Mehmet KOCA, Emrah ÖZAKAR, Rukiye SEVİNÇ ÖZAKAR

TRİİYODOANİLİN’İN SENTEZLENMESİ, NANOSÜSPANSİYONLARININ HAZIRLANMASI, İN VİTRO KARAKTERİZASYONU VE RADYOKONTRAST ÖZELLİKLERİNİN İNCELENMESİ

Amaç: Suda çözünürlüğü bulunmayan iyot bazlı triiyodoanilin (TIA) radyokontrast bileşiğinin sentezini ve nanosüspansiyonunu yapmak, karakterizasyonlarını gerçekleştirmek ve Bilgisayarlı Tomografi (BT) görüntülemede sıklıkla kullanılan iopromid ve ioheksol ile kıyaslamak.

SYNTHESIS OF TRIIODOANILINE, PREPARATION OF NANOSUSPENSIONS, IN VITRO CHARACTERIZATION AND INVESTIGATION OF RADIOCONTRAST PROPERTIES

Objective: Synthesis and nanosuspension preparation of iodine-based triiodoaniline (TIA) radiocontrast compound, which is not soluble in water, perform their characterization and compare with iopromide and iohexol, which are frequently used in Computed Tomography (CT) imaging.

Keywords:

CT imaging, nanocrystal nanosuspension, radiocontrast agent, triiodoaniline,

PDF

___

1. Caschera, L., Lazzara, A., Piergallini, L., Ricci, D., Tuscano, B., Vanzulli, A. (2016). Contrast agents in diagnostic imaging: Present and future. Pharmacological Research, 110, 65-75. https://doi.org/10.1016/j.phrs.2016.04.023
2. Koc, M.M., Aslan, N., Kao, A.P., Barber, A.H. (2019). Evaluation of X-ray tomography contrast agents: A review of production, protocols, and biological applications. Microscopy Research and Technique, 82(6), 812-848. https://doi.org/10.1002/jemt.23225
3. Almen, T. (1985). Development of nonionic contrast-media. Investigative Radiology, 20(1), 2- 9. https://doi.org/10.1097/00004424-198501002-00003.
4. Müller, R.H., Gohla, S., Keck, C.M. (2011). State of the art of nanocrystals – Special features, production,nanotoxicology aspects and intracellular delivery. European Journal of Pharmaceutics and Biopharmaceutics, 78, 1-9. https://doi.org/10.1016/j.ejpb.2011.01.007
5. Wang, Y., Zheng, Y., Zhang, L., Wang, Q., Zhang, D. (2013). Stability of nanosuspensions in drug delivery. Journal of Controlled Release, 172, 1126-1141. https://doi.org/10.1016/j.jconrel.2013.08.006
6. Gao, L., Liu, G., Ma, J., Wang, X., Zhou, L., Li, X. (2012). Drug nanocrystals: In vivo performances. Journal of Controlled Release, 160, 418-430. https://doi.org/10.1016/j.jconrel.2012.03.013
7. Wang, L.L., Du, J., Zhou, Y.Q., Wang, Y.C. (2017). Safety of nanosuspensions in drug delivery. Nanomedicine: Nanotechnology, Biology, and Medicine, 13(2), 455-469. https://doi.org/10.1016/j.nano.2016.08.007
8. Kamaly, N., He, J.C., Ausiello, D.A., Farokhzad, O.C. (2016). Nanomedicines for renal disease: current status and future applications. Nature Reviews Nephrology, 12(12), 738-753. https://doi.org/10.1038/nrneph.2016.156
9. Khan, I., Saeed, K., Khan, I. (2019). Nanoparticles: Properties, applications and toxicities. Arabian Journal of Chemistry, 12(7), 908-931. https://doi.org/10.1016/j.arabjc.2017.05.011
10. Williams, R.M., Jaimes, E.A., Heller, D.A. (2016). Nanomedicines for kidney diseases. Kidney International, 90(4), 740-745. https://doi.org/10.1016/j.kint.2016.03.041
11. Thurman, J.M., Serkova, N.J. (2013). Nanosized contrast agents to noninvasively detect kidney inflammation by magnetic resonance imaging. Advances in Chronic Kidney Disease, 20(6), 488-499. https://doi.org/10.1053/j.ackd.2013.06.001
12. Debbage, P., Jaschke, W. (2008). Molecular imaging with nanoparticles: Giant roles for dwarf actors. Histochemistry and Cell Biology, 130(5), 845-875. https://doi.org/10.1007/s00418-008- 0511-y
13. Chemical Book Web site. (2017). Retrieved September 28, from https://www.chemicalbook.com/ChemicalProductProperty_EN_cb5125267.htm.
14. Chemical Book Web site. (2017). Retrieved September 29, from https://www.chemicalbook.com/ChemicalProductProperty_EN_cb5110557.htm.
15. ChemSpider Web site. (2020). Retrieved September 29, from http://www.chemspider.com/Chemical-Structure.193223.html.
16. Sahu, B.P., Das, M.K. (2014). Nanosuspension for enhancement of oral bioavailability of felodipine. Applied Nanoscience, 4(2), 189-197. https://doi.org/10.1007/s13204-012-0188-3
