Flow NMR applications in combinatorial chemistry

Current Opinion in Chemical Biology

Volumn 7, Issue 3, 2003, Pages 388-394

  Keifer, Paul A ^a  

^a UNIVERSITY OF NEBRASKA MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COMBINATORIAL CHEMISTRY; DRUG DESIGN; DRUG RESEARCH; DRUG SCREENING; FLOW INJECTION ANALYSIS; FLOW KINETICS; MOLECULAR PROBE; NUCLEAR MAGNETIC RESONANCE; REVIEW; SOLID PHASE EXTRACTION;

EID: 0038537515     PISSN: 13675931     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1367-5931(03)00051-6     Document Type: Review

References (59)

1. Dorn HC: Flow NMR. In Encyclopedia of Nuclear Magnetic Resonance. Edited by Grant DM, Harris RK. West Sussex, England: John Wiley & Sons, Ltd; 1996:2026-2036.
2. Burton K.I., Everett J.R., Newman M.J., Pullen F.S., Richards D.S., Swanson A.G. Online liquid chromatography coupled with high field NMR and mass spectrometry (LC-NMR-MS): a new technique for drug metabolite structure elucidation. J. Pharm. Biomed. Anal. 15:1997;1903-1912.
3. Keifer P.A., Smallcombe S.H., Williams E.H., Salomon K.E., Mendez G., Belletire J.L., Moore C.D. Direct-injection NMR (DI-NMR): a flow NMR technique for the analysis of combinatorial chemistry libraries. J. Comb. Chem. 2:2000;151-171 This article contains the most complete description of DI-NMR. It explains the technique, it discusses data presentation and analysis, and it presents a real application using a combinatorial chemistry library.
4. Keifer PA: Flow injection analysis NMR (FIA-NMR) - a novel flow NMR technique that complements LC-NMR and direct injection NMR (DI-NMR) magnetic resonance in chemistry. Magn Reson Chem 2003, in press.
5. Yurek D.A., Branch D.L., Kuo M.S. Development of a system to evaluate compound identity, purity, and concentration in a single experiment and its application in quality assessment of combinatorial libraries and screening hits. J. Comb. Chem. 4:2002;138-148.
6. Lindon J.C., Farrant R.D., Sanderson P.N., Doyle P.M., Gough S.L., Spraul M., Hofmann M., Nicholson J.K. Separation and characterization of components of peptide libraries using on-flow coupled HPLC - NMR spectroscopy. Magn. Reson. Chem. 33:1995;857-863.
7. Chin J., Fell J.B., Jarosinski M., Shapiro M.J., Wareing J.R. HPLC/NMR in combinatorial chemistry. J. Org. Chem. 63:1998;386-390.
8. Bobzin S.C., Yang S., Kasten T.P. Application of liquid chromatography-nuclear magnetic resonance spectroscopy to the identification of natural products. J. Chromatogr. B. Biomed. Sci. Appl. 748:2000;259-267.
9. Sandvoss M., Weltring A., Preiss A., Levsen K., Wuensch G. Combination of matrix solid-phase dispersion extraction and direct on-line liquid chromatography-nuclear magnetic resonance spectroscopy-tandem mass spectrometry as a new efficient approach for the rapid screening of natural products: application to the total asterosaponin fraction of the starfish Asterias rubens. J. Chromatogr. A. 917:2001;75-86.
10. 1H NMR and high-performance liquid chromatography-UV. Drug Metab. Dispos. 29:2001;375-380.
11. Lindon J.C., Nicholson J.K., Wilson I.D. Directly coupled HPLC-NMR and HPLC-NMR-MS in pharmaceutical research and development. J. Chromatogr. B. Biomed. Sci. Appl. 748:2000;233-258.
12. 1H NMR, and MS). Anal. Chem. 74:2002;288-294.
13. 1H nuclear magnetic resonance spectroscopy and time-of-flight mass spectrometry: application to a mixture of nonsteroidal antiinflammatory drugs. Anal. Chem. 72:2000;3922-3926.
14. Shockcor J.P., Unger S.E., Savina P., Nicholson J.K., Lindon J.C. Application of directly coupled LC-NMR-MS to the structural elucidation of metabolites of the HIV-1 reverse-transcriptase inhibitor BW935U83. J. Chromatogr. B. Biomed. Sci. Appl. 748:2000;269-279.
15. Dear G.J., Plumb R.S., Sweatman B.C., Ayrton J., Lindon J.C., Nicholson J.K., Ismail I.M. Mass directed peak selection, an efficient method of drug metabolite identification using directly coupled liquid chromatography-mass spectrometry-nuclear magnetic resonance spectroscopy. J. Chromatogr. B. Biomed. Sci. Appl. 748:2000;281-293.
16. Wilson I.D. Multiple hyphenation of liquid chromatography with nuclear magnetic resonance spectroscopy, mass spectrometry and beyond. J. Chromatogr. A. 892:2000;315-327.
17. Dear G.J., Plumb R.S., Sweatman B.C., Parry P.S., Roberts A.D., Lindon J.C., Nicholson J.K., Ismail I.M. Use of directly coupled ion-exchange liquid chromatography-mass spectrometry and liquid chromatography-nuclear magnetic resonance spectroscopy as a strategy for polar metabolite identification. J. Chromatogr. B. Biomed. Sci. Appl. 748:2000;295-309.
