Guiding principles for natural product drug discovery

Future Medicinal Chemistry

Volumn 4, Issue 9, 2012, Pages 1067-1084

  Camp, David ^a   Davis, Rohan A ^a   Evans Illidge, Elizabeth A ^b   Quinn, Ronald J ^a  

^a GRIFFITH UNIVERSITY   (Australia)

^b AUSTRALIAN INSTITUTE OF MARINE SCIENCE   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

CAMPTOTHECIN; CASPOFUNGIN; ERIBULIN; IRINOTECAN; NATURAL PRODUCT; PACLITAXEL; PNEUMOCANDIN DERIVATIVE; RAPAMYCIN; TOPOTECAN; TRABECTEDIN;

DRUG DELIVERY SYSTEM; DRUG INDUSTRY; DRUG SCREENING; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; PHYSICAL CHEMISTRY; PRACTICE GUIDELINE; PRIORITY JOURNAL; REVIEW;

BIOLOGICAL AGENTS; BIOLOGICAL ASSAY; DRUG DISCOVERY;

EID: 84862569342     PISSN: 17568919     EISSN: 17568927     Source Type: Journal    
DOI: 10.4155/fmc.12.55     Document Type: Review

References (97)

1. Newman DJ, Cragg GM. Natural products as sources of new drugs over the 30 years from 1981 to 2010. J. Nat. Prod. 75(3), 311-335 (2012).
2. Grajal A. Biodiversity and the nation state: regulating access to genetic resources limits biodiversity research in developing countries. Conserv. Biol. 13(1), 6-10 (1999). (Pubitemid 29073136)
3. Young TR. The challenge of a new regime: the quest for certainty in access to genetic resources and benefit-sharing. Asian Biotechnol. Develop. Rev. 10(3), 113-136 (2008).
4. Macarron R. Critical review of the role of HTS in drug discovery. Drug Discov. Today 11(7-8), 277-279 (2006).
5. Leeson PD, Davis AM. Time-related differences in the physical property profiles of oral drugs. J. Med. Chem. 47(25), 6338-6348 (2004). (Pubitemid 39587257)
6. Leeson PD, Davis AM, Steele J. Drug-like properties: guiding principles for design-or chemical prejudice? Drug Discov. Today Technol. 1(3), 189-195 (2004). (Pubitemid 40197566)
7. Lipinski CA, Lombardo F, Dominy B, Feeney PJ. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv. Drug Del. Rev. 23(1-3), 3-25 (1997). (Pubitemid 27046991)
8. Hann MM. Molecular obesity, potency and other addictions in drug discovery. Med. Chem. Commun. 2(5), 349-355 (2011).
9. Macarron R, Luengo JI. Yin and Yang in medicinal chemistry: what does drug-likeness mean? Future Med. Chem. 3(5), 505-507 (2011).
10. Sugano K, Kansy M, Artursson P et al. Coexistence of passive and carrier-mediated processes in drug transport. Nat. Rev. Drug Discov. 9(8), 597-614 (2010).
11. Teague SJ, Davis AM, Leeson PD, Oprea T. The design of leadlike combinatorial libraries. Angew. Chem. Int. Ed. Engl. 38(24), 3743-3747 (1999).
12. Oprea TI, Bologa C, Olah MJ. Compound selection for virtual screening. In: Virtual Screening in Drug Discovery. Alvarez JC, Shoichet B (Eds) Marcel Dekker Inc., NY, USA, 89-106 (2004).
13. Hann MM, Oprea TI. Pursuing the leadlikeness concept in pharmaceutical research. Curr. Opin. Chem. Biol. 8(3), 255-263 (2004). (Pubitemid 38759400)
14. Hansch C. Quantitative approach to biochemical structure-activity relationships. Acc. Chem. Res. 2(8), 232-239 (1969).
15. Tute MS. Principles and practice of Hansch analysis. Guide to structure-activity correlation for the medicinal chemist. In: Advanced Drug Research. Harper NJ, Simmonds AB (Eds) Academic, New York, NY, USA, 1-77 (1971).
16. van de Waterbeemd H, Smith DA, Beaumont K, Walker DK. Property-based design: optimization of drug absorption and pharmacokinetics. J. Med. Chem. 44(9), 1313-1333 (2001). (Pubitemid 32852106)
17. Cronin MTD. The role of hydrophobicity in toxicity prediction. Curr. Comp. Aided Drug Des. 2(4), 405-413 (2006). (Pubitemid 46029596)