17. Ferreira, I.M., Casagrande, G.A., Pizzuti, L., Raminelli, C. (2014). Ultrasound-promoted rapid and efficient iodination of aromatic and heteroaromatic compounds in the presence of iodine and hydrogen peroxide in water. Synthetic Communications, 44(14), 2094-2102. https://doi.org/10.1080/00397911.2013.879900
18. Rao, J.P., Geckeler, K.E. (2011). Polymer nanoparticles: Preparation techniques and sizecontrol parameters. Progress in Polymer Science, 36(7), 887-913. https://doi.org/10.1016/j.progpolymsci.2011.01.001
19. Pirimoglu, B., Sade, R., Sakat, M.S., Ogul, H., Levent, A., Kantarci, M. (2018). Low-dose noncontrast examination of the paranasal sinuses using volumetric computed tomography. Journal of Computer Assisted Tomography, 42(3), 482-486. https://doi.org/10.1097/RCT.0000000000000699
20. Pirimoglu, B., Sade, R., Sakat, M.S., Polat, G., Kantarci, M. (2019). Low-dose non-contrast examination of the temporal bone using volumetric 320-row computed tomography. Acta Radiologica, 60(7), 908-916. https://doi.org/10.1177/0284185118802597
21. Ravichandran, R. (2009). Nanoparticles in drug delivery: Potential green nanobiomedicine applications. International Journal of Green Nanotechnology: Biomedicine, 1(2), 108-130. https://doi.org/10.1080/19430850903430427
22. De Simone, B., Ansaloni, L., Sartelli, M., Gaiani, F., Leandro, G., De' Angelis, G.L., Di Mario, F., Coccolini, F., Catena, F. (2018). Is the risk of contrast-induced nephropathy a real contraindication to perform intravenous contrast enhanced Computed Tomography for nontraumatic acute abdomen in Emergency Surgery Department?. Acta Biomedica, 89(9-S), 158- https://doi.org/172. 10.23750/abm.v89i9-S.7891.
23. Mohammed, N.M.A., Mahfouz, A., Achkar, K., Rafie, I.M., Hajar, R. (2013). Contrast-induced nephropathy. Heart View s : The Official Journal of the Gulf Heart Association, 14(3), 106-116. https://doi.org/10.4103/1995-705X.125926
24. Cosmai, L., Porta, C., Privitera, C., Gesualdo, L., Procopio, G., Gori, S., et al. (2020). Acute kidney injury from contrast-enhanced CT procedures in patients with cancer: White paper to highlight its clinical relevance and discuss applicable preventive strategies. ESMO Open, 5(2), 1-8. https://doi.org/10.1136/esmoopen-2019-000618.
25. Sovak, M., Ranganathan, R. (1980). Stability of nonionic water-soluble contrast media: implications for their design. Investigative Radiology, 15(6), S323-328. https://doi.org/10.1097/00004424-198011001-00068
26. The LibreTexts Web site. (2006). Retrieved January 05, 2021, from https://chem.libretexts.org/Bookshelves/General_Chemistry/Map%3A_Chemistry_- _The_Central_Science_(Brown_et_al.)/13%3A_Properties_of_Solutions
27. Cormode, D.P., Naha, P.C., Fayad, Z.A. (2014). Nanoparticle contrast agents for computed tomography: a focus on micelles. Contrast Media & Molecular Imaging, 9(1), 37-52. https://doi.org/10.1002/cmmi.1551
28. Ashton, J.R., West, J.L., Badea, C.T. (2015). In vivo small animal micro-CT using nanoparticle contrast agents. Frontiers in Pharmacology, 6, 1-22. https://doi.org/10.3389/fphar.2015.00256
29. Williams, R.M., Shah, J., Tian, H.S., Chen, X., Geissmann, F., Jaimes, E.A., Heller, D.A. (2018). Selective nanoparticle targeting of the renal tubules. Hypertension, 71(1), 87-94. https://doi.org/10.1161/HYPERTENSIONAHA.117.09843
30. Han, X.J., Xu, K., Taratula, O., Farsad, K. (2019). Applications of nanoparticles in biomedical imaging. Nanoscale, 11(3), 799-819. https://doi.org/10.3390/nano10091700
31. Hainfeld, J.F., Ridwan, S.M., Stanishevskiy, Y., Smilowitz, N.R., Davis, J., Smilowitz, H.M. (2018). Small, long blood half-life iodine nanoparticle for vascular and tumor imaging. Scientific Reports, 8, 1-10. https://doi.org/10.1038/s41598-018-31940-2
32. Kim, J., Lee, N., Hyeon, T. (2017). Recent development of nanoparticles for molecular imaging. Philosophical Transactions of the Royal Society A, 375(2107), 1-17. https://doi.org/10.1098/rsta.2017.0022
33. Patel, V.R., Agrawal, Y. (2011). Nanosuspension: An approach to enhance solubility of drugs. Journal of Advanced Pharmaceutical Technology & Research, 2(2), 81-87. https://doi.org/10.4103/2231-4040.82950
34. Sutradhar, K.B., Khatun, S., Luna, I.P. (2013). Increasing possibilities of nanosuspension. Journal of Nanotechnology, 2013, 346581. https://doi.org/10.1155/2013/346581
