Synthesis and antimicrobial activity of symmetrical two-tailed dendritic tricarboxylato amphiphiles

Bioorganic and Medicinal Chemistry

Volumn 15, Issue 11, 2007, Pages 3842-3853

  Sugandhi, Eko W ^a   Falkinham III, Joseph O ^a   Gandour, Richard D ^a  

^a VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

Author keywords

Antimicrobial activity; Dendritic amphiphiles; Hydrophobicity; Structure activity study

Indexed keywords

4 (2 CARBOXYETHYL) 4 (3,3 DIDECYLUREIDO)HEPTANEDIOIC ACID; 4 (2 CARBOXYETHYL) 4 (3,3 DIHEPTYLUREIDO)HEPTANEDIOIC ACID; 4 (2 CARBOXYETHYL) 4 (3,3 DINONYLUREIDO)HEPTANEDIOIC ACID; 4 (2 CARBOXYETHYL) 4 (3,3 DIOCTYLUREIDO)HEPTANEDIOIC ACID; 4 (2 CARBOXYETHYL) 4 (3,3 DIUNDECYLUREIDO)HEPTANEDIOIC ACID; 4 (2 CARBOXYETHYL) 4 [3 (1 DECYLUNDECYL)UREIDO]HEPTANEDIOIC ACID; 4 (2 CARBOXYETHYL) 4 [3 (1 DODECYLTRIDECYL)UREIDO]HEPTANEDIOIC ACID; 4 (2 CARBOXYETHYL) 4 [3 (1 HEPTYLOCTYL)UREIDO]HEPTANEDIOIC ACID; 4 (2 CARBOXYETHYL) 4 [3 (1 NONYLDECYL)UREIDO]HEPTANEDIOIC ACID; 4 (2 CARBOXYETHYL) 4 [3 (1 OCTYLNONYL)UREIDO]HEPTANEDIOIC ACID; 4 (2 CARBOXYETHYL) 4 [3 (1 UNDECYLDODECYL)UREIDO]HEPTANEDIOIC ACID; AMPHOPHILE; FUNCTIONAL GROUP; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ARTICLE; ASPERGILLUS NIGER; CANDIDA ALBICANS; CONTROLLED STUDY; CRYPTOCOCCUS NEOFORMANS; DRUG SOLUBILITY; DRUG SPECIFICITY; DRUG STRUCTURE; DRUG SYNTHESIS; ESCHERICHIA COLI; HYDROPHOBICITY; KLEBSIELLA PNEUMONIAE; LACTOBACILLUS PLANTARUM; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; MICROCOCCUS LUTEUS; MICROORGANISM; MINIMUM INHIBITORY CONCENTRATION; MYCOBACTERIUM SMEGMATIS; NONHUMAN; SACCHAROMYCES CEREVISIAE; STAPHYLOCOCCUS AUREUS;

ANTIFUNGAL AGENTS; BACTERIA; CANDIDA ALBICANS; CRYPTOCOCCUS NEOFORMANS; DENDRIMERS; HYDROPHOBICITY; SOLUBILITY; STRUCTURE-ACTIVITY RELATIONSHIP; WATER;

CANDIDA ALBICANS; FILOBASIDIELLA NEOFORMANS;

EID: 34247392455     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2007.03.017     Document Type: Article

References (44)

