Radioiodination of olmesartan medoxomil and biological evaluation of the product as a tracer for cardiac imaging
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M. H. Sanad
,
Ebtisam. A. Marzook
Abstract
The present study is oriented to synthesis of radioiodinated olmesartan medoxomil (OM) for potential cardiac imaging. Olmesartan medoxomil has been labeled with [125/131I] using chloramine-T (Ch-T) as an oxidizing agent. The key effective factors such as amount of oxidizing agent, amount of substrate, pH, reaction temperature and reaction time, have been systematically studied to get high radiochemical yield of the [125I]olmesartan medoxomil reaching values of 98.5%. The labeled compound was separated and purified using thin layer chromatography (TLC), paper electrophoresis and high performance liquid chromatography (HPLC). The biological distribution indicates the suitability of [125I]olmesartan medoxomil as a novel tracer to image heart with high heart/blood ratio within 30 min which was detected by gamma camera.
References
1. Nicholls, M. G., Richards, A. M., Agarwal, M.: The importance of the renin-angiotensin system in cardiovascular disease. J. Hum. Hypertens. 12, 295 (1998).10.1038/sj.jhh.1000638Search in Google Scholar PubMed
2. Balt, J. C., Mathy, M. J., Pfaffendorf, M., van Zwieten, P. A.: Inhibition of facilitation of sympathetic neurotransmission and angiotensin II-induced pressor effects in the pithed rat: comparison between valsartan, candesartan, eprosartan and embusartan. J. Hypertens. 19(12), 2241 (2001).10.1097/00004872-200112000-00018Search in Google Scholar PubMed
3. Kenakin, T.: Competitive antagonism. In: C. Boselli (Ed.), Pharmacologic Analysis of Drug-Receptor Interaction. 3rd ed. Philadelphia, Lippincot & Raven Publishers. 331 (1997).Search in Google Scholar
4. Skugor, M.: Thyroid Disorders. A Cleveland Clinic Guide. Cleveland Clinic Press, The Amazon Book Review, p. 82. ISBN 978-1-59624-021-6. (2006).Search in Google Scholar
5. Robbins, J., Schneider, A. B.: Thyroid cancer following exposure to radioactive iodine. Rev. Endocr. Metab. Disord. 1(3), 197 (2000).10.1023/A:1010031115233Search in Google Scholar
6. Narra, V. R., Howell, R. W., Harapanhalli, R. S., Sastry, K. S., Rao, D. V.: Radiotoxicity of some iodine-123, iodine-125 and iodine-131-labeled compounds in mouse testes: implications for radiopharmaceutical design. J. Nucl. Med. 33(12), 2196 (1992).Search in Google Scholar
7. Sanad, M. H., Sallam, Kh. M., Marzook, F. A., Abd-Elhaliem, S. M.: Radioiodination and biological evaluation of candesartan as a tracer for cardiovascular disorder detection J. Label Compd. Radiopharm. 59, 484 (2016).10.1002/jlcr.3435Search in Google Scholar PubMed
8. Liederer, B. M.: Case study: Olmesartan Medoxomil: a prodrug of olmesartan. In: V. J. Stella, R. T. Borchardt, M. J. Hageman, R. Oliyai, H. Maag, J. W. Tilley (Eds.), Prodrugs. Biotechnology: Pharmaceutical Aspects, vol V. Springer, New York, NY (2007).10.1007/978-0-387-49785-3_48Search in Google Scholar
9. Hans, R. B.: Olmesartan medoxomil current status of its use in monotherapy. Vasc. Health Risk Mangement. 2(4), 327 (2006).10.2147/vhrm.2006.2.4.327Search in Google Scholar PubMed PubMed Central
10. Ball, K. J., Williams, P. A., Stumpe, K. O.: Relative efficacy of an angiotensin II antagonist compared with other antihypertensive agents. Olmesartan medoxomil versus antihypertensives. J Hypertens 19(Suppl. 1), 49 (2001).10.1097/00004872-200106001-00007Search in Google Scholar PubMed
11. Chrysant, S. G., Marbury, T. C., Robinson, T. D.: Antihypertensive efficacy and safety of olmesartan medoxomil compared with amlodipine for mild-to moderate hypertension. J. Hum. Hypertens. 17, 425 (2003).10.1038/sj.jhh.1001577Search in Google Scholar PubMed
12. Gardner, S. F., Franks, A. M.: Olmesartan medoxomil: the seventh angiotensin receptor antagonist. Ann. Pharmacother. 37, 99 (2003).10.1345/aph.1C197Search in Google Scholar PubMed
13. Benicar (Olmesartan medoxomil) Drug Information: Clinical Pharmacology – Prescribing Information at RxList.” RxList. 27 June (2014). Web. 24 Apr. (2015).Search in Google Scholar
14. Huttunen, K. M., Raunio, H., Rautio, J.: Prodrugs – from serendipity to rational design. Pharmacol. Rev. 63, 750 (2011).10.1124/pr.110.003459Search in Google Scholar PubMed
15. Nandini, R. P., Seema, S. S.: Development and validation of new RP-HPLC method for determining impurity profiling in olmesartan medoxomil drug as well as in tablet dosage form. Der. Pharma. Chemica. 5(4), 274 (2013).Search in Google Scholar
16. Mohammad, A. K., Abolfazl, H.: An easy, safe and simple method for the iodination of heterocyclic compounds in water. Iran J. Org. Chem. 4, 270 (2009).Search in Google Scholar
