Chemoenzymatic synthesis and in vitro studies on the hydrolysis of antimicrobial monoglycosyl diglycerides by pancreatic lipase

Bioorganic and Medicinal Chemistry Letters

Volumn 17, Issue 7, 2007, Pages 1971-1978

  Cateni, Francesca ^a   Bonivento, Paolo ^a   Procida, Giuseppe ^a   Zacchigna, Marina ^a   Scialino, Giuditta ^a   Banfi, Elena ^a  

^a UNIVERSITY OF TRIESTE   (Italy)

Author keywords

1,2 Di O acyl 3 O d galactopyranosyl glycerols; 1,2 Di O acyl 3 O d glucopyranosyl glycerols; Antimicrobial activity; Monoglycosyl diglycerides; Pancreatic lipase; Synthesis

Indexed keywords

ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; GALACTOSYLDIACYLGLYCEROL; GLYCOLIPID; GLYCOSYLDIACYLGLYCEROL; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; DRUG HYDROLYSIS; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME SYNTHESIS; EUPHORBIA; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; IN VITRO STUDY; NONHUMAN; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

ANIMALS; ANTI-INFECTIVE AGENTS; ANTIFUNGAL AGENTS; CHEMISTRY, PHARMACEUTICAL; DIGLYCERIDES; DRUG DESIGN; FATTY ACIDS; HYDROLYSIS; LIPASE; MODELS, CHEMICAL; MOLECULAR CONFORMATION; MUCOR; PANCREAS; PSEUDOMONAS; TEMPERATURE;

EUPHORBIACEAE; FUNGI; NEGIBACTERIA; POSIBACTERIA;

EID: 33847650096     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2007.01.019     Document Type: Article

References (39)

1. Sastry P.S. Adv. Lipid Res. 12 (1974) 251
2. Doermann P. In: Murphy D.J. (Ed). Membrane Lipids. Plant Lipids (2005), CRC Press LLC, Boca Raton, FL 123
3. Ohta H., Awai K., and Takamiya K. Trends in Glycoscience and Glycotechnology 12 (2000) 241
4. Huis in't. Veld J.H.J., and Willers J.M.N. Antonie van Leeuwenhoek 39 (1973) 281
5. Matsubara K., Matsumoto H., Mizushina Y., Mori M., Nakajima N., Fuchigami M., Yoshida H., and Hada T. Oncol. Rep. 14 (2005) 157
6. Wang R., Furumoto T., Motoyama K., Okazaki K., Kondo A., and Fukui H. Biosci. Biotechnol. Biochem. 66 (2002) 248
7. Vairappan C.S. Sci. Int. (Lahore) 15 (2003) 49
8. Shirahashi H., Murakami N., Watanabe M., Nagatsu A., Sakakibara J., Tokuda H., Nishino H., and Iwashima A. Chem. Pharm. Bull. 41 (1993) 1664
9. Cateni F., Falsone G., and Zilic J. Mini-Rev. Med. Chem. 3 (2003) 425
10. Colombo D., Franchini L., Toma L., Ronchetti F., Nakabe N., Konoshima T., Nishino H., and Tokuda H. Eur. J. Med. Chem. 40 (2005) 69
11. Nagatsu A., Watanabe M., Ikemoto K., Hashimoto M., Murakami N., Sakakibara J., Tokuda H., Nishino H., Iwashima A., and Yazawa K. Bioorg. Med. Chem. Lett. 4 (1994) 1619
12. Nakata K. J. Biochem. 127 (2000) 731
13. Nakata K., Guo C.T., Matsufugi M., Yoshimoto A., Inagaki M., Higuchi R., and Suzuki Y. J. Biochem. 127 (2000) 191
14. Janwitayanuchit W., Suwanborirux K., Patarapanich C., Pummangura S., Lipipun V., and Vilaivan T. Phytochemistry 64 (2003) 1253
15. Bruno A., Rossi C., Marcolongo G., Di Lena A., Venzo A., Barrie C.P., and Corda D. Eur. J. Pharmacol. 524 (2005) 159
16. Tanaka R., Sakano Y., Nagatsu A., Shibuya M., Ebizuka Y., and Goda Y. Bioorg. Med. Chem. Lett. 15 (2005) 159
17. Cateni F., Zilic J., Falsone G., Scialino G., and Banfi E. Bioorg. Med. Chem. Lett. 13 (2003) 4345
18. Cateni F., Falsone G., Zilic J., Bonivento P., Zacchigna M., Zigon D., Sosa S., and Altinier G. ARKIVOC (2004) 54
19. Mannock D.A., Lewis R.N.A.H., and Mc Elhaney R.N. Chem. Phys. Lipids 55 (1990) 309
20. Colombo D., Ronchetti F., Scala A., Taino I.M., Marine Albini F., and Toma L. Tetrahedron: Asymmetry 5 (1994) 1377
21. Gurr M.I., Bonsen P.P.M., and Van Deenen L.L.M. Biochem. J. 106 (1968) 46P
22. Bashkatova A.I., Volynskaya V.N., Smirnova G.V., Shvets V.I., and Evstigneeva R.P. Zh. Org. Khim. 7 (1971) 1542
23. Batrakov, S. G.; Il' ina, E. F.; Panosyan, A. G. Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya 1976, 3, 643.
24. Gunstone, F. D. In Structured and Modified Lipids; Ed.; Marcel Decker: New York, 2001.
25. Haraldsson G.G., and Hjaltason B. In: Gunstone F.D. (Ed). Structured and Modified Lipids (2001), Marcel Decker, New York 313
26. Yamane T. In: Bornscheuer U.T. (Ed). Enzymes in Lipid Modification (2000), Wiley, Weinheim 148
27. Bottino N.R., Vandenburg G.A., and Reisen R. Lipids 2 (1967) 489
28. Yang L.Y., Kuksis A., and Myher J.J. J. Lipid Res. 31 (1990) 137
29. Babayan V.K. J. Am. Oil Chem. Soc. 58 (1981) 49
30. Mattson F.H., and Volpenhein R.A. J. Biol. Chem. 239 (1964) 2772
31. Christensen M.S., Hoy C.E., Becker C.C., and Redgrave T.G. Am. J. Clin. Nutr. 61 (1995) 56
32. Carrière F., Rogalska E., Cudrey C., Ferrato F., Laugier R., and Verger R. Bioorg. Med. Chem. 5 (1997) 429
33. +.
34. +.
35. Helrich, K. Association of Official Analytical Chemists, 'Official Methods of Analysis', 15th ed. Arlington VA, 1990; p 513, 514.
36. Barry A.L. In: Lorian V. (Ed). Antibiotics in Laboratory Medicine (1980), Williams & Wilkins, Baltimore 1
37. Banfi E., Scialino G., and Monti-Bragadin C. J. Antimicrob. Chemother. 52 (2003) 796
38. National Committee for Clinical Laboratory Standards, Reference method for broth dilution antifungal susceptibility testing of yeast. Approved standard M-27. NCCLS, Villanova, PA, USA, 1997.
39. Davis R., Markham A., and Balfour J.A. Drugs 51 (1996) 1019