Biblioteki związków chemicznych

Zwoliński, K. M.; Leśnikowski, Z. J.

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Tytuł artykułu

Biblioteki związków chemicznych

Autorzy

Zwoliński K. M. , Leśnikowski Z. J.

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Warianty tytułu

Libraries of chemical compounds

Języki publikacji

Abstrakty

Over the past decade one can observe a scientific revolution taking place resulting in an explosion of new biotechnologies. Moreover, with the end of the human genome project and following expansion of the extensive genetic research an unprecedented number of new biological targets useful in drug design have been identified. Simultaneously, new methods such as combinatorial synthesis have expanded the overall size of chemical libraries and high-throughtput technologies have enabled to screen more than one million compounds a day [43]. However, an increasing size of chemical libraries in a random fashion may not necessary increase a probability of success and the overall number of successfully identified leads. Thus, success of any drug discovery program depend heavily on the assumed selection criteria of appropriate molecules [58] which properties should maximize the chances of identifying ligands for any given target. Selection criteria used for compounds to generate diverse as well as focused chemical libraries are briefly discussed in the present overview. We describe the most important quality factors such as size, diversity and chemical tractability which should be always kept in mind during the design of chemical libraries. Chemical space is enormous and limited only by a chemist`s imagination. The number of possible drug-like molecules within chemical space has been estimated to be around 1060 [17]. In contrast the overall number of atoms in the observable Universe is approximately 1080. It is obvious that it is impossible to synthesize every possible molecule so one need to explore only those regions of chemical space which are enriched with molecules of appropriate structure and function. Recent strategies for the design of high-quality collections of structurally diverse sets of small molecules are discussed in the context of probing the chemical space in order to find new biologically active structures.

Słowa kluczowe

biblioteka chemiczna biblioteka wirtualna przestrzeń chemiczna związki naturalne leki

virtual library chemical library chemical space drugs natural products

Wydawca

Polskie Towarzystwo Chemiczne

Czasopismo

Wiadomości Chemiczne

Rocznik

2012

Tom

[Z] 66, 7-8

Strony

741--765

Opis fizyczny

Bibliogr. 123 poz., rys.

Twórcy

autor

Zwoliński K. M.

autor

Leśnikowski Z. J.

Pracownia Wirusologii Molekularnej i Chemii Biologicznej, Instytut Biologii Medycznej PAN ul. Lodowa 106, 93-232 Łódź, kzwolinski@cbm.pan.pl

