Abstract
There have been substantial improvements in radiopharmaceutical chemistry with respect to designing new diagnostic and therapeutic agents for combatting diseases. Porphyrin and phthalocyanine derivatives have been explored in this field because they possess unique photophysical properties, can accumulate in human and animal tumors, and their metal complexes are both thermodynamically and kinetically stable. A wide variety of radiolabeled metalloporphyrins and metallo phthalocyanines can be prepared that are stable in biological media. Radiolabeled compounds have been employed in preclinical applications for nuclear imaging, biodistribution studies, and photodynamic therapy. This chapter provides an overview of radiopharmaceutical applications of porphyins and phthalocyanines including small molecule and nanoparticle-based approaches.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
M. Biesaga, K. Pyrzyńska, M. Trojanowicz, Porphyrins in analytical chemistry. A review. Talanta 51(2), 209–224 (2000)
H. Huang, W. Song, J. Rieffel, J.F. Lovell, Emerging applications of porphyrins in photomedicine. Front Phys. 3, 23 (2015)
Y. Zhang, J.F. Lovell, Porphyrins as theranostic agents from prehistoric to modern times. Theranostics 2(9), 905–915 (2012)
D. Kessel, Hematoporphyrin and HPD: photophysics, photochemistry and phototherapy. Photochem. Photobiol. 39(s1), 851–859 (1984)
K.M. Smith, K.M. Kadish, R. Guilard, Handbook of Porphyrin Science: With Applications to Chemistry, Physics, Materials Science, Engineering, Biology and Medicine, vol 3, (World Scientific, 2012)
T.J. Dougherty, A brief history of clinical photodynamic therapy development at Roswell Park Cancer Institute. J. Clin. Laser Med. Surg. 14(5), 219–221 (1996)
R. Ackroyd, C. Kelty, N. Brown, M. Reed, The history of photodetection and photodynamic therapy. Photochem. Photobiol. 74(5), 656–669 (2001)
C.M. Allen, W.M. Sharman, J.E. Van Lier, Current status of phthalocyanines in the photodynamic therapy of cancer. J. Porphyr. Phthalocyannines 5(2), 161–169 (2001)
D.R. Tackley, G. Dent, W.E. Smith, Phthalocyanines: structure and vibrations. Phys. Chem. Chem. Phys. 3(8), 1419–1426 (2001)
V. Ščasnár, Lier J.E. Van, Biological activities of phthalocyanines—XV. Radiolabeling of the differently sulfonated 67Ga-phthalocyanines for photodynamic therapy and tumor imaging. Nucl. Med. Biol. 20(3), 257–262 (1993)
N. Sekkat, H. van den Bergh, T. Nyokong, N. Lange, Like a bolt from the blue: phthalocyanines in biomedical optics. Molecules 17(1), 98 (2012)
Y. Zhang, J.F. Lovell, Recent applications of phthalocyanines and naphthalocyanines for imaging and therapy. Wiley Interdiscip. Rev. Nanomed. Nanobiotechnol. 9(1), e1420 (2017)
H. Ali, J.E. van Lier, Metal Complexes as photo- and radiosensitizers. Chem. Rev. 99(9), 2379–2450 (1999)
F.R. Wrenn, M.L. Good, P. Handler, The use of positron-emitting radioisotopes for the localization of brain tumors. Science 113(2940), 525–527 (1951)
