Silanized biodegradable super paramagnetic metal oxides as contrast agents for imaging the gastrointestinal tract
Patent 5069216 Issued on December 3, 1991. Estimated Expiration Date: September 19, 2009. Estimated Expiration Date is calculated based on simple USPTO term provisions. It does not account for terminal disclaimers, term adjustments, failure to pay maintenance fees, or other factors which might affect the term of a patent.
This invention relates to materials exhibiting certain magnetic and biological properties which make them uniquely suitable for use as magnetic resonance imaging (MRI) agents to enhance MR images of animal organs and tissues. More particularly, the invention relates to the in vivo use of biologically degradable and metabolizable superparamagnetic metal oxides as MR contrast agents. Depending on their preparation, these metal oxides are in the form of superparamagnetic particle dispersoids or superparamagnetic fluids where the suspending medium is a physiologically-acceptable carrier, and may be uncoated or surrounded by a polymeric coating to which biological molecules can be attached. These materials are administered to animals, including humans, by a variety of routes and the metal oxides therein collect in specific target organs to be imaged; in the case of coated particles, the biological molecules can be chosen to target specific organs or tissues. The biodistribution of the metal oxides in target organs or tissues results in a more detailed image of such organs or tissues because the metal oxides, due to their superparamagnetic properties, exert profound effects on the hydrogen nuclei responsible for the MR image. In addition, the dispersoids and fluids are quite stable and, in the case of the fluids, can even be subjected to autoclaving without impairing their utility. Furthermore, the materials are biodegradable and, in the case of iron oxide compounds, can eventually be incorporated into the subject's hemoglobin, making them useful in treating anemia. Thus, the materials are well-suited for in vivo use.
Other References
Frei et al., J. App. Phys. 1986, 39(2), 999-1001
Frei et al., IEEE Transactions on Magnetics 1970, 6(2), 348-349
Wesbey et al., Physiological Chemistry and Physics and Medical NMR 1984, 16, 145-155
Lauterbur et al., Frontiers of Biological Energetics, vol. I: Electrons to Tissues, Dutton, P. L. et al., (Eds.), Academic Press, New York, NY (1978), pp. 752-759
Griffeth et al., in Book of Abstracts, The Society of Magnetic Resonance in Medicine 1983, 144-145
European Patent Application NO. 83112493, Filed 12/12/83, Inventor Steven A. Benner, Assignee Genetics Institute
Kronick et al., "Use of Superparamagnetic Particles for Isolation of Cells," J. Biochem'l Biophys'l Methods, 12:73-80 (1986)
Hassett et al., "Polymer-Anchored Metal Oxide Particles. 1. Superparamagnetic Magnetite Microcrystals Stabilized by Lignosulfanate," Inorg. Chem. 19(2):416-422 (1980)
Aharoni et al., "Superparamagnetism and Exchange Anisotropy in Microparticles of Magnetite Embedded in an Inert Carbonaceous Matrix," J. Appl. Phys. 42(1):352-356 (1971)
Griffiths et al., "The Structure, Magnetic Characterization, and Oxidation of Colloidal Iron Dispersions," J. Appl. Phys. 50(11, Pt. 1):7108-7115 (1979)