Bibliografia

[1] R . Casey, Designing Chemical Compound Libraries for Drug Discovery, December 1, 2005, [on-line], Business Intelligence Network, dostępny w Internecie: http://www.b-eye-network.com/view/2039.
[2] E .A. Martis, R. Radhakrishnan, R.R. Badve, J. Appl. Pharm. Sci., 2011, 1, 2.
[3] H.D. Holtje, W. Sippl, D. Rognan, G. Folkers, Molecular Modeling - Basic Principles and Applications, Wiley-VC H Verlag GmbH&Co. Winheim, 2008, 3rd ed.
[4] a) L.A. Thompson, J.A. Ellman, Chem. Rev., 1996, 96, 555; b) E.E. Kim, C.T. Baker, M.D. Dwyer, M.A. Murcko, B.G. Rao, R.D. Tung, M.A. Navia, J. Am. Chem. Soc., 1995, 117, 1181.
[5] a) M. Paturej, M. El Fray, Polimery, 2009, 54, 179; b) V. Kholodovych, A.V. Gubskaya, M. Bohrer, N. Harris, D. Knight, J. Kohn, W.J. Welsh, Polymer, 2008, 49, 2435; c) S. Brocchini, K. James, V. T angpasuthadol, J. Kohn, J. Biomed. Mater. Res., 1998, 42, 66; d) C.H. Reynolds, J. Comb. Chem., 1999, 1, 297.
[6] a) A. Knappik, L.M. Ge, A. Honegger, P. Pack, M. Fischer, G. Wellnhofer, A. Hoess, J. Wolle, A. P luckthun, B. Virnekas, J. Mol. Biol., 2000, 296, 57; b) M. Littre, M. Welschof, M. Braunagel, L. Hermes, C. Christ, A. Keller, P. Rohrbach, T. Kurschner, S. Schmidt, C. Kleist, P. Terness, J. I mmunol. Methods, 1999, 231, 3; c) K. Charlton, W.J. Harris, A.J. Porter, Biosens. Bioelectron., 2001, 16, 639; d) C.W. Cobaugh, J.C. Almagro, M. Pogson, B. Iverson, G. Georgiou, J. Mol. Biol., 2008, 378, 622.
[7] a) V.J. Hruby, J.-M. Ahn, S. Liao, Curr. Opin. Chem. Biol., 1997, 1, 114; b) P.J. Schatz, Curr. Opin. Biotechnol., 1994, 5, 487.
[8] M . Denault, J.N. Pelletier, Methods Mol. Biol., 2007, 352, 127.
[9] a) M. Famulok, A. Jenne, Curr. Opin. Chem. Biol., 1998, 2, 320; b) E.M. LeProust, B.J. Peck, K. S pirin, H.B. McCuen, B. Moore, E. Namsaraev, M.H. Caruthers, Nucl. Acids Res., 2010, 38, 2522.
[10] a) H.S. Zaher, P.J. Unrau, Methods in Molecular Biology, v. 288: Oligonucleotide Synthesis: Methods and Applications, P. Herdewijn (ed.), Humana Press Inc., b) M.A. Cleary, K. Kilian, Y. Wang, J. Bradshaw, G. Cavet, W. Ge, A. Kulkarni, K. Chang, N. Sheth, E. Leproust, E.M. Coffey, J. Burchard, W.R. McCombie, P. Linsley, G.J. Hannon, Nat. Methods, 2004, 1, 241.
[11] S . Rafique, M. Idrees, A. Nasim, H. Akbar, A. Athar, Biotech. Mol. Biol. Rev., 2010, 5, 38.
[12] D . Chen, V. Milacic, M. Frezza, Q.P. Dou, Curr. Pharm. Des., 2009, 15, 777.
[13] M .S. Arayne, N. Sultana, U. Haroon, M.A. Mesaik, Bioinorg. Chem. Appl., 2009, Article ID 914105.
[14] V . Badmaev, S. Prakash, M. Majeed, J. Altern. Complement. Med., 1999, 5, 273.
[15] a) http://www.cas.org/cgi-bin/cas/regreport.pl, b) 63,461,917 związków na dzień 15.01.2012.
