Abstract
Porphyrins are interesting derivatives with low toxicity, tumor avidity and rapid wash-out suggested as potential radiopharmaceuticals in radiolabeled form. In this work, [166Ho] labeled 5,10,15,20-tetrakis(phenyl) porphyrin ([166Ho]-TPP) was prepared using [166Ho]HoCl3 and 5,10,15,20-tetrakis(phenyl)porphyrin (H2TPP) for 12 h at 50 °C (radiochemical purity: >95 ± 2 % ITLC, >99 ± 0.5 % HPLC, specific activity: 0.9–1.1 GBq/mmol). Stability of the complex was checked in final formulation and human serum for 48 h. The partition coefficient was calculated for the compound (log P = 2.01). The biodistribution of the labeled compound in vital organs of wild-type rats was studied using scarification studies and SPECT. A detailed comparative pharmacokinetic study performed for 166Ho cation and [166Ho]-TPP performed up to 24 h. The complex is mostly washed out from the circulation through kidneys and in less extends from the liver. The kidney:blood, kidney:liver and kidney:muscle ratios 4 h post injection were 14, 3.6 and 7.38 respectively.
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Thomas SR, Khuntia D (2007) Motexafin gadolinium injection for the treatment of brain metastases in patients with non-small cell lung cancer. Int J Nanomed 2:79–87
Kahl SB, Koo MS (1992) Synthesis and properties of tetrakiscarborane-carboxylate esters of 2,4-bis (-dihydroxyethyl) deuteroporphyrin IX. In: Allen BJ, Moore DE, Harrington BV (eds) Progress in neutron capture therapy for cancer. Plenum Press, New York, pp 223–226
Sasaki K, Yumita N, Nishigaki R, Sakata I, Nakajima S, Umemura S-I (2001) Pharmacokinetic study of a indium-porphyrin photo- and sono-sensitizer in tumor-bearing mice. ATX-70. Jpn J Cancer Res 92:989–995
Fawwaz RA, Frye F, Loughman WD, Hemphill W (1974) Survival of skin homografts in dogs injected with 109Pd-protoporphyrin. J Nucl Med 15:997–1002
Fawwaz RA, Hemphill W, Winchell HS (1971) Potential use of 109Pd-porphyrin complexes for selective lymphatic ablation. J Nucl Med 12:231–236
Chakraborty S, Das T, Banerjee S, Sarma HD, Venkatesh M (2007) Preparation and preliminary biological evaluation of a novel 109Pd labeled porphyrin derivative for possible use in targeted tumor therapy. Q J Nucl Med Mol Imaging 15:16–23
Sarma HD, Das T, Banerjee S, Venkatesh M, Vidyasagar PB, Mishra KP (2010) Biologic evaluation of a novel 188Re-labeled porphyrin in mice tumor model. Cancer Biother Radiopharm 25:47–54
Murugesan S, Shettyc SJ, Srivastava TS, Noronha OPD, Samuel AM (2001) A technetium-99m-labelled cyclam acid porphyrin (CAP) for tumour imaging. Appl Radiat Isot 55:641–646
Wang A-Y, Lin J-L, Lin W-C (2010) Studies on the porphine labeled with 99mTc-pertechnetate. J Radioanal Nucl Chem 284:121–128
Nunn AD (1978) Medical radionuclides and the quality of radiopharmaceuticals, The kinetics of incorporation of 111In into m-tetraphenylporphine. J Radioanal Nucl Chem 53:291–298
Fazaeli Y, Jalilian AR, Amini MM, Rahiminejad-kisomi A, Rajabifar S, Bolourinovin F, Moradkhani S (2011) Preparation and preliminary evaluation of [67Ga]–tetra phenyl porphyrin complexes as possible imaging agents. J Radioanal Nucl Chem 288:17–24
Louis E, Boverie J, Dewit O, Baert F, De Vos M, D’Haens G, Belgian IBD Research Group (2007) Treatment of small bowel subocclusive Crohn’s disease with infliximab: an open pilot study. Acta Gastroenterol Belg 70(1):15–19
Teirstein AS, Machac J, Almeida O, Lu P, Padilla ML, Iannuzzi MC (2007) Results of 188 whole-body fluorodeoxyglucose positron emission tomography scans in 137 patients with sarcoidosis. Chest 132(6):1949–1953
Zielhuis SW, Nijsen JF, de Roos R, Krijger GC, van Rijk PP, Hennink WE, van het Schip AD (2006) Int J Pharm 31:69–74
Huh R, Park YS, Lee JD, Chung YS, Park YG, Chung SS, Chang JW (2005) Yonsei Med J 46:51–60
Seong SK, Ryu JM, Shin DH, Bae EJ, Shigematsu A, Hatori Y, Nishigaki J, Kwak C, Lee SE, Park KB (2005) Eur J Nucl Med Mol Imaging 32:910–917
Kropácek M, Melichar F, Henková K, Konopková M (2003) Nucl Med Rev Cent East Eur. 6(1):1–4
Breitz H, Wendt R, Stabin M, Bouchet L, Wessels B (2003) Dosimetry of high dose skeletal targeted radiotherapy (STR) with 166Ho-DOTMP. Cancer Biother Radiopharm. 18(2):225–230
Joh CW, Park CH, Kang HJ, Oh YT, Chun, Kim HS, Choi BI, Park KB, Kim YM, Kim KH, Vahc YW, Jang JS, Lee BK (2000) Nucl Med Commun 21(10):959–964
Majali MA, Saxena SK, Joshi SH, Unni PR, Ramamoorthy N (2001) Nucl Med Commun 22:97–103
Das T, Chakraborty S, Sarma HD, Venkatesh M, Banerjee S (2009) Nucl Med Commun 30:362–367
Chung YL, Lee JD, Bang D, Lee JB, Park KB, Lee MG (2000) Eur J Nucl Med 27:842–846
Falk JE (1975) Porohyrins and metalloporphyrins. Elsevier Science Publishing, New York
Manual for reactor produced radioisotopes, IAEA, VIENNA, 2003, IAEA-TECDOC-1340, ISBN 92-0-101103-2, ISSN 1011–4289, © IAEA, 2003, pp. 71, Printed by the IAEA in Austria, January 2003
Adler AD, Longo FR, Finarelli JD, Goldmacher J, Assour J, Korsakoff L (1967) A simplified synthesis for meso-tetraphenylporphine. J Org Chem 32:476
Jalilian AR, Rowshanfarzad P, Sabet M, Novinrooz A, Raisali G (2005) Preparation of [66Ga]bleomycin complex as a possible PET radiopharmaceutical. J Radioanal Nucl Chem 264:617
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Vahidfar, N., Jalilian, A.R., Fazaeli, Y. et al. Development and evaluation of a 166holmium labelled porphyrin complex as a possible therapeutic agent. J Radioanal Nucl Chem 295, 979–986 (2013). https://doi.org/10.1007/s10967-012-2034-1
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DOI: https://doi.org/10.1007/s10967-012-2034-1