A-94964, a novel inhibitor of bacterial translocase I, produced by Streptomyces sp. SANK 60404: I. Taxonomy, isolation and biological activity

Journal of Antibiotics

Volumn 61, Issue 9, 2008, Pages 537-544

  Murakami, Ryo ^a   Fujita, Yoko ^a   Kizuka, Masaaki ^a   Kagawa, Tomoka ^a   Muramatsu, Yasunori ^a   Miyakoshi, Shunichi ^b   Takatsu, Toshio ^a   Inukai, Masatoshi ^c  

^a DAIICHI SANKYO CO   (Japan)

^b GUNMA NATIONAL COLLEGE OF TECHNOLOGY   (Japan)

^c INTERNATIONAL UNIVERSITY OF HEALTH AND WELFARE   (Japan)

Author keywords

A 94964; Antimicrobial activity; Nucleoside antibiotic; Peptidoglycan; Streptomyces sp.; Translocase I; Tunicamycin

Indexed keywords

A 94964; ANTIINFECTIVE AGENT; CARRIER PROTEIN; TRANSLOCASE I; UNCLASSIFIED DRUG;

ARTICLE; DRUG ISOLATION; ENTEROCOCCUS FAECALIS; ENZYME INHIBITION; HUMAN; HUMAN CELL; IC 50; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; STAPHYLOCOCCUS AUREUS; STREPTOMYCES; UNINDEXED SEQUENCE;

ANTI-BACTERIAL AGENTS; BACTERIA; DISACCHARIDES; ENZYME INHIBITORS; HELA CELLS; HUMANS; PYRIMIDINE NUCLEOTIDES; STREPTOMYCES; TRANSFERASES (OTHER SUBSTITUTED PHOSPHATE GROUPS); TUNICAMYCIN;

BACTERIA (MICROORGANISMS); ENTEROCOCCUS FAECALIS; MAMMALIA; STAPHYLOCOCCUS AUREUS; STREPTOMYCES SP.;

EID: 57849092815     PISSN: 00218820     EISSN: None     Source Type: Journal    
DOI: 10.1038/ja.2008.71     Document Type: Article

References (33)