[16] A .D. Gorse, Curr. Top. Med. Chem., 2006, 6, 3.
[17] R .S. Bohacek, C. McMartin, W.C. Guida, Med. Res. Rev., 1996, 16, 3.
[18] P . Ertl, J. Chem. Inf. Comput. Sci., 2003, 43, 374.
[19] a) T. Fink, H. Bruggesser, J.-L. Reymond, Angew. Chem. Int. Ed., 2005, 44, 1504; b) T. Fink, J.-L. Reymond, J. Chem. Inf. Model., 2007, 47, 342.
[20] M . Feher, J. M. Schmidt, J. Chem. Inf. Comput. Sci., 2003, 43, 218.
[21] M olinspiration Cheminformatics virtual Screening Toolkit, ver. 2005.03, Molinspiration Cheminformatics: Slovensky Grob, Slovak Republic, 2005.
[22] L .C. Blum, J.-L. Reymond, J. Am. Chem. Soc., 2009, 131, 8732.
[23] J .-L. Reymond, R. van Deursen, L.C. Blum, L. Ruddigkeit, Med. Chem. Commun., 2010, 1, 30.
[24] C .A. Lipiński, A. Hopkins, Nature, 2004, 432, 855.
[25] G.V. Paolini, R.H. Shapland, W.P. van Hoorn, J.S. Mason, A.L. Hopkins, Nat. Biotechnol., 2006, 24, 805.
[26] C .M. Dobson, Nature, 2004, 432, 824.
[27] R . Todeschini, V. Consonni, Handbook of Molecular Descriptors, Wiley-VC H, Weinheim, 2000.
[28] J .L. Medina-Franco, K. Martinez-Mayorga, M.A. Giulianotti, R.A. Houghten, C. Pinilla, Curr. Comput.-Aided Drug Des., 2008, 4, 322.
[29] T .I. Oprea, J. Gottfries, J. Comb. Chem., 2001, 3, 157.
[30] J .-L. Reymond, R. van Deursen, Chem. Med. Chem., 2007, 2, 636.
[31] J .-L. Reymond, R. van Deursen, L.C. Blum, L. Ruddigkeit, Med. Chem. Commun., 2010, 1, 30.
[32] N . Nikolova, J. Jaworska, QSAR Comb. Sci., 2003, 22, 1006.
[33] H. Patel, M.J. Bodkin, B. Chen, V.J. Gillet, J. Chem. Inf. Model., 2009, 49, 1163.
[34] a) R. Kurczab, Przemysł Farmaceutyczny, 2011, 5, 88; b) S. Polak, B. Wiśniowska, Farmacja Polska, 2009, 65, 214; c) P. Setny, [on-line] dostępny na stronie www, http://www.icm.edu.pl/kdm/Projektowanie_leków.
[35] U . Schopfer, F. Hohn, M. Hueber, M. Girod, C. Engeloch, M. Popov, I. Muckenschnabel., J. Biomol. Screen., 2007, 12, 724.
[36] S . Lane, B. Boughtflower, I. Mutton, C. Paterson, D. Farrant, N. Taylor, Z. Blaxill, C. Carmody, P. Borman, Anal. Chem., 2005, 77, 4354.
[37] R . Lucena, S. Cardenas, M. Valcarcel., Anal. Bioanal. Chem., 2007, 388, 1663.
[38] K . Oldenburg, D. Pooler, K. Scudder, C. Lipinski, M. Kelly, Comb. Chem. High Throughput Screen., 2005, 8, 499.
[39] F . Li, C. Zhang, X. Guo, W. Feng, Biomed. Chromatogr., 2003, 17, 96.
[40] V . Pinciroli, R. Biancardi, N. Colombo, et al. J. Comb. Chem., 2001, 3, 434.
[41] A . Dalby, J.G. Nourse, W.D. Hounshell, A.K.I. Gushurst, D.L. Grier, B.A. Leland, J. Laufer., J. Chem. Inf. Comput. Sci., 1992, 32, 244.
[42] G.M. Rishton, Drug Discov. Today, 1997, 2, 382.
[43] L .M. Mayr, P. Fuerst, J. Biomol. Screen., 2008, 13, 443.