T.W. Liu, T.D. MacDonald, J. Shi, B.C. Wilson, G. Zheng, Intrinsically copper-64-labeled organic nanoparticles as radiotracers. Angew. Chem. Int. Ed. Engl. 51(52), 13128–13131 (2012)
P.A. Waghorn, Radiolabelled porphyrins in nuclear medicine. J. Label. Comp. Radiopharm. 57(4), 304–309 (2014)
A. Soucy-Faulkner, J.A. Rousseau, R. Langlois, V. Berard, R. Lecomte, F. Bénard et al., Copper-64 labeled sulfophthalocyanines for positron emission tomography (PET) imaging in tumor-bearing rats. J. Porphyr. Phthalocyanines 12(01), 49–53 (2008)
F.H. Figge, G.S. Weiland, L.O. Manganiello, Cancer detection and therapy. Affinity of neoplastic, embryonic, and traumatized tissues for porphyrins and metalloporphyrins. Proc. Soc. Exp. Biol. Med. 68(3), 640–641 (1948)
K.M. Smith, Porphyrins and Metalloporphyrins (Elsevier, Amsterdam, 1975)
W.R. Scheidt, Trends in metalloporphyrin stereochemistry. Acc. Chem. Res. 10(9), 339–345 (1977)
D. Dolphin, The Porphyrins, vol. 1 (Academic Press, New York, 1979)
K. Kasuga, M. Tsutsuo, Some new developments in the chemistry of metallophthalocyanines. Coord. Chem. Rev. 32(1), 67–95 (1980)
P. Hambright, J. Smart, J. McRae, M. Nohr, Y. Yano, P. Chu et al., Tumor imaging with 57cobalt (III)-sandwich complexes and 57cobalt (III)-porphyrins. Inorg. Nucl. Chem. Lett. 12(2), 217–222 (1976)
L. Anghileri, M. Heidbreder, R. Mathes, 57Co-hematoporphyrin accumulation by experimental tumors. Nuklearmedizin 15(4), 183 (1976)
M. Michael, C. Redvanly, Handbook of Radiopharmaceuticals (Wiley, England, 2003)
R. Bases, S.S. Brodie, S. Rubenfeld, Attempts at tumor localization using Cu64-labeled copper porphyrins. Cancer 11(2), 259–263 (1958)
P. Hambright, R. Fawwaz, P. Valk, J. McRae, A. Bearden, The distribution of various water soluble radioactive metalloporphyrins in tumor bearing mice. Bioinorg. Chem. 5(1), 87–92 (1975)
D. Cole, J. Mercer-Smith, S. Schreyer, J. Norman, D. Lavallee, The biological characteristics of a water soluble porphyrin in rat lymph nodes. Int. J. Rad. Appl. Instrum. B. 17(5), 457–464 (1990)
M.K. Bhalgat, J.C. Roberts, J.A. Mercer-Smith, B.D. Knotts, R.L. Vessella, D.K. Lavallee, Preparation and biodistribution of copper-67-labeled porphyrins and porphyrin-A6H immunoconjugates. Nucl. Med. Biol. 24(2), 179–185 (1997)
J.C. Roberts, S.L. Newmyer, J.A. Mercer-Smith, S.A. Schreyer, D.K. Lavallee, Labeling antibodies with copper radionuclides using N-4-nitrobenzyl-5-(4-carboxyphenyl)-10, 15, 20-tris (4-sulfophenyl) porphine. Int. J. Rad. Appl. Instrum. A. 40(9), 775–781 (1989)
Y. Fazaeli, A.R. Jalilian, M.M. Amini, M. Aboudzadeh, S. Feizi, A. Rahiminezhad et al., Preparation, nano purification, quality control and labeling optimization of (64Cu)-5, 10, 15, 20-tetrakis (penta fluoro phenyl) porphyrin complex as a possible imaging agent. J. Radioanal. Nucl. Chem. 295(1), 255–263 (2013)
J. Shi, T. Liu, J. Chen, D. Green, D. Jaffray, B.C. Wilson et al., Transforming a targeted porphyrin theranostic agent into a PET imaging probe for cancer. Theranostics 1, 363–370 (2011)
