Synthesis of 131I Labeled Quercetin through Oxidation Method Using Chloramine-T for Cancer Radiopharmaceuticals

https://doi.org/10.22146/ijc.34512

Maula Eka Sriyani(1*), Dian Ayu Utami(2), Mega Susilo Dwike(3), Eva Maria Widyasari(4), Muharram Marzuki(5), Rizky Juwita Sugiharti(6), Witri Nuraeni(7)

(1) National Nuclear Energy Agency, Jl. Tamansari No. 71 Bandung 40132, Indonesia
(2) Jenderal Achmad Yani University, Jl. Terusan Jenderal Sudirman Cimahi, Indonesia
(3) Jenderal Achmad Yani University, Jl. Terusan Jenderal Sudirman Cimahi, Indonesia
(4) National Nuclear Energy Agency, Jl. Tamansari No. 71 Bandung 40132, Indonesia
(5) Jenderal Achmad Yani University, Jl. Terusan Jenderal Sudirman Cimahi, Indonesia
(6) National Nuclear Energy Agency, Jl. Tamansari No. 71 Bandung 40132, Indonesia
(7) National Nuclear Energy Agency, Jl. Tamansari No. 71 Bandung 40132, Indonesia
(*) Corresponding Author

Abstract


Quercetin is one of the flavonoid groups with antioxidant activity. The objective of this study was to achieve the labeled compound of 131I-quercetin as a radiotracer for diagnosis and cancer therapy with high labeling efficiency and radiochemical purity. The labeling procedure was conducted by the oxidation reaction using chloramine-T. The effect of pH, reaction time, amount of oxidizing agent and ligand were evaluated in this research. Quercetin was successfully labeled with iodine-131 at pH 11 at room temperature for 10 min mixed in 1000 rpm with the amount of quercetin and chloramine-T is 0.4 and 0.3 mg, respectively. The results demonstrated that the ratio of quercetin/Na131I was 2 × 105. The 131I-quercetin labeling efficiency was 92.03 ± 2.20%, and radiochemical purity of 131I-quercetin was 99.34 ± 0.58%. The results showed that 131I-quercetin could be a radiotracer candidate for diagnosis and cancer therapy.


Keywords


131I-quercetin; iodination; natural compound; synthesis; anticancer

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References

[1] Hejmadi, M., 2010, Introduction to Cancer Biology, 2nd ed., http://csbl.bmb.uga.edu/mirrors/JLU/DragonStar2017/download/introduction-to-cancer-biology.pdf.

[2] Kementrian Kesehatan RI Pusat Data dan Informasi Kesehatan, 2015, Stop Kanker, infodatin-Kanker, 3.

[3] WHO, 2013, Media Center Cancer, Who Heal Organ, 1, 1–5.

[4] Loveland, W., Morrissey, D.J., and Seaborg, G.T., 2006, Modern Nuclear Chemistry, Wiley-Interscience, New York, United States, 671.

[5] Bagshawe, K.D., 1975, Recent Results in Cancer Research: Volume 46. Diagnosis and Therapy of Malignant Lymphomas, Immunology, 29 (4), 802.

[6] Mango, L., 2017, Theranostics: A unique concept to nuclear medicine, Arch. Cancer Sci. Ther., 1, 001–004.

[7] Ersahin, D., Doddamane, I., and Cheng, D., 2011, Targeted radionuclide therapy, Cancers, 3 (4), 3838–3855.

[8] Khan, F., Niaz, K., Maqbool, F., Hassan, F.I., Abdollahi, M., Venkata, K.C.N., Nabavi, S.M., and Bishayee, A., 2016, Molecular targets underlying the anticancer effects of quercetin: An update, Nutrients, 8 (9), 529.

[9] Katyal, P., Batra, N., and Khajuria, R., 2014, Flavonoids and their therapeutic potential as anti cancer agents: Biosynthesis and metabolism, World J. Pharm. Pharm. Sci., 3 (6), 2188–2216.