[44] D .J. Huggins, A.R. Venkitaraman, D.R. Spring., ACS Chem. Biol., 2011, 6, 208.
[45] M .D. Burke, S.L. Schreiber, Angew. Chem. Int. Ed., 2004, 43, 46.
[46] a) R.W. DeSimone, K.S. Currie, S.A. Mitchell, J.W. Darrow, D.A. Pippin, Comb. Chem. High Throughput Screen, 2004, 7, 473; b) C.D. Duarte, E.J. Barreiro, C.A.M. Fraga, Mini Rev. Med. Chem., 2007, 7, 1108.
[47] P .L. Myers, J.W. Greene, J. Saunders, S.L. Teig, Todays Chemist at work, 1997, 6, 47.
[48] D .R. Spring, Org. Biomol. Chem., 2003, 1, 3867.
[49] E .J. Corey, X.-M. Cheng, The logic of Chemical Synthesis, Wiley, New York, 1995.
[50] D .H. Drewry, S.S. Young, Chemom. Intell. Lab. Syst., 1999, 48, 1.
[51] a) L. Tan, E. Loukine, J. Bajorath, J. Chem. Inf. Model., 2008, 48, 2308; b) Z. Deng, C. Chuaqui, J. Singh, J. Med. Chem., 2006, 49, 490.
[52] a) D.E. Goldberg, Algorytmy genetyczne i ich zastosowania, Warszawa, WNT, 1998; b) A.L. Parrill, Drug Discov. Today, 1996, 1, 514.
[53] L . Weber, S. Wallbaum, C. Broger, K. Gubernator, Angew. Chem. Int. Ed., 1995, 34, 2280.
[54] a) O. Prien, ChemBioChem., 2005, 6, 500; b) G. Muller, Drug Discov. Today, 2003, 8, 681.
[55] R .L. Rice, J.M. Rusnak, F. Yokokawa, S. Yokokawa, D.J. Messner, A.L. Boynton, P. Wipf, J.S. Lazo, Biochemistry, 1997, 36, 15965.
[56] B.E. Evans, K.E. Rittle, M.G. Bock, R.M. DiPardo, R.M. Freidinger, W.L. Whitter, G.F. Lundell, D.F. Veber, P.S. Anderson, J. Med. Chem., 1988, 31, 2235.
[57] a) M.E. Welsch, S.A. Synder, B.R. Stockwell., Curr. Opin. Chem. Biol., 2010, 14, 347; b) R.W. DeSimone, K.S. Curie, S.A. Mitchell, J.W. Darrow, D.A. Pippin, Comb. Chem. High Throughput Screen., 2004, 7, 473.
[58] M .M. Olah, C.G. Bologa, T.I. Oprea, Curr. Drug. Discov. Technol., 2004, 1, 211.
[59] M . Olah, M. Mracec, L. Ostopovivi, R. Rad, A. Bora, N. Hadaruga, L. Olah, M. Banda, Z. Simon, M. Mracec, T.I. Oprea, Chemoinformatics in Drug Discovery, T.L. Oprea, Ed.; Wiley-VC H: New York, 2004, 223.
[60] E .A. Coats, 3D QSAR in Drug Design, Vol. 3, H. Kubinyi, G. Folkers, Y. C. Martin, Eds., Kluwer/ESCOM , Dordrecht, 1998, str. 199.
[61] a) D. Weininger, J. Chem. Inf. Comput. Sci., 1988, 28, 31; b) D. Weininger, A. Weininger, J.L. Weininger, J. Chem. Inf. Comput. Sci., 1989, 29, 97.
[62] a) O. Roche, P. Schneider, J. Zuegge, W. Guba, M. Kansy, A. Alanine, K. Bleicher, F. Danel., E.M. Gutknecht, M. Rogers-Evans, W. Neidhart, H. Stalder, M. Dillon, E. Sjogren, N. Fotouhi, P. Gillespie, R. Goodnow, W. Harris, P. Jones, M. Taniguchi, S. Tsujii, W. von der Saal, G. Zimmermann, G. Schneider, J. Med. Chem., 2002, 45, 137; b) S.L. McGovern, E. Caselli, N. Grigorieff, B.K. S hoichet, J. Med. Chem., 2002, 45, 1712; c) R.P. Sheridan, J. Chem. Inf. Comput. Sci., 2003, 43, 1037.
