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9. References
American Cancer Society (2004) Cancer Facts and Figures-2004, American Cancer Society, Atlanta.
Bonnett, R. (2000) Chemical aspects of photodynamic therapy, Gordon and Breach Science Publishers, Amsterdam.
Sternberg, E.D. and Dolphin, D. (1998) Porphyrin-based Photosensitizers for Use in Photodynamic Therapy, Tetrahedron 54, 4151–4202.
Leunig, M. et al. (1993) Tumour localisation kinetics of photofrin and three synthetic porphyrinoids in an amelanotic melanoma of the hamster, Br. J. Cancer 68, 225–234.
Paquette, B. and Van Lier, J.E. (1992) Phthalocyanines and related compounds: Structure-activity relationships, Photodyn. Ther. 145–156.
Sessler, J.L. et al. (1988) An "expanded porphyrin": the synthesis and structure of a new aromatic pentadentate ligand, J. Am. Chem. Soc. 110, 5586–5588.
Sessler, J.L. et al. (1993) Synthesis and structural characterization of lanthanide(III) texaphyrins, Inorg. Chem. 32, 3175–3187.
Sessler, J.L. et al. (1996) New texaphyrin-type expanded porphyrins, Pure Appl. Chem. 68, 1291–1295.
Young, S.W. et al. (1996) Gadolinium(III) texaphyrin: a tumor selective radiation sensitizer that is detectable by MRI, Proc. Nat. Acad. Sci. U S A 93, 6610–6615.
Miller, R.A. et al. (1999) In vivo animal studies with gadolinium(III) texaphyrin as a radiation enhancer, Int. J. Radiat. Oncol., Biol., Phys. 45, 981–989.
Sessler, J.L. and Miller, R.A. (2000) Texaphyrins: new drugs with diverse clinical applications in radiation and photodynamic therapy, Biochem. Pharmacol. 59, 733–739.
Rosenthal, D.I. et al. (1999) A phase I single-dose trial of gadolinium texaphyrin (Gd-Tex), a tumor selective radiation sensitizer detectable by magnetic resonance imaging, Clin. Cancer Res. 5, 739–745.
Carde, P. et al. (2001) Multicenter phase Ib/II trial of the radiation enhancer motexafin gadolinium in patients with brain metastases, J. Clin. Oncol. 19, 2074–2083.
Mehta, M.P. et al. (2002) Lead-in phase to randomized trial of motexafin gadolinium and whole-brain radiation for patients with brain metastases: centralized assessment of magnetic resonance imaging, neurocognitive, and neurologic end points, J. Clin. Oncol. 20, 3445–3453.
Mehta, M.P. et al. (2003) Survival and neurologic outcomes in a randomized trial of motexafin gadolinium and whole-brain radiation therapy in brain metastases, J. Clin. Oncol. 21, 2529–2536.
Sessler, J.L. et al. (1993) Gadolinium(III) texaphyrin: a novel MRI contrast agent, J. Am. Chem. Soc. 115, 10368–10369.
Young, S.W. et al. (1994) Preclinical evaluation of gadolinium(III) texaphyrin complex. A new paramagnetic contrast agent for magnetic resonance imaging, Invest Radiol. 29, 330–338.
Mody, T.D. and Sessler, J.L. (2001) Texaphyrins: a new approach to drug development, Journal of Porphyrins and Phthalocyanines 5, 134–142.
Chou, T.M. et al. (2002) Photodynamic therapy: applications in atherosclerotic vascular disease with motexafin lutetium, Catheterization and cardiovascular interventions: official journal of the Society for Cardiac Angiography & Interventions 57, 387–394.
Kereiakes, D.J. et al. (2003) Phase I drug and light dose-escalation trial of motexafin lutetium and far red light activation (phototherapy) in subjects with coronary artery disease undergoing percutaneous coronary intervention and stent deployment: procedural and long-term results, Circulation 108, 1310–1315.
Yeung, P.K.F. (2001) Motexafin lutetium (Pharmacyclics), IDrugs 4, 351–359.
Sessler, J.L. et al. (2001) Probing the reactivity of the radiation sensitizer motexafin gadolinium (Xcytrin) and a series of lanthanide(III) analogues in the presence of both hydroxyl radicals and aqueous electrons, J. Porphyrins Phthalocyanines 5, 593–599.
