It has long been known that the configurational isomers of biologically active compounds, e.g., nutrients, pesticides, and drugs, may exhibit different activities in a chiral environment such as the human body. Although the majority of drugs presently in development are chiral, analytical and preparative methods for the quantitative determination and purification of stereoisomers still lag behind. One reason is that commonly used chiral selectors for the direct resolution of enantiomers are not tailor-made for a specific analyte. The identification of suitable selectors for a particular pair of enantiomers still requires considerable experimentation and is generally demanding with regard to material, time and labor. The rational design of chiral host molecules, therefore, represents a challenge in facilitating enantiomer analysis. In this article, we describe how a combination of techniques ranging from organic synthesis to molecular biology yields antibodies of predetermined specificity and stereoselectivity that can be used as tailor-made chiral selectors for the chromatographic separation of enantiomers and their sensitive detection in immunosensors.
参考文献
| [1] | Stinson S C. Chem Eng News, 1997, 75: 38 |
| [2] | Stinson S C. Chem Eng News, 2001, 79: 79 |
| [3] | Eichelbaum M, Gross A S. Adv Drug Res, 1996, 28: 1 |
| [4] | De Camp W H. Chirality, 1989, 1: 2 |
| [5] | FDA. Policy Statement for the Development of New Stereoisomeric Drugs (5/1/1992). http://www.fda.gov/cder/guidance/stereo.htm (post date 1/3/1996) |
| [6] | Schurig V, Lindner W, Uray G. In: Helmchen G, Hoffmann R W, Mulzer J, Schaumann E, eds. Houben-Weyl, Methods of Organic Chemistry, Vol E21a, Part A.3. Stuttgart: Thieme, 1995. 147 |
| [7] | Tsukamoto M, Kagan H B. Adv Synth Catal, 2002, 344: 453 |
| [8] | Finn M G. Chirality, 2002, 14: 534 |
| [9] | Chankvetadze B. Chiral Separation. Amsterdam: Elsevier, 2001 |
| [10] | Maier N M, Franco P, Lindner W. J Chromatogr A, 2001, 906: 3 |
| [11] | Del Rio A, Piras P, Roussel C. Chirality, 2005, 17: S74 |
| [12] | http://chirbase.u-3mrs.fr/ |
| [13] | Hofstetter O, Lindstrom H, Hofstetter H. Anal Chem, 2002, 74: 2 119 |
| [14] | Hofstetter O, Lindstrom H, Hofstetter H. J Chromatogr A, 2004, 1 049: 85 |
| [15] | Hofstetter O, Hofstetter H, Wilchek M, Schurig V, Green B S. Chem Commun, 2000, (17): 1 581 |
| [16] | Silvaieh H, Schmid M G, Hofstetter O, Schurig V, Gübitz G. J Biochem Biophys Methods, 2002, 53: 1 |
| [17] | Hofstetter O, Hofstetter H, Wilchek M, Schurig V, Green B S. Nat Biotechnol, 1999, 17: 371 |
| [18] | Dutta P, Tipple C A, Lavrik N V, Datskos P G, Hofstetter H, Hofstetter O, Sepaniak M J. Anal Chem, 2003, 75: 2 342 |
| [19] | Tsourkas A, Hofstetter O, Hofstetter H, Weissleder R, Josephson L. Angew Chem Int Ed Engl, 2004, 43: 2 395 |
| [20] | Hofstetter O, Hertweck J K, Hofstetter H. J Biochem Biophys Methods, 2005, 63: 91 |
| [21] | Nezlin R. The Immunoglobulins. San Diego: Academic Press, 1998 |
| [22] | Rajewsky K. Nature, 1996, 381: 751 |
| [23] | Gellert M. Annu Rev Biochem, 2002, 71: 101 |
| [24] | Van Oss C J. In: Van Oss C J, van Regenmortel M H V, eds. Immunochemistry. New York: Marcel Dekker, 1994. 581 |
| [25] | Landsteiner K. The Specificity of Serological Reactions. New York: Dover Publications, 1962 |
