Chemical and Biological Approaches to Catalytic Antibodies

  • K. D. Janda
  • Chen Y.-C. Jack
Part of the Handbook of Experimental Pharmacology book series (HEP, volume 113)

Abstract

A long-standing goal of biochemists is the design and synthesis of catalysts endowed with particular activities and properties. For example, one might create an enzyme that can degrade drugs into inactive metabolites as a treatment for drug overdoses or an enzyme that acts on a prodrug to unmask its therapeutically useful form. Yet another enzyme could target the cleavage of a specific tumor or virus protein that is vital for development of that tumor or virus thus acting as a therapeutic agent. Other traits, such as thermostability, chemical stability, and oxidative stability, can also be incorporated into such catalysts.

Keywords

Catalysis Lipase Amide Proline Lysine 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Ashley JA, Janda KS (1992) Antibody catalysis in low water content media. J Org Chem 57:6691–6693CrossRefGoogle Scholar
  2. Baldwin J (1976) Rules for ring closure. J Chem Soc Chem Commun, pp 734–736Google Scholar
  3. Barbas CF, Kang AS, Lerner RA, Benkovic SJ (1991) Assembly of combinatorial antibody libraries on phage surfaces: the gene III site. Proc Natl Acad Sci USA 88:7978–7982PubMedCrossRefGoogle Scholar
  4. Bartlett PA, Johnson CA (1985) An inhibitor of chorismate mutase resembling the transition-state conformation. J Am Chem Soc 10:7792CrossRefGoogle Scholar
  5. Benkovic SJ, Napper AD, Lerner RA (1988) Catalysis of a stereospecific bimole-cular amide synthesis by an antibody. Proc Natl Acad Sci USA 85:5355–5538PubMedCrossRefGoogle Scholar
  6. Better M, Chang CP, Robinson RR, Horwitz AH (1988) Escherichia coli secretion of an active chimeric antibody fragement. Science 240:1041–1043PubMedCrossRefGoogle Scholar
  7. Bird RE, Hardman KD, Jacobson JW, Johnson S, Kaufman BM, Lee S-M, Lee T, Pope S, Riordan GS, Whitlow M (1988) Single-chain antigen-binding proteins. Science 242:423–426PubMedCrossRefGoogle Scholar
  8. Bishop DHL (1990) Gene expression using insect cells and viruses. Curr Opin Biotech 1:62–67PubMedCrossRefGoogle Scholar
  9. Bowdish K, Tang Y, Hicks JB, Hilvert D (1991) Yeast expression of a catalytic antibody with chorismate mutase activity. J Biol Chem 266:11901–11908PubMedGoogle Scholar
  10. Brinkley M (1992) A brief survey of methods for preparing protein conjugates with dyes, haptens, and cross-linking reagents. Bioconjugate Chem 3:2–13CrossRefGoogle Scholar
  11. Buckner J, Rudolph R (1991) Renaturation, purification and characterization of recombinant Fab-fragments produced in Escherichia coli. Bio/Technology 9: 157–162CrossRefGoogle Scholar
  12. Burand JP, Summers MD, Smith GE (1980) Transfection with baculovirus DNA. Virology 101:286–290PubMedCrossRefGoogle Scholar
  13. Cabilly S, Riggs AD, Pande H, Shively JE, Holmes WE, Rey M, Perry LJ, Wetzel R, Heyneker HL (1984) Generation of antibody activity from immunoglobulin polypeptide chains produced in Escherichia coli. Proc Natl Acad Sci USA 81:3273–3277PubMedCrossRefGoogle Scholar
  14. Carter P, Kelley RF, Rodrigues ML, Snedecor B, Covarrubias M, Velligan MD, Wong WLT, Rowland AM, Kotts CE, Carver ME, Yang M, Bourell JH, Shepard HM, Henner D (1992) High level Escherichia coli expression and production of a bivalent humanized antibody fragment. Bio/Technology 10: 163–167PubMedCrossRefGoogle Scholar
  15. Condra JH, Sardana W, Tomassini JE, Schlaback AJ, Davies M-E, Lineberger DW, Graham DJ, Gotlib L, Colonno RJ (1990) Bacterial expression of antibody fragments that block human rhinovirus infection of cultured cells. J Biol Chem 265:2292–2295PubMedGoogle Scholar
