Preliminary test of the radiopharmaceutical potential of PDI-Pyr radiolabeled with 131I

Abstract

Objective: Cancer is a fatal disease that arises as a result of unregulated growth and spread of malignant cells. According to the reports of World Health Organization (WHO), cancer related deaths are projected to increase in the future with the value of about 13.1 million deaths by the year 2030. In order to control this danger and growing burden, new technologies and therapeutic methods for improving the life quality of cancer patients are being developed. The overall aim of this work was to design of a new anti-cancer drug.

 

Methods: Radiolabeling and quality control studies of PDI-Pyr were carried out by using thin layer radiochromatography.  Scintigrams were obtained using a gamma camera (Infinia, GE), which was adjusted to detect g radiations of ¹³¹I.

Results: Radiolabeling yield of ¹³¹I-PDI-Pyr was obtained to be about 97%. Also, the highest uptakes of ¹³¹I-PDI-Pyr were observed in the stomach, the liver, the lung and the bladder.

Conclusion: The novel PDI-Pyr compound was successfully  radiolabeled with ¹³¹I using iodogen method for the first time. The preliminary results obtained in this study have indicated that in the case of verification of selective accumulation in some stomach liver, lung and bladder cancer cells, perylene chromophore derivatives promise to be used as new anticancer agents.

Keywords

• Radiolabelling, Thin Layer Radiochromatography, Scintigraphy, PDI Dyes

Preliminary test of the radiopharmaceutical potential of PDI-Pyr radiolabeled with 131I

Öz

References

1. Ghavami G, Sardari S, Shokrgozar MA. Anticancerous potentials of Achillea species against selected cell lines. The Journal of Medicinal Plants Research. 2010;4:2411–
2. Manjappa AS, Chaudhari KR, Venkataraju MP, Dantuluri P, Nanda B, Sidda C, et al. Antibody derivatization and conjugation strategies: application in preparation of stealth immunoliposome to target chemotherapeutics to tumor. Journal of controlled release : official journal of the Controlled Release Society. 2011;150(1):2-22.
3. Oku N. Anticancer therapy using glucuronate modified long-circulating liposomes. Advanced drug delivery reviews. 1999;40(1-2):63-73.
4. Conflict of Interest: The authors declared that they had no conflicts of interest. Franceschın M, Alvıno A, Ortaggı G, Bıanco A. A convenient naphthyl)propenoic Tetrahedron Letters. 2004;45: 9015-18. of naproxen acid (a precursor).
5. Han H, Cliff CL, Hurley LH. Accelerated assembly of G- quadruplex structures by a small molecule. Biochemistry. 1999;38(22):6981-6.
6. Tuntiwechapikul W, Lee JT, Salazar M. Design and synthesis of the G-quadruplex-specific cleaving reagent perylene-EDTA.iron(II). Journal of the American Chemical Society. 2001;123(23):5606-7.
7. Rossetti L, Franceschin M, Schirripa S, Bianco A, Ortaggi G, Savino M. Selective interactions of perylene derivatives having different side chains with inter- and intramolecular G-quadruplex DNA structures. A correlation with telomerase inhibition. Bioorganic & medicinal chemistry letters. 2005;15(2):413-20.
8. Kern JT, Thomas PW, Kerwin SM. The relationship between ligand aggregation and G-quadruplex DNA selectivity in a series of 3,4,9,10-perylenetetracarboxylic acid diimides. Biochemistry. 2002;41(38):11379-89.

9. Fedoroff OY, Salazar M, Han H, Chemeris VV, Kerwin SM, Hurley LH. NMR-Based model of a telomerase-inhibiting compound bound to G-quadruplex DNA. Biochemistry. 1998;37(36):12367-74.
10. Han H, Bennett RJ, Hurley LH. Inhibition of unwinding of G- quadruplex structures by Sgs1 helicase in the presence of N,N'-bis[2-(1-piperidino)ethyl]-3,4,9,10- perylenetetracarboxylic interactive ligand. Biochemistry. 2000;39(31):9311-6. a G-quadruplex
11. Kern JT, Kerwin SM. The aggregation and G-quadruplex DNA perylenetetracarboxylic acid diimides. Bioorganic & medicinal chemistry letters. 2002;12(23):3395-8. charged 3,4,9,10
12. Kern JT, Thomas PW, Kerwin SM. The relationship between ligand aggregation and G-quadruplex DNA selectivity in a series of 3,4,9,10-perylenetetracarboxylic acid diimides. Biochemistry. 2002;41(38):11379-89.
13. Juskowiak B, Galezowska E, Koczorowska N, Hermann TW. Aggregation and G-quadruplex DNA-binding study of 6a,12a-diazadibenzo-[a,g]fluorenylium Bioorganic 2004;14(14):3627-30. derivative. & medicinal chemistry letters.
14. Unak P, Unak T. Microscopic energy absorption of the DNA molecules from Auger electrons of International journal of radiation applications and instrumentation Part A, Applied radiation and isotopes. 1988;39(10):1037-40. iodine-125.
15. Ünak T, Ongun B, Ünak P. Microscopic Dose Calculations within the cell nucleus from Auger Auger electrons of iodine-125. Applied radiation and isotopes. 1995;46,661.
16. Hofer KG, Hughes WL. Radiotoxicity of intranuclear tritium, 125 iodine and 131 iodine. Radiation research. 1971;47(1):94-101.
17. Dincalp H, Kizilok S, Icli S. Targeted singlet oxygen generation using different DNA-interacting perylene diimide type photosensitizers. Journal of fluorescence. 2014;24(3):917-24.
18. Demiroglu H, Avcibasi U, Unak P, Muftuler FZ, Ichedef CA, Gumuser FG, et al. Radiolabeling of bleomycin-glucuronide with (131)I and biodistribution studies using xenograft model of human colon tumor in Balb/C mice. Cancer biotherapy & radiopharmaceuticals. 2012;27(6):371-83.
19. Avcibasi U, Demiroglu H, Ediz M, Akalin HA, Ozcaliskan E, Senay H, et al. Radiolabeling of new generation magnetic poly(HEMA-MAPA) nanoparticles with (131) I and preliminary investigation of its radiopharmaceutical potential using albino Wistar rats. Journal of labelled compounds & radiopharmaceuticals. 2013;56(14):708-16.
20. Avcibasi U, Demiroglu H, Ediz M, Akalin HA, Ozcaliskan E, Senay H, et al. Radiolabeling of new generation magnetic poly(HEMA-MAPA) nanoparticles with (131) I and preliminary investigation of its radiopharmaceutical potential using albino Wistar rats. Journal of labelled compounds & radiopharmaceuticals. 2013;56(14):708-16.
21. Avcibasi U, Dinçalp H, Ünak T, Yildirim Y, Avcibasi N, Duman radiopharmaceutical diisopropylphenyl)-N`-(4-pyridyl)-perylene-3,4,9,10- tetracarboxylic diimide radiolabeled with iodine-131. The Journal of Radioanalytical and Nuclear Chemistry. 2007;273(3): 669-675. tests of N-(2,6
22. Avcibasi U, Avcibasi N, Unak T, Unak P, Muftuler FZ, Yildirim Y, et al. Metabolic comparison of radiolabeled aniline- and phenol-phthaleins with (131)I. Nuclear medicine and biology. 2008;35(4):481-92.
23. Copyright © 2014 The Author(s); This is an open-access article distributed under the terms of the Creative Commons Attribution
24. License (http://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.