Hanzel et al., "Study of Colloidal Suspension of ଲ-Iron Oxide Hydroxide (FeOOH) Particles," Fizika (Zagreb) 9(Suppl. 1):102-103 (1977)
Saraswat et al., "Mossbauer Resonance Study of Brown Ferric Oxyhydroxide Gel," Indian J. Chem. Sect. A 15A(6):493-494 (1977)
Hanzel et al., "A Study of Thixotropic ଲ-FeOOH by Mossbauer Effect," J. Phys. (Paris) Collog. (6): 277-279 (1976)
Marshall et al., "Physical Investigations on Colloidal Iron-Dextran Complexes," J. Colloid Interface Sci. 37(2):390-402 (1971)
Chemical Abstracts 106(9):63060x (1986)
Chemical Abstracts 105(22):201689s, (1986)
Chemical Abstracts 105(14):123546b, (1986)
Chemical Abstracts 104(16):140717e, (1986)
Chemical Abstracts 104(4):121559p, (1986)
Chemical Abstracts 104(7):48280j, (1986)
Chemical Abstracts 103(26):225886p, (1985)
Chemical Abstracts 102(16):125150u, (1984)
Chemical Abstracts 102(12):104726g, (1985)
Chemical Abstracts 101(24):216942k, (1984)
Chemical Abstracts 101(18):155707p, (1984)
Chemical Abstracts 101(12):102641f, (1984)
Chemical Abstracts 100(26):219972k, (1983)
Chemical Abstracts 100(20):166887c, (1983)
Chemical Abstracts 100(10):78938q, (1983)
Chemical Abstracts 99(12):88918h, (1983)
Chemical Abstracts 98(22):190141r, (1983)
Chemical Abstracts 98(18):152319x, (1983)
Chemical Abstracts 98(14):118410k, (1982)
Chemical Abstracts 98(12):94518y, (1982)
Chemical Abstracts 98(12):90113q, (1982)
Chemical Abstracts 98(10):73414w, (1982)
Chemical Abstracts 97(26):226553x, (1982)
Chemical Abstracts 97(26):220200h, (1982)
Chemical Abstracts 97(22):192144x, (1982)
Chemical Abstracts 97(10):83808w, (1982)
Chemical Abstracts 96(12):96393m (1981)
Chemical Abstracts 96(2):14375v (1981)
Chemical Abstracts 95(16)136171a (1981)
Chemical Abstracts 95(16):135988k (1981)
Chemical Abstracts 94(26):211733v (1981)
Chemical Abstracts 94(17):134583s (1981)
Chemical Abstracts 94(6):40546e (1980)
Chemical Abstracts 93(14):141997n (1980)
Chemical Abstracts 93(4):32321s (1980)
Chemical Abstracts 92(26):225455b (1980)
Chemical Abstracts 92(16):139865d (1979)
Chemical Abstracts 92(14):121001j (1979)
Chemical Abstracts 92(14):115140n (1980)
Chemical Abstracts 92(12):103229k (1980)
Chemical Abstracts 91(20):167514m (1979)
Chemical Abstracts 91(18):150230t (1979)
Chemical Abstracts 90(12):96630n (1978)
Chemical Abstracts 90(12):95446v (1978)
Chemical Abstracts 90(12):95443s (1978)
Chemical Abstracts 89(22):190092q (1978)
Chemical Abstracts 89(6):51003y (1976)
Chemical Abstracts 89(4):35570a (1976)
Chemical Abstracts 88(24):180292v (1977)
Chemical Abstracts 88(20):145299f (1975)
Chemical Abstracts 88(16):112991x (1977)
Chemical Abstracts 88(14):98366p (1978)
Chemical Abstracts 87(24):192901k (1977)
Chemical Abstracts 86(18):132462n (1976)
Chemical Abstracts 86(14):98946m (1976)
Chemical Abstracts 85(16):114306q (1976)
Chemical Abstracts 84(12):80190j (1976)
Chemical Abstracts 84(12):76877w (1975)
Chemical Abstracts 84(2):11554u (1975)
Chemical Abstracts 82(16):105667u (1974)
Chemical Abstracts 80(18):98281s (1973)
Chemical Abstracts 79(24):140977e (1973)
Chemical Abstracts 79(10):59353b (1973)
Chemical Abstracts 79(4):25395b (1973)
Chemical Abstracts 77(24):157957e (1971)
Chemical Abstracts 76(22):133401x (1972)