  16. Craik CS, Largman C, Fletcher T, Roczniak S, Barr PJ, Fletterick R, Rutter WJ (1985) Redesigning trypsin: alteration of substrate specificity. Science 228:291–297PubMedCrossRefGoogle Scholar
  17. Crosby J, Stone R, Lienhard GE (1970) Mechanisms of thiazmine-catalyzed reactions. Decarboxylations. of 2-(l-carboxy-l-hydroxyethyl)-3,4-dimethylthiazolium chloride. J Am Chem Soc 92:2891–2900PubMedCrossRefGoogle Scholar
  18. Dafforn A, Koshland DE (1973) Proximity, entropy and orbital steering. Biochem Biophys Res Commun 52:779–783PubMedCrossRefGoogle Scholar
  19. Davis GT, Bedzyk WD, Voss EW, Jacobs TW (1991) Single chain antibody (SCA) encoding gene: one-step construction and expression in eukaryotic cells. Bio/Technology 9:165–169PubMedCrossRefGoogle Scholar
  20. Devlin JJ, Devlin PE, Clark R, O’Rourke EC, Levenson C, Mark DF (1989) Novel expression of chimeric plasminogen activators in insect cells. Bio/Technology 7:286–292CrossRefGoogle Scholar
  21. Durfor CN, Bolin RJ, Sugasawara RJ, Massey RJ, Jacobs JW, Schultz PG (1988) Antibody catalysis in reverse micelles. J Am Chem Soc 110:8713–8714CrossRefGoogle Scholar
  22. Eisenberg D, Wilcox W, Eshita SM, Pryciak PM, Ho SP, DeGrado WF (1986) The design, synthesis and crystallization of an alpha-helical peptide. Proteins 1:16–22PubMedCrossRefGoogle Scholar
  23. Engvall E (1980) Enzyme immunoassay ELISA and EMIT. Methods Enzymol 70:419–438PubMedCrossRefGoogle Scholar
  24. Erlanger B (1980) The preparation of antigenic hapten-carrier conjugates: a survey. Methods Enzymol 70:85–103PubMedCrossRefGoogle Scholar
  25. Evnin LB, Vásquez JR, Craik CS (1990) Substrate specificity of trypsin investigated by using a genetic selection. Proc Natl Acad Sci USA 87:6659–6663PubMedCrossRefGoogle Scholar
  26. Gallacher G, Jackson CS, Searcey M, Badman GT, Goel R, Topham CM, Mellor GW, Brocklehurst K (1991) A polyclonal antibody preparation with Michaelian catalytic properties. Biochem J 279:871–881PubMedGoogle Scholar
  27. Gong B, Lesley SA, Schultz PG (1992) A chromogenic assay for screening large antibody libraries. J Am Chem Soc 114:1486–1487CrossRefGoogle Scholar
  28. Goraj K, Renard A, Martial JA (1990) Purification and initial structural characterization of octarellin, a de novo polypeptide modelled on the α/β barrel proteins. Protein Eng 3:259–266PubMedCrossRefGoogle Scholar
  29. Grossberg AL, Pressman D (1960) Nature of the combining site of antibody against a hapten bearing a positive charge. J Am Chem Soc 82:5478–5482CrossRefGoogle Scholar
  30. Hahn KW, Wieslaw AK, Stewart JM (1990) Design and synthesis of a peptide having chymotrypsin-like esterase activity. Science 248:1544–1547PubMedCrossRefGoogle Scholar
  31. Handel TM, DeGrado WF (1990) De novo design of a Zn2+ binding protein. J Am Chem Soc 112:6710–6711CrossRefGoogle Scholar
  32. Hasemann CA, Capra JD (1990) High-level production of a functional immunoglobulin heterodimer in a baculovirus expression system. Proc Natl Acad Sci USA 87:3942–3946PubMedCrossRefGoogle Scholar
  33. Hasemann CA, Capra JD (1992) Baculovirus expression of antibodies: a method for the expression of complete immunoglobulins in a eukaryotic host. Methods 2:146–158CrossRefGoogle Scholar
  34. Hilvert D, Nared KD (1988) Stereospecific Claisen rearrangement catalyzed by an antibody. J Am Chem Soc 110:5593–5594CrossRefGoogle Scholar
  35. Hilvert D, Carpenter SH, Nared KD, Auditor M-TM (1988) Catalysis of concerted reactions by antibodies: the Claisen rearrangement. Proc Natl Acad Sci USA 85:4953–4955PubMedCrossRefGoogle Scholar
  36. Ho SP, DeGrado WF (1987) Design of a 4-helix bundle protein: synthesis of peptides which self-associate into a helical protein. J Am Chem Soc 109:6751–6758CrossRefGoogle Scholar