1. Brandish PE, Kimura K, Inukai M, Southgate R, Lonsdale JT, Bugg TD. Modes of action of tunicamycin, liposidomycin B and mureidomycin A: Inhibition of phospho-N-acetylmuramyl-pentapeptide translocase from Escherichia coli. Antimicrob Agents Chemother 40: 1640-1644 (1996)
2. Inukai M, Isono F, Takahashi S, Enokita R, Sakaida Y, Haneishi T. Mureidomycin A~D, novel peptidylnucleoside antibiotics with spheroplast forming activity. I. Taxonomy, fermentation, isolation and physico-chemical properties. J Antibiot 42: 662-666 (1989)
3. Karwowski JP, Jackson M, Theriault RJ, Chen RH, Barlow GJ, Maus ML. Pacidamycins, a novel series of antibiotics with anti-Pseudomonas aeruginosa activity. I. Taxonomy of the producing organism and fermentation. J Antibiot 42: 506-511 (1989)
4. Chatterjee S, Nadkarni SR, Vijayakumar EK, Patel MV, Ganguli BN, Fehlhaber HW, Vertesy L. Napsamycins, new Pseudomonas activity antibiotics of mureidomycin family from Streptomyces sp. HIL Y-82, 11372. J Antibiot 47: 595-598 (1994)
5. Ubukata M, Isono K. The structure of liposidomycin B, an inhibitor of bacterial peptidoglycan synthesis. J Am Chem Soc 110: 4416-4417 (1988)
6. Takatsuki A, Arima K, Tamura G. Tunicamycin, a new antibiotic. I. Isolation and characterization of tunicamycin. J Antibiot 24: 215-223 (1971)
7. Yamaguchi H, Sato S, Yoshida S, Takada K, Itou M, Seto H, Otake N. Capuramycin, a new nucleoside antibiotic. Taxonomy, fermentation, isolation and characterization. J Antibiot 39: 1047-1053 (1986)
8. Seto H, Otake N. The structure of a new nucleoside antibiotic, capuramycin. Tetrahedron Lett 29: 2343-2346 (1988)
9. Muramatsu Y, Muramatsu A, Ohnuki T, Ishi MM, Kizuka M, Enokita R, Tsutsumi S, Arai M, Ogawa Y, Suzuki T, Takatsu T, Inukai M. Studies on novel bacterial translocase I inhibitors. I. Taxonomy, fermentation, isolation, physicochemical properties and structure elucidation of A-500359A, C, D and G. J Antibiot 57: 243-252 (2003)
10. Muramatsu Y, Ishii MM, Inukai M. Studies on novel bacterial translocase I inhibitors, A-500359s. II. Biological activities of A-500359 A, C, D and G. J Antibiot 56: 253-258 (2003)
11. Muramatsu Y, Miyakoshi S, Ogawa Y, Ohnuki T, Ishii MM, Arai M, Inukai M. Studies on novel bacterial translocase I inhibitors, A-500359s. III. Deaminocaprolactam derivaties of capuramycin: A-500359 E, F, H, M-1 and M-2. J Antibiot 56: 259-267 (2003)
12. Ohnuki T, Muramatsu Y, Miyakoshi S, Takatsu T, Inukai M. Studies on novel bacterial translocase I inhibitors, A-500359s. IV. Biosynthesis of A-500359s. J Antibiot 56: 268-279 (2003)
13. Muramatsu Y, Arai M, Sakaida Y, Takamatsu Y, Miyakoshi S, Inukai M. Studies on novel bacterial translocase I inhibitors, A-500359s. V. Enhanced production of capuramycin and A-500359A in Streptomyces griseus SANK 60196. J Antibiot 59: 601-606 (2006)
14. McDonald LA, Barbieri LR, Carter GT, Lenoy E, Lotvin J, Petersen PJ, Singh G, Williamson RT. Structures of the muraymycins, novel peptidoglycan biosynthesis inhibitors. J Am Chem Soc 124: 10260-10261 (2002)
15. Igarashi M, Nakagawa N, Doi N, Hattori S, Naganawa H, Hamada M. Caprazamycin B, a novel anti-tuberculosis antibiotic, from Streptomyces sp. J Antibiot 56: 580-583 (2003)
16. Igarashi M, Takahashi Y, Shibata T, Nakamura H, Naganawa H, Miyake T, Akamatsu Y. Caprazamycins, novel liponucleoside antibiotics, from Streptomyces sp. II. Structure elucidation of caprazamycins. J Antibiot 58: 327-337 (2005)
17. Fernandes PB, Swanson RN, Hardy DJ, Hanson CW, Coen L, Rasmussen RR, Chen RH. Pacidamycins, a novel series of antibiotics with anti-Pseudomonas aeruginosa activity. III. Microbiologic profile. J Antibiot 42: 521-526 (1989)
18. Isono F, Kodama K, Inukai M. Susceptibility of Pseudomonas species to the novel antibiotics mureidomycins. Antimicrob Agents Chemother 36: 1024-1027 (1992)
19. Shirling EB, Gottlieb D. Methods for characterization of Streptomyces species. Int J Syst Bacteriol 16: 313-340 (1966)
20. Waksman SA. Classification, identification and description of genera and species. The Actinomycetes. Vol. II, pp. 328-334, Williams & Wilkins (1961)
21. Hasegawa T, Takizawa M, Tanida S. A rapid analysis for chemical grouping of aerobic actinomycetes. J Gen Appl Microbiol 29: 319-322 (1983)
22. Nakagawa Y, Kawasaki H. Identification Manual of Actinomycetes. (edited by The Society for Actinomycetes Japan, Business Center for Academic Societies Japan, Tokyo, Japan), pp. 83-117 (2001) (Japanese)
23. Saitou N, Nei M. The neighbor-joining method: a new method of constructing phylogenetic tree. Mol Biol Evol 6: 514-525 (1987)
24. Tamura K, Dudley J, Nei M, Kumar S. MEGA4: Molecular Evolutionary Genetics Analysis (MEGA) Software Version 4.0. Mol Biol Evol 24: 1596-1599 (2007)
25. Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxic assays. J Immunol Methods 65: 55-63 (1983)
26. Heifetz A, Keenan RW, Elbein, AD. Mechanism of action of tunicamycin on the UDP-GlcNAc: dolichyl phosphate GlcNAc-1-phosphate transferase. Biochemistry 18: 2186-2192 (1979)
27. Constantine GB, Remy CL, Johanne B, Nicole GV, Karin AS, Angela M, Suzanne C, Scott JH, Ving JL. Synthetic dihydropacidamycin antibiotics: A modified spectrum of activity for the pacidamycin class. Bioorg Med Chem Lett 13: 3305-3309 (2003)
28. Dini C, Didier-Laurent S, Drochon N, Feteanu S, Guillot JC, Monti F, Uridat E, Zhang J, Aszodi J. Synthesis of submicromolar inhibitors of MraY by exploring the region originally occupied by the diazepanone ring in the liposidomycin structure. Bioorg Med Chem Lett 12: 1209-1213 (2002)
29. Hotoda H, Furukawa M, Daigo M, Murayama K, Kaneko M, Muramatsu Y, Ishi MM, Miyakoshi S, Takatsu T, Inukai M, Kakuta M, Abe T, Harasaki T, Fukuoka T, Utsui Y, Ohya S. Synthesis and antimycobacterial activity of capuramycin analogues. Part 1: Substitution of the azepan-2-one moiety of capuramycin. Bioorg Med Chem Lett 13: 2829-2832 (2003)
30. Hotoda H, Daigo M, Furukawa M, Murayama K, Hasegawa AC, Kaneko M, Muramatsu Y, Ishi MM, Miyakoshi S, Takatsu T, Inukai M, Kakuta M, Abe T, Fukuoka T, Utsui Y, Ohya S. Synthesis and antimycobacterial activity of capuramycin analogues. Part 2: Acylated derivatives of capuramycin-related compounds. Bioorg Med Chem Lett 13: 2833-2836 (2003)
31. Miyake T, Takahashi Y, Igarashi M, Doi N, Shitara T, Sohtome H, Iijima K, Masuda T, Hattori S, Nakagawa N, Akamatsu Y. Novel semisynthetic antibiotics from caprazamycins (Part 1): Caprazene derivatives and their anti-Mycobacterium tuberculosis activity. 43rd Interscience Conference on Antimicrobial Agents and Chemotherapy (ICAAC), Abstracts F-2140 (2003)
32. Miyake T, Shitara T, Igarashi M, Doi N, Takahashi Y, Sohtome H, Iijima K, Masuda T, Hattori S, Nakagawa N, Akamatsu Y. Novel semisynthetic antibiotics from caprazamycins (Part 2): Caprazol derivatives and their anti- Mycobacterium tuberculosis activity. 43rd Interscience Conference on Antimicrobial Agents and Chemotherapy (ICAAC), Abstracts F-2141 (2003)
33. Price NPJ, Tsvetanova B. Biosynthesis of the Tunicamycins: A Review. J Antibiot 60: 485-491 (2007)