17. Abolfazl, H., Mohammad, A. K., Masoumeh, H., Mahmoud, T. A.: A simple method for iodination of heterocyclic compounds using HIO4/NaCl/silica gel/H2SO4 in water. Monatsh Chem. 143, 619 (2012).10.1007/s00706-011-0611-6Search in Google Scholar
18. Sanad, M. H., Shweeta, H. A.: Preparation and bio-evaluation of 99mTc-carbonyl complex of ursodeoxycholic acid for heptobiliary imaging. J. Mol. Imag. Dynamic. 5, 1 (2015).Search in Google Scholar
19. Sanad, M. H.: Labeling of Omeprazole with technetium-99m for diagnosis of stomach. Radiochemistry 55(6), 605 (2013).10.1134/S1066362213060076Search in Google Scholar
20. Ramalingaiah, H., Jagadeesh, R. V., Puttaswamy, M.: Os (VIII)-catalyzed and uncatalyzed oxidation of biotin by chloramine-T in alkaline medium: comparative mechanistic aspects and kinetic modeling. J. Mol. Cat. A: Chem. 265(1–2), 70 (2007).10.1016/j.molcata.2006.09.047Search in Google Scholar
21. Siddiqui, N., Husain, A., Chaudhry, L., Alam, M., Mitra, M., Bhasin, P.: Pharmacological and pharmaceutical profile of valsartan: a review. J. Appl. Pharm. Sci. 1(4), 12 (2011).Search in Google Scholar
22. Kuchar, M., Oliveira, M. C., Gano, L., Santos, I., Kniess, T.: Radioiodinated sunitinib as a potential radiotracer for imaging angiogenesis-radiosynthesis and first radiopharmacological evaluation of 5-[125I]Iodo-sunitinib. Bioorg. Med. Chem. Lett. 22(8), 2850 (2012).10.1016/j.bmcl.2012.02.068Search in Google Scholar
23. Abi-Dargham, A., Zea-Ponce, Y., Terriere, D., Al-Tikriti, M., Baldwin, R. M., Hoffer, P., Charney, D., Leysen, J. E., Laruelle, M., Mertens, J., Innis, R. B.: Preclinical evaluation of [123I] R93274 as a SPECT radiotracer for imaging 5-HT2A receptors. Eur. J. Pharmacol. 321(3), 285 (1997).10.1016/S0014-2999(96)00906-5Search in Google Scholar
24. Attila, V., Sandor, N., Zoltan, K., Rezso, G. L., Rösch, F.: Handbook of Nuclear Chemistry, 2nd ed. Springer, New York (2011).Search in Google Scholar
25. Sanad, M. H., Talaat, H. M.: Radioiodination and biological evaluation of rabeprazole as a peptic ulcer localization radiotracer. Radiochemistry 59(3), 307 (2017).10.1134/S1066362217030158Search in Google Scholar
26. Sanad, M. H.: Labeling and biological evaluation of 99mTc-azithromycin for infective inflammation diagnosis. Radiochemistry 55(5), 539 (2013).10.1134/S1066362213050159Search in Google Scholar
27. Sanad, M. H., Abdel-Ghaney, I. Y.: Synthesis of 99mTc-erythromycin complex as a model for infection sites imaging. Radiochemistry 55(4), 418 (2013).10.1134/S1066362213040139Search in Google Scholar
28. Sanad, M. H.: Novel radiochemical and biological characterization of 99mT-histamine as a model for brain imaging. J. Anal. Sci. Technol. 5, 23 (2014).10.1186/s40543-014-0023-4Search in Google Scholar
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Articles in the same Issue
- Frontmatter
- Redox behavior and solubility of plutonium under alkaline, reducing conditions
- Effects of temperature on the extraction of U(VI) and Pu(IV) by tris(2-methylbutyl) phosphate from nitric acid media
- Interaction of salicylic acid with zirconium diphosphate and its reactivity toward uranium (VI)
- Complexation of a macrocyclic ligand, 2,6-di (N-methyl)formamide-calix[4]pyridine, with Eu(III) and extraction of Eu(III) and Am(III)
- Feasibility studies of using N,N-dihexyloctanamide (DHOA) for fast reactor fuel reprocessing applications
- Encapsulated polymeric beads impregnating unexplored amide, N,N′-bis(2-ethyl hexyl) α-hydroxy acetamide (BEHGA) – preparation, sorption and kinetic studies for tri-, tetra- and hexavalent radionuclides
- Radioiodination of olmesartan medoxomil and biological evaluation of the product as a tracer for cardiac imaging
- Investigation of chemical composition and moisture content for different materials on the attenuation of γ rays
Articles in the same Issue
- Frontmatter
- Redox behavior and solubility of plutonium under alkaline, reducing conditions
- Effects of temperature on the extraction of U(VI) and Pu(IV) by tris(2-methylbutyl) phosphate from nitric acid media
- Interaction of salicylic acid with zirconium diphosphate and its reactivity toward uranium (VI)
- Complexation of a macrocyclic ligand, 2,6-di (N-methyl)formamide-calix[4]pyridine, with Eu(III) and extraction of Eu(III) and Am(III)
- Feasibility studies of using N,N-dihexyloctanamide (DHOA) for fast reactor fuel reprocessing applications
- Encapsulated polymeric beads impregnating unexplored amide, N,N′-bis(2-ethyl hexyl) α-hydroxy acetamide (BEHGA) – preparation, sorption and kinetic studies for tri-, tetra- and hexavalent radionuclides
- Radioiodination of olmesartan medoxomil and biological evaluation of the product as a tracer for cardiac imaging
- Investigation of chemical composition and moisture content for different materials on the attenuation of γ rays
