Tailoring modification of deoxysugars during biosynthesis of the antitumour drug chromomycin A3 by Streptomyces griseus ssp. griseus

Molecular Microbiology

Volumn 53, Issue 3, 2004, Pages 903-915

  Menéndez, Nuria ^a   Nur E Alam, Mohammad ^b   Braña, Alfredo F ^a   Rohr, Jürgen ^b   Salas, José A ^a   Méndez, Carmen ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

^b University of Kentucky   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; CHROMOMYCIN; CHROMOMYCIN A3; DEOXYSUGAR; METHYLTRANSFERASE; MITHRAMYCIN;

ACETYLATION; ACYLATION; ANTIBIOTIC BIOSYNTHESIS; ANTIMICROBIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; BACTERIAL GENE; BACTERIAL STRAIN; BIOTRANSFORMATION; CHEMICAL MODIFICATION; CMMA GENE; CMMMIII GENE; CONTROLLED STUDY; DRUG STRUCTURE; ENZYME SUBSTRATE; GENE INACTIVATION; HUMAN; HUMAN CELL; METHYLATION; MICROCOCCUS LUTEUS; NONHUMAN; PRIORITY JOURNAL; STREPTOMYCES ALBUS; STREPTOMYCES GRISEUS; TUMOR CELL LINE;

ACETYLATION; AMINO ACIDS; BASE SEQUENCE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CHROMOMYCIN A3; DEOXY SUGARS; DISACCHARIDES; DNA PRIMERS; GENE EXPRESSION REGULATION, BACTERIAL; MASS SPECTROMETRY; METHYLATION; POLYMERASE CHAIN REACTION; STREPTOMYCES GRISEUS;

ACTINOBACTERIA (CLASS); BACTERIA (MICROORGANISMS); MICROCOCCUS; MICROCOCCUS LUTEUS; STREPTOMYCES; STREPTOMYCES ALBUS; STREPTOMYCES GRISEUS; UNCULTURED ACTINOMYCETE;

EID: 3843111327     PISSN: 0950382X     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1365-2958.2004.04166.x     Document Type: Article

References (51)

