Isotopic exchange method for preparation of io-dine-125-n-(1-p-nitrobenzaldhydephenyl)-2- (2-iodophenyl)-4-(4-nitrobenzilidene)-imidazolin -5-one and its biological evaluation

  • Authors

    • Atteyat Labib Qassim University
    2014-03-23
    https://doi.org/10.14419/ijbas.v3i2.1766

  • Abstract

    N-(1-p-nitrobenzaldhydephenyl)-2-(2-iodophenyl)-4-(4-nitrobenzilidene)-imidazolin-5-one was labeled with radioactive iodine-125.via nucleophilic substitution reaction, the isotopic exchange labeling process was carried out in  dry state at 330oC for 20 min. The radiochemical yield was determined by using electrophoresis and the yield is equal to 93%.Ammonium sulphate was used as catalyst to facilitate the exchange reaction in melt state. Maximum heated with iodine-125 at 330oC for 20 min in a reaction mixture with pH between 6 and 8. The results referred to the importance of use NaOH in a molarity of less than 0.02M to prevent the decomposition of the produced tracer due to the change in pH of the reaction mixture. The biodistrubution pattern of the labeled compound was examined in normal as well as in tumor bearing mice and the data show high clearance from the blood as the activity remind in the blood 11.2% at 4 hours post injection. The labeled compound was extracted via liver as the accumulated activity in the liver and intestine were 14.4, 15.4% respectively at 4 hours post injection The biodistrubution of labeled compound in tumor bearing mice accumulation in ascites with high percentage  equal to 55.3 % at 24 hours post injection. This demonstrate the ability of this tracer concentrate in tumor site which primate its possible application as therapeutic agent.

     

    Keywords: Imidazoline Derivatives, Isotopic Exchange Method, Tumor Targeting, Tissues Distribution.

  • References

    1. Zha, Z. et al. (2011). Synthesis and evaluation of two novel 2-nitroimidazole derivatives as potential PET radioligands for tumor imaging. Nuclear medicine and biology 38(4), 501-508. http://dx.doi.org/10.1016%2Fj.nucmedbio.2010.11.001
    2. Williams, J. (1999).The Academy of Radiology Research: the imaging community's advocate for change. Journal of nuclear medicine 40(6), 9N-22N. http://jnm.snmjournals.org/content/40/6/9N.full.pdf+html
    3. Eschmann, S. M. et al. (2005). Prognostic impact of hypoxia imaging with 18F-misonidazole PET in non-small cell lung cancer and head and neck cancer before radiotherapy. Journal of nuclear medicine 46, 253-260.
    4. Nickols, N. G., Jacobs, C. S., Farkas, M. E., and Dervan. P. B. (2007). Improved nuclear localization of DNA-binding polyamides. Nucleic acids research 35, 363-370. http://dx.doi.org/10.1093%2Fnar%2Fgkl1042
    5. Harki, D. A., Satyamurthy,N. D., Stout, B., Phelps, M. E., and Dervan, P. B. (2008). In vivo imaging of pyrrole-imidazole polyamides with positron emission tomography. Proceedings of the National Academy of Sciences 105(35), 13039-13044 doi: 10.1073/pnas.0806308105
    6. MacInnes, N., and Duty, S. (2004). Locomotor effects of imidazoline I2-site-specific ligands and monoamine oxidase inhibitors in rats with a unilateral 6-hydroxydopamine lesion of the nigrostriatal pathway. British Journal of Pharmacology 143(8), 952-959 http://dx.doi.org/10.1038/sj.bjp.0706019
    7. Liu, H., and Du, D-M. (2009). Recent advances in the synthesis of 2-imidazolines and their applications in homogeneous catalysis. Advanced Synthesis & Catalysis, 351(4), 489–519. http://dx.doi.org/10.1002/adsc.200800797
    8. Graczyk, P. P., Khan, A., Bhatia, G. S., Palmer, V. Medland, D. and Numata, H. (2005). The neuroprotective action of JNK3 inhibitors based on the 6, 7-dihydro-5H-pyrrolo [1, 2-a] imidazoles scafold. Bioorg Med Chem Lett, 15, 4666-4670. http://europepmc.org/abstract/MED/16153829
    9. Uaucu, R., Karaburun, N. G. and Isikdag, I. (2001). Synthesis and analgesic activity of some 1-benzyl-2- substituted-4, 5-diphenyl-1Himidazole derivatives. Farmaco, 56, 285-290. http://europepmc.org/abstract/MED/11421256
    10. Bellina, F., Cauteruccio, S., and Rossi, R. (2007). Synthesis and biological activity of vicinal diaryl-substituted 1H-imidazoles. Tetrahedron 63(22), 4571-4624. http://dx.doi.org/10.1016/j.tet.2007.02.075‎
    11. Kawamura, K. et al. (2010). Imaging of I2-imidazoline receptors by small-animal PET using 2-(3-fluoro-[4-11C] tolyl)-4, 5-dihydro- 1H-imidazole ([11C]FTIMD). Nuclear Medicine and Biology 37, p. 625. http://dx.doi.org/10.1016/j.nucmedbio.2010.02.013‎
    12. Hikasa Y. Mizushima H. (2013). Effects of imidazoline and non-imidazoline α-adrenergic agents on rabbit platelet aggregation. Pharmacology 91, 135-144. http://www.karger.com/DOI/10.1159/000346269
    13. Labib A. A. (2013). Synthesis, radioiodination and biodistribution evaluation of 5-(2-amimo-4-styryl pyrimidine-4-yl)-4-methoxybenzofuran-
    14. -ol. Asia Oceania Journal of Nuclear Medicine and Biology 1 32, 32-38. http://www.oalib.com/paper/2032386#.Uy4KjfmSxZ0

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  • How to Cite

    Labib, A. (2014). Isotopic exchange method for preparation of io-dine-125-n-(1-p-nitrobenzaldhydephenyl)-2- (2-iodophenyl)-4-(4-nitrobenzilidene)-imidazolin -5-one and its biological evaluation. International Journal of Basic and Applied Sciences, 3(2), 78-85. https://doi.org/10.14419/ijbas.v3i2.1766

    Received date: 2014-01-16

    Accepted date: 2014-02-13

    Published date: 2014-03-23