[63] a) H. van De Waterbeemd, D.A. Smith, K. Beaumont, D.K. Walter, J. Med. Chem., 2001, 44, 1313; b) D .F. Veber, S.R. Johnson, H.Y. Cheng, B.R. Smith, K.W. Ward, K.D. Kopple., J. Med. Chem., 2002, 45, 2615.
[64] a) J. Ashby, D. Paton, Mutation Res., 1993, 286, 3; b) N. Green, Adv. Drug Deliv. Rev, 2002, 54, 417.
[65] a) P.S. Charifson, W.P. Walters, J. Comput. Aided Mol. Des., 2002, 16, 311; b) M. Hann, B. Hudson, X. Lewell, R. Lifely, L. Miller, N. Ramsden, J. Chem. Inf. Comput. Sci., 1999, 39, 897.
[66] a) T.I. Oprea, J. Comput. Aided Mol. Des., 2000, 14, 251; b) S. Sirois, G. Hatzakis, D. Wei, Q. Du, K.-Ch. Chou, Comput. Biol. Chem., 2005, 29, 55; c) G.M. Rishton, Drug. Disc. Today, 1997, 2, 382.
[67] a) R.C. Onderwater, J.N. Commandeur, E.J. Groot, A. Sitters, W.M. Menge, N.P. Vermeulen, Toxicology, 1998, 125, 117; b) G.F. Smith., Prog. Med. Chem., 2011, 50, 1.
[68] FILTER OpenEye Scientific Software, http://zinc.docking.org
[69] Chemia leków, Ewaryst Pawełczyk (ed.), Państwowy Zakład Wydawnictw Lekarskich, Warszawa 1978, str. 557.
[70] H. Xu, Curr. Top. Med. Chem., 2002, 2, 1305.
[71] a) E. Estrada, E. Uriarte, Curr. Med. Chem., 2001, 8, 1573; b) S. Fergus, A. Bender, D.R. Spring, Curr. Opin. Chem. Biol., 2005, 9, 304.
[72] a) R. Todeschini, V. Consonni, Handbook of Molecular Descriptors, WILEY -VC H, 2000; b) R . T odeschini, V. Consonni, Molecular Descriptors for Chemoinformatics (2 volumes), Wiley-VC H, 2009; c) C. Bologa, T. K. Allu, M.Olah, M. A. Kappler, T. I. Oprea, J. Comput. Aided Mol. Des. 2005, 19, 625; d) V.J. Sykora, D.E. Leahy, J. Chem. Inf. Model., 2008, 48, 1931.
[73] E .J. Martin, J.M. Blaney, M.A. Siani, D.C. Spellmeyer, A.K. Wong, W.H. Moos, J. Med. Chem., 1995, 38, 1431.
[74] a) M. Hahn, J. Chem. Inf. Comput. Sci., 1997, 37, 80; b) S. Renner, G. Schneider, Chem. Med. Chem., 2006, 1, 181.
[75] a) S. Nikolić, N, Trinajstić, I.M. Tolić, J. Chem. Inf. Comput. Sci., 2000, 40, 920; b) R.J. Spandl, A. Bender, D.R. Spring, Org. Biomol. Chem., 2008, 6, 1149.
[76] A .L. Hopkins, J.S. Mason, J.P. Overington, Curr. Opin. Struct. Biol., 2006, 16, 127.
[77] I . Kola, J. Landis, Nat. Rev. Drug. Discov., 2004, 3, 711.
[78] a) C.A. Lipinski, F. Lombardo, B.W. Dominy, P.J. Feeney, Adv. Drug Deliv. Rev., 1997, 23, 3; b) C.A. Lipinski, F. Lombardo, B.W. Dominy, P.J. Feeney, Adv. Drug Deliv. Rev., 2001, 46, 3.
[79] C .A. Lipiński, Drug Discov. Today: Technologies, 2004, 1, 337.
[80] D .E. Clark, S.D. Pickett., Drug Discov. Today, 2000, 5, 49.
[81] D .F. Veber, S.R. Johnson, H.Y. Cheng, B.R. Smith, K.W. Ward, K.D. Kopple, J. Med. Chem., 2002, 45, 2615.