1. 2+ complexes with DNA. Biochemistry 31: 2988-2997.
2. Altschul, S.F., Gish, W., Miller, W., Myers, E.W., and Lipman, D.J. (1990) Basic local alignment search tool. J Mol Biol 215: 403-410.
3. Arisawa, A., Tsunekawa, H., Okamura, K., and Okamoto, R. (1995) Nucleotide sequence analysis of the carbomycin biosynthetic genes including the 3-O-acyltransferase gene from Streptomyces thermotolerans. Biosci Biotechnol Biochem 59: 582-588.
4. Bate, N., and Cundliffe, E. (1999) The mycinose-biosynthetic genes of Streptomyces fradiae, producer of tylosin. J Ind Microbiol Biotechnol 23: 118-122.
5. Bianchi, N., Osti, F., Rutigliano, C., Corradini, F.G., Borsetti, E., Tomassetti, M., et al. (1999) The DNA-binding drugs mithramycin and chromomycin are powerful inducers of erythroid differentiation of human K562 cells. Br J Haematol 104: 258-265.
6. Chakrabarti, S., Bhattacharyya, D., and Dasgupta, D. (2001) Structural basis of DNA recognition by anticancer antibiotics, chromomycin A(3) and mithramycin: roles of minor groove width and ligand flexibility. Biopolymers 56: 85-95.
7. Chater, K.F., and Wilde, L.C. (1980) Streptomyces albus G mutants defective in the Sa/GI restriction-modification system. J Gen Microbiol 116: 323-334.
8. 3 are potent inhibitors of neuronal apoptosis induced by oxidative stress and DNA damage in cortical neurons. Ann Neurol 49: 345-354.
9. Epp, J.K., Huber, M.L., Turner, J.R., Goodson, T., and Schnöner, B.E. (1989) Production of a hybrid macrolide antibiotic in Streptomyces ambofaciens and Streptomyces lividans by introduction of a cloned carbomycin biosynthetic gene from Streptomyces thermotolerans. Gene 85: 293-301.
10. Fernández, E., Weissbach, U., Reillo, C.S., Braña, A.F., Méndez, C., Rohr, J., and Salas, J.A. (1998) Identification of two genes from Streptomyces argillaceus encoding glycosyltransferases involved in transfer of a disaccharide during biosynthesis of the antitumor drug mithramycin. J Bacteriol 180: 4929-4937.
11. Fernández-Lozano, M.J., Remsing, L.L., Quirós, L.M., Braña, A.F., Fernández, E., Sánchez, C., et al. (2000) Characterization of two polyketide methyltransferases involved in the biosynthesis of the antitumor drug mithramycin by Streptomyces argillaceus. J Biol Chem 275: 3065-3074.
12. Flett, F., Mersinias, V., and Smith, C.P. (1997) High efficiency intergeneric conjugal transfer of plasmid DNA from Escherichia coli to methyl DNA-restricting streptomycetes. FEMS Microbiol Lett 155: 223-229.
13. Gao, X., and Patel, D.J. (1989) Solution structure of the chromomycin-DNA complex. Biochemistry 28: 751-762.
14. González, A., Remsing, L.L., Lombó, F., Fernández Lozano, M.J., Prado, L., Braña, A.F., et al. (2001) The mtmVUC genes of the mithramycin gene cluster in Streptomyces argillaceus are involved in the biosynthesis of the sugar moieties. Mol Gen Genet 264: 827-835.
15. Hara, O., and Hutchinson, C.R. (1992) A macrolide 3-O-acyltransferase gene from the midecamycin-producing species Streptomyces mycarofaciens. J Bacteriol 174: 5141-5144.
16. Jayasuriya, H., Lingham, R.B., Graham, P., Quamina, D., Herranz, L., Genilloud, O., et al. (2002) Durhamycin A, a potent inhibitor of HIV Tat transactivation. J Nat Prod 65: 1091-1095.
17. Kawano, T., Hidaka, T., Furihata, K., Mochizuki, J., Nakayama, H., Hayakawa, Y., and Seto, H. (1990) Isolation and structures of mono- and di-deacetyl chromomycin antibiotics 02-3D and 02-3G from Streptomyces avellaneus. J Antibiot 43: 110-113.
18. Kieser, T., Bibb, M.J., Buttner, M.J., Chater, K.F., and Hopwood, D.A. (2000) Practical Streptomyces Genetics. Norwich: The John Innes Foundation.
19. Kirschning, A., Bechthold, A., and Rohr, J. (1997) Chemical and biochemical aspects of deoxysugars and therefrom derived oligosaccharides. Topics Curr Chem 188: 1-84.
20. Korzybski, T., Kowszyk-Gindifer, Z., and Kurilowicz, W. (1978) Antibiotics. Origin, Nature and Properties. Washington, DC: American Society for Microbiology Press, pp. 1401-1404.
21. Krogh, A., Larsson, B., von Heijne, G., and Sonnhammer, E.L. (2001) Predicting transmembrane protein topology with a hidden Markov model: application to complete genomes. J Mol Biol 305: 567-580.
22. Liu, H.-W., and Thorson, J.S. (1994) Pathways and mechanisms in the biogenesis of novel deoxysugars by bacteria. Annu Rev Microbiol 48: 223-256.
23. 3 and mithramycin with poly (dG-dC) x poly (dC-dG) and poly (dG) x poly (dC). Biochem 36: 2291-2299.
24. Mazodier, P., Petter, R., and Thompson, C.J. (1989) Intergeneric conjugation between Escherichia coli and Streptomyces species. J Bacteriol 171: 3583-3585.
