Assessing the drug-likeness of lamellarins, a marine-derived natural product class with diverse oncological activities

European Journal of Medicinal Chemistry

Volumn 45, Issue 6, 2010, Pages 2165-2172

  Chittchang, Montakarn ^a,b   Paul Gleeson, M ^a,c   Ploypradith, Poonsakdi ^a,b   Ruchirawat, Somsak ^a,b  

^a Toxicology and Management of Chemicals   (Thailand)

^b Research and Innovation   (Thailand)

^c KASETSART UNIVERSITY   (Thailand)

Author keywords

Drug likeness; In silico descriptors; Lamellarins; Lipophilicity; Physicochemical profiling; Principal components analysis (PCA)

Indexed keywords

ANTINEOPLASTIC AGENT; LAMELLARIN; LAMELLARIN A; LAMELLARIN ALPHA; LAMELLARIN B; LAMELLARIN BETA; LAMELLARIN C; LAMELLARIN D; LAMELLARIN E; LAMELLARIN F; LAMELLARIN G; LAMELLARIN GAMMA; LAMELLARIN H; LAMELLARIN I; LAMELLARIN J; LAMELLARIN K; LAMELLARIN L; LAMELLARIN M; LAMELLARIN N; LAMELLARIN S; LAMELLARIN T; LAMELLARIN THETA; LAMELLARIN U; LAMELLARIN V; LAMELLARIN W; LAMELLARIN X; LAMELLARIN Y; LAMELLARIN Z; NATURAL PRODUCT; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; COMPUTER MODEL; CONTROLLED STUDY; HYDROXYLATION; LIPOPHILICITY; PHYSICAL CHEMISTRY; PRINCIPAL COMPONENT ANALYSIS; THEORETICAL MODEL;

ADMINISTRATION, ORAL; ANTINEOPLASTIC AGENTS; BIOLOGICAL PRODUCTS; COMPUTATIONAL BIOLOGY; DRUG DISCOVERY; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; LABORATORIES; OCEANS AND SEAS; PHYSICOCHEMICAL PROCESSES; PRINCIPAL COMPONENT ANALYSIS; REPRODUCIBILITY OF RESULTS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 77950924384     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2010.01.053     Document Type: Article

References (70)

