Production of the Bengamide Class of Marine Natural Products in Myxobacteria: Biosynthesis and Structure-Activity Relationships

Angewandte Chemie - International Edition

Volumn 54, Issue 51, 2015, Pages 15560-15564

  Wenzel, Silke C ^a   Hoffmann, Holger ^b   Zhang, Jidong ^b   Debussche, Laurent ^b   Haag Richter, Sabine ^b   Kurz, Michael ^b   Nardi, Frederico ^b   Lukat, Peer ^a   Kochems, Irene ^a   Tietgen, Heiko ^b,c   Schummer, Dietmar ^d   Nicolas, Jean Paul ^b,c   Calvet, Loreley ^b,c   Czepczor, Valerie ^b,c   Vrignaud, Patricia ^b,c   Mühlenweg, Agnes ^f   Pelzer, Stefan ^e   Müller, Rolf ^a   Brönstrup, Mark ^a  

^a HELMHOLTZ CENTRE FOR INFECTION RESEARCH   (Germany)

^b SANOFI   (France)

^c TH Mittelhessen ^*  (France)

^d TECHNISCHE HOCHSCHULE MITTELHESSEN   (Germany)

^e Evonik Nutrition and Care   (Germany)

^f TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

Author keywords

bengamides; biosynthesis; drug discovery; natural products; resistance

Indexed keywords

AMINO ACIDS; BIOCHEMISTRY; BIOSYNTHESIS; ELECTRIC RESISTANCE; MAMMALS; SYNTHESIS (CHEMICAL);

ANTICANCER COMPOUNDS; BACTERIAL RESISTANCE; BENGAMIDES; DRUG DISCOVERY; MARINE NATURAL PRODUCTS; MULTIDISCIPLINARY PROJECTS; NATURAL PRODUCTS; STRUCTURE ACTIVITY RELATIONSHIPS;

DRUG PRODUCTS;

AZEPINE DERIVATIVE; BIOLOGICAL PRODUCT;

ANIMAL; AREA UNDER THE CURVE; C57BL MOUSE; EXPERIMENTAL MELANOMA; FEMALE; HALF LIFE TIME; MARINE BIOLOGY; METABOLISM; MOUSE; MYXOCOCCALES; PATHOLOGY; SPONGE (PORIFERA); STRUCTURE ACTIVITY RELATION;

ANIMALS; AREA UNDER CURVE; AZEPINES; BIOLOGICAL PRODUCTS; FEMALE; HALF-LIFE; MARINE BIOLOGY; MELANOMA, EXPERIMENTAL; MICE; MICE, INBRED C57BL; MYXOCOCCALES; PORIFERA; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84955172598     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201508277     Document Type: Article

References (35)