  37. Huse WD, Sastry L, Iverson SA, Kang AS, Alting-Mees M, Burton DR, Benkovic SJ, Lerner RA (1989) Generation of a large combinatorial library of the immunoglobulin repertoire in phage lambda. Science 246:1275–1281PubMedCrossRefGoogle Scholar
  38. Ikeda S, Weinhouse MI, Janda KD, Lerner RA (1991) Asymmetric induction via a catalytic antibody. J Am Chem Soc 113:7763–7764CrossRefGoogle Scholar
  39. Jackson DY, Jacobs JW, Sugasawara R, Reich SH, Bartlett PA, Schultz PG (1988) An antibody-catalyzed Claisen rearrangment. J Am Chem Soc 110:4841–4842CrossRefGoogle Scholar
  40. Jacobs J, Schultz PG (1987) Catalytic antibodies. J Am Chem Soc 109:2174–2176CrossRefGoogle Scholar
  41. Jacobson NE, Bartlett PA (1981) A phosphonamidate dipeptide analogue as an inhibitor of carboxypeptidase A. J Am Chem Soc 103:654–657CrossRefGoogle Scholar
  42. Janda KD, Schloeder D, Benkovic SJ, Lerner RA (1988a) Induction of an antibody that catalyzes the hydrolysis of an amide bond. Science 241:1188–1191PubMedCrossRefGoogle Scholar
  43. Janda KD, Lerner RA, Tramontano A (1988b) Antibody catalysis of bimolecular amide formation. J Am Chem Soc 110:4835–4837CrossRefGoogle Scholar
  44. Janda KD, Benkovic SB, Lerner RA (1989) Catalytic antibodies with lipase activity and R or S substrate selectivity. Science 244:437–440PubMedCrossRefGoogle Scholar
  45. Janda KD, Weinhouse MI, Schloeder DM, Lerner RA, Benkovic SJ (1990a) Bait and switch strategy for obtaining catalytic antibodies with acyl-transfer capabilities. J Am Chem Soc 112:1274–1275CrossRefGoogle Scholar
  46. Janda KD, Ashley JA, Jones TM, Mcleod DA, Schloeder DM, Weinhouse MI (1990b) Immobilized catalytic antibodies in aqueous and organic solvents. J Am Chem Soc 112:8886–8888CrossRefGoogle Scholar
  47. Janda KD, Shevlin CG, Lerner RA (1993) Antibody catalysis of a disfavored chemical transformation. Science 259:490–493PubMedCrossRefGoogle Scholar
  48. Jarvis DL, Fleming J-AGW, Kovacs GR, Summers MD, Guarino LA (1990) Use of early baculovirus promoters for continuous expression and efficient processing of foreign gene products in stably transformed lepidopteran cells. Bio/Technology 8:950–955PubMedCrossRefGoogle Scholar
  49. Jencks WP (1975) Binding energy, specificity, and enzymic catalysis: the Circe effect. Adv Enzymol 43:219–410PubMedGoogle Scholar
  50. Jencks WP (1987) Catalysis in chemistry and enzymology. Dover MineolaGoogle Scholar
  51. Johnson LN (1992) Time-resolved protein crystallography. Protein Sci 1:1237–1243PubMedCrossRefGoogle Scholar
  52. Jones JB (1976) On the potential of soluble and immobilized enzymes in synthetic organic chemistry. Methods Enzymol 44:831–843PubMedCrossRefGoogle Scholar
  53. Kang AS, Barbas CF, Janda KD, Benkovic SJ, Lerner RA (1991) Linkage of recognition and replication functions by assembling combinatorial antibody Fab libraries along phage surfaces. Proc Natl Acad Sci USA 88:4363–4366PubMedCrossRefGoogle Scholar
  54. Kang AS, Jones TM, Burton DR (1992) Antibody redesign by chain shuffling from random combinatorial immunoglobulin libraries. Proc Natl Acad Sci USA 88:11120–11123CrossRefGoogle Scholar
  55. Kemp DS, Paul KG (1975) The physical organic chemistry of benzisoxazoles. III. The mechanism and the effects of solvents on rates of decarboxylation of benzisoxazole-3-carboxylic acids. J Am Chem Soc 97:7305–7317CrossRefGoogle Scholar
  56. Knowles JR (1987) Tinkering with enzymes: what are we learning? Science 236: 1252–1258PubMedCrossRefGoogle Scholar
  57. Köhler G, Milstein C (1975) Continuous cultures of fused cells secreting antibodies of predefined specificities. Nature 256:495–497PubMedCrossRefGoogle Scholar