18. Ganesan A. The impact of natural products upon modern drug discovery. Curr. Opin. Chem. Biol., 12(3), 306-317 (2008).
19. Williams J, Read C, Norton A et al.Biodiversity, Australia State of the Environment Report 2001 (Theme Report). Heritage D (Ed.) CSIRO Publishing, Melbourne, Australia (2001).
20. Cordell GA, Colvard MD. Natural products and traditional medicine: turning on a paradigm. J. Nat. Prod. 75(3), 514-525 (2012).
21. Evans-Illidge EA, Battershill CN. Marine natural products discovery in Australia-from reef to royalty, and the pursuit of Convention for Biological Diversity (CBD) compliance. J. Biolaw Bus. Special SUPPL. Aus. 23-27 (2007).
22. Kate K, Laird SA. The Commercial Use of Biodiversity-Access to Genetic Resources and Benefit Sharing. Earthscan, London, UK (1999).
23. Glowka L. A Guide to Designing Legal Frameworks to Determine Access to Genetic Resourcesl. International Union for Conservation of Nature, Switzerland(1998).
24. McConnell K. The Biodiversity Convention-A Negotiating History. Kluwer Law International, London, UK (1996).
25. Gollin M. An Intellectual Property Rights Framework for Biodiversity Prospecting. WRI, Washington, DC, USA (1993).
26. Bindseil KU, Jakupovic J, Wolf D, Lavayre J, Leboul J, van der Pyl D. Pure compound libraries; a new perspective for natural product based drug discovery. Drug Discov. Today 6(16), 840-847 (2001). (Pubitemid 32734512)
27. Abel U, Koch C, Speitling M, Hansske FG. Modern methods to produce natural-product libraries. Curr. Opin. Chem. Biol. 6(4), 453-458 (2002). (Pubitemid 34804767)
28. Quinn RJ, Carroll AR, Pham NB et al. Developing a drug-like natural product library. J. Nat. Prod. 71(3), 464-468 (2008). (Pubitemid 351549376)
29. Pereira DA, Williams JA. Origin and evolution of high throughput screening. Br. J. Pharmacol. 152(1), 53-61 (2007). (Pubitemid 47339909)
30. Quinn RJ. High-throughput screening in natural product drug discovery in Australia utilising Australia's biodiversity. Drug Dev. Res. 46(3-4), 250-254 (1999). (Pubitemid 29258922)
31. Quinn RJ. QPRI's system for screening of natural products. In: Bioassay Methods in Natural Product Research and Drug Development. Bohlin L, Bruhn JG (Eds). Kluwer Academic Publishers, Dordrecht, The Netherlands, 151-157 (1999).
32. Wagenaar MM. Pre-fractionated microbial samples-the second generation natural products library at Wyeth. Molecules 13(6), 1406-1426 (2008).
33. Baell JB, Holloway GA. New substructure filters for removal of pan assay interference compounds (PAINS) from screening libraries and for their exclusion in bioassays. J. Med. Chem. 53(7), 2719-2740 (2010).
34. Baell JB. Observations on screening-based research and some concerning trends in the literature. Future Med. Chem. 2(10), 1529-1546 (2010).
35. Eldridge GR, Veroort HC, Lee CM et al. High-throughput method for the production and analysis of large natural product libraries for drug discovery. Anal. Chem. 74(16), 3963-3971 (2002). (Pubitemid 34912891)
36. Appleton DR, Buss AD, Butler MS. A simple method for high-throughput extract prefractionation for biological screening. Chimia 61(6), 327-331 (2007).
37. Tu Y, JC, Ruan H et al. Automated high-throughput system to fractionate plant natural products for drug discovery. J. Nat. Prod. 73(4), 751-754 (2010).
38. Camp D, Davis RA, Campitelli M, Ebdon J, Quinn RJ. Drug-like properties: guiding principles for the design of natural product libraries. J. Nat. Prod. 75(1), 72-85 (2012).
