Biopharmaceutics of boronated radiosensitizers: Liposomal formulation of MnBOPP (manganese chelate of 2,4-(α,β-dihydroxyethyl) deuterioporphyrin IX) and comparative toxicity in mice

Journal of Pharmaceutical Sciences

Volumn 88, Issue 9, 1999, Pages 912-917

  Zhou, Rong ^b,d   Balasubramanian, Sathyamangalam V ^a   Kahl, Stephen B ^c   Straubinger, Robert M ^a  

^a UNIVERSITY AT BUFFALO   (United States)

^b ROSWELL PARK CANCER INSTITUTE   (United States)

^c UNIVERSITY OF CALIFORNIA   (United States)

^d UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHELATE; LIPOSOME; MANGANESE; METALLOPORPHYRIN; RADIOSENSITIZING AGENT;

ARTICLE; DRUG ACCUMULATION; DRUG DETERMINATION; DRUG FORMULATION; DRUG SELECTIVITY; DRUG TARGETING; ENCAPSULATION; FEMALE; MOUSE; NEUTRON CAPTURE THERAPY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE IMAGING; PHOTODYNAMIC THERAPY; RADIOSENSITIZATION;

EID: 0032823007     PISSN: 00223549     EISSN: None     Source Type: Journal    
DOI: 10.1021/js980454i     Document Type: Article

References (35)