25. 3 in Streptomyces griseus: analysis of the gene cluster and rational design of novel chromomycin analogues. Chem Biol 11: 21-32.
26. 3. Bioorg Med Chem 11: 2791-2801.
27. 3. Tetrahedron Lett 43: 5513-5516.
28. 3 by Streptomyces griseus. J Antibiot 43: 883-889.
29. Patallo, E.P., Blanco, G., Fischer, C., Braña, A.F., Rohr, J., Méndez, C., and Salas, J.A. (2001) Deoxysugar methylation during biosynthesis of the antitumor polyketide elloramycin by Streptomyces olivaceus. J Biol Chem 276: 18765-18774.
30. Paulus, T.J., Tuan, J.S., Luebke, V.E., Maine, G.T., DeWitt, J.P., and Katz, L. (1990) Mutation and cloning of eryG, the structural gene for erythromycin O-methyltransferase from Saccharopolyspora erythraea, and expression of eryG in Escherichia coli. J Bacteriol 172: 2541-2546.
31. Pelzer, S., Sussmuth, R., Heckmann, D., Recktenwald, J., Huber, P., Jung, G., and Wohlleben, W. (1999) Identification and analysis of the balhimycin biosynthetic gene cluster and its use for manipulating glycopeptide biosynthesis in Amycolatopsis mediterranei DSM5908. Antimicrob Agents Chemother 43: 1565-1573.
32. Piepersberg, W. (1994) Pathway engineering in secondary metabolite-producing actinomycetes. Crit Rev Biotech 14: 251-285.
33. Pojer, F., Li, S.M., and Heide, L. (2002) Molecular cloning and sequence analysis of the clorobiocin biosynthetic gene cluster: new insights into the biosynthesis of aminocoumarin antibiotics. Microbiology 148: 3901-3911.
34. Quirós, L.M., Aguirrezabalaga, I., Olano, C., Méndez, C., and Salas, J.A. (1998) Two glycosyltransferases and a glycosidase are involved in oleandomycin modification during its biosynthesis by Streptomyces antibioticus. Mol Microbiol 28: 1177-1185.
35. Remers, W.A. (1979) The Chemistry of Antitumor Antibiotics, Vol. 1. New York: Wiley-Interscience, pp. 133-175
36. Rodríguez, L., Rodríguez, D., Olano, C., Braña, A.F., Méndez, C., and Salas, J.A. (2001) Functional analysis of OleY L-oleandrasyl 3-O-methyltransferase of the oleandomycin biosynthetic pathway in Streptomyces antibioticus. J Bacteriol 183: 5358-5363.
37. Rohr, J., Méndez, C., and Salas, J.A. (1999) The biosynthesis of aureolic acid group antibiotics. Bioorg Chem 27: 41-54.
38. Sambrook, J., Fritsch, E.F., and Maniatis, T. (1989) Molecular Cloning: A Laboratory Manual. Cold Spring Harbor, NY: Cold Spring Harbor Laboratory Press.
39. 2+ complex in methanol: role of the carbohydrates in complex formation. J Am Chem Soc 115: 7962-7970.
40. 3 stabilize the Mg (2+)-dimer complex. Biochemistry 32: 463-471.
41. Skarbek, J.D., and Speedie, M.K. (1981) Antitumor Compounds of Natural Origin: Chemistry and Biochemistry. Aszalos, A. (ed.). Boca Raton: CRC Press, pp. 191-235.
42. Skehan, P., Storeng, R., Scudiero, D., Monks, A., McMahon, J., Vistica, D., et al. (1990) New colorimetric cytotoxicity assay for anticancer-drug screening. J Natl Cancer Inst 82: 1107-1112.
43. Sun, Y., Zhou, X., Liu, J., Bao, K., Zhang, G., Tu, G., et al. (2002) Streptomyces nanchangensis, a producer of the insecticidal polyether antibiotic nanchangmycin and the antiparasitic macrolide meilingmycin, contains multiple polyketide gene clusters. Microbiology 148: 361-371.
44. Trefzer, A., Salas, J.A., and Bechthold, A. (1999) Genes and enzymes of deoxysugar biosyntheses. Nat Prod Report 16: 283-299.
45. Vieira, J., and Messing, J. (1991) New pUC-derived cloning vectors with different selectable markers and DNA replication origins. Gene 100: 189-194.
46. Vilches, C., Mendez, C., Hardisson, C., and Salas, J.A. (1990) Biosynthesis of oleandomycin by Streptomyces antibioticus: influence of nutritional conditions and development of resistance. J Gen Microbiol 136: 1447-1454.
47. Vilches, C., Hernández, C., Méndez, C., and Salas, J.A. (1992) Role of glycosylation and deglycosylation in biosynthesis of and resistance to oleandomycin in the producer organism, Streptomyces antibioticus. J Bacteriol 174: 161-165.
48. Volchegursky, Y., Hu, Z., Katz, L., and McDaniel, R. (2000) Biosynthesis of the anti-parasitic agent megalomicin: transformation of erythromycin to megalomicin in Saccharopolyspora erythraea. Mol Microbiol 40: 1045-1046.
49. Waldron, C., Matsushima, P., Rosteck, P.R., Jr, Broughton, M.C., Turner, J., Madduri, K., et al. (2001) Cloning and analysis of the spinosad biosynthetic gene cluster of Saccharopolyspora spinosa. Chem Biol 8: 487-499.
50. Weymouth-Wilson, A.C. (1997) The role of carbohydrates in biologically active natural products. Nat Prod Report 14: 99-110.
51. Yanisch-Perron, C., Viera, J., and Messing, J. (1985) Improved M13 phage cloning vectors and host strains, nucleotide sequences of the M13mp18 and pUC19 vectors. Gene 33: 103-119.