Chemical Abstracts 76(18):105589w (1971)
Chemical Abstracts 75(4):28012c (1971)
Chemical Abstracts 75(4):27293h (1971)
Chemical Abstracts 74(10):47297v (1971)
Chemical Abstracts 73(2):8659z (1970)
Chemical Abstracts 70(4):15369w (1968)
Chemical Abstracts 106(5):30227d (1986)
Chemical Abstracts 105(11):94705v (1986)
Chemical Abstracts 104(2):8911j (1985)
Chemical Abstracts 103(10):79717r (1985)
Chemical Abstracts 102(25):217087t (1985)
Chemical Abstracts 101(20):182361c (1984)
Chemical Abstracts 101(8):64609s (1984)
Chemical Abstracts 101(8):60893g (1984)
Chemical Abstracts 101(4):26265u (1984)
Chemical Abstracts 100(26):220449b (1984)
Chemical Abstracts 100(12):94062e (1983)
Chemical Abstracts 100(10):76840c (1983)
Chemical Abstracts 99(12):98084x (1983)
Chemical Abstracts 98(24):208985f (1983)
Chemical Abstracts 98(12):92800k (1982)
Chemical Abstracts 97(22):192028n (1982)
Chemical Abstracts 97(12):96402j (1982)
Chemical Abstracts 97(8):58985u (1982)
Chemical Abstracts 97(4):27036f (1981)
Chemical Abstracts 96(2):14597u (1981)
Chemical Abstracts 95(22):190200x (1981)
Chemical Abstracts 94(4):24045k (1979)
Chemical Abstracts 93(8):75922f (1979)
Chemical Abstracts 93(6):60362z (1979)
Chemical Abstracts 92(16):132247v (1980)
Chemical Abstracts 92(10):79598g (1980)
Chemical Abstracts 90(23):185487p (1979)
Chemical Abstracts 90(7):53689w (1978)
Chemical Abstracts 90(4):334198e (1978)
Chemical Abstracts 89(20):170803u (1978)
Chemical Abstracts 89(20):167339s (1978)
Chemical Abstracts 89(4):28735e (1975)
Chemical Abstracts 88(22):155807j (1977)
Chemical Abstracts 88(20):139486y (1977)
Chemical Abstracts 88(8):57643h (1977)
Chemical Abstracts 87(26):209656j (1975)
Chemical Abstracts 87(24):192818p (1977)
Chemical Abstracts 87(18):144987w (1974)
Chemical Abstracts 86(24):180256v (1974)
Chemical Abstracts 86(20):148377z (1976)
Chemical Abstracts 86(18):127890w (1976)
Chemical Abstracts 85(24):180273c (1975)
Chemical Abstracts 85(22):163807n (1976)
Chemical Abstracts 85(20):153490q (1976)
Chemical Abstracts 85(16):115907y (1976)
Chemical Abstracts 84(24):171849x (1976)
Chemical Abstracts 84(24):167382x (1975)
Chemical Abstracts 83(10):82870j (1975)
Chemical Abstracts 83(2):13387v (1975)
Chemical Abstracts 80(20):114136f (1974)
Chemical Abstracts 77(10):67350x (1972)
Chemical Abstracts 76(8):37768b (1971)
Chemical Abstracts 75(22):132964a (1971)
Chemical Abstracts 75(4):27045d (1971)
Chemical Abstracts 74(18):92769m (1970)
Chemical Abstracts 73(26):133165m (1970)
Chemical Abstracts 73(8):39644v (1970)
Chemical Abstracts 73(8):37267a (1970)
Chemical Abstracts 73(4):19805v (1970)
Chemical Abstracts 72(24):126644t (1969)
Chemical Abstracts 72(2):5048t (1969)
Chemical Abstracts 68(4):17110n (1967)
Chemical Abstracts 65:158c (1966)
Chemical Abstracts 65:3155c (1966)
Chemical Abstracts 58:5137c (1963)
Hemmingsson, A., et al., Acta Radiologica (1987), 28(6), 703
Ogan, M. D., et al., Invest. Radiol. (1987), 22, 665
Englestad, B. L., Diag. Imag. (1987), 144, Mar
Bacon, B. R., et al., J. Lab. Clin. Med. (1987), 110, 164
Saini, S., et al., Radiol. (1987), 162, 211
Hahn, P. F., et al., Radiol. (1987), 164, 37
Kent, T. A., et al., Soc. of Magn. Res. in Med. (abstract) (1987), 5 (Aug.)