1. Bayliss M. J. Bacteriol. 31 (1936) 489
2. Walker J.E. J. Infect. Dis. 35 (1924) 557
3. Vorum H., Brodersen R., Kragh-Hansen U., and Pedersen A.O. Biochim. Biophys. Acta 1126 (1992) 135
4. Williams A.A., Sugandhi E.W., Macri R.V., Falkinham III J.O., and Gandour R.D. J. Antimicrob. Chemother. 59 (2007) 451
5. Newkome G.R., Behera R.K., Moorefield C.N., and Baker G.R. J. Org. Chem. 56 (1991) 7162
6. Csizmadia, F. Log P and log D calculator , accessed November 15, 2006.
7. Newkome G.R., Weis C.D., Moorefield C.N., and Fronczek F.R. Tetrahedron Lett. 38 (1997) 7053
8. Nagase A., Kuwahara Y., Tominaga Y., and Sugawara R. Agric. Biol. Chem. 47 (1983) 53
9. Djedovič N., Ferdani R., Harder E., Pajewska J., Pajewski R., Weber M.E., Schlesinger P.H., and Gokel G.W. New J. Chem. 29 (2005) 291
10. Boal A.K., Das K., Gray M., and Rotello V.M. Chem. Mater. 14 (2002) 2628
11. Baykut F. Rev. Fac. Sci. Univ. Istanbul. 19 (1954) 121
12. Breusch F.L., and Sokullu S. Chem. Ber. 86 (1953) 678
13. Meakins R.J., and Sack R.A. Aust. J. Sci. Res. 4A (1951) 213
14. Overmars F.J.J., Engberts J.B.F.N., and Weringa W.D. Recl. Trav. Chim. Pays-Bas 113 (1994) 293
15. Meekel A.A.P., Wagenaar A., Šmisterová J., Kroeze J.E., Haadsma P., Bosgraaf B., Stuart M.C.A., Brisson A., Ruiters M.H.J., Hoekstra D., and Engberts J.B.F.N. Eur. J. Org. Chem. 2000 (2000) 665
16. Malanga C., Mannucci S., and Lardicci L. J. Chem. Res. Synop. 6 (2000) 701
17. Wescott L.D., and Mattern D.L. J. Org. Chem. 68 (2003) 10058
18. Kaneko D., Olsson U., and Sakamoto K. Langmuir 18 (2002) 4699
19. Kanicky J.R., and Shah D.O. Langmuir 19 (2003) 2034
20. Bates R.G., and Allen G.F. J. Res. Natl. Bur. Stand. (US) 64A (1960) 343
21. Boris S., and Barbes C. Microbes Infect. 2 (2000) 543
22. Kondo E., and Kanai K. Jpn. J. Med. Sci. Biol. 25 (1972) 1
23. Seidel V., and Taylor P.W. Int. J. Antimicrob. Agents 23 (2004) 613
24. Masuoka J., and Hazen K.C. Glycobiology 9 (1999) 1281
25. Genco C.A., Maloy W.L., Kari U.P., and Motley M. Int. J. Antimicrob. Agents 21 (2003) 75
26. Quinn F.R., Driscoll J.S., and Hansch C. J. Med. Chem. 18 (1975) 332
27. Jiang S., Wang L., Yu H., and Chen Y. React. Funct. Polym. 62 (2005) 209
28. Langsrud S., Sundheim G., and Borgmann-Strahsen R. J. Appl. Microbiol. 95 (2003) 874
29. Walsh S.E., Maillard J.-Y., Russell A.D., Catrenich C.E., Charbonneau D.L., and Bartolo R.G. J. Appl. Microbiol. 94 (2003) 240
30. Oya A., Funato Y., and Sugiyama K. J. Mater. Sci. 29 (1994) 11
31. Cox, J. M.; Marsden, J. H. E.; Elmore, N.; Shephard, M. C.; Burrell, R. A. US Patent 4146716, 1979, 17 pp
32. Grier N., Dybas R.A., Strelitz R.A., Witzel B.E., and Dulaney E.L. J. Pharm. Sci. 71 (1982) 365
33. Carballeira N.M., Ortiz D., Parang K., and Sardari S. Arch. Pharm. 337 (2004) 152
34. Carballeira N.M., O'Neill R., and Parang K. Chem. Phys. Lipids 136 (2005) 47
35. Carballeira N.M., Sanabria D., and Parang K. Arch. Pharm. 338 (2005) 441
36. Carballeira N.M., Sanabria D., Cruz C., Parang K., Wan B.J., and Franzblau S. Lipids 41 (2006) 507
37. Sugandhi, E. W.; Macri, R. V.; Kite, B. L.; Williams, A. A.; Slebodnick, C.; Falkinham, J. O., III; Esker, A. R.; Gandour, R. D. J. Med. Chem. 2007, 50, doi:10.1021/jm061240d. Available online 9 March 2007.
38. Newkome G.R., Weis C.D., and Childs B.J. Des. Monomers Polym. 1 (1998) 3
39. Troyanskii E.I., Ioffe V.A., Mizintsev V.V., and Nikishin G.I. Izv. Akad. Nauk SSSR, Ser. Khim. 8 (1984) 1814
40. Gall, R.; Bosies, E. Germany Patent DE 3623397 A1, 1988, 12 pp
41. Froger C., and Parisot A. Compt. Rend. 238 (1954) 1589
42. Yoshioka Y., and Tashiro K. J. Phys. Chem. B 107 (2003) 11835
43. Rao H.S.P., and Bharathi B. Indian J. Chem. B 41 (2002) 1072
44. Wright J.B., and Elderfield R.C. J. Org. Chem. 11 (1946) 111