Essramycin: A first triazolopyrimidine antibiotic isolated from nature

Journal of Antibiotics

Volumn 61, Issue 3, 2008, Pages 149-157

  El Gendy, Mervat M A ^b   Shaaban, Mohamed ^b   Shaaban, Khaled A ^a   El Bondkly, Ahmed M ^b   Laatsch, Hartmut ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

^b NATIONAL RESEARCH CENTRE   (Egypt)

Author keywords

Essramycin; Marine Streptomyces sp.; Triazolopyrimidine

Indexed keywords

ANTIBIOTIC AGENT; ESSRAMYCIN; UNCLASSIFIED DRUG; ANTIINFECTIVE AGENT; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; PYRIMIDINE DERIVATIVE; TRIAZOLE DERIVATIVE;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; BACTERIAL STRAIN; BIOLOGICAL ACTIVITY; COLUMN CHROMATOGRAPHY; DRUG DECOMPOSITION; DRUG IDENTIFICATION; DRUG ISOLATION; DRUG SCREENING; DRUG STRUCTURE; ELECTROSPRAY MASS SPECTROMETRY; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; HETERONUCLEAR MULTIPLE QUANTUM COHERENCE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MARINE SPECIES; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STREPTOMYCES; CONFORMATION; DRUG EFFECT; FERMENTATION; INFRARED SPECTROPHOTOMETRY; ISOLATION AND PURIFICATION; MASS SPECTROMETRY; METABOLISM; MICROBIOLOGICAL EXAMINATION; MOLECULAR WEIGHT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; THIN LAYER CHROMATOGRAPHY; ULTRAVIOLET SPECTROPHOTOMETRY;

NEGIBACTERIA; POSIBACTERIA; STREPTOMYCES SP.;

ANTI-BACTERIAL AGENTS; CHEMISTRY, PHYSICAL; CHROMATOGRAPHY, THIN LAYER; FERMENTATION; GRAM-NEGATIVE BACTERIA; GRAM-POSITIVE BACTERIA; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MICROBIAL SENSITIVITY TESTS; MOLECULAR CONFORMATION; MOLECULAR WEIGHT; PYRIMIDINES; SPECTROPHOTOMETRY, INFRARED; SPECTROPHOTOMETRY, ULTRAVIOLET; STREPTOMYCES; TRIAZOLES;

EID: 54049118862     PISSN: 00218820     EISSN: None     Source Type: Journal    
DOI: 10.1038/ja.2008.124     Document Type: Article

References (37)