1. D. J. Newman, G. M. Cragg, J. Nat. Prod. 2012, 75, 311-335;
2. A. Bauer, M. Brönstrup, Nat. Prod. Rep. 2014, 31, 35-60;
3. M. S. Butler, A. A. Robertson, M. A. Cooper, Nat. Prod. Rep. 2014, 31, 1612-1661.
4. J. W. Blunt, B. R. Copp, R. A. Keyzers, M. H. Munro, M. R. Prinsep, Nat. Prod. Rep. 2015, 32, 116-211;
5. T. F. Molinski, D. S. Dalisay, S. L. Lievens, J. P. Saludes, Nat. Rev. Drug Discovery 2009, 8, 69-85.
6. K. L. Jackson, J. A. Henderson, A. J. Phillips, Chem. Rev. 2009, 109, 3044-3079.
7. C. Cuevas, A. Francesch, Nat. Prod. Rep. 2009, 26, 322-337.
8. T. L. Simmons, R. C. Coates, B. R. Clark, N. Engene, D. Gonzalez, E. Esquenazi, P. C. Dorrestein, W. H. Gerwick, Proc. Natl. Acad. Sci. USA 2008, 105, 4587-4594;
9. T. Hoffmann, S. Müller, S. Nadmid, R. Garcia, R. Müller, J. Am. Chem. Soc. 2013, 135, 16904-16911.
10. E. Quiñoà, M. Adamczeski, P. Crews, G. J. Bakus, J. Org. Chem. 1986, 51, 4494-4497;
11. M. Adamczeski, E. Quiñoà, P. Crews, J. Org. Chem. 1990, 55, 240-242;
12. C. García-Ruiz, F. Sarabia, Mar. Drugs 2014, 12, 1580-1622.
13. D. D. Xu, O. Repič, T. J. Blacklock, L. Waykole, J. V. Calienni, L. Ciszewski, G. T. Lee, W. Liu, J. Szewczyk, K. Vargas, K. Prasad, Org. Process Res. Dev. 2003, 7, 856-865.
14. F. R. Kinder, Jr., etal., J. Med. Chem. 2001, 44, 3692-3699;
15. Z. Thale, F. R. Kinder, K. W. Bair, J. Bontempo, A. M. Czuchta, R. W. Versace, P. E. Phillips, M. L. Sanders, S. Wattanasin, P. Crews, J. Org. Chem. 2001, 66, 1733-1741.
16. H. Dumez, H. Gall, R. Capdeville, C. Dutreix, A. T. VanOosterom, G. Giaccone, Anticancer Drugs 2007, 18, 219-225.
17. H. Towbin, etal., J. Biol. Chem. 2003, 278, 52964-52971.
18. J. L. Mauriz, J. Martin-Renedo, A. Garcia-Palomo, M. J. Tunon, J. Gonzalez-Gallego, Curr. Drug Targets 2010, 11, 1439-1457.
19. J. P. Lu, X. H. Yuan, H. Yuan, W. L. Wang, B. Wan, S. G. Franzblau, Q. Z. Ye, ChemMedChem 2011, 6, 1041-1048.
20. F. Sarabia, F. Martin-Galvez, C. Garcia-Ruiz, A. Sanchez-Ruiz, C. Vivar-Garcia, J. Org. Chem. 2013, 78, 5239-5253;
21. P. K. Metri, R. Schiess, K. R. Prasad, Chem. Asian J. 2013, 8, 488-493;
22. W. Zhang, Q. Liang, H. Li, X. Meng, Z. Li, Tetrahedron 2013, 69, 664-672.
23. H. Hoffmann, S. Haag-Richter, M. Kurz, H. Tietgen, 2005, WO 2005/044803.
24. J. Zhang, Y. Benedetti, A. Commercon, WO2007/135295;
25. J. Zhang, N. Bhatnagar, WO2006/056695.
26. T. A. Johnson, J. Sohn, Y. M. Vaske, K. N. White, T. L. Cohen, H. C. Vervoort, K. Tenney, F. A. Valeriote, L. F. Bjeldanes, P. Crews, Bioorg. Med. Chem. 2012, 20, 4348-4355.
27. S. C. Wenzel, R. Müller, Curr. Opin. Drug Discovery Dev. 2009, 12, 220-230.
28. C. Hertweck, Angew. Chem. Int. Ed. 2009, 48, 4688-4716;
29. Angew. Chem. 2009, 121, 4782-4811.
30. M. A. Marahiel, J. Pept. Sci. 2009, 15, 799-807.
31. Y. A. Chan, A. M. Podevels, B. M. Kevany, M. G. Thomas, Nat. Prod. Rep. 2009, 26, 90.
32. G. Liu, Y. M. Ma, W. Y. Tai, C. M. Xie, Y. L. Li, J. Li, F. J. Nan, ChemMedChem 2008, 3, 74-78.
33. D. D. Kim, J. Krishnarajah, S. Lillioja, F. deLooze, J. Marjason, J. Proietto, S. Shakib, B. G. Stuckey, J. E. Vath, T. E. Hughes, Diabetes Obes. Metab. 2015, 17, 566-572;
34. A. A. Joharapurkar, N. A. Dhanesha, M. R. Jain, Diabetes Metab. Syndr. Obes. 2014, 7, 73-84.
35. S. Kim, K. LaMontagne, M. Sabio, S. Sharma, R. W. Versace, N. Yusuff, P. E. Phillips, Cancer Res. 2004, 64, 2984-2987.