From Wikipedia, the free encyclopedia
18F-EF5
Names
Preferred IUPAC name
2-(2-Nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide
Other names
NSC-684681; EF-5
Identifiers
3D model ( JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C8H7F5N4O3/c9-7(10,8(11,12)13)4-15-5(18)3-16-2-1-14-6(16)17(19)20/h1-2H,3-4H2,(H,15,18) checkY
    Key: JGGDSDPOPRWSCX-UHFFFAOYSA-N checkY
  • O=[N+]([O-])c1nccn1CC(=O)NCC(F)(F)C(F)(F)F
Properties
C8H7F5N4O3
Molar mass 302.161 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY  verify ( what is checkY☒N ?)

EF5 is a nitroimidazole derivative used in oncology research. [1] Due to its similarity in chemical structure to etanidazole, EF5 binds in cells displaying hypoxia. [2]

Non-labeled EF5 has been extensively used in immunohistochemical studies for several years and its hypoxia specificity has been comprehensively evaluated [3] [4] The 18F- radiolabeled derivative of EF5 is being studied for its possibility to be used in positron emission tomography (PET) to detect low levels of oxygen in brain tumors and several other malignant tumors. [5] This can help show how a tumor will respond to treatment.

Targeting tumor hypoxia in cancer treatment aims to overcome radiotherapy resistance of hypoxic tumors. Thus, a major clinical implication for 18F-EF5-PET imaging is expected to be guiding of radiotherapy dose modulation. Clinical studies on 18F-EF5-PET/CT imaging have indicated clinically acceptable biodistribution and dosimetric profile, [6] and in head and neck cancer also favorable imaging characteristics, [7] prognostic value [8] and repeatability. [9] A recent 18F-EF5-PET/MR study showed promising potential in detecting tumor hypoxia in cervical cancer. [10] However, 18F-EF5-PET/CT is not feasible in imaging of ovarian cancer due to physiological intra-abdominal 18F-EF5-accumulation. [11] Further studies evaluating the clinical use of 18F-EF5 PET imaging in head and neck cancer are ongoing.

