Structure activity relationship studies on the antimicrobial activity of novel edeine A and D analogues

Journal of Peptide Science

Volumn 12, Issue 10, 2006, Pages 653-662

  Czajgucki, Zbigniew ^a   Andruszkiewicz, Ryszard ^a   Kamysz, Wojciech ^b  

^a GDANSK UNIVERSITY OF TECHNOLOGY   (Poland)

^b MEDICAL UNIVERSITY OF GDANSK   (Poland)

Author keywords

Antimicrobial activity; Edeine analogues; Edeine antibiotics; Peptide synthesis

Indexed keywords

2,3 DIAMINOPROPIONIC ACID; AZIDE; DIPEPTIDE; EDEINE; EDEINE A DERIVATIVE; EDEINE D DERIVATIVE; ESTER; METHYL GROUP; TRIPEPTIDE; UNCLASSIFIED DRUG; VALERIC ACID DERIVATIVE;

AMINO TERMINAL SEQUENCE; ANTIMICROBIAL ACTIVITY; ARTICLE; BACTERIAL STRAIN; CARBOXY TERMINAL SEQUENCE; CHEMICAL MODIFICATION; CHEMICAL PROCEDURES; CONTROLLED STUDY; DRUG SYNTHESIS; FUNGAL STRAIN; ISOMER; NONHUMAN; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

ANTI-BACTERIAL AGENTS; EDEINE; MICROBIAL SENSITIVITY TESTS; PEPTIDES; SPERMIDINE; STRUCTURE-ACTIVITY RELATIONSHIP;

FUNGI;

EID: 33750077285     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.775     Document Type: Article

References (34)

