Synthesis and antimicrobial evaluation of farnesyl diphosphate mimetics

Bioorganic Chemistry

Volumn 31, Issue 1, 2003, Pages 80-97

  Fairlamb, Ian J S ^a,b   Dickinson, Julia M ^a   O'Connor, Rachael ^a   Cohen, Louis H ^c   Van Thiel, Christa F ^c  

^a MANCHESTER METROPOLITAN UNIVERSITY   (United Kingdom)

^b UNIVERSITY OF YORK   (United Kingdom)

^c TNO   (Netherlands)

Author keywords

Antimicrobial agents; Copper(I) catalysed tetrahydropyranyl ether displacements; Farnesyl protein transferase; Inhibitors; Squalene synthase

Indexed keywords

10 PHENYL 5,9 DIMETHYLDECADIENOIC ACID; 2 (DIETHOXYPHOSPHINYL) 10 PHENYL 5,9 DIMETHYLDECADIENOIC ACID; 2 PHOSPHONO 10 PHENYL 5,9 DIMETHYLDECADIENOIC ACID; 3,7 DIMETHYLOCTADIEN 1 PHENYLSULFONE; 8 BENZOXY 3,7 DIMETHYLOCTADIEN 1 OL; 8 HYDROXY 3,7 DIMETHYLOCTADIEN 1 PHENYLSULFONE; ANTIINFECTIVE AGENT; FARNESYL DIPHOSPHATE; FUNCTIONAL GROUP; SQUALENE SYNTHASE; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ARTICLE; BROMINATION; CANDIDA ALBICANS; CONTROLLED STUDY; DRUG INHIBITION; DRUG MECHANISM; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; NONHUMAN; OXIDATION; PRIORITY JOURNAL; SACCHAROMYCES CEREVISIAE; STEROL SYNTHESIS; STRUCTURE ANALYSIS;

CANDIDA ALBICANS; ESCHERICHIA COLI; PSEUDOMONAS; PSEUDOMONAS AERUGINOSA; SACCHAROMYCES CEREVISIAE; SALMONELLA TYPHIMURIUM; TYPHIMURIUM;

EID: 0037306133     PISSN: 00452068     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0045-2068(03)00025-7     Document Type: Article

References (29)

1. (a) For two excellent reviews in this area see, Nadin A., Nicolaou K.C. Angew. Chem. Int. Ed. Engl. 35:1996;1622
2. (b) Biller S.A., Neuenschwander K., Ponpipom M.M., Poulter C.D. Curr. Pharm. Des. 2:1996;1.
3. Grunler J. Biochem. Biophys. Acta. 1212:1994;259.
4. (a) Bhide R.S., Patel D.V., Patel M.M., Robinson S.P., Hunihan L.W., Gordon E.M. Biorg. Med. Chem. Lett. 4:1994;2107
5. (b) Clarke S. Ann. Rev. Biochem. 61:1992;355
6. (c) Schafer W.R., Rine J. Annu. Rev. Genet. 30:1992;209
7. (d) Omer C.A., Gibbs J.B. Mol. Microbiol. 11:1994;219
8. (e) Casey P.J., Seabra M.C. J. Biol. Chem. 271:1996;5289.
9. Mechelke M., Wiemer D.F. Tetrahedron Lett. 39:1998;783
10. (b) Mechelke M., Wiemer D.F. J. Org. Chem. 64:1999;4821
11. (c) Spencer T.A., Onofrey T.J., Cann R.O., Russell J.S., Lee L.E., Blanchard D.E., Castro A., Gu P., Jiang G., Schechter I. J. Org. Chem. 64:1999;807.
12. Gaon I., Turek T.C., Weller V.A., Edelstein R.L., Singh S.K., Distefano M.D. J. Org. Chem. 61:1996;7738.
13. Long S.B., Casey P.J., Beese S. Biochemistry. 37:1998;9612.
14. Holstein S., Cermak D.M., Hohl R., Lewis K., Wiemer D.F. Bioorg. Med. Chem. 6:1998;687.
15. Corey E.J., Kim C.U., Takeda M. Tetrahedron Lett. 42:1972;4339.
16. 4 . E-Selectivity was confirmed by quantitative n.O.e studies (pulse delay=5 s, IRATN=150): a small n.O.e is observed between the terminal vinyl proton and the Z-methyl protons (0.2%), whereas an n.O.e of 1.9% is observed from the terminal vinyl proton to the E-methylene protons.
17. National Committee for Clinical Laboratory Standards. Reference method for broth dilution for antifungal susceptibility testing of yeast. National Committee for Clinical Laboratory Standards, Villanova, PA (USA).
18. (a) Squalestatin S1 is a potent nanomolar inhibitor of SQS. In our antimicrobial assay the MIC for S1 against C. albicans was determined to be <2 μ g/mL. The reported MIC for S1 against C. albicans is between 6-16 μg/mL Dufresne C., Wilson K.E., Zink D., Smith J., Bergstrom J.D., Kurtz M., Rew D., Nallin M., Jenkins R., Bartizal K., Trainor C., Bills G., Meinz M., Huang L., Onishi J., Milligan J., Mojena M., Pelaez F. Tetrahedron. 48:1992;10221
19. (b) Dufresne C., Wilson K.E., Zink D.L., Bergstrom J.D., Rew D., Smith J., Singh D.L., Lingham R.B., Mojena M., Cascales C., Pelaez F., Gibbs J.B. J. Nat. Prod. 56:1993;1923
20. (c) Watson N.S., Bell R., Chan C., Cox B., Hutson J.L., Keeling S.E., Kirk B.E., Procopiou P.A., Steeples I.P., Widdowson J. Bioorg. Med. Chem. Lett. 3:1993;2541.
21. SQS is an active enzyme in E. coli: see http://www.genome.ad.jp/kegg/kegg2.htm.
22. The MIC was determined using a micro-dilution procedure (see Ref. [10]). The agar media was prepared by incorporation of compound 15 at various concentrations. The MIC was determined as the lowest concentration of 15 where no visible growth of the organism was observed.
23. Cohen L.H., Valentijn A.R.P.M., Roodenburg L., van Leeuwen R.E.W., Holger Huisman R., Lutz R.J., van der Marel G.A., van Boom J.H. Biochem. Phamacol. 49:1995;839.
24. Cohen L.H., Pieterman E., van Leeuwen R.E.W., Du J., Negre-Aminou P., Valentijn A.R.P.M., Overhand M., van der Marel G.A., van Boom J.H. Biochem. Phamacol. 57:1999;365.
25. Chehade K.A.H., Andres D.A., Morimoto H., Spielmann H.P. J. Org. Chem. 65:2000;3027.
26. Szkopinska A., Swieewska G., Karst F. Biochem. Biophys. Res. Commun. 267:2000;473.
27. Brown M.S., Goldstein J.L. Science. 232:1986;34.
28. Campbell R.V.M., Crombie L., Findley D.A.R., King R.W., Pattenden G., Whiting D.A. J. Chem. Soc. Perkin Trans. 1:1975;897.
29. Marshall J.A., Andrews R.C. J. Org. Chem. 50:1985;1602.