39. Bugni TS, Richards B, Bhoite L, Cimbora D, Harper MK, Ireland CM. Marine natural product libraries for high-throughput screening and rapid drug discovery. J. Nat. Prod. 71(6), 1095-1098 (2008). (Pubitemid 352008917)
40. Johnson TA, Sohn J, Inman WD et al. Natural product libraries to accelerate the high-throughput discovery of therapeutic leads. J. Nat. Prod. 74(12), 2545-2555 (2011).
41. Shoichet BK. Screening in a spirit haunted world. Drug Discov. Today 11, 607-615 (2006).
42. Thorne N, Auld DS, Inglese J. Apparent activity in high-throughput screening: origins of compound-dependent assay interference. Curr. Opin. Chem. Biol. 14, 315-324 (2010).
43. Macarron R, Banks MN, Bojanic D et al. Impact of high-throughput screening in biomedical research. Nat. Rev. Drug Discov. 10(3), 188-195 (2011).
44. Munos B. Lessons from 60 years of pharmaceutical innovation. Nat. Rev. Drug Discov. 8(12), 959-968 (2009).
45. Lombardo F, Shalaeva MY, Tupper KA, Gao F, Abraham MH. ElogPoct: a tool for lipophilicity determination in drug discovery. J. Med. Chem. 43(15), 2922-2928 (2000). (Pubitemid 30599650)
46. Avery VM, Camp D, Carroll AR, Jenkins ID, Quinn RJ. The identification of bioactive natural products by high throughput screening (HTS). In: Comprehensive Natural Products II. Chemistry and Biology. Mander LN, Lui HW (Eds). Elsevier, Oxford, UK, 177-203 (2010).
47. Hopkins AL, Groom CR, Alex A. Ligand efficiency: a useful metric for lead selection. Drug Discov. Today 9(10), 430-431 (2004). (Pubitemid 38510559)
48. Buchanan MS, Davis RA, Duffy S, Avery VM, Quinn RJ. Antimalarial benzylisoquinoline alkaloid from the rainforest tree Doryphora sassafras. J. Nat. Prod. 72, 1541-1543 (2009).
49. Mueller D, Davis RA, Duffy S, Avery VM, Camp D, Quinn RJ. Antimalarial activity of azafluorenone alkaloids from the australian tree Mitrephora diversifolia. J. Nat. Prod. 72(8), 1538-1540 (2009).
50. Davis RA, Duffy S, Avery VM, Camp D, Hooper JNA, Quinn RJ. (+)-7-bromotrypargine, an antimalarial b-carboline from the australian marine sponge, Ancorina sp. Tetra. Lett. 51(4), 583-585 (2010).
51. Yang X, Davis RA, Buchanan MS et al. Antimalarial bromotyrosine derivatives from the Australian marine sponge Hyattella sp. J. Nat. Prod. 73(5), 985-987 (2010).
52. Feng Y, Davis RA, Sykes ML et al. Antitrypanosomal pyridoacridine alkaloids from the Australian ascidian, Polysyncraton echinatum. Tetra. Lett. 51(18), 2477-2479 (2010).
53. Feng Y, Davis RA, Sykes ML, Avery VM, Camp D, Quinn RJ. Pseudoceratinazole A: a novel bromotyrosine alkaloid from the Australian sponge Pseudoceratina sp. Tetra. Lett. 51(37), 4847-4850 (2010).
54. Feng Y, Davis RA, Sykes ML, Avery VM, Camp D, Quinn RJ. Antitrypanosomal cyclic polyketide peroxides from the Australian marine sponge Plakortis sp. J. Nat. Prod. 73(4), 716-719 (2010).
55. Davis RA, Sykes ML, Avery VM, Camp D, Quinn RJ. Convolutamines I and J, antitrypanosomal alkaloids from the bryozoan Amathia tortusa. Bioorg. Med. Chem. 19(22), 6615-6619 (2011).
56. Yin S, Davis RA, Shelper T et al. Pseudoceramines A-D, new antibacterial bromotyrosine alkaloids from the marine sponge Pseudoceratina sp. Org. Biomol. Chem. 9(19), 6755-6760 (2011).
57. Dictionary of Natural Products on DVD. Taylor and Francis Group/CRC Press, London, UK (2011).
58. Hillgren JM, Öberg CT, Elofsson M. Syntheses of pseudoceramines A-D and a new synthesis of spermatinamine, bromotyrosine natural products from marine sponges. Org. Biomol. Chem. 10(6), 1246-1254 (2012).
59. Bhal SK, Kassam K, Peirson IG, Pearl GM. The rule of five revisited: applying log D in place of log P in drug-likeness filters. Mol. Pharm. 4, 556-560 (2007). (Pubitemid 47310166)