H. Huang, J.F. Lovell, Advanced functional nanomaterials for theranostics. Adv. Funct. Mater. 27(2), 1603524 (2017)
D. Luo, K.A. Carter, J.F. Lovell, Nanomedical engineering: shaping future nanomedicines. Wiley Interdiscip. Rev. Nanomed. Nanobiotechnol. 7(2), 169–188 (2015)
S.M. Janib, A.S. Moses, J.A. MacKay, Imaging and drug delivery using theranostic nanoparticles. Adv. Drug Deliv. Rev. 62(11), 1052–1063 (2010)
X. Ma, Y. Zhao, X.-J. Liang, Theranostic nanoparticles engineered for clinic and pharmaceutics. Acc. Chem. Res. 44(10), 1114–1122 (2011)
T.W. Liu, T.D. MacDonald, J. Shi, B.C. Wilson, G. Zheng, Intrinsically copper-64-labeled organic nanoparticles as radiotracers. Angew. Chem. Intl. Ed. Engl. 51(52), 13128–13131 (2012)
T.W. Liu, T.D. MacDonald, C.S. Jin, J.M. Gold, R.G. Bristow, B.C. Wilson et al., Inherently multimodal nanoparticle-driven tracking and real-time delineation of orthotopic prostate tumors and micrometastases. ACS Nano 7(5), 4221–4232 (2013)
J. Rieffel, U. Chitgupi, J.F. Lovell, Recent advances in higher-order, multimodal, biomedical imaging agents. Small 11(35), 4445–4461 (2015)
H. Huang, R. Hernandez, J. Geng, H. Sun, W. Song, F. Chen et al., A porphyrin-PEG polymer with rapid renal clearance. Biomaterials 76, 25–32 (2016)
Y. Zhang, D. Wang, S. Goel, B. Sun, U. Chitgupi, J. Geng et al., Surfactant-stripped frozen pheophytin micelles for multimodal gut imaging. Adv. Mater. 28(38), 8524–8530 (2016)
J. Rieffel, F. Chen, J. Kim, G. Chen, W. Shao, S. Shao et al., Hexamodal imaging with porphyrin-phospholipid-coated upconversion nanoparticles. Adv. Mater. 27(10), 1785–1790 (2015)
Y. Li, Lin T-y, Y. Luo, Q. Liu, W. Xiao, W. Guo et al., A smart and versatile theranostic nanomedicine platform based on nanoporphyrin. Nat. Commun. 5, 4712 (2014)
L. Feng, L. Cheng, Z. Dong, D. Tao, T.E. Barnhart, W. Cai et al., Theranostic liposomes with hypoxia-activated prodrug to effectively destruct hypoxic tumors post photodynamic therapy. ACS Nano. (2016)
Y. Fazaeli, A.R. Jalilian, M.M. Amini, A. Rahiminejad-kisomi, S. Rajabifar, F. Bolourinovin et al., Preparation and preliminary evaluation of (67Ga)-tetra phenyl porphyrin complexes as possible imaging agents. J. Radioanal. Nucl. Chem. 288(1), 17–24 (2011)
K. Sasaki, N. Yumita, R. Nishigaki, I. Sakata, S. Nakajima, Umemura Si. Pharmacokinetic study of a gallium-porphyrin photo- and sono-sensitizer, ATX-70, in tumor-bearing mice. Cancer Sci. 92(9), 989–995 (2001)
Y. Fazaeli, A.R. Jalilian, M.M. Amini, K. Ardaneh, A. Rahiminejad, F. Bolourinovin et al., Development of a 68Ga-fluorinated porphyrin complex as a possible PET imaging agent. Nucl. Med. Mol. Imaging 46(1), 20–26 (2012)
F. Zoller, P.J. Riss, F.-P. Montforts, D.K. Kelleher, E. Eppard, F. Rösch, Radiolabelling and preliminary evaluation of 68 Ga-tetrapyrrole derivatives as potential tracers for PET. Nucl. Med. Biol. 40(2), 280–288 (2013)
S. Jurisson, D. Berning, W. Jia, D. Ma, Coordination compounds in nuclear medicine. Chem. Rev. (U. S.) 93(3), 11371156 (1993)