References

  1. ^ Evans SM, Fraker D, Hahn SM, Gleason K, Jenkins WT, Jenkins K, et al. (March 2006). "EF5 binding and clinical outcome in human soft tissue sarcomas". International Journal of Radiation Oncology, Biology, Physics. 64 (3): 922–7. doi: 10.1016/j.ijrobp.2005.05.068. PMID  16458778.
  2. ^ Lord EM, Harwell L, Koch CJ (December 1993). "Detection of hypoxic cells by monoclonal antibody recognizing 2-nitroimidazole adducts". Cancer Research. 53 (23): 5721–6. PMID  8242628.
  3. ^ Koch CJ, Evans SM (March 2015). "Optimizing hypoxia detection and treatment strategies". Seminars in Nuclear Medicine. 45 (2): 163–76. doi: 10.1053/j.semnuclmed.2014.10.004. PMC  4365940. PMID  25704388.
  4. ^ Koch CJ (2002). "[1] Measurement of absolute oxygen levels in cells and tissues using oxygen sensors and 2-nitroimidazole EF5". Measurement of absolute oxygen levels in cells and tissues using oxygen sensors and 2-nitroimidazole EF5. Methods in Enzymology. Vol. 352. Elsevier. pp. 3–31. doi: 10.1016/s0076-6879(02)52003-6. ISBN  978-0-12-182255-2. PMID  12125356.
  5. ^ Ziemer LS, Evans SM, Kachur AV, Shuman AL, Cardi CA, Jenkins WT, et al. (February 2003). "Noninvasive imaging of tumor hypoxia in rats using the 2-nitroimidazole 18F-EF5". European Journal of Nuclear Medicine and Molecular Imaging. 30 (2): 259–66. doi: 10.1007/s00259-002-1037-5. PMID  12552344. S2CID  22002592.
  6. ^ Lin LL, Silvoniemi A, Stubbs JB, Rengan R, Suilamo S, Solin O, et al. (September 2012). "Radiation dosimetry and biodistribution of the hypoxia tracer (18)F-EF5 in oncologic patients". Cancer Biotherapy & Radiopharmaceuticals. 27 (7): 412–9. doi: 10.1089/cbr.2011.1130. PMID  22897720.
  7. ^ Komar G, Seppänen M, Eskola O, Lindholm P, Grönroos TJ, Forsback S, et al. (December 2008). "18F-EF5: a new PET tracer for imaging hypoxia in head and neck cancer". Journal of Nuclear Medicine. 49 (12): 1944–51. doi: 10.2967/jnumed.108.053785. PMID  18997048. S2CID  16561341.
  8. ^ Komar G, Lehtiö K, Seppänen M, Eskola O, Levola H, Lindholm P, et al. (November 2014). "Prognostic value of tumour blood flow, [18F]EF5 and [18F]FDG PET/CT imaging in patients with head and neck cancer treated with radiochemotherapy". European Journal of Nuclear Medicine and Molecular Imaging. 41 (11): 2042–50. doi: 10.1007/s00259-014-2818-3. PMID  24898846. S2CID  6276936.
  9. ^ Silvoniemi A, Suilamo S, Laitinen T, Forsback S, Löyttyniemi E, Vaittinen S, et al. (February 2018). "Repeatability of tumour hypoxia imaging using [18F]EF5 PET/CT in head and neck cancer". European Journal of Nuclear Medicine and Molecular Imaging. 45 (2): 161–169. doi: 10.1007/s00259-017-3857-3. PMC  5745570. PMID  29075831.
  10. ^ Narva, Sara I.; Seppänen, Marko P.; Raiko, Juho R.H.; Forsback, Sarita J.; Orte, Katri J.; Virtanen, Johanna M.; Hynninen, Johanna; Hietanen, Sakari (December 2021). "Imaging of Tumor Hypoxia With 18F-EF5 PET/MRI in Cervical Cancer". Clinical Nuclear Medicine. 46 (12): 952–957. doi: 10.1097/RLU.0000000000003914. ISSN  1536-0229. PMID  34619699.
  11. ^ Laasik M, Hynninen J, Forsback S, Noponen T, Seppänen M, Hietanen S (September 2020). "The feasibility of [18F]EF5-PET/CT to image hypoxia in ovarian tumors: a clinical study". EJNMMI Research. 10 (1): 103. doi: 10.1186/s13550-020-00689-z. PMC  7483702. PMID  32910291.
From Wikipedia, the free encyclopedia
18F-EF5
Names
Preferred IUPAC name
2-(2-Nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide
Other names
NSC-684681; EF-5
Identifiers
3D model ( JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C8H7F5N4O3/c9-7(10,8(11,12)13)4-15-5(18)3-16-2-1-14-6(16)17(19)20/h1-2H,3-4H2,(H,15,18) checkY
    Key: JGGDSDPOPRWSCX-UHFFFAOYSA-N checkY
  • O=[N+]([O-])c1nccn1CC(=O)NCC(F)(F)C(F)(F)F
Properties
C8H7F5N4O3
Molar mass 302.161 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY  verify ( what is checkY☒N ?)

EF5 is a nitroimidazole derivative used in oncology research. [1] Due to its similarity in chemical structure to etanidazole, EF5 binds in cells displaying hypoxia. [2]

Non-labeled EF5 has been extensively used in immunohistochemical studies for several years and its hypoxia specificity has been comprehensively evaluated [3] [4] The 18F- radiolabeled derivative of EF5 is being studied for its possibility to be used in positron emission tomography (PET) to detect low levels of oxygen in brain tumors and several other malignant tumors. [5] This can help show how a tumor will respond to treatment.

Targeting tumor hypoxia in cancer treatment aims to overcome radiotherapy resistance of hypoxic tumors. Thus, a major clinical implication for 18F-EF5-PET imaging is expected to be guiding of radiotherapy dose modulation. Clinical studies on 18F-EF5-PET/CT imaging have indicated clinically acceptable biodistribution and dosimetric profile, [6] and in head and neck cancer also favorable imaging characteristics, [7] prognostic value [8] and repeatability. [9] A recent 18F-EF5-PET/MR study showed promising potential in detecting tumor hypoxia in cervical cancer. [10] However, 18F-EF5-PET/CT is not feasible in imaging of ovarian cancer due to physiological intra-abdominal 18F-EF5-accumulation. [11] Further studies evaluating the clinical use of 18F-EF5 PET imaging in head and neck cancer are ongoing.