[82] J . Clardy, C. Walsh., Nature, 2004, 432, 829.
[83] T .I. Oprea, Mol. Divers., 2002, 5, 199.
[84] a) T.H. Keller, A. Pichota, Z. Yin, Curr. Opin. Chem. Biol., 2006, 10, 357; b) T. Fichert, M. Yazdanian, J.R. Proudfoot, Bioorg. Med. Chem. Lett., 2003, 13, 719; c) I. Muegge, Med. Res. Rev., 2003, 23, 302; d) M.C. Wenlock, R.P. Austin, P. Barton, A.M. Davis, P.D. Leeson, J. Med. Chem., 2003, 46, 1250.
[85] A . Luch, The Carcinogenic Effects of Polycyclic Aromatic Hydrocarbons, 2005, Imperial College Press.
[86] K . Muller, Ch. Faeh, F. Diederich, Science, 2007, 317, 1881.
[87] a) D.C. Rees, M.S. Congreve, C.W. Murray, R. Carr., Nat Rev. Drug Discov., 2004, 3, 660; b) D.A. Erlanson, R.S. McDowell, T. O`Brien, J. Med. Chem., 2004, 47, 3463.
[88] a) M. Congreve, R. Carr, C. Murray, H. A. Jhoti, Drug Discov. Today, 2003, 8, 876; b) M. Cherry, T. M itchell, Introduction to Fragment-Based Drug Discovery, [w:] Fragment-Based Drug Discovery: A Practical Approach, 2008, John Wiley&Sons, Ltd., rozdział 1.
[89] A .L. Hopkins, C.R. Groom, A. Alex, Drug Discov. Today, 2004, 9, 430.
[90] C . Abad-Zapatero, J.T. Metz, Drug Discov. Today, 2005, 10, 464.
[91] J . Baker, T. Hesterkamp, D. Whittaker, Drug Discov. World., 2008, 3, 67.
[92] a) L. Di, E.H. Kerns, Drug Discov. Today, 2006, 11, 446; b) A. Schuffenhauer, S. Ruedisser, A.L. Marzinzik, W. Jahnke, M.J. Blommers, P. Selzer, E. Jacoby, Curr. Top. Med. Chem., 2005, 5, 751.
[93] M . Hohwy, L. Spadola, B. Lundquist, P. Hawtin, J. Dahmen, I. Groth-Clausen, E. Nilsson, S. Persdotter, K. von Wachenfeldt, R.H.A. Folmer, K. Edman, J. Med. Chem., 2008, 51, 2178.
[94] P .J. Hajduk, R.P. Meadows, S.W. Fesik, Science, 1997, 278, 497.
[95] G.W. Bemis, M.A. Murcko, J. Med. Chem., 1996, 39, 2887.
[96] G.W. Bemis, M.A. Murcko, J. Med. Chem., 1999, 42, 5095.
[97] a) J. Fejzo, C.A. Lepre, J.W. Peng, G.W. Bemis, Ajay, M.A. Murcko, J.M. Moore, Chem. Biol., 1999, 6, 755; b) C.A. Lepre, J. Peng, J. Fejzo, N. Abdul-Manan, J. Pocas, M. Jacobs, X. Xie, J.M. Moore, Comb. Chem. High Throughput Screen., 2002, 5, 583.
[98] X. Q. Lewell, D.B. Judd, S.P. Watson, M.M. Hann, J. Chem. Inf. Comput. Sci., 1998, 38, 511.
[99] K . Babaoglu, B.K. Shoichet, Nat. Chem. Biol., 2006, 2, 720.
[100] A . Schuffenhauer, Curr. Top. Med. Chem., 2005, 5, 751.
[101] a) J.C. Priscu, C.H. Fritsen, E.E. Adams, S.J. Giovannoni, H.W. Paerl, C.P. McKay, P.T. Doran, D.A. Gordon, B.D. Lanoil, J.L. Pinckney, Science, 1998, 280, 2095; b) J.T. Staley, J.J. Gosink, Annu. Rev. Microbiol., 1999, 53, 189.