18. Keifer PA: The NMR toolkit for compound characterization. In Integrated Drug Discovery Technologies. Edited by Mei H-Y, Czarnik AW. New York, NY: Marcel Dekker Inc.; 2002:485-541.
19. Keifer PA: NMR spectroscopy in drug discovery: tools for combinatorial chemistry, natural products, and metabolism research. In Progress in Drug Research, vol 55. Edited by Jucker E. Basel: Birkhauser Verlag; 2000:137-211.
20. Keifer P.A. New methods for obtaining high-resolution NMR spectra of solid-phase synthesis resins, natural products, and solution-state combinatorial chemistry libraries. Drugs Future. 23:1998;301-317.
21. Keifer P.A. High-resolution NMR techniques for solid-phase synthesis and combinatorial chemistry. Drug Discov. Today. 2:1997;468-478.
22. 1H-NMR and MS). J. Pharm. Biomed. Anal. 27:2002;191-200 This is a nice illustration of an FIA-NMR application.
23. 1H-nuclear magnetic resonance spectroscopy and time-of-flight mass spectrometry. Analyst. 125:2000;927-931.
24. 1H NMR and HPLC characterization of a 96-member substituted methylene malonamic acid library. J. Comb. Chem. 1:1999;140-150.
25. Lewis K., Phelps D., Sefler A. Automated high-throughput quantification of combinatorial arrays. Am. Pharm. Rev. 3:2000;63-68.
26. Kalelkar S., Dow E.R., Grimes J., Clapham M., Hu H. Automated analysis of proton NMR spectra from combinatorial rapid parallel synthesis using self-organizing maps. J. Comb. Chem. 4:2002;622-629 This article discusses how to use self-organizing maps to facilitate the analysis of DI-NMR data.
27. Combs A., Rafalski M. N-arylation of sulfonamides on solid supports. J. Comb. Chem. 2:2000;29-32.
28. Gmeiner W.H., Cui W., Konerding D.E., Keifer P.A., Sharma S.K., Soto A.M., Marky L.A., Lown J.W. Shape-selective recognition of a model Okazaki fragment by geometrically-constrained bis-distamycins. J. Biomol. Struct. Dyn. 17:1999;507-518.
29. Stockman B.J., Farley K.A., Angwin D.T. Screening of compound libraries for protein binding using flow-injection nuclear magnetic resonance spectroscopy. Methods Enzymol. 338:2001;230-246 This contains a good discussion of the use of DI-NMR for NMR screening.
30. Potts B.C.M., Deese A.J., Stevens G.J., Reily M.D., Robertson D.G., Theiss J. NMR of biofluids and pattern recognition: assessing the impact of NMR parameters on the principal component analysis of urine from rat and mouse. J. Pharm. Biomed. Anal. 26:2001;463-476 This is a detailed study of how NMR parameters can affect the results from automated data analyses. Although the application is to metabonomics, the lessons learned may prove to be applicable to combinatorial chemistry.
31. Kraus W.E., Houmard J.A., Duscha B.D., Knetzger K.J., Wharton M.B., McCartney J.S., Bales C.W., Henes S., Samsa G.P., Otvos J.D.et al. Effects of the amount and intensity of exercise on plasma lipoproteins. N. Engl. J. Med. 347:2002;1483-1492.
32. Griffiths L., Horton R. Optimization of LC-NMR. III. Increased signal-to-noise ratio through column trapping. Magn. Reson. Chem. 36:1998;104-109.
33. de Koning J.A., Hogenboom A.C., Lacker T., Strohschein S., Albert K., Brinkman U.A.T. Online trace enrichment in hyphenated liquid chromatography-nuclear magnetic resonance spectroscopy. J. Chromatogr. A. 813:1998;55-61.
34. Bao D., Thanabal V., Pool W.F. Determination of tacrine metabolites in microsomal incubate by high performance liquid chromatography-nuclear magnetic resonance/mass spectrometry with a column trapping system. J. Pharm. Biomed. Anal. 28:2002;23-30 This is a recent application of the SPE-NMR method. SPE-NMR isn't currently used in combinatorial chemistry, but it bears watching.
35. Nyberg N.T., Baumann H., Kenne L. Application of solid-phase extraction coupled to an NMR flow-probe in the analysis of HPLC fractions. Magn. Reson. Chem. 39:2001;236-240.
36. Haner R.L., Llanos W., Mueller L. Small volume flow probe for automated direct-injection NMR analysis: design and performance. J. Magn. Reson. 143:2000;69-78.
37. Lacey M.E., Tan Z.J., Webb A.G., Sweedler J.V. Union of capillary high-performance liquid chromatography and microcoil nuclear magnetic resonance spectroscopy applied to the separation and identification of terpenoids. J. Chromatogr. A. 922:2001;139-149.