  58. Lewis C, Kramer T, Robinson S, Hilvert D (1991) Medium effects in antibody-catalyzed reactions. Science 253:1019–1022PubMedCrossRefGoogle Scholar
  59. Lin YY, Risk M, Ray SM, Van Engen D, Clardy JC, Golick J, James JC, Nakanishi K (1981) Isolation and structure of brevetoxin B from the “red tide” dinoflagel-late Ptychodicus brevis (Gymnodiniumbreve). J Am Chem Soc 107:6773–6775CrossRefGoogle Scholar
  60. Mandecki W, Shallcross MA, Sowadski J, Tomazic-Allen S (1991) Mutagenesis of conserved residues within the active site of Escherichia coli alkaline phosphatase yields enzymes with increased k cat. Protein Eng 4:801–804PubMedCrossRefGoogle Scholar
  61. Marlier JF, O’Leary MH (1986) Solvent dependence of the carbon kinetic isotope effect on the decarboxylation of 4-pyridylacetic acid. A model for enzymatic decarboxylations. J Am Chem Soc 108:4896–4899CrossRefGoogle Scholar
  62. Mayers GL, Grossberg AL, Pressman D (1973) Arginine and lysine in binding sites of anti-4-azophthalate antibodies. Immunol Chem 10:37–41CrossRefGoogle Scholar
  63. Medin JA, Hunt L, Gathy K, Evans RK, Coleman MS (1990) Efficient, low-cost protein factories: expression of human adenosine deaminase in baculovirus-infected insect larvae. Proc Natl Acad Sci USA 87:2760–2764PubMedCrossRefGoogle Scholar
  64. Miyamoto C, Smith GE, Farrell-Towt J, Chizzonite R, Summers MD, Ju G (1985) Production of human c-myc protein in insect cells infected with baculovirus expression vector. Mol Cell Biol 5:2860–2865PubMedGoogle Scholar
  65. Napper AD, Benkovic SJ, Tramantano A, Lerner RA (1987) A stereospecific cyclization catalyzed by an antibody. Science 237:1041–1043PubMedCrossRefGoogle Scholar
  66. Nishima T, Tsuji A, Fukushima DK (1974) Site of conjugation of bovine serum albumin to corticosteroid hormones and specificity of antibodies. Steroids 24:861–874CrossRefGoogle Scholar
  67. Paul S, Volle DJ, Beach CM, Johnson DR, Powell MJ, Massey RJ (1989) Catalytic hydrolysis of vasoactive intestinal peptide by human autoantibody. Science 244:1158–1162PubMedCrossRefGoogle Scholar
  68. Paul S, Volle DJ, Powell MJ, Massey RJ (1990) Site-specificity of a catalytic vasoactive intestinal peptide antibody: an inhibitory VIP subsequence distant from the scissile peptide bond. J Biol Chem 265:11910–11913PubMedGoogle Scholar
  69. Paul S, Johnson DJ, Massey R (1991) Binding and multiple hydrolytic sites in epitopes recognized by catalytic anti-peptide antibodies. Ciba Found Symp 159:156–173PubMedGoogle Scholar
  70. Pauling L (1948) Chemical achievement and hope for the future. Am Sci 36:51–58PubMedGoogle Scholar
  71. Pollack SJ, Jacobs JW, Schultz PG (1986) Selective chemical catalysis by an antibody. Science 234:1570–1573PubMedCrossRefGoogle Scholar
  72. Pressman D, Grossberg AC, Pence LH, Pauling L (1946) The reactions of antiserum homologous to the p-azophenyltrimethylammonium group. J Am Chem Soc 68:250–255CrossRefGoogle Scholar
  73. Raso V, Stollar D (1975) The antibody-enzyme analogy. Comparison of enzymes and antibodies specific for phosphopyridoxyltyrosine. Biochemistry 14:584–599PubMedCrossRefGoogle Scholar
  74. Regan L, Clarke ND (1990) A tetrahedral zinc(II)-binding site introduced into a designed protein. Biochemistry 29:10879–10883CrossRefGoogle Scholar
  75. Regan L, DeGrado WF (1988) Characterization of a helical protein designed from first principles. Science 241:976–978PubMedCrossRefGoogle Scholar
  76. Sastry L, Alting-Mees M, Huse WD, Short JM, Sorge JA, Hay BN, Janda KD, Benkovic SJ, Lerner RA (1989) Cloning of the immunological repertoire in Eschericia coli for generation of monoclonal catalytic antibodies: construction of a heavy chain variable region-specific cDNA library. Proc Natl Acad Sci USA 86:5728–5732PubMedCrossRefGoogle Scholar
