Pharmaceutical agents from filamentous marine cyanobacteria

Drug Discovery Today

Volumn 18, Issue 17-18, 2013, Pages 863-871

  Tan, Lik Tong ^a  

^a NANYANG TECHNOLOGICAL UNIVERSITY   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

ANANDAMIDE; ANTIBIOTIC AGENT; ANTINEOPLASTIC AGENT; ANTIPROTOZOAL AGENT; AURILIDE; BISEBROMOAMIDE; BRENTUXIMAB VEDOTIN; CARMAPHYCINS A; CARMAPHYCINS B; DOLASTATIN 10; DOLASTATIN 15; EPOXOMICIN; GAMMA UROGASTRONE; GRASSYSTATIN C; HISTONE DEACETYLASE INHIBITOR; HOIAMIDE A; HOIAMIDE D; ISOMALYNGAMIDE A; ISOMALYNGAMIDE A1; LARGAZOLE; METHIONINE SULFONE; METHIONINE SULFOXIDE; NATURAL PRODUCT; PROTEASOME INHIBITOR; SERINOLAMIDE A; SOBLIDOTIN; TASIAMIDE B; UNCLASSIFIED DRUG; UNINDEXED DRUG; VEDOTIN; VORSETUZUMAB MAFODOTIN;

ACTIN FILAMENT; ANTINEOPLASTIC ACTIVITY; ANTIPROTOZOAL ACTIVITY; BIOLOGICAL ACTIVITY; CANCER CELL; CYANOBACTERIUM; DOLABELLA AURICULARIA; DRUG DOSE; DRUG STRUCTURE; HODGKIN DISEASE; HUMAN; IC 50; IN VITRO STUDY; KIDNEY CARCINOMA; LARGE CELL LYMPHOMA; LEUKEMIA; LYNGBYA; LYNGBYA MAJUSCULA; MICROTUBULE; NEUROTOXICITY; NONHUMAN; OSCILLATORIA; PERIPHERAL NEUROPATHY; PHORMIDIUM GRACILE; PLASMODIUM FALCIPARUM; REVIEW; SACCHAROMYCES CEREVISIAE; SCHIZOTHRIX; SYMPLOCA;

ANIMALS; ANTINEOPLASTIC AGENTS; ANTIPROTOZOAL AGENTS; CYANOBACTERIA; DRUG DISCOVERY; HUMANS; MOLECULAR STRUCTURE; NEUROTRANSMITTER AGENTS; PROTEASE INHIBITORS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84883215375     PISSN: 13596446     EISSN: 18785832     Source Type: Journal    
DOI: 10.1016/j.drudis.2013.05.010     Document Type: Review

References (64)

