Synthesis and antibacterial activity of aminosugar-functionalized intercalating agents

Carbohydrate Research

Volumn 345, Issue 1, 2010, Pages 10-22

  Shi, Wei ^a   Marcus, Sandra L ^a   Lowary, Todd L ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

Anthracyclines; Antibacterial; Synthesis

Indexed keywords

96-WELL; AMINO SUGAR; ANTHRACYCLINES; ANTI-BACTERIAL ACTIVITY; BACILLUS ATROPHAEUS; E. COLI; FUNCTIONALIZED; INTERCALATING AGENTS; MICRODILUTION; STRUCTURE ACTIVITY RELATIONSHIPS;

AMINES; BACTERIOLOGY; ESCHERICHIA COLI; SUGAR (SUCROSE); SUGARS;

COMPLEXATION;

AMINOGLYCOSIDE DERIVATIVE; INTERCALATING AGENT;

ANTIBACTERIAL ACTIVITY; ARTICLE; BACILLUS; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; ESCHERICHIA COLI; INFRARED SPECTROSCOPY; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION;

AMINO SUGARS; ANTI-BACTERIAL AGENTS; BACILLUS; ESCHERICHIA COLI; GLYCOSIDES; INTERCALATING AGENTS; STRUCTURE-ACTIVITY RELATIONSHIP;

BACILLUS ATROPHAEUS; ESCHERICHIA COLI;

EID: 71649107623     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2009.10.010     Document Type: Article

References (29)

1. Di Marco A., Gaetani M., Dorigotti L., Soldati M., and Bellini O. Nature 201 (1964) 706-707
2. Cassinelli F., and Orezzi P. Gen. Microbiol. 11 (1963) 167-174
3. Arcamone F., Cassinelli G., Fantini G., Grein A., Orezzi P., Pol C., and Spalla C. Biotechnol. Bioenerg. 11 (1969) 1101-1110
4. Arcamone F., Bernardi L., Giardino P., Patelli B., Di Marco A., Casazza A.M., Pratesi G., and Reggiani P. Cancer Treat. Rep. 60 (1976) 829-834
5. Israel M., Modest E.J., and Frei E. Cancer Res. 35 (1975) 1365-1368
6. Coukell A.J., and Faulds D. Drugs 53 (1997) 453-482
7. Umezawa H., Takahashi Y., Kinoshita M., Naganawa H., Masuda T., Ishizuka M., Tatsuta K., and Takeuchi T. J. Antibiot. 32 (1979) 1082-1084
8. Oki T., Matsuzawa Y., Yoshimoto A., Numata K., and Kitamura I. J. Antibiot. 28 (1975) 830-834
9. Hori S., Shirai M., Hirano S., Oki T., Inui T., Tsukagoshi S., Ishizuka M., Takeuchi T., and Umezawa H. Gann 68 (1977) 685-690
10. Weiss R.B. Semin. Oncol. 19 (1992) 670-686
11. Arcamone F.M. Anthracyclines. In: Cragg G.M., Kingston D.G.I., and Newmann D.J. (Eds). Anticancer Agents from Natural Products (2005), CRC Press, Boca Raton, FL 299-320
12. Minotti G., Menna P., Salatorelli E., Cairo G., and Gianni L. Pharmacol. Rev. 56 (2004) 185-229
13. Gewirtz D.A. Biochem. Pharmacol. 57 (1999) 727-741
14. Qu X., Wan C., Becker H.C., Zhong D., and Zewail A.H. Proc. Natl. Acad. Sci. U.S.A. 98 (2001) 14212-14217
15. Wang A.H.J., Ughetto G., Quigley G.J., and Rich A. Biochemistry 26 (1987) 1152-1163
16. Lown J.W. Chem. Soc. Rev. 22 (1993) 165-176
17. Pani B., Monti-Bragadin C., and Samer L. Cell. Mol. Life Sci. 31 (1975) 787-788
18. Dornberger K., Eckardt K., Ihn W., Tresselt D., and Schumann G. J. Basic Microbiol. 29 (1989) 241-245
19. Kim B.S., Moon S.S., and Hwang B.K. J. Agric. Food Chem. 48 (2000) 1875-1881
20. Shi W., Coleman R.S., and Lowary T.L. Org. Biomol. Chem. (2009) 3709-3722
21. National Committee for Clinical Laboratory Standards. Performance standards for antimicrobial disk and dilution susceptibility tests for bacteria isolated from animals. Approved standard M31-A. National Committee for Clinical Laboratory Standards: Wayne, Pa. 1999.
22. Elangovan A., Wang Y.H., and Ho T.I. Org. Lett. 5 (2003) 1841-1844
23. Alami M., Ferri F., and Linstrumelle G. Tetrahedron Lett. 34 (1993) 6403-6406
24. Erdelyi M., and Gogoll A. J. Org. Chem. 66 (2001) 4165-4169
25. Lal B., Pramanik B.N., Manhas M.S., and Bose A.K. Tetrahedron Lett. 23 (1977) 1977-1980
26. Lautens M., Schmid G.A., and Chau A. J. Org. Chem. 67 (2002) 8043-8053
27. Sengupta S., Duan H., Lu W., Petersen J.L., and Shi X. Org. Lett. 10 (2008) 1493-1496
28. Garg N.K., Sarpong R., and Stoltz B.M. J. Am. Chem. Soc. 124 (2002) 13179-13184
29. Silverstein R.M., and Webster F.X. Spectrometric Identification of Organic Compounds. 6th ed. (1998), John Wiley & Sons, New York Chapter 4