1. Li J.W.-H., and Vederas J.C. Science 325 (2009) 161-165
2. Butler M.S. J. Nat. Prod. 67 (2004) 2141-2153
3. Butler M.S. Nat. Prod. Rep. 25 (2008) 475-516
4. Ganesan A. Curr. Opin. Chem. Biol. 12 (2008) 306-317
5. Andersen R.J., Faulkner D.J., He C.-H., Van Duyne G.D., and Clardy J. J. Am. Chem. Soc. 107 (1985) 5492-5495
6. Lindquist N., Fenical W., Van Duyne G.D., and Clardy J. J. Org. Chem. 53 (1988) 4570-4574
7. Carroll A.R., Bowden B.F., and Coll J.C. Aust. J. Chem. 46 (1993) 489-501
8. Urban S., and Capon R.J. Aust. J. Chem. 49 (1996) 711-713
9. Reddy M.V.R., Faulkner D.J., Venkateswarlu Y., and Rao M.R. Tetrahedron 53 (1997) 3457-3466
10. Davis R.A., Carroll A.R., Pierens G.K., and Quinn R.J. J. Nat. Prod. 62 (1999) 419-424
11. Ham J., and Kang H. Bull. Korean Chem. Soc. 23 (2002) 163-166
12. Krishnaiah P., Reddy V.L.N., Venkataramana G., Ravinder K., Srinivasulu M., Raju T.V., Ravikumar K., Chandrasekar D., Ramakrishna S., and Venkateswarlu Y. J. Nat. Prod. 67 (2004) 1168-1171
13. Reddy S.M., Srinivasulu M., Satyanarayana N., Kondapi A.K., and Venkateswarlu Y. Tetrahedron 61 (2005) 9242-9247
14. Urban S., Butler M.S., and Capon R.J. Aust. J. Chem. 47 (1994) 1919-1924
15. Urban S., Hobbs L., Hooper J.N.A., and Capon R.J. Aust. J. Chem. 48 (1995) 1491-1494
16. Bailly C. Curr. Med. Chem. Anti-Cancer Agents 4 (2004) 363-378
17. Fan H., Peng J., Hamann M.T., and Hu J.-F. Chem. Rev. 108 (2008) 264-287
18. Quesada A.R., García Grávalos M.D., and Fernández Puentes J.L. Br. J. Cancer 74 (1996) 677-682
19. Reddy M.V.R., Rao M.R., Rhodes D., Hansen M.S.T., Rubins K., Bushman F.D., Venkateswarlu Y., and Faulkner D.J. J. Med. Chem. 42 (1999) 1901-1907
20. Ishibashi F., Tanabe S., Oda T., and Iwao M. J. Nat. Prod. 65 (2002) 500-504
21. Ridley C.P., Reddy M.V.R., Rocha G., Bushman F.D., and Faulkner D.J. Bioorg. Med. Chem. 10 (2002) 3285-3290
22. Facompré M., Tardy C., Bal-Mahieu C., Colson P., Perez C., Manzanares I., Cuevas C., and Bailly C. Cancer Res. 63 (2003) 7392-7399
23. Tardy C., Facompré M., Laine W., Baldeyrou B., García-Gravalos D., Francesch A., Mateo C., Pastor A., Jiménez J.A., Manzanares I., Cuevas C., and Bailly C. Bioorg. Med. Chem. 12 (2004) 1697-1712
24. Marco E., Laine W., Tardy C., Lansiaux A., Iwao M., Ishibashi F., Bailly C., and Gago F. J. Med. Chem. 48 (2005) 3796-3807
25. Chittchang M., Batsomboon P., Ruchirawat S., and Ploypradith P. ChemMedChem 4 (2009) 457-465
26. Baunbæk D., Trinkler N., Ferandin Y., Lozach O., Ploypradith P., Ruchirawat S., Ishibashi F., Iwao M., and Meijer L. Mar. Drugs 6 (2008) 514-527
27. J.L.F. Puentes, D. Garcia Gravalos, A. Rodriguez Quesada, World Patent WO/1997/001336 (1997).
28. J.L.F. Puentes, D. Garcia Gravalos, A. Rodriguez Quesada, U.S. Patent 5,852,033 (1998).
29. J.L.F. Puentes, D. Garcia Gravalos, A. Rodriguez Quesada, U.S. Patent 6,087,370 (2000).
30. A PharmaMar's report on. http://www.pharmamar.com/ElementoPrensa.aspx?prensa=247 (Presentations at AACR-NCI-EORTC International Conference demonstrate breadth and depth of PharmaMar's product pipeline, November 2003)
31. A PharmaMar's report on. http://www.pharmamar.com/ElementoPrensa.aspx?prensa=239 (PharmaMar presents preclinical data affirming the potential of its main compounds in sarcomas and leukaemias at the AACR Annual Meeting, April 2004)
32. A PharmaMar's report on. http://www.pharmamar.com/ElementoPrensa.aspx?prensa=145 (PharmaMar presents 13 posters at AACR highlighting clinical and preclinical development pipeline, April 2005)
33. Lipinski C.A., Lombardo F., Dominy B.W., and Feeney P.J. Adv. Drug Deliv. Rev. 23 (1997) 3-25
34. Martin Y.C. J. Med. Chem. 48 (2005) 3164-3170
35. Gleeson M.P. J. Med. Chem. 51 (2008) 817-834