1. El-Gendy MM, PhD Thesis, Isolation of antibiotic compounds from marine Streptomyces collected from Mediterranean Sea, Faculty of Agriculture, Cairo University, Egypt, 2006
2. Fenical W. Chemical studies of marine bacteria: developing a new resource. Chem Rev 93: 1673-1683 (1993)
3. Fenical W, Jensen PR, Attaway DH, Zaborsky OR. Marine microorganisms: a new biomedical resource, Marine Biotechnology, Eds.; Plenum Press, New York, Vol. 1, pp. 419-457 (1993)
4. Pietra F. Nat Prod Rep 14: 453-464 (1997)
5. Faulkner D. J Nat Prod Rep 17: 7-55 (2000) Laatsch H. Marine Bacterial Metabolites, In: Frontiers in Marine Biotechnology, P. Proksch, WE.G. Müller, Eds., pp. 225-288, Horizon Bioscience, Norfolk, UK 2006. ISBN 1-904933-18-1
6. Laatsch H. AntiBase 2007, A Data Base for Rapid Dereplication and Structure Determination of Microbial Natural Products, Wiley-VCH, Weinheim, Germany; see http://wwwuser.gwdg.de/~ucoc/laatsch/AntiBase.htm
7. a) Anzai K, Nagatsu J, Suzuki S. Pathocidin, a new antifungal antibiotic. I. Isolation, physical and chemical properties, and biological activities. J Antibiot 14: 340-342 (1961)
8. b) Anzai K, Suzuki S. Chemical structure of pathocidin. J Antibiot 14: 253 (1961)
9. Nagatsu J, Anzai K, Suzuki S. Pahocidin, a new antifungal antibiotic. II, Taxonomic studies on the pathocidin-producing organism Streptomyces albus var. pathocidicus. J Antibiot 15: 103-106 (1962)
10. Hirasawa K, Isono K. Formation of 8-azaguanine from guanine by Streptomyces albus. J Antibiot 31: 628-629 (1978)
11. Bru-Magniez N, Guengor T, Teulon JM. Triazolopyrimidine derivatives which are angiotensin II receptor antagonists, their methods of preparation and pharmaceutical compositions in which they are present. Patent US 93-39382 19930416; US 92-863955 19920406 [Chem Abstr 123: 228204]
12. Eriguchi A, Mimura T, Kuretani M, Katakura S, Nishida K. Preparation of triazolopyrimidine derivatives as atherosclerotics and smooth muscle cell growth inhibitors. Patent JP 90-218676 19900820 [Chem Abstr 117: 150806]
13. Chipkin RE, Witkowski JT. 4,7-Dimethyl-2-(4-pyridinyl)-1,2,4-triazolo[1, 5-a]pyrimidin-5(4H)-one. Patent Application: WO 84-EP410 19841218 [Chem Abstr 104: 50891]
14. Benecke Ch, Grund R, Hohberger R, Kerber A, Laue R, Wieland Th., Molgen Vers. 3, Univ. Bayreuth (Germany), 2000
15. calculated with AMI using SPARTAN' 04, Wavefunction Inc., Irvine, CA 92612
16. ACD NMR simulation programs Vers. 6.00, 2002, Advanced Chemistry Development Inc., Toronto, Canada
17. 15N NMR study of 1,2,4-triazolo[1,5-a]pyrimidines with one tautomerism-introducing substituent. J Mol Structure 355: 273-285 (1995)
18. Anzai K, Nagatsu J, Suzuki S. J Antibiot 14: 340-342 (1961)
19. Selby TP (du Pont de Nemours, E. I., and Co., USA). Preparation of substituted phenyltriazolopyrimidine herbicides. Eur. Pat. 353902 [Chem Abstr 113: 191375 (1990)]
20. Malkomes HP. Influence of some newer herbicides on microbial activities in the soil and on some fungi isolated from the soil under laboratory conditions Biologische Bundesanstalt für Land- und Forstwirtschaft 58: 165-173 (2006)
21. Coulter TS, Taylor S, Murfin S, Thammalaksa V, Aicher B, Jaekel S, Reuter T. Preparation of pyrazolopyrimidines as inhibitors of kinase activity, Patent 2005, EP13907 20051222; 2004, EP 30674 20041223 [Chem. Abstr. 145: 124588]
22. Jaekel S, Murfin S, Taylor S, Aicher B, Kelter AR, Coulter T Thienopyrimidines for pharmaceutical compositions and their preparation and use as kinase inhibitors, Patent 2006, EP5980 20060621; 2005, EP 13500 20050622 [Chem Abstr 146: 100711]
23. Srivastava RP, Kumar VV, Bhatia S, Sharma S. Studies in antiparasitic agents. Part 24. Synthesis of 5-(2-furyl)-2-substituted-amino-1,3,4-triazoles and substituted 1,3,4-triazolo[1,5-a]pyrimidines as potential antifilarial and leishmanicidal agents. Indian J Chem 34B: 209-214 (1995)
24. Magan R, Marin C, Salas JM, Barrera-Perez M, Rosales MJ, Sanchez-Moreno M. Cytotoxicity of three new triazolopyrimidine derivatives against the plant trypanosomatid Phytomonas sp. isolated from Euphorbia characias, Memorias do Institute Oswaldo Cruz 99: 651-656 (2004)
25. Dictionary of Natural Products on CD-ROM, Chapman & Hall Chemical Database, 2006
26. search in the Chemical Abstracts by SciFinder®, 2007
27. Moore BS, Trischman JA, Seng D, Kho D, Jensen RP, Fenical W. Salinamides, anti inflammatory depsipeptide from a marine Streptomycetes. J Org Chem 64: 1145-1150 (1999)
28. Shirling EB, Gottlieb D. Methods for characterization of Streptomyces species. Int J Syst Bacteriol 16: 313-340 (1966)
29. Shirling EB, Gottlieb D. Cooperative description of type cultures of Streptomyces. II - species description from first study. Int J Syst Bacteriol 18: 69-100 (1968);
30. Cooperative description of type cultures of Streptomyces. III - additional species description from first and second studies. 18: 279-345 (1968);
31. Cooperative description of type cultures of Streptomyces. IV - species description from 2nd, 3rd and 4th studies. 19: 391-512 (1969);
32. Cooperative description of type strain of Streptomyces. V - additional description. The 2nd, 3rd and 4th studies. 22: 265-300 (1972)
33. Waksman SA. The Actinomycetes, Classification, identification and description of genera and species, The Williams and Wilkins Co., Baltimore, USA, 1961, II
34. Yamaguchi T. Comparison of the cell-wall composition of morphologically distinct Actinomycetes. J Bacteriol 89: 444-453 (1965)
35. Yan LP, Hong K, Hu S, Liu LH. 16S rDNA diversity analysis of 30 Streptomycetes isolates displaying significant cytotoxic activity against B 16 cells from near - shore sediments of Hainan Island. Wei Sheng Wu Xue Bae Apr 45: 185-190 (2005)
36. Williams ST, Davies FL. Use of a scanning electron microscope for the examination of Actinomycetes. J Gen Microbiol 48: 171-177 (1967)
37. Kenneth LK. Prepared research paper RP 2911, Central Nations for the revised ISCC-NBS colour name blocks. J Res NBS 16: 427 (1958)