[102] a) E. Blochl, R. Rachel, S. Burggraf, D. Hafenbradl, H.W. Jannasch, K.O. Stetter, Extremophiles, 1997, 1, 14; b) H. Takami, K. Kobata, T. Nagahama, H. Kobayashi, A. Inoue, K. Horikoshi, Extremophiles, 1999, 3, 97.
[103] L . Groth, P. Schumann, B. Schuetze, K. Augsten, I. Kramer, E. Stackebrandt, Int. J. Syst. Bacteriol., 1999, 49, 1733.
[104] S .L. Pimm, G.J. Russell, J.L. Gittleman, T.M. Brooks, Science, 1995, 269, 347.
[105] R . Vapoorte., Drug Discov. Today, 1998, 3, 232.
[106] a) A. Sittenfeld, R. Villers, Curr. Opin. Biotechnol., 1993, 4, 280; b) B. M. Olivera, C. Walker, G.E. C artier, D. Hooper, A.D. Santos, R. Schoenfeld, R. Shetty, M. Watkins, P. Bandyopadhyay, D.R. Hillyard, Ann. New York Acad. Sci., 1999, 870, 223.
[107] a) R. Verpoorte, J. Pharm. Pharmacol., 2000, 52, 253; b) J. D. Phillipson, L.A. Anderson, J. Ethnopharmacol., 1989, 25, 61; c) A.D. Kinghorn, Biotechnology, 1994, 26, 81.
[108] E . Williamson, D.T. Okpako, F.J. Evans, Selection, Preparation and Pharmacological Evaluation of Plant Material, 1996, Wiley, Chichester.
[109] S .M. Rates, Toxicon, 2001, 39, 603.
[110] M . Zhu, J.D. Phillipson, P.M. Greengrass, N.E. Bowery, Y. Cai, Phytochemistry, 1999, 44, 441.
[111] M .S. Butler, J. Nat. Prod., 2004, 67, 2141.
[112] R . Verpoorte, J. Ethnopharmacol., 1989, 25, 43.
[113] E .M. Williamson, Phytomedicine, 2001, 8, 401.
[114] B. Gilbert, L.F. Alves, Curr. Med. Chem., 2003, 10, 13.
[115] M . Hamburger, K. Hostettmann, Phytochem., 1991, 30, 12, 3864.
[116] P .A. Keifer, Curr. Opin. Chem. Biol., 2003, 7, 388.
[117] a) N. Bross-Walch, T. Kuhn, D. Moskau, O. Zerbe, Chem. Biodiversity, 2005, 2, 147; b) G.E. Martin, R.C. Crouch, Two-Dimensional NMR Spectroscopy: Applications for Chemists and Biochemists, R.M.K. Carlton, W.R. Croasmun (eds.), 1994, Wiley-VC H, Weinheim,.
[118] a) Ginkgo Biloba, T.A. van Beek (ed.), 2000, Amsterdam, Harwood Academic Publ.; b) S. Furukawa, Scientific Papers of the Institute of Physical and Chemical Research, Tokio, 1932, 19, 27.
[119] a) K. Ingkaninan, A. Hazekamp, A.C. Hoek, S. Balconi, R. Verpoorte, J. Liq. Chrom. Rel. Technol. 2000, 23, 2195; b) G.A. Cordell, Y.G. Shin, Pure Appl. Chem., 1999, 71 1089;
[120] J .D. McChesney, Chemistry of the Amazon, Biodiversity, Nature Products and Environmental Issues, ACS Symposium Series No. 88 American Chemical Society, Washington, DC , 1995.
[121] M . Wani, H. Taylor, M. Wall, P. Coggon, A. McPhail, J. Am. Chem. Soc., 1971, 93, 2325.
[122] Ł. Szoka, Gazeta Farmaceutyczna, 2009, 9, 34.
[123] a) C.T. Walsh, Science, 2004, 303, 1805; b) J. Lau, S. Frykman, R. Regentin, S. Ou, H. Tsuruta, P. Licari, Biotechnol. Bioeng., 2002, 78, 280.

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