60. DiMasi JA, Hansen RW, Grabowski HG. The price of innovation: new estimates of drug development costs. J. Health Econ. 22(2), 151-185 (2003). (Pubitemid 36279392)
61. DiMasi JA, Grabowski HG. The cost of biopharmaceutical R&D: is biotech different? Manage. Decis. Econ. 28(4-5), 469-479 (2007).
62. Davis RA, Fechner GA, Sykes ML et al. (-)-Dibromophakellin: an alpha 2B adrenoceptor agonist isolated from the Australian marine sponge, Acanthella costata. Bioorg. Med. Chem. 17(6), 2497-2500 (2009).
63. Davis RA, Carroll AR, Duffy S et al. Endiandrin A, a potent glucocorticoid receptor binder isolated from the Australian plant Endiandra anthropophagorum. J. Nat. Prod. 70(7), 1118-1121 (2007). (Pubitemid 47279902)
64. Mickel SJ, Sedelmeier GH, Niederer D et al. Large-scale synthesis of the anti-cancer marine natural product (+)-discodermolide. Part 1: synthetic strategy and preparation of a common precursor. Org. Proc. Res. Dev. 8(1), 92-100 (2004). (Pubitemid 38175718)
65. Mickel SJ, Sedelmeier GH, Niederer D et al. Large-scale synthesis of the anti-cancer marine natural product (+)-discodermolide. Part 2: synthesis of fragments C1-6 and C9-14. Org. Proc. Res. Dev. 8(1), 101-106 (2004). (Pubitemid 38175719)
66. Mickel SJ, Sedelmeier GH, Niederer D et al. Large-scale synthesis of the anti-cancer marine natural product (+)-discodermolide. Part 3: synthesis of fragment C15-21. Org. Proc. Res. Dev. 8(1), 107-112 (2004). (Pubitemid 38175720)
67. Mickel SJ, Sedelmeier GH, Niederer D et al. Large-scale synthesis of the anti-cancer marine natural product (+)-discodermolide. Part 4: preparation of fragment C7-24. Org. Proc. Res. Dev. 8(1), 113-121 (2004). (Pubitemid 38175721)
68. Mickel SJ, Niederer D, Daeffler R et al. Large-scale synthesis of the anti-cancer marine natural product (+)-discodermolide. Part 5: linkage of fragments C1-6 and C7-24 and finale. Org. Proc. Res. Dev. 8(1), 122-130 (2004). (Pubitemid 38175722)
69. Koehn FE, Carter GT. The evolving role of natural products in drug discovery. Nat. Rev. Drug Discov. 4(3), 206-220 (2005). (Pubitemid 40372555)
70. Kennedy J. Mutasynthesis, chemobiosynthesis, and back to semi-synthesis: combining synthetic chemistry and biosynthetic engineering for diversifying natural products. Nat. Prod. Rep. 25(1), 25-34 (2008). (Pubitemid 351207544)
71. Ikeda Y, Idemoto H, Hirayama F et al. Safracins, new antitumor antibiotics. I. Producing organism, fermentation and isolation. J. Antibiot. 36(10), 1279-1283 (1983). (Pubitemid 14232192)
72. Cuevas C, Pérez M, Martín MJ et al. Synthesis of ecteinascidin ET-743 and phthalascidin Pt-650 from cyanosafracin B. Org. Lett. 2(16), 2545-2548 (2000).
73. Evans-Illidge E. Natural ways-learning from nature's 4.5 billion year biotechnology project. Aust. Sci. 67, 36-39 (2004).
74. Camp D, Quinn RJ. Biodiscovery for natural product pharmaceuticals: an Australian experience. J. Biolaw Bus. Special SUPPL. Aus. 39-43 (2007).
75. Dalton R. Bioprospects less than golden. Nature 429(6992), 598-600 (2004). (Pubitemid 38812295)
76. Carrizosa S, Brush SB, Wright BD, McGuire PE. Accessing Biodiversity and Sharing the Benefits: Lessons from Implementing the Convention on Biological Diversity. International Union for Conservation of Nature, Switzerland (2004).
77. Benavidez P II. The challenges in the implementation of the Philippine ABS regulations: monitoring and enforcement of bioprospecting activities. Presented at: International Expert Workshop on Access to Genetic Resources and Benefit Sharing. Cuernavaca, Mexico, 24-27 October 2004.