[10] Maalik. A., Khan, F.A., Mumtaz, A., Mehmood, A., Azhar, S., Atif, M., Karim, S., Altaf, Y., and Tariq, I., 2014, Pharmacological applications of quercetin and its derivatives: A short review, Trop. J. Pharm. Res., 13 (9), 1561–1566.

[11] Tahir; I., Wijaya, K., Widianingsih, D., 2003, Hubungan kuantitatif struktur-aktivitas antiradikal senyawa turunan flavon/flavonol berdasarkan pendekatan Free-Wilson, Makalah Seminar Nasional Kimia Fisik III, Universitas Diponegoro, 19 March 2003.

[12] Kakizoe, T., 2003, Chemoprevention of cancer-focusing on clinical trials, Jpn. J. Clin. Oncol., 33 (9), 421–442.

[13] Russo, N., Toscano, M., and Uccella, N., 2000, Semiempirical molecular modeling into quercetin reactive site: Structural, conformational, and electronic features, J. Agric. Food Chem., 48 (8), 3232–3237.

[14] Choi, M.H., Rho, J.K., Kang, J.A., Shim, H.E., Nam, Y.R., Yoon, S., Kim, H.R., Choi, D.S., Park, S.H., Jang, B.S., and Jeon, J., 2016, Efficient radiolabeling of rutin with 125I and biodistribution study of radiolabeled rutin, J. Radioanal. Nucl. Chem., 308 (2), 477–483.

[15] Barolli, M.G., and Pomilio, A.B., 1997, Synthesis of [131-I]-iodinated quercetin, J. Labelled Compd. Radiopharm., 39 (11), 927–933.

[16] Hosseinimehr, S.J., Tolmachev, V., and Stenerlöw, B., 2011, 125I-labeled quercetin as a novel DNA-targeted radiotracer, Cancer Biother. Radiopharm., 26 (4), 469–475.

[17] Park, B., Choe, Y.S., Lee, S.Y., Lee, K.H., Chi, D.Y., Kim, S.E., Choi, Y., Lee, J., and Kim, B.T., 2001, Synthesis of iodine-123 labeled quercetin and catechin as radical seeking agents, J. Labelled Compd. Radiopharm., 44, S957–S958.

[18] Xie, Q., Li, X., Wang, G., Hou, X., Wang, Y., Yu, H., Qu, C., Luo, S., Cui, Y., Xia, C., and Wang, R., 2017, Preparation and evaluation of 131I-quercetin as a novel radiotherapy agent against dedifferentiated thyroid cancer, J. Radioanal. Nucl. Chem., 311 (3), 1697–1708.

[19] Sriyani, M.E., Utami, D.A., Widyasari, E.M., and Marzuki, M., 2015, Iodination method of quercetin for synthesis of anticancer labelled compound, Procedia Chem., 16, 245–250.

[20] Neacsu, B., Cimpeanu, C., and Barna, C., 2013, Radionuclidic purity-An essential parameter in quality control of radiopharmaceuticals, Rom. Rep. Phys., 65 (1), 155–167.

[21] Kowalsky, R.J., and Falen, S.W., 2004, Radiopharmaceuticals in Nuclear Pharmacy and Nuclear medicine, 2nd ed., American Pharmacists Association (APhA), Washington, DC.

[22] Saha, G.B., 2010, Fundamentals of Nuclear Pharmacy, Springer-Verlag, New York.

[23] Setiawan, D., Hastiawan I., and Bashiroh, N.A., 2018, Synthesis, radiochemical purity control and stability of Scandium-46-1,4,7-triazacyclononane-1,4,7-triacetic acid (46Sc-NOTA), Indones. J. Chem., 18 (1), 153–158.

[24] Sims-Mourtada, J., Yang, D., Tworowska, I., Larson, R., Smith, D., Tsao, N., Opdenaker, L., Mourtada, F., and Woodward, W., 2012, Detection of canonical hedgehog signaling in breast cancer by 131-iodine-labeled derivatives of the sonic hedgehog protein, J. Biomed. Biotechnol., 2012, 639562.



DOI: https://doi.org/10.22146/ijc.34512

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