Synthesis and biological activity of dialkylphosphocholines

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 22, 2009, Pages 6346-6349

  Lukáč, Miloš ^a   Mrva, Martin ^a   Fischer Fodor, Eva ^b   Lacko, Ivan ^a   Bukovský, Marián ^a   Miklášová, Natalia ^a   Ondriska, František ^c   Devínsky, Ferdinand ^a  

^a Physics and Informatics   (Slovakia)

^b Cancer Institute Ion Chiricuta Cluj Napoca   (Romania)

^c HPL spol s ro   (Slovakia)

Author keywords

Acanthamoeba lugdunensis; Candida albicans; Cytotoxic activity; Dialkylphosphocholines; Miltefosine

Indexed keywords

DIALKYLPHOSPHOCHOLINE; MILTEFOSINE; PHOSPHORYLCHOLINE; UNCLASSIFIED DRUG;

ACANTHAMOEBA; ACANTHAMOEBA LUGDUNENSIS; ANTINEOPLASTIC ACTIVITY; ANTIPROTOZOAL ACTIVITY; ARTICLE; BIOLOGICAL ACTIVITY; CANDIDA ALBICANS; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG SYNTHESIS; FEMALE; FUNGICIDAL ACTIVITY; HUMAN; HUMAN CELL; NONHUMAN; TUMOR CELL;

ACANTHAMOEBA; ANTI-BACTERIAL AGENTS; ANTIFUNGAL AGENTS; ANTINEOPLASTIC AGENTS; ANTIPROTOZOAL AGENTS; CANDIDA ALBICANS; DRUG SCREENING ASSAYS, ANTITUMOR; INHIBITORY CONCENTRATION 50; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; PHOSPHORYLCHOLINE; PLANT EXTRACTS; STRUCTURE-ACTIVITY RELATIONSHIP;

ACANTHAMOEBA LUGDUNENSIS; CANDIDA ALBICANS;

EID: 71049123327     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.09.079     Document Type: Article

References (58)

