: 27453908 Free PMC Article7:PET imaging of tumor hypoxia using 18F-labeled pimonidazole. Busk M, Jakobsen S, Horsman MR, Mortensen LS, Iversen AB, Overgaard J, Nordsmark M, Ji X, Lee DY, Raleigh JR.Acta Oncol. 2013 Oct;52(7):1300-7. doi: 10.3109/0284186X.2013.815797. Epub 2013 Aug 21. PMID: 23962243 8:Radiosensitivity of pimonidazole-unlabelled intratumour quiescent cell population to γ-rays, accelerated carbon ion beams and boron neutron capture reaction. Masunaga S, Sakurai Y, Tanaka H, Hirayama R, Matsumoto Y, Uzawa A, Suzuki M, Kondo N, Narabayashi M, Maruhashi A, Ono K.Br J Radiol. 2013 Jan;86(1021):20120302. doi: 10.1259/bjr.20120302. PMID: 23255546 Free PMC Article9:Wortmannin efficiently suppresses the recovery from radiation-induced damage in pimonidazole-unlabeled quiescent tumor cell population. Masunaga S, Sakurai Y, Tanaka H, Suzuki M, Kondo N, Narabayashi M, Maruhashi A, Ono K.J Radiat Res. 2013 Mar 1;54(2):221-9. doi: 10.1093/jrr/rrs094. Epub 2012 Oct 24. PMID: 23097299 Free PMC Article10:Enhanced radiosensitization by liposome-encapsulated pimonidazole for anticancer effects on human melanoma cells. Kato S, Kimura M, Kageyama K, Tanaka H, Miwa N.J Nanosci Nanotechnol. 2012 Jun;12(6):4472-7. PMID: 22905487