1. P.N. Leao The chemical ecology of cyanobacteria Nat. Prod. Rep. 29 2012 372 391
2. W.H. Gerwick Nitrogen-containing metabolites from marine cyanobacteria G.A. Cordell, The Alkaloids: Chemistry and Biology 2001 Elsevier 75 184
3. L.T. Tan Bioactive natural products from marine cyanobacteria for drug discovery Phytochemistry 68 2007 954 979
4. L.T. Tan Marine cyanobacteria: a treasure trove of bioactive secondary metabolites for drug discovery Stud. Nat. Prod. Chem. 36 2012 67 110
5. A.C. Jones The unique mechanistic transformations involved in the biosynthesis of modular natural products from marine cyanobacteria Nat. Prod. Rep. 27 2010 1048 1065
6. W.H. Gerwick, and B.S. Moore Lessons from the past and charting the future of marine natural products drug discovery and chemical biology Chem. Biol. 19 2012 85 98
7. J. Poncet The dolastatins, a family of promising antineoplastic agents Curr. Pharm. Des. 5 1999 139 162
8. H. Luesch Isolation of dolastatin 10 from the marine cyanobacterium Symplca species VP642 and total stereochemistry and biological evaluation of its analogue symplostatin 1 J. Nat. Prod. 64 2001 907 910
9. C. Deng Brentuximab vedotin Clin. Cancer Res. 19 2013 22 27
10. G.R. Pettit Antineoplastic agents. 592. Highly effective cancer cell growth inhibitory structural modifications of dolastatin 10 J. Nat. Prod. 74 2011 962 968
11. D.A. Gianolio Targeting HER2-positive cancer with dolastatin 15 derivatives conjugated to trastuzumab, novel antibody-drug conjugates Cancer Chemother. Pharmacol. 70 2012 439 449
12. T. Teruya Bisebromoamide, a potent cytotoxic peptide from the marine cyanobacterium Lyngbya sp.: isolation, stereostructure, and biological activity Org. Lett. 11 2009 5062 5065
13. X. Gao Total synthesis and stereochemical reassignment of bisebromoamide Org. Lett. 12 2010 3018 3021
14. H. Sasaki Revised structure and structure-activity relationship of bisebromoamide and structure of norbisebromoamide from the marine cyanobacterium Lyngbya sp Tetrahedron 67 2011 990 994
15. W. Li Total synthesis and cytotoxicity of bisebromoamide and its analogues Tetrahedron Lett. 52 2011 2124 2127
16. E. Sumiya Cell-morphology profiling of a natural product library identifies bisebromoamide and miuraenamide A as actin filament stabilizers ACS Chem. Biol. 6 2011 425 431
17. K. Suzuki 307 Bisebromoamide, as a novel molecular target drug inhibiting phosphorylation of both extracellular signal-regulated kinase and AKT in renal cell carcinoma J. Urol. 187 2012 e124 e125
18. K. Taori Structure and activity of largazole, a potent antiproliferative agent from the Floridian marine cyanobacterium Symploca sp J. Am. Chem. Soc. 130 2008 1806 1807
19. S. Li Synthetic routes and biological evaluation of largazole and its analogues as potent histone deacetylase inhibitors Molecules 16 2011 4681 4694
20. J. Hong, and H. Luesch Largazole: from discovery to broad-spectrum therapy Nat. Prod. Rep. 29 2012 449 456
21. Y. Liu Anticolon cancer activity of largazole, a marine-derived tunable histone deacetylase inhibitor J. Pharmacol. Exp. Ther. 335 2010 351 361
22. S.U. Lee In vitro and in vivo osteogenic activity of largazole ACS Med. Chem. Lett. 2 2011 248 251
23. Y. Liu A histone deacetylase inhibitor, largazole, decreases liver fibrosis and angiogenesis by inhibiting transforming growth factor-b and vascular endothelial growth factor signaling Liver Int. 33 2013 504 515
24. G. Giannini Histone deacetylase inhibitors in the treatment of cancer: overview and perspectives Future Med. Chem. 4 2012 1439 1460
25. M.E. Law Glucocorticoids and histone deacetylase inhibitors cooperate to block the invasiveness of basal-like breast cancer cells through novel mechanisms Oncogene 32 2013 1316 1329
26. S.K. Ghosh Histone deacetylase inhibitors are potent inducers of gene expression in latent EBV and sensitize lymphoma cells to nucleoside antiviral agents Blood 119 2012 1008 1017
27. D. Ungermannova Largazole and its derivatives selectively inhibit ubiquitin activating enzyme (E1) PLoS ONE 7 2012 e29208
28. A.R. Pereira The carmaphycins: new proteasome inhibitors exhibiting an α,β-epoxyketone warhead from a marine cyanobacterium Chembiochem 13 2012 810 817
29. A.F. Kisselev Proteasome inhibitors: an expanding army attacking a unique target Chem. Biol. 19 2012 99 115
30. H. Luesch Total structure determination of apratoxin A, a potent cytotoxin from the marine cyanobacterium Lyngbya majuscula J. Am. Chem. Soc. 123 2001 5418 5423
31. Y. Liu Apratoxin a reversibly inhibits the secretory pathway by preventing cotranslational translocation Mol. Pharmacol. 76 2009 91 104