Weissleder, R., et al., Am. J. Roentgen. (1987), 149, 723
Widder, K. J., et al., Europ. J. Cancer Clin. Oncol. (1983), 19, 141
Molday, R. S.; Mackenzie, D., J. Immunol. Methods, (1982), 52, 353
Gehr, P., et al., Nature (1983), 302, 336
Sato, S. B., et al., J. Biochem. (1986), 100, 1481
Ohnishi, S. I., Studia Biophysica (1985), 110, 123
Gibb, F. R.; Morrow, P. E. J. Appl. Physiol. (1962), 17(3), 429
Morrow, P. E., et al., Health Physics (1964), 10(8), 543
Cohen, D., et al., Science (1979), 204, 514
Weissleder, R., et al., Am. J. Roentgen. (1988), 150, 115, 561
Weissleder, R., et al., Am. J. Roentgen. (1987), 149, 1161
Weissleder, R., et al., Radiol. (1988), 166, 423
Tsang, Y. M., et al., Radiol. (1988), 167, 21
Hersh and Yaverbaum, Clin. Chim. Acta, 63: 69-72 (1975)
Robinson, et al., Biotech, Bioeng., XV: 603-606 (1973)
Guesdon and Avrameas, Immunochemistry, 14: 443-447 (1977)
Kaiser and Miskolczy, J. of Applied Physics, 41(3): 1064-1072
Molday et al., Nature 268: 437-438 (1977)
Rembaum, Pure & Appl. Chem. 52: 1275-1278 (1980)
Rembaum and Margel, T. British Polymer Journal 10: 275-280 (Dec. 1978)
Rembaum and Yen, J. Macromol. Sci.-Chem., A13 (5): 603-632 (1979)
Rembaum et al., Chemtech, 182-190 (Mar. 1978)
Carter, Clin. Chem 24:362-364 (1978)
Dawes and Gardner, Clin. Chim. Acta 86: 353-356 (1978)
Freifelder, Physical Biochemistry: Applications to Biochemistry and Molecular Biology, p. 259, W. H. Freeman and Company, San Francisco (1976)
Guesdon et al., J. Allergy Clin. Immunol. 61(1): 23-27 (1978)
Halling and Dunnill, Enzyme Microb. Technol. 2: 2-10 (1980)
Hirschbein et al., Chemtech, Mar. 1982: 172-179 (1982)
Ithakissios and Kubiatowicz, Clin. Chem. 23(11): 2072-2079 (1977)
Ithakissios et al., Clin. Chim. Acta, 84: 69-84 (1978)
Jacobs, The Ligand Quarterly, 4(4): 23-33 (1981)
Kamel and Gardner, Clin. Chim. Acta, 89: 363-370 (1978)
Kamel et al., Clin. Chem., 25(12): 1997-2002 (1979)
Kamel et al., Clin. Chem., 26(9): 1281-1284 (1980)
Klibanov, Science, 219: 722 (1983)
Mosbach and Anderson, Nature, 270: 259-261 (1977)
Nayak, The Ligand Quarterly 4(4): 34 (1981)
Nye et al., Clin. Chim. Acta, 69: 387-396 (1976)
Parsons, in: Methods in Enzymology, J. Langone (ed.), 73: 224-239 (1981)
Pourfarzaneh, The Ligand Quarterly 5(1): 41-47 (1982)
Pourfarzaneh et al., Clin. Chem., 26(6): 730-733 (1980)
Weetall, in: Methods in Enzymology, K. Mosbach (ed.), 44: 134-148 (1976