1. Houlihan W.J., Lohmeyer M., Workman P., and Cheon S.H. Med. Res. Rev. 15 (1995) 157
2. Brachwitz H., and Vollgraf C. Pharmacol. Ther. 66 (1995) 39
3. Koufaki M., Polychroniou V., Calogeropoulou T., Tsotinis A., Drees M., Fiebig H.H., LeClerc S., Hendriks H.R., and Makriyannis A. J. Med. Chem. 39 (1996) 2609
4. Hilgard P., Klenner T., Stekar J., Nössner G., Kutscher B., and Engel J. Eur. J. Cancer 33 (1997) 442
5. Nair H.K., Peterson A.C., Yazdi P.T., and Franzmair R. Bioorg. Med. Chem. Lett. 7 (1997) 2379
6. Holý A., Otová B., Buděšínský M., Emerson D., and Wiles M.E. J. Med. Chem. 44 (2001) 4462
7. Papazafiri P., Avlonitis N., Angelou P., Calogeropoulou T., Koufaki M., Scoulica E., and Fragiadaki I. Cancer Chemother. Pharmacol. 56 (2005) 261
8. Pinchuk A.N., Rampy M.A., Longino M., Skinner R.W.S., Gross M.D., Weichert J.P., and Counsell R.E. J. Med. Chem. 49 (2006) 2155
9. Gajate C., Gonzales-Camacho F., and Mollinedo F. Plos 1 4 (2009) e5044
10. Lukáč, M.; Mojžiš, J.; Mojžišová, G.; Mrva, M.; Ondriska, F.; Valentová, J.; Lacko, I.; Bukovský, M.; Devínsky, F.; Karlovská, J. Eur. J. Med. Chem., in press. doi:10.1016/j.ejmech.2009.08.011.
11. Mollinedo F., Fernandez-Luna J.L., Gajate C., Martin-Martin B., Benito A., Martinez-Dalmau R., and Modolell M. Cancer Res. 57 (1997) 1320
12. Gajate C., Fonteriz R.I., Cabaner C., Alvarez-Noves G., Alvarez-Rodriquez Y., Modolell M., and Mollinedo F. Int. J. Cancer 85 (2000) 674
13. Gajate C., and Mollinedo F. Blood 98 (2001) 3860
14. Gajate C., Del Canto-Janez E., Acuña A.U., Amat-Guerri F., Geijo E., Santos-Beneit A.M., Veldman R.J., and Mollinedo F. J. Exp. Med. 200 (2004) 353
15. Gajate C., and Mollinedo F. Blood 109 (2007) 711
16. Leonard R., Hardy J., van Tienhoven G., Houston S., Simmononds S., David M., and Mansi J. Clin. Oncol. 19 (2001) 4150
17. Vink S.R., Schellens J.H., van Blitterswijk W.J., and Verheij M. Invest. New Drugs 23 (2005) 279
18. Obando D., Widmer F., Wright L.C., Sorrell T.C., and Jolliffe K.A. Bioorg. Med. Chem. 15 (2007) 5158
19. Widmer F., Wright L.C., Obando D., Handke R., Ganandren R., Ellis D.H., and Sorrell T.C. Antimicrob. Agents Chemother. 50 (2006) 414
20. Tong Z., Widmer F., Sorrell T.C., Guse Z., Jolliffe K.A., Halliday C., Lee O.C., Kong F., Wright L.C., and Chen S.C.A. Antimicrob. Agents Chemother. 51 (2007) 2219
21. Bierer D.E., Garber R.E., Jolad S.D., Ubillas R.P., Randle J., Nauka E., Latour J., Dener J.M., Fort D.M., Kuo J.E., Inman W.D., Dubenko L.G., Ayala F., Ozioko A., Obialor C., Elisabetsky E., Carlson T., Truong T.V., and Bruening R.C. J. Org. Chem. 60 (1995) 7022
22. Lu Q., Ubillas R.P., Zhou Y., Dubenko L.G., Dener J.M., Litvak J., Phuan P.W., Flores M., Ye Z.J., Gerber R.E., Truong T., and Biere D.E. J. Nat. Prod. 62 (1999) 824
23. Hornillos V., Saugar J.M., de la Torre B.G., Andreu D., Rivas L., Acuña A.U., and Amat-Guerri F. Bioorg. Med. Chem. Lett. 16 (2006) 5190
24. Seifert K., Lemke A., Croft S.L., and Kayser O. Antimicrob. Agents Chemother. 51 (2007) 4525
25. Calogeropoulou T., Angelou P., Detsi A., Fragiadaki I., and Scoulica E. J. Med. Chem. 51 (2008) 897
26. Coghi P., Vaiana N., Pezzano M.G., Rizzi L., Kaiser M., Brun R., and Romeo S. Bioorg. Med. Chem. Lett. 18 (2008) 4658
27. Hornillos V., Carrillo E., Rivas L., Amat-Guerri F., and Acuña A.U. Bioorg. Med. Chem. Lett. 18 (2008) 6336