32. S. Shen Cyclodepsipeptide toxin promotes the degradation of Hsp90 client proteins through chaperone-mediated autophagy J. Cell Biol. 185 2009 629 639
33. Z. Nahleh Heat shock proteins in cancer: targeting the 'chaperones' Future Med. Chem. 4 2012 927 935
34. Q.Y. Chen Systematic chemical mutagenesis identifies a potent novel apratoxin A/E hybrid with improved in vivo antitumor activity ACS Med. Chem. Lett. 2 2011 861 865
35. R.V. Grinberg Single cell genome amplification accelerates identification of the apratoxin biosynthetic pathway from a complex microbial assemblage PLoS ONE 6 2011 e18565
36. K. Suenaga Isolation and stereostructure of aurilide, a novel cyclodepsipeptide from the Japanese sea hare Dolabella auricularia Tetrahedron Lett. 37 1994 6771 6774
37. S. Sato Marine natural product aurilide activates the OPA1-mediated apoptosis by binding to prohibitin Chem. Biol. 18 2011 131 139
38. A.L. Theiss, and S.V. Sitaraman The role and therapeutic potential of prohibitin in disease Biochim. Biophys. Acta 1813 2011 1137 1143
39. A. Tripathi Biochemical studies of the lagunamides, potent cytotoxic cyclic depsipeptides from the marine cyanobacterium Lyngbya majuscula Mar. Drugs 10 2012 1126 1137
40. T. Takahashi Solid phase library synthesis of cyclic depsipeptides: aurilide and aurilide analogues J. Comb. Chem. 5 2003 414 428
41. K. Suenaga Synthesis and cytotoxicity of aurilide analogs Bioorg. Med. Chem. Lett. 18 2008 3902 3905
42. Y. Takada The total synthesis and structure-activity relationships of a highly cytotoxic depsipeptide kulokekahilide-2 and its analogs Tetrahedron 68 2012 659 669
43. M. Umehara Structure-related cytotoxic activity of derivatives from kulokekahilide-2, a cyclodepsipeptide in Hawaiian marine mollusk Bioorg. Med. Chem. Lett. 22 2012 7422 7425
44. D. Pei Regulation of p53: a collaboration between Mdm2 and Mdmx Oncotarget 3 2012 228 235
45. S. Shangary, and S. Wang Small-molecule inhibitors of the MDM2-p53 protein-protein interaction to reactivate p53 function: a novel approach for cancer therapy Annu. Rev. Pharmacol. Toxicol. 49 2009 223 241
46. K.L. Malloy Hoiamide D, a marine cyanobacteria-derived inhibitor of p53/MDM2 interaction Bioorg. Med. Chem. Lett. 22 2012 683 688
47. T.T. Chang Isomalyngamide A, A-1 and their analogs suppress cancer cell migration in vitro Eur. J. Med. Chem. 46 2011 3810 3819
48. R. Araoz Neurotoxic cyanobacterial toxins Toxicon 56 2010 813 828
49. V. Zuliani Sodium channel blockers for neuropathic pain Expert Opin. Ther. Pat. 20 2010 755 779
50. M. Mantegazza Voltage-gated sodium channels as therapeutic targets in epilepsy and other neurological disorders Lancet Neurol. 9 2010 413 424
51. A. Pereira Hoiamide A, a sodium channel activator of unusual architecture from a consortium of two Papua New Guinea cyanobacteria Chem. Biol. 16 2009 893 906
52. M. Gutierrez A cannabinomimetic lipid from a marine cyanobacterium J. Nat. Prod. 74 2011 2313 2317
53. R. Montaser Marine cyanobacterial fatty acid amides acting on cannabinoid receptors Chembiochem 13 2012 2676 2681
54. L.M. Sanchez Almiramides A-C: discovery and development of a new class of leishmaniasis lead compounds J. Med. Chem. 53 2010 4187 4197
55. T. Conroy Total synthesis and antimalarial activity of symplostatin 4 Org. Lett. 12 2010 5576 5579
56. K. Taori Combinatorial strategies by marine cyanobacteria: symplostatin 4, an antimitotic natural dolastatin 10/15 hybrid that synergizes with the coproduced HDAC inhibitor largazole Chembiochem 10 2009 1634 1639
57. T. Conroy Total synthesis, stereochemical assignment, and antimalarial activity of gallinamide A Chemistry 17 2011 13544 13552
58. S.C. Stolze The antimalarial natural product symplostatin 4 is a nanomolar inhibitor of the food vacuole falcipains Chem. Biol. 19 2012 1546 1555
59. M. Marco, and J.M. Coteron Falcipain inhibition as a promising antimalarial target Curr. Top. Med. Chem. 12 2012 408 444
60. M. Drag, and G.S. Selvesen Emerging principles in protease-based drug discovery Nat. Rev. Drug Discov. 9 2010 690 701
61. J.C. Kwan Grassystatins A-C from marine cyanobacteria, potent cathepsin E inhibitors that reduce antigen presentation J. Med. Chem. 52 2009 5732 5747
62. S. Yang Total synthesis of grassystatin A, a probe for cathepsin E function Bioorg. Med. Chem. 20 2012 4774 4780
63. Y. Liu Cyanobacterial peptides as a prototype for the design of potent β-serectase inhibitors and the development of selective chemical probes for other aspartic proteases J. Med. Chem. 55 2012 10749 10765
64. M. Sathya BACE1 in Alzheimer's disease Clin. Chim. Acta 414 2012 171 178