35. Rabinow, B., Kipp, J., Papadopoulos, P., Wong, J., Glosson, J., Gass, J., Sun, C.S., Wielgos, T., White, R., Cook, C., Barker, K., Wood, K. (2007). Itraconazole IV nanosuspension enhances efficacy through altered pharmacokinetics in the rat. International Journal of Pharmaceutics, 339(1-2), 251-260. https://doi.org/10.1016/j.ijpharm.2007.02.030
36. Merisko-Liversidge, E., Liversidge, G.G., Cooper, E.R. (2003). Nanosizing: A formulation approach for poorly-water-soluble compounds. European Journal of Pharmaceutical Sciences, 18(2), 113-120. https://doi.org/10.1016/S0928-0987(02)00251-8
37. Peters, K., Leitzke, S., Diederichs, J.E., Borner, K., Hahn, H., Müller, R.H., Ehlers, S. (2000). Preparation of a clofazimine nanosuspension for intravenous use and evaluation of its therapeutic efficacy in murine Mycobacterium avium infection. Journal of Antimicrobial Chemotherapy, 45(1), 77-83. https://doi.org/10.1093/jac/45.1.77
38. Kalvakuntla, S., Deshpande, M., Attari, Z., Kunnatur, K. (2016). Preparation and characterization of nanosuspension of aprepitant by H96 process. Advanced Pharmaceutical Bulletin, 6(1), 83-90. https://doi.org/10.15171/apb.2016.013
39. Singare, D.S., Marella, S., Gowthamrajan, K., Kulkarni, G.T., Vooturi, R., Rao, P.S. (2010). Optimization of formulation and process variable of nanosuspension: An industrial perspective. International Journal of Pharmaceutics, 402(1-2), 213-220. https://doi.org/10.1016/j.ijpharm.2010.09.041
40. Singh, S., Singh, S.K., Chauhan, M.G., Kumar, B., Pandey, N.K., Kaur, B., Kumar, A., Mohanta, S., Gulati, M., Wadhwa, S., Yadav, A.K., Singh, P.K., Kumari, Y., Kaur, G., Khursheed, R., Clarisse, A. (2019). Quality by design-based optimization of formulation and process variables for controlling particle size and zeta potential of spray dried incinerated copper nanosuspension. Recent Innovations in Chemical Engineering, 12(3), 248-260. https://doi.org/10.2174/2405520412666190627144845
41. Karakucuk, A., Celebi, N. (2020). Investigation of formulation and process parameters of wet media milling to develop etodolac nanosuspensions. Pharmaceutical Research, 37(6), 111. https://doi.org/10.1007/s11095-020-02815-x
42. Ali, H.S., York, P., Blagden, N. (2009). Preparation of hydrocortisone nanosuspension through a bottom-up nanoprecipitation technique using microfluidic reactors. International Journal of Pharmaceutics, 375(1-2), 107-113. https://doi.org/10.1016/j.ijpharm.2009.03.029
43. Patravale, V.B., Date, A.A., Kulkarni, R.M. (2004). Nanosuspensions: A promising drug delivery strategy. Journal of Pharmacy and Pharmacology, 56, 827-840. https://doi.org/10.1211/0022357023691
44. Moorthi, C., Krishnan, K., Manavalan, R., Kathiresan, K. (2012). Preparation and characterization of curcumin–piperine dual drug loaded nanoparticles. Asian Pacific Journal of Tropical Biomedicine, 2(11), 841-848. https://doi.org/10.1016/S2221-1691(12)60241-X
45. Afifi, S.A., Hassan, M.A., Abdelhameed, A.S., Elkhodairy, K.A. (2015). Nanosuspension: An emerging trend for bioavailability enhancement of etodolac. International Journal of Polymer Science, 2015, 938594. http://dx.doi.org/10.1155/2015/938594
46. Wiśniewska, M., Ostolska, I., Szewczuk-Karpisz, K., Chibowski, S., Terpiłowski, K., Gun’ko, V.M., Zarko, V.I. (2015). Investigation of the polyvinyl alcohol stabilization mechanism and adsorption properties on the surface of ternary mixed nanooxide AST 50 (Al2O3–SiO2–TiO2). Journal of Nanoparticle Research, 17(12), 1-14. http://dx.doi.org/10.1007/s11051-014-2831-2
47. Abdelbary, A.A., Li, X., El-Nabarawi, M., Elassasy, A., Jasti, B. (2013). Effect of fixed aqueous layer thickness of polymeric stabilizers on zeta potential and stability of aripiprazole nanosuspensions. Pharmaceutical Development and Technology, 18(3), 730-735. http://dx.doi.org/10.3109/10837450.2012.727001.
48. Müller, R., Jacobs, C. (2002). Buparvaquone mucoadhesive nanosuspension: preparation, optimisation and long-term stability. International Journal of Pharmaceutics, 237(1-2), 151- 161. http://dx.doi.org/10.1016/s0378-5173(02)00040-6.