Mutasynthesis of lincomycin derivatives with activity against drug-resistant staphylococci

Antimicrobial Agents and Chemotherapy

Volumn 54, Issue 2, 2010, Pages 927-930

  Ulanova, Dana ^a   Novotná, Jitka ^a   Smutná, Yvona ^a,c   Kameník, Zdeněk ^a,b   Gažák, Radek ^a   Šulc, Miroslav ^a   Sedmera, Petr ^a   Kadlčík, Stanislav ^a   Plháčková, Kamila ^a   Janata, Jiří ^a  

^a INSTITUTE OF MICROBIOLOGY   (Czech Republic)

^b CHARLES UNIVERSITY   (Czech Republic)

^c CZECH UNIVERSITY OF LIFE SCIENCES PRAGUE   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

4' BUTYL 4' DEPROPYLLINCOMYCIN; 4' PENTYL 4' DEPROPYLLINCOMYCIN; ANTIBIOTIC AGENT; LINCOMYCIN; UNCLASSIFIED DRUG;

ANTIBIOTIC RESISTANCE; ANTIMICROBIAL ACTIVITY; ARTICLE; BACTERIAL STRAIN; CHEMICAL MODIFICATION; DRUG STRUCTURE; DRUG SYNTHESIS; GENE DELETION; GENE SYNTHESIS; MUTANT; PRIORITY JOURNAL; STAPHYLOCOCCACEAE; STREPTOMYCES; STREPTOMYCES LINCOLNENSIS;

ANTI-BACTERIAL AGENTS; BACTERIAL PROTEINS; HUMANS; LINCOMYCIN; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; PROLINE; STAPHYLOCOCCAL INFECTIONS; STAPHYLOCOCCUS; STREPTOMYCES;

EID: 75749124216     PISSN: 00664804     EISSN: 10986596     Source Type: Journal    
DOI: 10.1128/AAC.00918-09     Document Type: Article

References (25)

