Drug – bio-affecting and body treating compositions – Antigen – epitope – or other immunospecific immunoeffector – Conjugate or complex
Patent
1995-03-29
2000-04-11
Minnifield, Nita
Drug, bio-affecting and body treating compositions
Antigen, epitope, or other immunospecific immunoeffector
Conjugate or complex
4241931, 4241941, 4242781, 530300, 530326, 530327, 530333, 530334, 530335, 530344, A61K 39385, A61K 3800, C07K 500, C07K 1600
Patent
active
060485299
ABSTRACT:
The invention relates to a procedure for synthesis of well-defined conjugates of peptides to the tolerogenic polymer monomethoxypolyethylene glycol (mPEG) or polyvinyl alcohol (PVA). This method results in the preparation of conjugates in which one molecule of tolerogenic polymer is specifically coupled to one or the other or both of the termini of an otherwise unaltered peptide molecule. A synthetic peptide synthesized using this method and corresponding to a myasthenogenic region of an acetylcholine receptor was conjugated to monomethoxypolyethylene glycol. Injection of animals with the mPEG-conjugate and subsequent immunization with whole receptor suppressed the development of experimental autoimmune myasthenia gravis (EAMG) by electrophysiological criteria. Specifically-conjugated, tolerogenic peptides are also disclosed for diseases as diverse as ragweed pollen allergy and Grave's disease.
REFERENCES:
patent: 4261973 (1981-04-01), Lee et al.
patent: 5068177 (1991-11-01), Carson et al.
patent: 5130297 (1992-07-01), Sharma et al.
patent: 5194425 (1993-03-01), Sharma et al.
patent: 5256641 (1993-10-01), Yatvin et al.
patent: 5260422 (1993-11-01), Clark et al.
patent: 5268454 (1993-12-01), Barstad et al.
patent: 5284935 (1994-02-01), Clark et al.
patent: 5370871 (1994-12-01), Dintzis et al.
patent: 5468481 (1995-11-01), Sharma et al.
patent: 5468730 (1995-11-01), Hahn
patent: 5552529 (1996-09-01), Rearden
patent: 5578496 (1996-11-01), Atassi et al.
patent: 5614192 (1997-03-01), Vandenbark
patent: 5759834 (1998-06-01), Atassi
patent: 5800815 (1998-09-01), Chestnut et al.
Suppression of Reaginic Antibodies with Modified Allergens, "III. Preparation of Tolerogenic Conjugates of common Allergens with Monomethoxypolyethylene Glycols of Different Molecular Weights by the Mixed Anhydride Method," by S.I. Wie, C.W. Wie, W.Y. Lee, L.G. Filion, A.H. Sehon and E. Akerblom, International Archives of Allergy and Applied Immunology, vol. 64 (1981).
Suppression of Reaginic Antibodies with Modified Allergens, III. Down-regulation of secondary in vitro antibody responses by suppressor T cells of mice treated with a tolerogenic conjugate of ovalbumin and monomethoxypolyethylene glycol, OVA (mPEG).sub.13, by S. suppressor T cells of mice treated with a tolerogenic conjugate of ovalbumin and monomethoxypolyethylene glycol, OVA(mPEG).sub.13, by S. Mokashi, V. Holford-Strevens, G. Sterrantino, C.J.C. Jackson and A.H. Sehon, Immunology Letters, 23 (1989/1990) 95-102.
Preparation and Immunochemical Properties of Methoxypolyethylene Glycol-Coupled and N-Carboxymethylted Derivatives of Ragweed Pollen Allergen, Antigen E.sup.1, by TePiao King, Loucia Kochoumian, and Lawrence M. Lichtenstein, Archives of Biochemistry and Biophysics, Lawrence M. vol. 178, pp. 442-450 (1977).
Abrogation of reaginic antibodies with modified allergens, by Weng Y. Lee and Alec H. Sehon, Nature, vol. 267, pp. 618-619, Jun. 16, 1977.
Suppression of Reaginic Antibodies with Modified Allergens, "IV. Induction of Suppressor T Cells by Conjugates of Polyethylene Glycol (PEG) and Monomethoxy PEG with Ovalbumin," by W.Y. Lee, A.H. Sehon and E. Akerblom, International Archives of Allergy and Applied Immunology, vol. 64, pp. 100-114 (1981).
Suppression of Reaginic Antibodies with Modified Allergens, "I. Reduction in Allergenicity of Protein Allergens by Conjugation to Polyethylene Glycol," by Weng Y. Lee and Alec H. Sehon, International Archives of Allergy and Applied Immunology, vol. 56, pp. 193-206 (1978).
Suppression of Reaginic Antibodies with Modified Allergens, "II. Abrogation of Reaginic Antibodies with Allergens Conjugated to Polyethylene Glycol," by Weng Y. Lee and Alec H. Sehon, International Archives of Allergy and Applied Immunology, vol. 56, pp. 193-206 (1978).
Hyposensitization in asthmatics with mPEG-modified and unmodified house dust mite extract, "IV. Occurrence and prediction of side effects," by H. Mosbech, A. Dirksen, S. Dreborg, L. Frolund, J.H. Heinig, U.G. Svendsen, M. Soborg, E. Taudorf & B. Weeke, Allergy, No. 45, pp. 142-150 (1990).