38. Kautz R.A., Lacey M.E., Wolters A.M., Foret F., Webb A.G., Karger B.L., Sweedler J.V. Sample concentration and separation for nanoliter-volume NMR spectroscopy using capillary isotachophoresis. J. Am. Chem. Soc. 123:2001;3159-3160.
39. Wolters A.M., Jayawickrama D.A., Larive C.K., Sweedler J.V. Capillary isotachophoresis/NMR: extension to trace impurity analysis and improved instrumental coupling. Anal. Chem. 74:2002;2306-2313.
40. Eldridge G.R., Vervoort H.C., Lee C.M., Cremin P.A., Williams C.T., Hart S.M., Goering M.G., O'Neil-Johnson M., Zeng L. High-throughput method for the production and analysis of large natural product libraries for drug discovery. Anal. Chem. 74:2002;3963-3971 This paper illustrates how microcoil probes could be used, and the whole field of microcoil probes is worth watching. Automated microcoil flow probes will be very useful tools when they become available.
41. 1H NMR characterization of the product from single solid-phase resin beads using capillary NMR flow probes. J. Magn. Reson. 153:2001;215-222.
42. Rashid M.A., Gustafson K.R., Crouch R.C., Groweiss A., Pannell L.K., Van Q.N., Boyd M.R. Application of high-field NMR and cryogenic probe technologies in the structural elucidation of poecillastrin a, a new antitumor macrolide lactam from the sponge Poecillastra species. Org. Lett. 4:2002;3293-3296.
43. Keun H.C., Beckonert O., Griffin J.L., Richter C., Moskau D., Lindon J.C., Nicholson J.K. Cryogenic probe 13C NMR spectroscopy of urine for metabonomic studies. Anal. Chem. 74:2002;4588-4593.
44. Macnaughtan M.A., Hou T., Macnamara E., Santini R.E., Raftery D. NMR difference probe. A dual-coil probe for NMR difference spectroscopy. J. Magn. Reson. 156:2002;97-103.
45. Zhang X., Sweedler J.V., Webb A.G. A probe design for the acquisition of homonuclear, heteronuclear, and inverse detected NMR spectra from multiple samples. J. Magn. Reson. 153:2001;254-258.
46. Hou T., Smith J., Macnamara E., Macnaughtan M., Raftery D. Analysis of multiple samples using multiplex sample NMR: selective excitation and chemical shift imaging approaches. Anal. Chem. 73:2001;2541-2546 Chemical shift imaging for multiplex NMR has the potential to make NMR acquisitions parallel. It remains to be seen whether it can yet be applied to real problems.
47. Ross A., Schlotterbeck G., Senn H., Von Kienlin M. Application of chemical shift imaging for simultaneous and fast acquisition of NMR spectra on multiple samples. Angew. Chem. Int. Ed. Engl. 40:2001;3243-3245.
48. Spitzer T., Sefler A.M., Rutkowske R. An improved DEPT-HMQC sequence for high-throughput NMR analysis. Magn. Reson. Chem. 39:2001;539-543.
49. Hodge P., Monvisade P., Morris G.A., Preece I. A novel NMR method for screening soluble compound libraries. Chem. Commun. 1:2001;239-240.
50. 1H NMR. Quantitation with a convenient and novel internal standard. J. Comb. Chem. 3:2001;434-440.
51. 1H NMR. J. Comb. Chem. 2:2000;39-41 The limitations of conventional NMR standards are well discussed. This is a good thought-provoking article about reference and quantification standards.
52. Elyashberg M.E., Blinov K.A., Williams A.J., Martirosian E.R., Molodtsov S.G. Application of a new expert system for the structure elucidation of natural products from their 1D and 2D NMR data. J. Nat. Prod. 65:2002;693-703.
53. 1H NMR chemical shifts using neural networks. Anal. Chem. 74:2002;80-90.
54. 1H NMR spectra: part 3. Confirmation of postulated chemical structure. Magn. Reson. Chem. 40:2002;623-634.
55. Rosse G., Neidig P., Schroder H. Automated structure verification of small molecules libraries using 1D and 2D NMR techniques. Methods. Mol. Biol. 201:2002;123-139.
56. Hu H., De Angelis A.A., Mandelshtam V.A., Shaka A.J. The multidimensional filter diagonalization method. J. Magn. Reson. 144:2000;357-366 It appears as if only a few people really understand FDM, but it will be great for combinatorial chemistry if FDM proves to be worthwhile.
57. Nyberg N.T., Baumann H., Kenne L. Solid-phase extraction NMR studies of chromatographic fractions of saponins from Quillaja saponaria. Anal. Chem. 75:2003;268-274.
58. Wolters A.M., Jayawickrama D.A., Sweedler J.V. Microscale NMR. Curr. Opin. Chem. Biol. 6:2002;711-716.
59. Spraul M., Freund A.S., Nast R.E., Withers R.S., Maas W.E., Corcoran O. Advancing NMR sensitivity for LC-NMR-MS using a cryoflow probe: application to the analysis of acetaminophen metabolites in urine. Anal. Chem. 75:2003;1536-1541.