  77. Shimizo Y, Chou H-N, Bandu H, Van Dvyne G, Varky JC (1986) Structure of brevetoxin A (GB-1 toxin), the most potent toxin in the Florida red tide organism, Gymnodinium breve (Ptychodiscus brevis). J Am Chem Soc 108: 514–515CrossRefGoogle Scholar
  78. Shokat KM, Schultz PG (1991) The generation of antibody combining sites containing catalytic residues. Ciba Found Symp 159:118–135PubMedGoogle Scholar
  79. Shokat KM, Leumann CL, Sugasawara R, Schultz PG (1989) A new strategy for the generation of catalytic antibodies. Nature 338:269–271PubMedCrossRefGoogle Scholar
  80. Smith GE, Summers MD, Fraser MJ (1983a) Production of human beta interferon in insect cells infected with a baculovirus expression vector. Mol Cell Biol 3:2156–2165PubMedGoogle Scholar
  81. Smith GE, Fraser MJ, Summers MD (1983b) Molecular engineering of the Auto-grapha californica nuclear polyhedrosis virus genome: deletion mutations within the polyhedron gene. J Virol 46:584–593PubMedGoogle Scholar
  82. Smith GE, Ju G, Ericson BL, Moschera J, Lahm H-W, Chizzonite R, Summers MD (1985) Modification and secretion of human interleukin 2 produced in insect cells by a baculovirus expression vector. Proc Natl Acad Sci USA 82:8404–8408PubMedCrossRefGoogle Scholar
  83. Summers JB (1983) Catalytic principles of enzyme chemistry. PhD thesis, Harvard University, New HavenGoogle Scholar
  84. Summers MD, Smith GE (1987) A manual of methods for baculovirus vectors and insect cell culture procedures. Texas Agricultural Experiment Station, College Station, TexasGoogle Scholar
  85. Tang Y, Hicks JB, Hilvert D (1991) In vivo catalysis of a metabolically essential reaction by an antibody. Proc Natl Acad Sci USA 88:8784–8786PubMedCrossRefGoogle Scholar
  86. Taylor PJ (1972) The decarboxylation of some heterocyclic acetic acids. J Chem Soc, pp 1077–1086Google Scholar
  87. Tramantano A, Janda KD, Lerner RA (1986a) Chemical reactivity at an antibody binding site elicited by mechanistic design of a synthetic antigen. Proc Natl Acad Sci USA 83:6736–6740CrossRefGoogle Scholar
  88. Tramantano A, Janda KD, Lerner RA (1986b) Catalytic antibodies. Science 234:1566–1570CrossRefGoogle Scholar
  89. Tramantano A, Ammann AA, Lerner RA (1988) Antibody catalysis approaching the activity of enzymes. J Am Chem Soc 110:2282–2286CrossRefGoogle Scholar
  90. Udaka K, Chua M-M, Tong L-H, Karush F, Goodgal SH (1990) Bacterial expression of immunoglobulin VH proteins. Mol Immunol 27:25–35PubMedCrossRefGoogle Scholar
  91. Webb NR, Madoulet C, Tosi P-F, Broussard DR, Sneed L, Nicolau C, Summers MD (1989) Cell-surface expression and purification of human CD4 produced in baculovirus-infected insect cells. Proc Natl Acad Sci USA 86:7731–7735PubMedCrossRefGoogle Scholar
  92. Wirsching PJ, Ashley JA, Benkovic SJ, Janda KD, Lerner RA (1991) An unexpectedly efficient catalytic antibody operating by ping-pong and induced fit mechanisms. Science 252:680–685PubMedCrossRefGoogle Scholar
  93. Wood CR, Boss MA, Kenten JH, Calvert JE, Roberts NA, Emtage JS (1985) The synthesis and in vivo assembly of functional antibodies in yeast. Nature 314:446–449PubMedCrossRefGoogle Scholar
  94. Zu Putlitz J, Kubasek WL, Duchêne M, Marget M, von Specht B-U, Domdey H (1990) Antibody production in baculovirus-infected insect cells. Bio/Technology 8:651–654PubMedCrossRefGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 1994

Authors and Affiliations

  • K. D. Janda
  • Chen Y.-C. Jack

There are no affiliations available

Personalised recommendations