1. Dougherty, T. J.; Gomer, C. J.; Henderson, B. W.; Jori, G.; Kessel, D.; Korbelik, M.; Moan, J.; Peng, Q. Photodynamic therapy. J. Natl. Cancer Inst. 1998, 90, 889-905.
2. Popovic, E. A.; Kaye, A. H.; Hill, J. S. Photodynamic therapy of brain tumors. J. Clin. Laser Med. Surg. 1996, 14, 251-261.
3. Barth, R. F.; Soloway, A. H.; Fairchild, R. D.; Brugger, R. M. Boron neutron capture therapy for cancer. Realities and prospects. Cancer 1992, 70, 2995-3007.
4. Hawthorne, M. F. The role of chemistry in the development of boron neutron capture therapy of cancer. Angew. Chem., Int. Ed. Engl. 1993, 32, 950-984.
5. Fairchild, R. G.; Kahl, S. B.; Laster, B. H.; Kalef, E. J.; Popenoe, E. A. In vitro determination of uptake, retention, distribution, biological efficacy, and toricity of boronated compounds for neutron capture therapy: a comparison of porphyrins with sulfhydryl boron hydrides. Cancer Res. 1990, 50, 4860-4865.
6. Kahl, S. B.; Koo, M. Synthesis of tetrakis-carborane-carboxylate ester of 2,4-bis-(a,b-dihydroxyethyl) deuterioporphyrin IX. J. Chem. Soc., Chem. Commun. 1990, 24, 1769-1771.
7. Hill, J. S.; Kahl, S. B.; Kaye, A. H.; Stylli, S. S.; Koo, M.; Gonzales, M. F.; Vardaxis, N. J.; Johnson, C. I. Selective tumor uptake of a boronated porphyrin in an animal model of cerebral glioma. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 1785-1789.
8. Chen, C. W.; Cohen, J. S.; Myers, C. E.; Sohn, M. Paramagnetic metalloporphyrins as potential contrast agents in NMR imaging. FEBS Lett. 1984, 168, 70-74.
9. Lyon, R. C.; Faustino, P. J.; Cohen, J. S. Tissue distribution and stability of metalloporphyrin MRI contrast agents. Magn. Reson. Med. 1987, 4, 24-33.
10. Huang, L.; Straubinger, R.; Kahl, S.; Koo, M.; Alletto, J.; Mazurchuk, R.; Chau, R.; Thamer, S.; Fiel, R. Boronated metalloporphyrins: a novel approach to the diagnosis and treatment of cancer using contrast-enhanced MR imaging and neutron capture therapy. J. Magn. Reson. Imaging 1993, 3, 351-356.
11. Weizsaecker, M.; Deen, D. F.; Rosenblum, M. L.; Hoshino, T.; Gutin, P. H.; Barker, M. The 9L rat brain tumor: description and application of an animal model. J. Neurol. 1981, 224, 183-192.
12. Huang, L. R. Magnetic resonance imaging: contrast enhancement of brain tumor pathology through chemical intervention. State University of New York at Buffalo, Ph.D. Dissertation, 1994.
13. Szoka, F. C., Jr.; Papahadjopoulos, D. Procedure for preparation of liposomes with large internal aqueous space and high capture by reverse-phase evaporation. Proc. Natl. Acad. Sci. U.S.A. 1978, 75, 4194-4198.
14. Bartlett, G. R. Phosphorus assay in column chromatography. J. Biol. Chem. 1959, 234, 466-468.
15. Sharma, A.; Straubinger, R. M. Novel taxol formulations: preparation and characterization of taxol-containirig liposomes. Pharm. Res. 1994, 11, 889-896.
16. Szoka, F. C., Jr.; Olson, F.; Heath, T.; Vail, W.; Mayhew, E.; Papahadjopoulos, D. Preparation of unilamellar liposomes of intermediate size (0.1-0.2 μm) by a combination of reverse phase evaporation and extrusion through polycarbonate membranes. Biochim. Biophys. Acta 1980, 601, 559-571.
17. Gabizon, A.; Papahadjopoulos, D. Liposome formulations with prolonged circulation time in blood and enhanced uptake by tumors. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 6949-6953.
18. Papahadjopoulos, D.; Allen, T. M.; Gabizon, A.; Mayhew, E.; Matthay, K.; Huang, S. K.; Lee, K-D.; Woodle, M. C.; Lasic, D. D.; Redemann, C.; Martin, F. J. Sterically stabilized liposomes: improvements in pharmacokinetics and antitumor therapeutic efficacy. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 11460-11464.
19. Sharma, U. S.; Sharma, A.; Chau, R. I.; Straubinger, R. M. Liposome-mediated therapy of intracranial brain tumors in a rat model. Pharm. Res. 1997, 14, 992-998.
20. Allen, T. M.; Chonn, A. Large unilamellar liposomes with low uptake into the reticuloendothelial system. FEBS Lett. 1987, 223, 42-46.
21. Hawthorne, M. F.; Shelly, K. Liposomes as drug delivery vehicles for boron agents. J. Neur. Oncol. 1997, 33, 53-58.
22. Feakes, D. A.; Shelly, K.; Hawthorne, M. F. Selective boron delivery to murine tumors by lipophilic species incorporated in the membranes of unilamellar liposomes. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 1367-1370.
23. 3]: synthesis and liposomal delivery to murine tumors. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 3029-3033.
24. Yanagie, H.; Tomita, T.; Kobayashi, H.; Fujii, Y.; Nonaka, Y.; Saegusa, Y.; Hasumi, K.; Eriguchi, M.; Kobayashi, T.; Ono, K. Inhibition of human pancreatic cancer growth in nude mice by boron neutron capture therapy. Br. J. Cancer 1997, 75, 660-665.
25. Mayhew, E.; Rustum, Y. M.; Szoka, F.; Papahadjopoulos, D. Role of cholesterol in enhancing the antitumor activity of cytosine arabinoside entrapped in liposomes. Cancer Treat. Rep. 1979, 63, 1923-1928.
26. Senior, J.; Gregoriadis, G. Stability of small unilamellar vesicles in serum and clearance from the circulation: the effect of the phospholipid and cholesterol components. Life Sci. 1982, 30, 2123-2136.
27. Hunt, C. A. Liposome disposition in vivo. V. Liposome stability in plasma and implications for drug carrier function. Biochim. Biophys. Acta 1982, 719, 450-463.
28. Balasubramanian, S. V.; Straubinger, R. M. Taxol-lipid interactions: taxol-dependent effects on the physical properties of model membranes. Biochemistry 1994, 33, 8941-8947.
29. Janoff, A. S.; Boni, L. T.; Popescu, M. C.; Minchey, S. R., Cullis, P. R.; Madden, T. D.; Taraschi, T.; Gruner, S. M.; Shyamsunder, E.; Tate, M. W.; Mendelsohn, R.; Bonner, D. Unusual lipid structures selectively reduce the toxicity of amphotericin B. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 6122-6126.
30. Szoka, F. C., Jr.; Papahadjopoulos, D. Comparative properties and methods of preparation of lipid vesicles (liposomes). Annu. Rev. Biophys. Bioeng. 1980, 9, 467-508.
31. 2H NMR study. Biochemistry 1990, 29, 10676-10684.
32. Sankaram, M. B.; Thompson, T. E. Cholesterol-induced fluid phase immiscibility in membranes. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 8686-8690.
33. Semple, S. C.; Chonn, A.; Cullis, P. R. Influence of cholesterol on the association of plasma proteins with liposomes. Biochemistry 1996, 35, 2521-2525.
34. Lasic, D.; Martin, F.; Gabizon, A.; Huang, S.; Papahadjopoulos, D. Sterically stabilized liposomes: a hypothesis on the molecular origin of the extended circulation times. Biochim. Biophys. Acta 1991, 1070, 187-192.
35. Sharma, A.; Mayhew, E.; Straubinger, R. M. Antitumor effect of taxol-containing liposomes in a taxol-resistant murine tumor model. Cancer Res. 1993, 53, 5877-5881.