1. Kurylo-Borowska Z. Antibiotical properties of the strain Bacillus brevis Vm4. Bull. Inst. Marine Med. Gdańsk 1959; 10: 83-98.
2. Kurylo-Borowska Z. Isolation and properties of pure edeine, an antibiotic of the strain Bacillus brevis Vm4. Bull. Inst. Marine Med. Gdańsk 1959; 10: 151-163.
3. Borowski E, Chmara H, Jereczek-Morawska E. The antibiotic edeine. VI. Paper and thin-layer chromatography of components of the edeine complex. Biochim. Biophys. Acta 1966; 130: 560-563.
4. 1. Biochemistry 1970; 9: 1224-1232.
5. Wojciechowska H, Zgoda W, Borowski E, Dziegielewski K, Ulikowski S. The antibiotic Edeine. XII. Isolation and structure of edeine F. J. Antibiot. 1983; 36: 793-798.
6. Wojciechowska H, Konitz A, Borowski E. The antibiotic edeine. XI. Chemical structure of edeine D. Int. J. Pept. Protein Res. 1985; 26: 279-293.
7. Chmara H, Borowski E. Antibiotic Edeine: VII. Biological activity of edeine A and B. Acta Microbiol. Pol. 1968; 17: 59-66.
8. Borysiewicz J. Effect of various inhibitors of protein and deoxyribonucleic acid synthesis on the growth of Mycoplasmas. Appl. Microbiol. 1966; 14: 1049-1050.
9. Borowski J, Borowski E, Ciepat A, Dzierzanowska D, Jakubicz P, Smorczewski A. Elimination of plasmids determining bacterial antibiotic resistance by edeine. Drugs Exp. Clin. Res. 1977; 3: 189-191.
10. Borowski J, Jakoniuk P, Jabłońska W, Borowski E. Effect of edeine on primary immunologic response in mice. Arch. Immun. Therap. Exp. 1975; 23: 195-199.
11. Kierońska D, Rózalska B, Zabłocki B. Immunosuppressive properties of the antibiotic edeine. Bull. Acad. Pol. Sci., Ser. Sci. Biol. 1976; 24: 705-710.
12. Borowski J, Jakoniuk P, Borowski E. Edeine as an immunosuppressive agent. Drugs Exp. Clin. Res. 1977; 3: 183-188.
13. Kuryło-Borowska Z. On the mode of action of edeine. Effect of edeine on the bacterial DNA. Biochim. Biophys. Acta 1964; 87: 305-313.
14. Borowski E, Chmara H. The antibiotic edeine. VIII: The mode of action of edeine A and B. Acta Microbiol. Pol. 1968; 17: 241-248.
15. Kuryło-Borowska Z, Szer W. Inhibition of bacterial DNA synthesis by edeine. Effect on Escherichia coli mutants lacking DNA polymerase I. Biochim. Biophys. Acta 1972; 287: 236-245.
16. Woynarowska B, Chmara H, Borowski E. Differential mechanism of action of the antibiotic edeine on prokaryotic and eukaryotic organism points to new basis for selective toxicity. Drugs Exp. Clin. Res. 1979; 5: 181-186.
17. Hierowski M, Kuryło-Borowska Z. On the mode of action of edeine. I. Effect of edeine on the synthesis of polyphenylalanine in a cell-free system. Biochim. Biophys. Acta 1965; 95: 578-589.
18. Obrig T, Irvin J, Culp W, Hardesty B. Inhibition of peptide initiation on reticulocyte ribosomes by edeine. Eur. J. Biochem. 1971; 21: 31-41.
19. Pioletti M, Schlunzen F, Harms J, Zarivach R, Gluhmann M, Avila H, Bashan A, Bartels H, Auerbach T, Jacobi C. Hartsch T, Yonath A, Franceschi F. Crystal structures of complexes of the small rlbosomal subunit with tetracycline, edeine and IF3. EMBO J. 2001; 20: 1829-1839.
20. Mazerski J, Wojciechowska H, Zgoda W, Woynarowska B, Borowski E. Esters and amides of edeine A. J. Antibiot. 1981; 34: 28-33.
21. Gumieniak J, Andruszkiewicz R, Czerwiński A, Grzybowska J, Borowski E. Synthesis of the decarboxy analog of edeine D. J. Antibiot. 1983; 36: 1239-1241.
22. Grzybowska J, Wojciechowska H, Andruszkiewicz R, Borowski E. Syntheses of edeine antibiotics and their analogs. Part IV. Synthesis of N-terminal peptide fragments corresponding to active and inactive isomers of edeine D. Pol. J. Chem. 1979; 53: 1533-1539.
23. Kuehne P, Linden A, Hesse M. Asymmetric synthesis of the alkaloids mayfoline and N(1)-acetyl-N(1)-deoxymayfoline. Helv. Chim. Acta 1996; 79: 1085-1094.
24. Andruszkiewicz R, Wyszogrodzka M. Efficient synthesis of N-benzyloxycarbonyl- and N-tert-butoxycarbonyl-(S)-isoserine and their derivatives. Synlett 2002; 12: 2101-2103.
25. α -protected L-asparagines with iodosobenzene diacetate. A practical route to β-amino-L-alanine derivatives. J. Org. Chem. 1997; 62: 6918-6920.
26. Andruszkiewicz R, Treder A. A convenient synthesis of (S)-O-benzyl-N-tert-butoxycarbonyl-β-tyrosine. Pol. J. Chem. 2004; 78: 1081-1084.
27. 2-benzyloxycarbonyl-(S)-2-amino-3-(dimethylamino)propanoic acid. Org. Prep. Proced. Int. 2001; 33: 379-381.
28. Czajgucki Z, Sowiński P, Andruszkiewicz R. Synthesis of orthogonally protected (3R,4S)- and (3S,4S)-4,5-diamino-3-hydroxypentanoic acids. Amino Acids 2003; 24: 289-291.
29. Andruszkiewicz R, Radowski M, Czajgucki Z. Efficient synthesis of orthogonally protected spermidine and norspermidine derivatives. Synth. Commun. 2005; 35: 1085-1094.
30. Czerwiński A, Wojciechowska H, Andruszkiewicz R, Grzybowska J, Gumieniak J, Borowski E. Total synthesis of edeine D. J. Antibiot. 1983; 36: 1001-1006.
31. Andruszkiewicz R, Wojciechowska H, Borowski E. Syntheses of edeine antibiotics and their analogs. Part II. Synthesis of some analogs of C-terminal moiety of peptide chain of edeines A and D. Pol. J. Chem. 1978; 52: 2147-2156.
32. Grzybowska J, Wojciechowska H, Andruszkiewicz R, Borowski E. Syntheses of edeine antibiotics and their analogs. Part III. Synthesis of some analogs of N-terminal moiety of peptide chain of edeine D. Pol. J. Chem. 1979; 53: 1267-1273.
33. Shioiri T, Ninomiya K, Yamada S. Diphenylphosphoryl azide. A new convenient reagent for a modified Curtius reaction and for the peptide synthesis. J. Am. Chem. Soc. 1972; 94: 6203-6205.
34. Anderson GW, Zimmerman JE, Callahan FM. The use of esters of N-hydroxysuccinimide in peptide synthesis. J. Am. Chem. Soc. 1964; 86: 1839-1842.