36. Oprea T.I., Davis A.M., Teague S.J., and Leeson P.D. J. Chem. Inf. Comput. Sci. 41 (2001) 1308-1315
37. Hann M.M., and Oprea T.I. Curr. Opin. Chem. Biol. 8 (2004) 255-263
38. Lajiness M.S., Vieth M., and Erickson J. Curr. Opin. Drug Discov. Devel. 7 (2004) 470-477
39. Gleeson M.P. J. Med. Chem. 50 (2007) 101-112
40. FILTER Manual version 2.0.1 on. http://www.eyesopen.com
41. Xu Y.-J., and Gao H. QSAR Comb. Sci. 22 (2003) 422-429
42. Weaver S., and Gleeson M.P. J. Mol. Graph. Model. 26 (2008) 1315-1326
43. Hollósy F., Seprödi J., Örfi L., Erös D., Kéri G., and Idei M. J. Chromatogr. B 780 (2002) 355-363
44. Hallgas B., Patonay T., Kiss-Szikszai A., Dobos Z., Hollósy F., Ero{combining double acute accent}s D., O{combining double acute accent}rfi L., Kéri G., and Idei M. J. Chromatogr. B 801 (2004) 229-235
45. Hallgas B., Dobos Z., O{combining double acute accent}sz E., Hollósy F., Schwab R.E., Szabó E.Z., Ero{combining double acute accent}s D., Idei M., Kéri G., and Lóránd T. J. Chromatogr. B 819 (2005) 283-291
46. Hallgas B., Dobos Z., Agócs A., Idei M., Kéri G., Lóránd T., and Mészáros G. J. Chromatogr. B 856 (2007) 148-155
47. Leach A.G., Jones H.D., Cosgrove D.A., Kenny P.W., Ruston L., MacFaul P., Wood J.M., Colclough N., and Law B. J. Med. Chem. 49 (2006) 6672-6682
48. Vrecl M., Uršič M., Pogačnik A., Zupančič-Kralj L., and Jan J. Toxicol. Appl. Pharmacol. 204 (2005) 170-174
49. Abraham M.H., Duce P.P., Prior D.V., Barratt D.G., Morris J.J., and Taylor P.J. J. Chem. Soc. Perkin Trans. 2 (1989) 1355-1375
50. Proudfoot J.R. Bioorg. Med. Chem. Lett. 15 (2005) 1087-1090
51. Oprea T.I., Allu T.K., Fara D.C., Rad R.F., Ostopovici L., and Bologa C.G. J. Comput. Aided Mol. Des. 21 (2007) 113-119
52. Wenlock M.C., Austin R.P., Barton P., Davis A.M., and Leeson P.D. J. Med. Chem. 46 (2003) 1250-1256
53. Ritchie T.J., Luscombe C.N., and Macdonald S.J.F. J. Chem. Inf. Model. 49 (2009) 1025-1032
54. O'Shea R., and Moser H.E. J. Med. Chem. 51 (2008) 2871-2878
55. Pla D., Francesch A., Calvo P., Cuevas C., Aligué R., Albericio F., and Álvarez M. Bioconjug. Chem. 20 (2009) 1100-1111
56. Pla D., Martí M., Farrera-Sinfreu J., Pulido D., Francesch A., Calvo P., Cuevas C., Royo M., Aligué R., Albericio F., and Álvarez M. Bioconjug. Chem. 20 (2009) 1112-1121
57. Ploypradith P., Petchmanee T., Sahakitpichan P., Litvinas N.D., and Ruchirawat S. J. Org. Chem. 71 (2006) 9440-9448
58. PubChem on. http://pubchem.ncbi.nlm.nih.gov/
59. Valko K., My Du C., Bevan C., Reynolds D.P., and Abraham M.H. Curr. Med. Chem. 8 (2001) 1137-1146
60. OECD Guidelines for Testing of Chemicals on. http://www.oecd.org/document/40/0,3343,en_2649_34377_37051368_1_1_1_1,00 .html
61. SPSS; 16.0. SPSS Inc., Chicago, IL, USA, (2008).
62. FILTER; 2.0.1. OpenEye Scientific Software, Santa Fe, NM, USA, (2007) on http://www.eyesopen.com
63. SIMCA-P; 10.0. Umetrics AB, Umeå, Sweden, (2002) on. http://www.umetrics.com
64. Molinspiration Property Engine; 2009.01. Molinspiration Cheminformatics, Slovensky Grob, Slovak Republic, (2009) on http://www.molinspiration.com.
65. FAF-Drugs: Free ADME/tox Filtering. Ressource Parisienne en Bioinformatique Structurale (RPBS), Paris, France, (2006) on http://bioserv.rpbs.univ-paris-diderot.fr/Help/FAFDrugs.html.
66. Miteva M.A., Violas S., Montes M., Gomez D., Tuffery P., and Villoutreix B.O. Nucleic Acids Res. 34 (2006) W738-744
67. ACD/ChemSketch; 12.01. Advanced Chemistry Development, Inc., Toronto, ON, Canada, (2009) on http://www.acdlabs.com.
68. Bio-Loom; 1.5. BioByte Corporation, Claremont, CA, USA, (2005) on http://www.biobyte.com.
69. ChemBioDraw Ultra; 11.0.1 (2007), CambridgeSoft Corporation, Cambridge, MA, USA
70. ®; 2.0 (2007), Accelrys Software Inc., San Diego, CA, USA