References

  1. ^ Evans SM, Fraker D, Hahn SM, Gleason K, Jenkins WT, Jenkins K, et al. (March 2006). "EF5 binding and clinical outcome in human soft tissue sarcomas". International Journal of Radiation Oncology, Biology, Physics. 64 (3): 922–7. doi: 10.1016/j.ijrobp.2005.05.068. PMID  16458778.
  2. ^ Lord EM, Harwell L, Koch CJ (December 1993). "Detection of hypoxic cells by monoclonal antibody recognizing 2-nitroimidazole adducts". Cancer Research. 53 (23): 5721–6. PMID  8242628.
  3. ^ Koch CJ, Evans SM (March 2015). "Optimizing hypoxia detection and treatment strategies". Seminars in Nuclear Medicine. 45 (2): 163–76. doi: 10.1053/j.semnuclmed.2014.10.004. PMC  4365940. PMID  25704388.
  4. ^ Koch CJ (2002). "[1] Measurement of absolute oxygen levels in cells and tissues using oxygen sensors and 2-nitroimidazole EF5". Measurement of absolute oxygen levels in cells and tissues using oxygen sensors and 2-nitroimidazole EF5. Methods in Enzymology. Vol. 352. Elsevier. pp. 3–31. doi: 10.1016/s0076-6879(02)52003-6. ISBN  978-0-12-182255-2. PMID  12125356.
  5. ^ Ziemer LS, Evans SM, Kachur AV, Shuman AL, Cardi CA, Jenkins WT, et al. (February 2003). "Noninvasive imaging of tumor hypoxia in rats using the 2-nitroimidazole 18F-EF5". European Journal of Nuclear Medicine and Molecular Imaging. 30 (2): 259–66. doi: 10.1007/s00259-002-1037-5. PMID  12552344. S2CID  22002592.
  6. ^ Lin LL, Silvoniemi A, Stubbs JB, Rengan R, Suilamo S, Solin O, et al. (September 2012). "Radiation dosimetry and biodistribution of the hypoxia tracer (18)F-EF5 in oncologic patients". Cancer Biotherapy & Radiopharmaceuticals. 27 (7): 412–9. doi: 10.1089/cbr.2011.1130. PMID  22897720.
  7. ^ Komar G, Seppänen M, Eskola O, Lindholm P, Grönroos TJ, Forsback S, et al. (December 2008). "18F-EF5: a new PET tracer for imaging hypoxia in head and neck cancer". Journal of Nuclear Medicine. 49 (12): 1944–51. doi: 10.2967/jnumed.108.053785. PMID  18997048. S2CID  16561341.
  8. ^ Komar G, Lehtiö K, Seppänen M, Eskola O, Levola H, Lindholm P, et al. (November 2014). "Prognostic value of tumour blood flow, [18F]EF5 and [18F]FDG PET/CT imaging in patients with head and neck cancer treated with radiochemotherapy". European Journal of Nuclear Medicine and Molecular Imaging. 41 (11): 2042–50. doi: 10.1007/s00259-014-2818-3. PMID  24898846. S2CID  6276936.
  9. ^ Silvoniemi A, Suilamo S, Laitinen T, Forsback S, Löyttyniemi E, Vaittinen S, et al. (February 2018). "Repeatability of tumour hypoxia imaging using [18F]EF5 PET/CT in head and neck cancer". European Journal of Nuclear Medicine and Molecular Imaging. 45 (2): 161–169. doi: 10.1007/s00259-017-3857-3. PMC  5745570. PMID  29075831.
  10. ^ Narva, Sara I.; Seppänen, Marko P.; Raiko, Juho R.H.; Forsback, Sarita J.; Orte, Katri J.; Virtanen, Johanna M.; Hynninen, Johanna; Hietanen, Sakari (December 2021). "Imaging of Tumor Hypoxia With 18F-EF5 PET/MRI in Cervical Cancer". Clinical Nuclear Medicine. 46 (12): 952–957. doi: 10.1097/RLU.0000000000003914. ISSN  1536-0229. PMID  34619699.
  11. ^ Laasik M, Hynninen J, Forsback S, Noponen T, Seppänen M, Hietanen S (September 2020). "The feasibility of [18F]EF5-PET/CT to image hypoxia in ovarian tumors: a clinical study". EJNMMI Research. 10 (1): 103. doi: 10.1186/s13550-020-00689-z. PMC  7483702. PMID  32910291.

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