Modulation of Antibody Responses by Conjugates of Antigens With Monomethoxypolyethylene Glycol, by Alec. H. Sehon, Immunobiology of Proteins and Peptides V Vaccines, pp. 341-351.
New Model Visual Pigments, Spectroscopy of Poly(ethylene glycol) Peptide Schiff bases of Retinal, by P.K. Das, Ralph S. Becker, Dieter Hannak, and Ernst Baver, Journal of the American Chemical Society, vol. 101, No. 1, Jan. 3, 1979.
Soluble Polymers in Organic Syntheses: II. Use of Polyethylene Glycol-Bound Reagents for Peptide Syntheses, by Manfred Mutter, Tetrahedron Letters, No. 31, Jul. 1978.
Syntheses of Poly(ethylene Glycol)-Bound NADP by Selective Modification at the 6-amino group of NADP, by Keiko Okuda, Itaru Urabe, and Hirosuke Okada, European Journal of Biochemistry, vol., 151, No. 1, Aug. 11, 1985.
A Poly(oxyethylene)-Supported Cys-Pro-Leu-Cys/Fe(II) Complex as a Rubredoxin Model: Protection of the Fe-Cys Coordination from Hydrolysis in Aqueous Solution, by Norikazu Ueyama, Michio Kanata, and Akira Nakamura, Polymer Journal, vol. 17, No. 5, pp. 721-727 (1985).
Development of new Functionalized Polymers and Their Utilization in Peptide Chemistry, by Shmuel Zalipsky, Ph.D., University of Minnesota (1987), Dissertation Abstracts International (The Sciences and Engineering), vol. 48, No. 8 (Feb. 1988).
Engineering Proteins to Enhance Their Partition Coefficients in Aqueous Two-Phase Systems, by Kristina Kohler, Charlotta Ljungquist Akihiko Kondo, Andres Veide, and Bjorn Nilsson, Biotechnology, vol. 9, No. 7, Jul. 1991.
Preparation of Polyethylene Glycol Derivatives with two Different Functional groups at the Termini, by Shmuel Zalipsky and George Barany, Polymer Preprints, vol. 27, No. 1, Apr. 1986.
Investigation into the Spectroscopy and Photoisomerization of a Series of Ploy(Ethylene Glycol) peptide Schiff Bases of 11-cis Retinal, by Kenn Freedman, Ralph S. Becker, Dieter Hannak, and Ernst Bayer, Photochemistry and Photobiology, vol. 43, No. 3, Mar. 1986.
Modification of Batroxobin with Activated Polyethylene Glycol: Reduction of Binding Ability Towards Anti-Batroxobin Antibody and Retention of Defibrinogenation Activity in Circulation of Preimmun-Dogs, by Hiroyuki Nushimura, Katsunobu Takahashi, Katsukiyo Sakurai Kazunobu Fujinuma, Yasushi Imamura, Mitsuoki Ooba, and Yuji Inada, Life Sciences, vol. 33, No. 15, Oct. 10, 1983.
A Double-Blind Study Comparing Monomethoxy Polyethylene Glycol-Modified Honeybee Venom and Unmodified Honeybee Venom for Immunotherapy, by Ulrich Muller, M.D., Arthur R. Rabson, M.R.C.Path., Marium Bischof, M.D., Ruth Lomnitzer, Ph.D., Sten Dreborg, M.D., and Ake Lanner, M.Sc., The Journal of Allergy and Clinical Immunoology, vol. 80, No. 1 (1987).
Synthesis, Isolation, and Characterization of Conjugates of Ovalbumin with Monomethoxypolyethylene Glycol Using Cyanuric Chloride as the Coupling Agent, by Chung-Ja C. Jackson, James L. Charlton, Kimberly Kuzminski, Glen M. Lang, and Alex H. Sehon, Analytical Biochemistry, vol. 165, pp. 114-127 (1987).
A convenient general Method for synthesis of N.sub.x or N.sup.w Dithiasuccinoyl (Dts) Amino Acids and Dipeptides: Application of Polyethylene Glycol as a Carrier for Functional Purification, by Shmuel Zalipsky, Fernando Albericio, Utszula Slomczynska, and George Barany.
Characterization of a Polyethylene Glycol Conjugate of Recombinant Human Interferon, by Kita Yoshiko, Michael F. Rohde, Rsutomu Arakawa, Katerina D. Fagin, Eleanor N. Fish, and Kris Banerjee, Drug Design and Delivery, vol. 6, pp. 157-167 (1990).
Soluble Polymers in Organic Syntheses 3. Polyethylene Glycol as Acid Labile Solubilizing Protecting Group, by h. Anzinger and M. Mutter, Polymer Bulletin, No. 66, Nov. 22, 1982.
Enzyme Modification by MPEG with an Amino Acid or Peptide as Spacer Arms, by Luciana Sartore, Paolo Caliceti, Oddone Schiavon, and Francesco M. Veronese, Applied Biochemistry and Biotechnology, vol. 27, No. 1, Jan. 1991.
Tsuji, Hisashi et al., "Modified Interleukin-2", English language Abstract of Japanese Patent No. 63,258,896 in Chemical Abstracts
Ashizawa Tetsuo
Atassi M. Zouhair
McDaniel C. Steven
Minnifield Nita
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