Magda, D.J. et al. (2004) Synthesis of texaphyrin conjugates, Pure Appl. Chem. 76, 365–374.
Sessler, J.L. et al. (1987) Synthesis and crystal structure of a novel tripyrrane-containing porphyrinogen-like macrocycle, J. Org. Chem. 52, 4394–4397.
Hannah, S. et al. (2001) Synthesis of a Metal-Free Texaphyrin, Org. Lett. 3, 3911–3914.
Sessler, J.L. et al. (1994) Texaphyrins: Synthesis and Applications, Acc. Chem. Res. 27, 43–50.
Sessler, J.L. et al. (1988) The coordination chemistry of planar pentadentate "porphyrin-like" ligands, Comments Inorg. Chem. 7, 333–350.
Mody, T.D. et al. (2001) Texaphyrins: synthesis and development of a novel class of therapeutic agents, Prog. Inorg. Chem. 49, 551–598.
Harriman, A. et al. (1989) Metallotexaphyrins: a new family of photosensitisers for efficient generation of singlet oxygen, Chem. Commun. 314–316.
Sessler, J.L. et al. (1991) Tripyrroledimethine-derived ("texaphyrin"-type) macrocycles: potential photosensitizers which absorb in the far-red spectral region, Proc. SPIE-The International Society for Optical Engineering 1426, 318–329.
Ehrenberg, B. et al. (1992) Spectroscopy, photokinetics and cellular effect of far-red and near infrared absorbing photosensitizers, Proc. SPIE-The International Society for Optical Engineering 1645, 259–263.
Shimanovich, R. et al. (2001) Mn(II)-Texaphyrin as a Catalyst for the Decomposition of Peroxynitrite, J. Amer. Chem. Soc. 123, 3613–3614.
Crow, J. (in press) in: Medicinal Inorganic Chemistry, ACS Symposium Series, (Sessler, J.L. et al., Eds.).
Hannah, S. et al. (2002) Late First-Row Transition-Metal Complexes of Texaphyrin, J. Am. Chem. Soc. 124, 8416–8427.
Young, S.W. et al. (1996) Lutetium texaphyrin (PCI-0123): a near-infrared, water-soluble photosensitizer, Photochem. Photobiol. 63, 892–897.
Geraldes, C.F. et al. (1995) Nuclear magnetic relaxation dispersion studies of water-soluble gadolinium(III)-texaphyrin complexes, J. Magn. Reson. Imag. 5, 725–729.
Sessler, J.L. et al. (1996) Water soluble texaphyrin metal complex preparation, US Pat. 5,569,759.
Meyers, C.A. et al. (2004) Neurocognitive function and progression in patients with brain metastases treated with whole-brain radiation and motexafin gadolinium: results of a randomized phase III trial, J. Clin. Oncol. 22, 157–165.
Anonymous (2004) Motexafin gadolinium: gadolinium (III) texaphyrin, gadolinium texaphyrin, Gd-Tex, GdT2B2, PCI 0120, Drugs in R&D 5, 52–57.
Rosenthal, D.I. et al. (2000) Reversible renal toxicity resulting from high single doses of the new radiosensitizer gadolinium texaphyrin, Department of Radiation Oncology, University of Pennsylvania Medical Center, Philadelphia 19104-4283, USA, 593–598.
Dimofte, A. et al. (2002) In vivo light dosimetry for motexafin lutetium-mediated PDT of recurrent breast cancer, Lasers Surg. Med. 31, 305–312.
Renschler, M.F. et al. (1998) Photodynamic therapy trials with lutetium texaphyrin (Lu-Tex) in patients with locally recurrent breast cancer, Proceedings of SPIE-The International Society for Optical Engineering 3247, 35–39.
Woodburn, K.W. et al. (2002) Photodynamic therapy for choroidal neovascularization: a review, Retina 22, 391–405.
Rockson, S.G. et al. (2000) Photoangioplasty for human peripheral atherosclerosis: Results of a phase I trial of photodynamic therapy with motexafin lutetium (antrin), Circulation 102, 2322–2324.