S.S. Jurisson, J.D. Lydon, Potential technetium small molecule radiopharmaceuticals. Chem. Rev. (U. S.) 99(9), 2205–2218 (1999)
D.W. Wong, A. Mandal, I.C. Reese, J. Brown, R. Siegler, In vivo assessment of 99mTc-labeled hematoporphyrin derivative in tumor-bearing animals. Int. J. Nucle. Med. Biol. 10(4), 211–218 (1983)
A.-Y. Wang, J.-L. Lin, W.-C. Lin, Studies on the porphine labeled with 99 mTc–pertechnetate. J. Radioanal. Nucl. Chem. 284(1), 21–28 (2010)
S. Shetty, S. Murugesan, S. Chatterjee, S. Banerjee, T. Srivastava, O.P. Noronha et al., A new 99mTc labeled porphyrin for specific imaging of Sarcoma 120: Synthesis and biological study in a Swiss mouse model. J. Label. Comp. Radiopharm. 38(5), 411–418 (1996)
S.R. Chatterjee, S. Murugesan, J. Kamat, S. Shetty, T. Srivastava, O. Noronha et al., Photodynamic effects induced by meso-tetrakis (4-(carboxymethyleneoxy) phenyl) porphyrin using rat hepatic microsomes as model membranes. Arch. Biochem. Biophys. 339(1), 242–249 (1997)
D.W. Wong, A. Mandal, I.C. Reese, J. Brown, R. Siegler, In vivo assessment of 99mTc-labeled hematoporphyrin derivative in tumor-bearing animals. Int. J. Nucl. Med. Biol. 10(4), 211–218 (1983)
J.-H. Lee, S. Shao, K.T. Cheng, J.F. Lovell, C.H. Paik, 99mTc-labeled porphyrin–lipid nanovesicles. J. Liposome Res. 25(2), 101–106 (2015)
S. Murugesan, S. Shetty, T. Srivastava, O. Noronha, A. Samuel, A technetium-99m-labelled cyclam acid porphyrin (CAP) for tumour imaging. Appl. Radiat. Isot. 55(5), 641–646 (2001)
M. Subbarayan, S.J. Shetty, T.S. Srivastava, O.P. Noronha, A.M. Samuel, H. Mukhtar, Water-soluble 99mTc-labeled dendritic novel porphyrins tumor imaging and diagnosis. Biochem. Biophys. Res. Commun. 281(1), 32–36 (2001)
M. Subbarayan, S. Shetty, T. Srivastava, O. Noronha, A. Samuel, Evaluation studies of technetium-99m-porphyrin (T3, 4BCPP) for tumor imaging. J. Porphyr. Phthalocyanines. 5(12), 824–828 (2001)
Y. Liu, B. Shen, F. Liu, B. Zhang, T. Chu, J. Bai et al., Synthesis, radiolabeling, biodistribution and fluorescent imaging of histidine-coupled hematoporphyrin. Nucl. Med. Biol. 39(4), 579–585 (2012)
R.A. Fawwaz, W. Hemphill, H. Winchell, Potential use of 109Pd-porphyrin complexes for selective lymphatic ablation. J. Nucl. Med. 12(5), 231–236 (1971)
R. Fawwaz, F. Frye, W. Loughman, W. Hemphill, Survival of skin homografts in dogs injected with 109Pd-protoporphyrin. J. Nucl. Med. 15(11), 997–1002 (1974)
S. Chakraborty, T. Das, S. Banerjee, H. Sarma, M. Venkatesh, 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 51(1), 16 (2007)
T. Das, S. Chakraborty, H. Sarma, S. Banerjee, A novel (109Pd) palladium labeled porphyrin for possible use in targeted radiotherapy. Radiochim. Acta 96(7), 427–433 (2008)
D.W. Wong, A. Mandal, J. Brown, I.C. Reese, R. Siegler, S. Hyman, In vivo assessment of 111In-labeled hematoporphyrin derivative in breast tumor-bearing animals. Int. J. Rad. Appl. Instrum. B. 16(3), 269–281 (1989)