28. Wadhone P., Maiti M., Agarwal R., Kamat V., Martin S., and Saha B. J. Immunol. 182 (2009) 7146
29. Croft S.L., Snowdon W., and Yardley V. J. Antimicrob. Chemother. 38 (1996) 1041
30. Walochnik J., Duchêne M., Seifert K., Obwaller A., Hottkowitz T., Wiedremann G., Eibl H., and Aspöck H. Antimicrob. Agents Chemother. 46 (2002) 695
31. McBride J., Ingram P.R., Henriquez F.L., and Roberts C. J. Clin. Microbiol. 43 (2005) 629
32. Schuster F.L., Guglielmo B.J., and Visvesvara G.S. J. Eukaryot. Microbiol. 53 (2006) 121
33. McBride J., Mullen A.B., Carter K.C., and Roberts C.W. J. Antimicrob. Chemother. 60 (2007) 521
34. Lukáč M., Mrva M., Ondriska F., Lacko I., and Devínsky F. Chem. Listy 102 (2008) s199
35. Aichelburg A.C., Walochnik J., Assadian O., Prosch H., Steuer A., Perneczky G., Visvesvara G.S., Aspöck H., and Vetter N. Emerg. Infect. Dis. 14 (2008) 1743
36. Walochnik J., Obwaller A., Gruber F., Mildner M., Tschachler E., Suchomel M., Duchêne M., and Auer H. J. Antimicrob. Chemother. 64 (2009) 539
37. Seifert K., Duchêne M., Wernsdorfer W.H., Kollaritsch H., Scheiner O., Wiedermann G., Hottkowitz T., and Eibl H. Antimicrob. Agents Chemother. 45 (2001) 1505
38. Blaha C., Duchêne M., Aspöck H., and Walochnik J. J. Antimicrob. Chemother. 57 (2006) 273
39. Steinberg J.P., Galindo R.L., Kraus E.S., and Ghanem K.G. Clin. Infect. Dis. 35 (2002) e43
40. Duarte A.G., Sattar F., Granwehr B., Aronson J.F., Wang Z., and Lick S. J. Heart Lung Transplant. 25 (2006) 237
41. Fürnkranz U., Nagl M., Gottardi W., Köhsler M., Aspöck H., and Walochnik J. Antimicrob. Agents Chemother. 52 (2008) 470
42. Croft S.L., Seifert K., and Duchêne M. Mol. Biochem. Parasitol. 126 (2003) 165
43. Lorenzo-Morales J., Klieščiková J., Martinez-Carretero E., De Pablos L.M., Profotová B., Nohýnková E., Osuna A., and Valladares B. Eukaryot. Cell 7 (2008) 509
44. Peresypkin A.V., and Menger F.M. Org. Lett. 1 (1999) 1347
45. Kumar A., Alami E., Holmberg K., Seredyuk V., and Menger F.M. Colloids Surf. A: Physicochem. Eng. Asp. 228 (2003) 197
46. Seredyuk V., Alami E., Nydén M., Holmberg K., Peresypkin A.V., and Menger F.M. Langmuir 17 (2001) 5160
47. Seredyuk V., Alami E., Nydén M., Holmberg K., Peresypkin A.V., and Menger F.M. Colloids Surf. A: Physicochem. Eng. Asp. 203 (2002) 245
48. Sun Y., Feng Y., Dong H., Chen Z., and Han L. Cent. Eur. J. Chem. 5 (2007) 620
49. Menger F.M., Seredyuk V.A., Apkarain R.P., and Wright E.R. J. Am. Chem. Soc. 124 (2002) 12408
50. Ukawa K., Imamiya E., Yamamoto H., Mizuno K., Tasaka A., Terashita Z., Okutani T., Nomura H., Kasukabe T., Hozumi M., Kudo I., and Inoue K. Chem. Pharm. Bull. 37 (1989) 1249
51. McKennon M.J., Meyers A.I., Darauz K., and Schwarm M. J. Org. Chem. 58 (1993) 3568
52. Clarke H.T., Gillespie H.B., and Weisshaus S.Z. J. Am. Chem. Soc. 55 (1933) 4571
53. Imam T., Devínsky F., Lacko I., and Mlynarčík D. Pharmazie 38 (1983) 308
54. Lukáč M., Lacko I., and Devínsky F. Acta Facult. Pharm. Univ. Comenianae 55 (2008) 141
55. -1 3427, 2919, 2851, 1635, 1469, 1242, 1100, 1067, 822.
56. Ondriska F., Mrva M., Lichvár M., Žiak P., Murgašová Z., and Nohýnková E. Ann. Agric. Environ. Med. 11 (2004) 335
57. Fischer-Fodor E., Moldovan N., Virag P., Soritau O., Brie I., Lonnecke P., Hey-Hawkins E., and Silaghi-Dumitrescu L. Dalton Trans. 45 (2008) 6393
58. 50 values, the experiments for all compounds were performed for a concentration series (from 1 to 200 μg/ml).