Yeung, A. (2004) Vulnerable Plaque: Pathophysiology, Detection and Therapeutic Intervention, Cardiovascular Research Foundation 16th Annual Scientific Meeting of Transcatheter Cardiovascular Therapeutics (TCT), Washington, DC.
Griffin, G.M. et al. (2001) Preclinical evaluation of motexafin lutetium-mediated intraperitoneal photodynamic therapy in a canine model, Clin. Cancer Res. 7, 374–81.
Hsi, R.A. et al. (2001) Photodynamic therapy in the canine prostate using motexafin lutetium, Clin. Cancer Res. 7, 651–660.
Viala, J. et al. (1999) Phases IB and II multidose trial of gadolinium texaphyrin, a radiation sensitizer detectable at MR imaging: preliminary results in brain metastases, Radiology 212, 755–759.
Kessel, D. et al. (2003) Localization and photodynamic efficacy of two cationic porphyrins varying in charge distribution, Photochem. Photobiol. 78, 431–435.
Kessel, D. (2002) Relocalization of cationic porphyrins during photodynamic therapy, Photochem. Photobiol. Sci. 1, 837–840.
Jori, G. et al. (1984) In Vitro and In Vivo Studies on the Interaction of Hematoporphyrin and its Dimethyl Ester with Normal and Malignant Cells in: Porphyrin Localization and Treatment of Tumors, Progress in Clinical and Biological Research, Vol. 170, pp. 471–482 (Doiron, D.R. and Gomer, C.J., Eds.) Liss, NY.
El-Far, M. and Pimstone, N. (1984) Porphyrin: Protoporphyrin: Plasma Protein Interaction-The Metabolic Basis for Tumor Localization of Hematoporphyrin Derivative-A Preliminary Report in: Porphyrin Localization and Treatment of Tumors, Progress in Clinical and Biological Research, Vol. 170, pp. 657–660 (Doiron, D.R. and Gomer, C.J., Eds.) Liss, NY.
Ruck, A. and Diddens, H. (1996) Upake and Subcellular Distribution of Photosensitizing Drugs in Malignant Cells in: The Fundamental Basis of Phototherapy (Honigsman, H.J., G.; Young, A., Ed.) OEMF, Milano.
Vorndran, C. et al. (1995) New fluorescent calcium indicators designed for cytosolic retention or measuring calcium near membranes, Biophys. J. 69, 2112–2124.
Peng, Q. et al. (1996) Correlation of subcellular and intratumoral photosensitizer localization with ultrastructural features after photodynamic therapy, Ultrastruct. Path. 20, 109–129.
Synytsya, A. et al. (2003) In vitro interaction of macrocyclic photosensitizers with intact mitochondria: a spectroscopic study, Biochim. Biophys. Acta 1620, 85–96.
Synytsya, A. et al. (2004) Biodistribution assessment of a lutetium(III) texaphyrin analogue in tumor-bearing mice using NIR Fourier-transform Raman spectroscopy, Photochem. Photobiol. 79, 453–460.
Woodburn, K.W. et al. (1997) Localization and efficacy analysis of the phototherapeutic lutetium texaphyrin (PCI-0123) in the murine EMT6 sarcoma model, Photochem. Photobiol. 65, 410–415.
Woodburn, K.W. (2001) Intracellular localization of the radiation enhancer motexafin gadolinium using interferometric Fourier fluorescence microscopy, J. Pharm. Exper. Ther. 297, 888–894.
Zellweger, M. et al. (2000) Fluorescence pharmacokinetics of Lutetium Texaphyrin (PCI-0123, Lu-Tex) in the skin and in healthy and tumoral hamster cheek-pouch mucosa, J. Photochem. Photobiol., B 55, 56–62.
Hayase, M. et al. (2001) Photoangioplasty with local motexafin lutetium delivery reduces macrophages in a rabbit post-balloon injury model, Cardiovascular Research 49, 449–455.
Woodburn, K.W. et al. (1996) Phototherapy of cancer and atheromatous plaque with texaphyrins, Journal of clinical laser medicine & surgery 14, 343–8.
Woodburn, K.W. et al. (1996) Selective uptake of texaphyrins by atheromatous plaque, Proceedings of SPIE-The International Society for Optical Engineering 2671, 62–71.