G. Robinson Jr., A. Alavi, R. Vaum, M. Staum, Imaging of lymph node uptake after intravenous administration. J. Nucl. Med. 27, 239 (1986)
C. Ljungquist, Delineation of a transplanted malignant melanoma with indium-111-labeled porphyrin. J. Nucl. Med. 26, 756–760 (1985)
S. Nakajima, H. Yamauchi, I. Sakata, H. Hayashi, K. Yamazaki, T. Maeda et al., 111In-labeled Mn-metalloporphyrin for tumor imaging. Nucl. Med. Biol. 20(2), 231–237 (1993)
C.H. Bedel-Cloutour, L. Mauclaire, A. Saux, M. Pereyre, Syntheses of functionalized indium porphyrins for monoclonal antibody labeling. Bioconjug. Chem. 7(6), 617–627 (1996)
R. Firestone, V. Shirley, C. Baglin, S. Chu, J. Zipkin, Table of Isotopes (A Wiley-Interscience Publication. Wiley, New York, 1996)
M. Aboudzadeh, Y. Fazaeli, H. Khodaverdi, H. Afarideh, Production, nano-purification, radiolabeling and biodistribution study of (140Nd) 5, 10, 15, 20-tetraphenylporphyrin complex as a possible imaging agent. J. Radioanal. Nucl. Chem. 295(1), 105–113 (2013)
N. Vahidfar, A.R. Jalilian, Y. Fazaeli, A. Bahrami-Samani, D. Beiki, A. Khalaj, Development and evaluation of a 166holmium labelled porphyrin complex as a possible therapeutic agent. J. Radioanal. Nucl. Chem. 295(2), 979–986 (2013)
H.D. Sarma, T. Das, S. Banerjee, M. Venkatesh, P.B. Vidyasagar, K.P. Mishra, Studies on efficacy of a novel 177Lu-labeled porphyrin derivative in regression of tumors in mouse model. Curr. Radiopharm. 4(2), 150–160 (2011)
J. Crudo, M. Edreira, E. Obenaus, S. de Castiglia, Labeling of the anti-melanoma 14f7 monoclonal antibody with rhenium-188-MAG3 chelate: conjugation optimization, in vitro stability and animal studies. J. Radioanal. Nucl. Chem. 261(2), 337–342 (2004)
K.M. Kadish, K.M. Smith, R. Guilard, Handbook of Porphyrin Science (World Scientific, Singapore, 2010), pp. 1–35 2014
S. Banerjee, T. Das, G. Samuel, H. Sarma, M. Venkatesh, M. Pillai, A novel (186/188Re)-labelled porphyrin for targeted radiotherapy. Nucl. Med. Commun. 22(10), 1101–1107 (2001)
H.D. Sarma, T. Das, S. Banerjee, M. Venkatesh, P.B. Vidyasagar, K.P. Mishra, Biologic evaluation of a novel 188Re-labeled porphyrin in mice tumor model. Cancer Biother. Radiopharm. 25(1), 47–54 (2010)
Z. Jia, H. Deng, M. Pu, Synthesis and preliminary biological studies of the novel conjugate 188Re-labeled meso-tetrakis (4-sulfophenyl) porphyrin in mice. Nucl. Med. Biol. 34(6), 643–649 (2007)
Jia Z-y, Pu Deng H-f, Luo S-z M-f, Rhenium-188 labelled meso-tetrakis (3, 4-bis (carboxymethyleneoxy) phenyl) porphyrin for targeted radiotherapy: preliminary biological evaluation in mice. Eur. J. Nucl. Med. Mol. Imaging 35(4), 734–742 (2008)
E.R. Ranyuk, N. Cauchon, H. Ali, R. Lecomte, B. Guérin, J.E. van Lier, PET imaging using 64Cu-labeled sulfophthalocyanines: synthesis and biodistribution. Bioorg. Med. Chem. Lett. 21(24), 7470–7473 (2011)
Y. Zhang, M. Jeon, L.J. Rich, H. Hong, J. Geng, Y. Zhang et al., Non-invasive multimodal functional imaging of the intestine with frozen micellar naphthalocyanines. Nat. Nanotechnol. 9(8), 631–638 (2014)