78. Lettington RJL. National access laws, continuing monitoring, and enforcement issues. Presented at: International Expert Workshop on Access to Genetic Resources and Benefit Sharing. Cuernavaca, Mexico, 24-27 October 2004.
79. Buck M, Hamilton C. The Nagoya Protocol on access to genetic resources and the fair and equitable sharing of benefits arising from their utilization to the Convention on Biological Diversity. RECIEL 20(1), 47-61 (2011).
80. Young TR. A simple solution: using certificates of legal provenance as a workable component of a functional regime on ABS. Presented at: International Expert Workshop on Access to Genetic Resources and Benefit Sharing. Cuernavaca, Mexico, 24-27 October 2004.
81. Fernandez JC. Elements for the design of a certificate of legal provenance. Presented at: International Expert Workshop on Access to Genetic Resources and Benefit Sharing. Cuernavaca, Mexico, 24-27 October 2004.
82. Mukherjee J, Llewellyn LE, Evans-Illidge EA. A tropical marine microbial natural products geobibliography as an example of desktop exploration of current research using web visualisation tools. Mar. Drugs 6(4), 550-577 (2008). (Pubitemid 352774413)
83. Burton G. Australia-staying ahead of the game. Presented at: 2nd National Biodiscovery Forum. Adelaide, Australia, 4-5 August, 2011.
84. Philips B. New incentives for conserving biodiversity. Presented at: 2nd National Biodiscovery Forum. Adelaide, Australia, 4-5 August 2011.
85. Harrigan GG, Goetz GH. Chemical and biological integrity in natural products screening. Comb. Chem. High Throughput Screen. 8(6), 529-534 (2005). (Pubitemid 41242957)
86. Harvey AL. Natural products as a screening resource. Curr. Opin. Chem. Biol. 11(5), 480-484 (2007). (Pubitemid 47593079)
87. Harvey AL. Medicines from nature: are natural products still relevant to drug discovery? Trends Pharmacol. Sci. 20(5), 196-198 (1999).
88. Catalan J, Diaz C, Garcia-Blanco F. Characterization of Binary solvent mixtures of DMSO with water and other cosolvents. J. Org. Chem. 66(17), 5846-5852 (2001). (Pubitemid 32867483)
89. Zitha-Bovens E, Maas P, Wife D et al. COMDECOM: predicting the lifetime of screening compounds in DMSO solution. J. Biomol. Screening 14(5), 557-565 (2009).
90. Kozikowski BA, Burt TM, Tirey DA et al. The effect of freeze/thaw cycles on the stability of compounds in DMSO. J. Biomol. Screening 8(2), 210-215 (2003).
91. Camp D, Avery VM, Street I, Quinn RJ. Progress towards establishing an open access molecular screening capability in the Australasian region. ACS Chem. Biol. 2(12), 764-767 (2007). (Pubitemid 351166048)
92. Hofmann A, Wang CK, Osman A, Camp D. Merging structural biology with chemical biology: structural chemistry at Eskitis. Struct. Chem. 21(5), 1117-1129 (2010).
93. Harvey AL. Strategies for discovering drugs from previously unexplored natural products. Drug Discov. Today 5(7), 294-300 (2000).
94. Sashidhara KV, White KN, Crews P. A selective account of effective paradigms and significant outcomes in the discovery of inspirational marine natural products. J. Nat. Prod. 72(3), 588-603 (2009).
95. Harvey AL. Natural products in drug discovery. Drug Discov. Today 13(19-20), 894-901 (2008).
96. Kritzer JA. Beyond discovery: probes that see, grab and poke. Nat. Chem. Biol. 6(12), 868-870 (2010).
97. Rishton GM. Molecular diversity in the context of leadlikeness: compound properties that enable effective biochemical screening. Curr. Opin. Chem. Biol. 12(3), 340-351 (2008).