Woodburn, K.W. et al. (1997) Photoeradication and imaging of atheromatous plaque with texaphyrins, Proc. SPIE-The International Society for Optical Engineering 2970, 44–50.
Sessler, J.L. et al. (1997) Biomedical applications of lanthanide(III) texaphyrins. Lutetium(III) texaphyrins as potential photodynamic therapy photosensitizers, J. Alloys Compd. 249, 146–152.
Magda, D. et al. (2001) Redox cycling by motexafin gadolinium enhances cellular response to ionizing radiation by forming reactive oxygen species, Int. J. Radiat. Oncol. Biol. 51, 1025–1036.
Sessler, J.L. et al. (1999) One-Electron Reduction and Oxidation Studies of the Radiation Sensitizer Gadolinium(III) Texaphyrin (PCI-0120) and Other Water Soluble Metallotexaphyrins, J. Phys. Chem. A 103, 787–794.
Sessler, J.L. et al. (2001) Pulse Radiolytic Studies of Metallotexaphyrins in the Presence of Oxygen: Relevance of the Equilibrium with Superoxide Anion to the Mechanism of Action of the Radiation Sensitizer Motexafin Gadolinium (Gd-Tex2+, Xcytrin), J. Phys. Chem. B 105, 1452–1457.
Magda, D. et al. (2002) Motexafin gadolinium reacts with ascorbate to produce reactive oxygen species, Chem. Commun. 2730–2731.
Chari, R.V.J. (1998) Targeted delivery in chemotherapeutics: tumor activated prodrug therapy, Adv. Drug Delivery Rev. 31, 89–104.
Meister, A. (1995) Mitochondrial changes associated with glutathione deficiency, Biochim. Biophys. Acta 1271, 35–42.
Hall, E.J. (1994) Radiobiology for the Radiobiologist, J. B. Lippincott Co., Philadelphia.
Brown, J.M. et al. (1981) SR-2508: a 2-nitroimidazole amide which should be superior to misonidazole as a radiosensitizer for clinical use, Int. J. Radiat. Oncol. Biol. 7, 695–703.
Adams, G.E. et al. (1980) Toxicity of nitro compounds toward hypoxic mammalian cells in vitro: dependence on reduction potential, J. Nat. Cancer Inst. 64, 555–560.
Stratford, I.J. et al. (1981) Cytotoxic Properties of 4-Nitroimidazole (NSC 38087): A Radiosensitizer of Hypoxic Cells In Vitro, Br. J. Cancer 44, 109–116.
Simpson, J.R. et al. (1982) Large Fraction Radiotherapy Plus Misonidazole for Treatments of Advanced Lung Cancer: Report of a Phase I/II Trial, Int. J. Radiation Oncology Biol. Phys. 8, 303–308.
Berlin, V. and Haseltine, W.A. (1981) Reduction of adriamycin to a semiquinone-free radical by NADPH cytochrome P-450 reductase produces DNA cleavage in a reaction mediated by molecular oxygen, J. Biol. Chem. 256, 4747–4756.
Doroshow, J.H. (1983) Effect of anthracycline antibiotics on oxygen radical formation in rat heart, Cancer Res. 43, 460–472.
Yeh, G.C. et al. (1987) Adriamycin resistance in human tumor cells associated with marked alterations in the regulation of the hexose monophosphate shunt and its response to oxidant stress, Cancer Res. 47, 5994–5999.
Lau, D.H. et al. (1989) Association of DNA cross-linking with potentiation of the morpholino derivative of doxorubicin by human liver microsomes, J. Nat. Cancer Inst. 81, 1034–1038.
Rumyantseva, G.V. et al. (1989) Hydroxyl radical generation and DNA strand scission mediated by natural anticancer and synthetic quinones, FEBS letters 242, 397–400.
Sinha, B.K. et al. (1989) Adriamycin activation and oxygen free radical formation in human breast tumor cells: protective role of glutathione peroxidase in adriamycin resistance, Cancer Res. 49, 3844–3848.
Lewis, A.D. et al. (1992) Role of cytochrome P-450 from the human CYP3A gene family in the potentiation of morpholino doxorubicin by human liver microsomes, Cancer Res. 52, 4379–4384.