| [26] | Landsteiner K, van der Scheer J. J Exp Med, 1928, 48: 315 |
| [27] | Cook C E. In: Wainer I W, ed. Drug Stereochemistry: Analytical Methods and Pharmacology. 2nd ed. New York: Marcel Dekker, 1993. 35 |
| [28] | Erlanger B F. Methods Enzymol, 1980, 70: 85 |
| [29] | Hermanson G T. In: Bioconjugate Techniques. San Diego: Academic Press, 1996. 419 |
| [30] | Harlow E, Lane D. Antibodies: a Laboratory Manual. Cold Spring Harbor: Cold Spring Harbor Laboratory Press, 1988 |
| [31] | Hofstetter O, Hofstetter H, Wilchek M, Schurig V, Green B S. J Am Chem Soc, 1998, 120: 3 251 |
| [32] | Catty D, Raykundalia C. In: Catty D, ed. Antibodies: a Practical Approach, Vol 2. Oxford: IRL Press, 1989. 97 |
| [33] | Zeleke T K, Zeleke J M, Hofstetter H, Hofstetter O. J Mol Recognit, 2005, 18: 334 |
| [34] | K hler G, Milstein C. Nature, 1975, 256: 495 |
| [35] | Goding J W. Monoclonal Antibodies: Principles and Practice. 3rd ed. San Diego: Academic Press, 1996 |
| [36] | Hofstetter O, Hofstetter H, Wilchek M, Schurig V, Green B S. Int J Bio-Chromatogr, 2000, 5: 165 |
| [37] | U.S. Department of Agriculture. Alternatives to Ascites Production of Monoclonal Antibodies. http://www.nal.usda.gov/awic/newsletters/v8n3/8n3mcard.htm |
| [38] | Falkenberg F W, Hengelage T, Krane M, Bartels I, Albrecht A, Holtmeier N, Wuthrich M. J Immunol Methods, 1993, 165: 193 |
| [39] | Jackson L R, Trudel L J, Lipman N S. Lab Animal, 1999, 28: 38 |
| [40] | Konterman R, Dübel S. Antibody Engineering. Berlin: Springer, 2001 |
| [41] | Lo B K C. Antibody Engineering, Methods and Protocols, Methods in Molecular Biology, Vol 248. Totowa: Humana Press, 2004 |
| [42] | Hofstetter H, Cary J R, Eleniste P P, Hertweck J K, Lindstrom H J, Smith G B, Ranieri D I, Undesser L P, Zeleke J M, Zeleke T K, Hofstetter O. Chirality, 2005, 17: S9 |
| [43] | Nevanen T K, Hellman M-L, Munck N, Wohlfahrt G, Koivula A, S derlund H. Prot Eng, 2003, 16: 1 089 |
| [44] | Marks J D, Hoogenboom H R, Bonnert T P, McCafferty J, Griffiths A D, Winter G. J Mol Biol, 1991, 222: 581 |
| [45] | Kay B K, Winter J, McCafferty J. Phage Display of Peptides and Proteins. San Diego: Academic Press, 1996 |
| [46] | Phillips T M. Adv Chromatogr, 1989, 29: 133 |
| [47] | Cutler P. Immunoaffinity Chromatography. In: High Resolution Chromatography: a Practical Approach. Millner P, ed. Oxford: Oxford University Press, 1999. 233 |
| [48] | Mertens R, Stüning M, Weiler E W. Naturwissenschaften, 1982, 69: 595 |
| [49] | Knox J P, Galfre G. Anal Biochem, 1986, 115: 92 |
| [50] | Nevanen T K, S derholm L, Kukkonen K, Suortti T, Teerinen T, Linder M, S derlund H, Teeri T T. J Chromatogr A, 2001, 925: 89 |
| [51] | Lua A C, Chou T-Y. J Chromatogr A, 2002, 967: 191 |
| [52] | Afeyan N B, Gordon N F, Mazsaroff I, Varady L, Fulton S P, Yang Y B, Regnier F E. J Chromatogr, 1990, 519: 1 |
| [53] | Regnier F E. Nature, 1991, 350: 634 |
| [54] | Allenmark S G, Andersson S. J Chromatogr A, 1994, 666: 167 |
| [55] | Haginaka J. J Chromatogr A, 2001, 906: 253 |
| [56] | Aboul-Enein H Y, Ali I. In: Chiral Separations by Liquid Chromatography and Related Techniques. New York: Marcel Dekker, 2003. 209 |
| [57] | Malmqvist M. Nature, 1993, 361: 186 |
| [58] | Josephson L, Perez J M, Weissleder R. Angew Chem Int Ed, 2001, 40: 3 204 |
上一张
下一张
上一张
下一张
计量
- 下载量()
- 访问量()
文章评分
- 您的评分：
-
10%
-
20%
-
30%
-
40%
-
50%