M. Obochi, R. Boyle, Lier J. Van, Biological activities of phthalocyanines. XIII. The effects of human serum components on the in vitro uptake and photodynamic activity of zinc phthalocyanine. Photochem. Photobiol. 57(4), 634–640 (1993)
J. Rousseau, R. Boyle, A. MacLennan, T. Truscott, J. Van Lier, Biodistribution and tumor uptake of (67Ga) chlorogallium-tetraoctadecyloxy phthalocyanine and its sulfonation products in tumor bearing C3H mice. Int. J. Rad. Appl. Instrum. B. 18(7), 777–782 (1991)
J. Rousseau, D. Autenrieth, J.E. Van Lier, Synthesis, tissue distribution and tumor uptake of (99Tc) tetrasulfophthalocyanine. Int. J. Appl. Radiat. Isot. 34(3), 571–579 (1983)
C.P. Gros, A. Eggenspiller, A. Nonat, J.-M. Barbe, F. Denat, New potential bimodal imaging contrast agents based on DOTA-like and porphyrin macrocycles. Med. Chem. Commun. 2(2), 119–125 (2011)
B. Laster, S. Kahl, J. Kalef-Ezra, E. Popenoe, R.G. Fairchild, Biological Efficacy of a Boronated Porphyrin as Measured in Cell Culture (Brookhaven National Lab, Upton, NY (USA), 1987)
F. Benard, S. Kudrevich, J. Rousseau, J. van Lier, Radiolabeled phthalocyanines as tumor imaging agents. Clin. Nucl. Med. 21(6), 512 (1996)
D.K. Lavallee, R. Fawwaz, The synthesis and characterization of 111 in hematoporphyrin derivative. Int. J. Rad. Appl. Instrum. B 13(6), 639–641 (1986)
D.W. Wong, A simple and efficient method of labeling hematoporphyrin derivative with 111In. Appl. Radiat. Isot. 35(7), 691–692 (1984)
N. Maric, S.M. Chan, P.B. Hoffer, P. Duray, Radiolabeled porphyrin vs gallium-67 citrate for the detection of human melanoma in athymic mice. Int. J. Rad. Appl. Instrum. B. 15(5), 543–551 (1988)
R.R. Kavali, B. Chul Lee, B. Seok Moon, S. Dae Yang, K. Soo Chun, C. Woon Choi et al., Efficient methods for the synthesis of 5-(4-(18F) fluorophenyl)-10, 15, 20-tris (3-methoxyphenyl) porphyrin as a potential imaging agent for tumor. J. Label. Comp Radiopharm. 48(10), 749–758 (2005)
G.M. Entract, F. Bryden, J. Domarkas, H. Savoie, L. Allott, S.J. Archibald et al., Development of PDT/PET theranostics: Synthesis and biological evaluation of an 18F-radiolabeled water-soluble porphyrin. Mol. Pharm. 12(12), 4414–4423 (2015)
T. Das, S. Chakraborty, H.D. Sarma, S. Banerjee, M. Venakatesh, A novel 177 Lu-labeled porphyrin for possible use in targeted tumor therapy. Nucl. Med. Biol. 37(5), 655–663 (2010)
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2018 Springer International Publishing AG, part of Springer Nature
About this chapter
Cite this chapter
Rajendiran, V., Ghosh, S., Lovell, J.F. (2018). Porphyrin and Phthalocyanine Radiolabeling. In: Lee, D. (eds) Radionanomedicine. Biological and Medical Physics, Biomedical Engineering. Springer, Cham. https://doi.org/10.1007/978-3-319-67720-0_3
Download citation
DOI: https://doi.org/10.1007/978-3-319-67720-0_3
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-319-67719-4
Online ISBN: 978-3-319-67720-0
eBook Packages: Physics and AstronomyPhysics and Astronomy (R0)