Feinstein, E. et al. (1993) Dependence of nucleic acid degradation on in situ free-radical production by Adriamycin, Biochemistry 32, 13156–61.
Gao, J.-P. et al. (1993) The role of reduced nicotinamide adenine dinucleotide phosphate in glucose-and temperature-dependent doxorubicin cytotoxicity, Cancer Chemother. Pharmacol. 33, 191–196.
Minotti, G. et al. (1995) Secondary alcohol metabolites mediate iron delocalization in cytosolic fractions of myocardial biopsies exposed to anticancer anthracyclines: novel linkage between anthracycline metabolism and iron-induced cardiotoxicity, J. Clin. Invest. 95, 1595–605.
Lau, D.H. et al. (1994) Metabolic conversion of methoxymorpholinyl doxorubicin: from a DNA strand breaker to a DNA cross-linker, Br. J. Cancer 70, 79–84.
Miller, R.A. et al. (2001) Motexafin gadolinium: A redox active drug that enhances the efficacy of bleomycin and doxorubicin, Clin. Cancer Res. 7, 3215–3221.
Lottner, C., Bart, K.-C., Bernhart, G., Brunner, H. (2002) Hematoporphyrin-Derived Soluble Porphyrin-Platinum Conjugates with Combined Cytotoxic and Phototoxic Antitumor Activity, J. Med. Chem. 45, 2064–2078.
Zhang, J.-G., Lindup, E. (1994) Cisplatin Nephrotoxicity: Decreases in Mitochondrial Protein Sulphydryl Concentration and Calcium Uptake by Mitochondria from Rat Renal Cells, Biochem. Pharmacol. 47, 1127–1135.
Pasini, A. and Zunino, F. (1987) New Cisplatin Analogues-On the Way to Better Antitumor Agents, Angew. Chem. Int. Ed. Engl. 26, 615–625.
Di Francesco, A.M. et al. (2002) Cellular and molecular aspects of drugs of the future: Oxaliplatin, Cell. Molec. Life Sciences 59, 1914–1927.
Ohndorf, U.-M. et al. (1999) Basis for recognition of cisplatin-modified DNA by high-mobility-group proteins, Nature 399, 708–712.
Dolling, J.A. et al. (1999) Cisplatin-modification of DNA repair and ionizing radiation lethality in yeast, Saccharomyces cerevisiae, Mutation Res. 433, 127–136.
Legendre, F. and Chottard, J.-C. (1999) Kinetics and Selectivity of DNA-Platination in: Cisplatin: Chemistry and Biochemistry of a Leading Anticancer Drug, pp. 223–245 (Lippert, B., Ed.) Verlag Helvitica Chimica Acta, Zurich.
Messman, R.A. and Allegra, C.J. (2001) Antifolates in Cancer Chemotherapy and Biotherapy in: Cancer chemotherapy and biotherapy: principles and practice, pp. 139 (Chabner, B.A. and Longo, D.L., Eds.) Lippincott Williams & Wilkins, Philadelphia.
Piper, J.R. et al. (1982) Syntheses of alpha-and gamma-substituted amides, peptides, and esters of methotrexate and their evaluation as inhibitors of folate metabolism, J. Med. Chem. 25, 182–187.
Wright, J.E. et al. (1993) Methotrexate and gamma-tert-butyl methotrexate transport in CEM and CEM/MTX human leukemic lymphoblasts, Biochem. Pharmacol. 46, 871–6.
Endo, N. et al. (1987) Target-selective cytotoxicity of methotrexate conjugated with monoclonal anti-MM46 antibody, Cancer Immunol. Immunother. 25, 1–6.
Umemoto, N. et al. (1989) Preparation and in vitro cytotoxicity of a methotrexate-anti-MM46 monoclonal antibody conjugate via an oligopeptide spacer, Int. J. Cancer 43, 677–654.
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Wei, WH., Fountain, M.E., Sessler, J.L., Magda, D.J., Wang, Z., Miller, R.A. (2005). Texaphyrin Conjugates. Progress Towards Second Generation Diagnostic and Therapeutic Agents. In: Gloe, K. (eds) Macrocyclic Chemistry. Springer, Dordrecht. https://doi.org/10.1007/1-4020-3687-6_25
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