1. Brisson-Noel, A., and P. Courvalin. 1986. Nucleotide sequence of gene linA encoding resistance to lincosamides in Staphylococcus haemolyticus. Gene 43:247-253.
2. Chesneau, O., H. Ligeret, N. Hosan-Aghaie, A. Morvan, and E. Dassa. 2005. Molecular analysis of resistance to streptogramin A compounds conferred by the Vga proteins of staphylococci. Antimicrob. Agents Chemother. 49:973-980.
3. Chung, S. T., J. J. Manis, S. J. McWethy, T. E. Patt, D. F. Witz, H. J. Wolf, and M. G. Wovcha. 1997. Fermentation, biosynthesis and molecular genetics of linkomycin, p. 165-186. In W. R. Strohl (ed.), Biotechnology of industrial antibiotics, 2nd ed. Dekker, New York, NY.
4. Gust, B., G. L. Challis, K. Fowler, T. Kieser, and K. F. Chater. 2003. PCR-targeted Streptomyces gene replacement identifies a protein domain needed for biosynthesis of the sesquiterpene soil odor geosmin. Proc. Natl. Acad. Sci. U. S. A. 100:1541-1546.
5. Hu, Y., V. Phelan, I. Ntai, C. M. Farnet, E. Zazopoulos, and B. O. Bachmann. 2007. Benzodiazepine biosynthesis in Streptomyces refuineus. Chem. Biol. 14:691-701.
6. Kamenik, Z., J. Kopecky, M. Mareckova, D. Ulanova, J. Novotna, S. Pospisil, and J. Olsovska. 2009. HPLC-fluorescence detection method for determination of key intermediates of the lincomycin biosynthesis in fermentation broth. Anal. Bioanal. Chem. 393:1779-1787.
7. Koberska, M., J. Kopecky, J. Olsovska, M. Jelinkova, D. Ulanova, P. Man, M. Flieger, and J. Janata. 2008. Sequence analysis and heterologous expression of the lincomycin biosynthetic cluster of the type strain Streptomyces lincolnensis ATCC 25466. Folia Microbiol. (Praha) 53:395-401.
8. Lau, J., D. E. Cane, and C. Khosla. 2000. Substrate specificity of the loading didomain of the erythromycin polyketide synthase. Biochemistry 39:10514-10520.
9. Lell, B., and P. G. Kremsner. 2002. Clindamycin as an antimalarial drug: review of clinical trials. Antimicrob. Agents Chemother. 46:2315-2320.
10. Li, W., S. Chou, A. Khullar, and B. Gerratana. 2009. Cloning and characterization of the biosynthetic gene cluster for tomaymycin, an SJG-136 monomeric analog. Appl. Environ. Microbiol. 75:2958-2963.
11. Li, W., A. Khullar, S. Chou, A. Sacramo, and B. Gerratana. 2009. Biosynthesis of sibiromycin, a potent antitumor antibiotic. Appl. Environ. Microbiol. 75:2869-2878.
12. Magerlein, B. J. 1971. Modification of lincomycin. Adv. Appl. Microbiol. 14:185-229.
13. Magerlein, B. J., R. D. Birkenmeyer, and F. Kagan. 1967. Lincomycin. 6. 4′-Alkyl analogs of lincomycin. Relationship between structure and antibacterial activity. J. Med. Chem. 10:355-359.
14. Magerlein, B. J., and F. Kagan. 1969. Lincomycin. 8. 4′-Alkyl-1′-demethyl-4′-depropylclindamycins, potent antibacterial and antimalarial agents. J. Med. Chem. 12:780-784.
15. Novotna, G., V. Adamkova, J. Janata, O. Melter, and J. Spizek. 2005. Prevalence of resistance mechanisms against macrolides and lincosamides in methicillin-resistant coagulase-negative staphylococci in the Czech Republic and occurrence of an undefined mechanism of resistance to lincosamides. Antimicrob. Agents Chemother. 49:3586-3589.
16. Novotna, G., and J. Janata. 2006. A new evolutionary variant of the streptogramin A resistance protein, Vga(A)LC, from Staphylococcus haemolyticus with shifted substrate specificity towards lincosamides. Antimicrob. Agents Chemother. 50:4070-4076.
17. Novotna, G., J. Spizek, and J. Janata. 2007. In vitro activity of telithromycin and quinupristin/dalfopristin against methicillin-resistant coagulase-negative staphylococci with defined resistance genotypes. Folia Microbiol. (Praha) 52:593-599.
18. Olsovska, J., M. Jelinkova, P. Man, M. Koberska, J. Janata, and M. Flieger. 2007. High-throughput quantification of lincomycin traces in fermentation broth of genetically modified Streptomyces spp. Comparison of ultra-performance liquid chromatography and high-performance liquid chromatography with UV detection. J. Chromatogr. A 1139:214-220.
19. Pohl, N. L., M. Hans, H. Y. Lee, Y. S. Kim, D. E. Cane, and C. Khosla. 2001. Remarkably broad substrate tolerance of malonyl-CoA synthetase, an enzyme capable of intracellular synthesis of polyketide precursors. J. Am. Chem. Soc. 123:5822-5823.
20. Ross, J. I., E. A. Eady, J. H. Cove, W. J. Cunliffe, S. Baumberg, and J. C. Wootton. 1990. Inducible erythromycin resistance in staphylococci is encoded by a member of the ATP-binding transport super-gene family. Mol. Microbiol. 4:1207-1214.
21. Salas, J. A., and C. Mendez. 2007. Engineering the glycosylation of natural products in actinomycetes. Trends Microbiol. 15:219-232.
22. Spizek, J., and T. Rezanka. 2004. Lincomycin, clindamycin and their applications. Appl. Microbiol. Biotechnol. 64:455-464.
23. Thakker-Varia, S., A. C. Ranzini, and D. T. Dubin. 1985. Ribosomal RNA methylation in Staphylococcus aureus and Escherichia coli: effect of the "MLS" (erythromycin resistance) methylase. Plasmid 14:152-161.
24. Urbaskova, P. 1998. Rezistence bakterií k antibiotik[ring]um. Vybrané metody. Trios, Prague, Czech Republic. (In Czech.)
25. Visser, J. July 1972. Preparation of lincomycin analogues. U.S. patent 3,674,647.