2-(Arylpropionylamino)- and 2-(arylacryloylamino)benzophenones: Farnesyltransferase inhibition and antimalarial activity

Pharmazie

Volumn 59, Issue 10, 2004, Pages 744-752

  Fucik, K ^a   Kettler, K ^a   Wiesner, J ^b   Ortmann, R ^a   Unterreitmeier, D ^a   Krauss, J ^a   Bracher, F ^a   Jomaa, H ^b   Schlitzer, Martin ^a  

^a UNIVERSITY OF MUNICH   (Germany)

^b JUSTUS LIEBIG UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

2 ACYLAMINO DERIVATIVE; ACRYLOYLAMINOBENZOPHENONE DERIVATIVE; BENZOPHENONE DERIVATIVE; N [3 BENZOYL 4 [3 (4 TRIFLUOROMETHYLPHENYL)PROPIONYLAMINO]PHENYL] 3 [5 (4 NITROPHENYL) 2 FURYL]ACRYLIC ACID AMIDE; N ACYLAMINO ACID; PROPIONYLAMINOBENZOPHENONE DERIVATIVE; PROTEIN FARNESYLTRANSFERASE INHIBITOR; UNCLASSIFIED DRUG;

ANTIMALARIAL ACTIVITY; ARTICLE; DRUG ACTIVITY; DRUG CYTOTOXICITY; DRUG STRUCTURE; ENZYME INHIBITION; IC 50; INHIBITION KINETICS; NONHUMAN; STRUCTURE ANALYSIS;

ALKYL AND ARYL TRANSFERASES; ANIMALS; ANTIMALARIALS; BENZOPHENONES; DRUG SCREENING ASSAYS, ANTITUMOR; ESCHERICHIA COLI; FARNESYLTRANSTRANSFERASE; HL-60 CELLS; HUMANS; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; PLASMODIUM FALCIPARUM; SPECTROMETRY, FLUORESCENCE; STRUCTURE-ACTIVITY RELATIONSHIP; TETRAZOLIUM SALTS; THIAZOLES;

EID: 6344225688     PISSN: 00317144     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (29)

1. Ancelin ML, Calas M, Bompart J, Cordina G, Martin D, Bari MB, Jei T, Druilhe P, Vial HJ (1998) Antimalarial activity of 77 phospholipid polar head analogs: close correlation between inhibition of phospholipid metabolism and in vitro Plasmodium falciparum growth. Blood 91: 1426-1437.
2. Bell IM (2000) Inhibitors of protein prenylation 2000. Exp Opin Ther Patents 10: 1813-1831.
3. Böhm M, Mitsch A, Wißner P, Sattler I, Schlitzer M (2001) Exploration of novel aryl binding sites of farnesyltransferase using molecular modeling and benzophenone-based farnesyltransferase inhibitors. J Med Chem 44: 3117-3124.
4. Buckner FS, Yokoyama K, Nguyen L, Grewal A, Erdjument-Bromage H, Tempst P, Strickland CL, Xiao L, Van Voorhis WC, Gelb MH (2000) Cloning, heterologous expression, and distinct substrate specificity of protein farnesyltransferase from Trypanosoma brucei. J Biol Chem 275: 21870-21876.
5. Buckner FS, Eastman RT, Nepumuceno-Silva JL, Speelmon EC, Myler PJ, Van Voorhis WC, Yokoyama K (2002) Cloning, heterologous expression, and substrate specificities of protein farnesyltransferases from Trypanosoma cruzi and Leishmania major. Mol Biochem Parasitol 122: 181-188.
6. Chakrabarti D, Azam T, DelVecchio C, Qiu L, Park Y, Allen CM (1998) Protein prenyl transferase activities of Plasmodium falciparum. Mol Biochem Parasitol 94: 175-184.
7. Chakrabarti D, Da Silva T, Barger J, Paquette S, Patel H, Patterson S, Allen CM (2002) Protein farnesyltransferase and protein prenylation in Plasmodium falciparum. J Biol Chem 277: 42066-42073.
8. Cox AD, Der CJ (2002) Farnesyltransferase inhibitors: promises and realities. Curr Op Pharm 2: 388-393.
9. Del Villar K, Mitsuzawa H, Yang W, Sattler I, Tamanoi F (1997) Amino acid substitutions that convert the protein substrat specificity of farnesyltransferase to that of geranylgeranyltransferase type I. J Biol Chem 272: 680-687.
10. Desjardins RE, Canfield CJ, Haynes JD, Chulay JD (1979) Quantitative assessment of antimalarial activity in vitro by a semiautomated microdilution technique. Antimicrob. Agents Chemother. 16: 710-718.
11. Fu H-W, Casey PJ (1999) Enzymology and biology of CaaX protein prenylation. Rec Prog Hormon Res 54: 315-343.
12. Ibrahim M, Azzouz N, Gerald P, Schwarz RT (2001) Identification and characterisation of Toxoplasma gondii protein farnesyltransferase. Int J Parasitol 31: 1489-1497.
13. Kettler K, Sakowski J, Silber K, Sattler I, Klebe G, Schlitzer M (2003) Non-thiol farnesyltransferase inhibitors: N-(4-acylamino-3-benzoylphenyl)-3-[5- (4-nitrophenyl)-2-furyl]acrylic acid amides. Bioorg Med Chem 11: 1521-1530.
14. 1B-like receptor. J Med Chem 42: 2504-2526.
15. Mosmann T (1983) Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxic assays. J Immun Meth 65: 55-63.
16. Pompliano DL, Gomez RP, Anthony NJ (1992) Intramolecular fluorescece enhancement: a continuous assay of ras farnesyl: protein transferase. J Am Chem Soc 114: 7945-7946.
17. Purcell WT, Donehower RC (2002) Evolving therapies: Farnesyltransferase inhibitors. Curr One Rep 4: 29-36.
18. Ridley RG (2002) Medical need, scientific opportunity and the drive for antimalarial drugs. Nature 415: 686-693.
19. Sachs J, Malaney P (2002) The economic and social burden of malaria. Nature 415: 680-685.
20. Schlitzer M (2002) Structure based design of benzophenone-based nonthiol farnesyltransferase inhibitors. Curr Pharm Design 8: 1713-1722.
21. Trager W, Jensen JB (1976) Human malaria parasites in continous culture. Science 193: 673-675.
22. Wiesner J, Kettler K, Sakowski J, Ortmann R, Jomaa H, Schlitzer M (2003a) Structure-activity relationships of novel anti-malarial agents: 5. N-(4-Acylamino-3-benzoylphenyl)-[5-(4-nitrophenyl)-2-furyl]acrylic acid amides. Bioorg Med Chem Lett 13: 361-363.
23. Wiesner J, Fucik K, Kettler K, Sakowski J, Ortmann R, Jomaa H, Schlitzer M (2003b) Structure-activity relationships of novel anti-malarial agents: 6. N-(4-arylpropionylamino-3-benzoylphenyl)-[5-(4-nitrophenyl)-2-furyl]acrylic acid amides. Bioorg Med Chem Lett 13: 1539-1541.
24. Wiesner J, Ortmann R, Mitsch A, Wißner P, Sattler I, Jomaa H, Schützer M (2003c) Farnesyltransferase-inhibitors: 5- arylacryloylaminobenzophenones show anti-malarial activity. Pharmazie 58: 289-290.
25. Wiesner J, Kettler K, Sakowski J, Ortmann R, Katzin AM, Kimura EA, Silber K, Klebe G, Jomaa H, Schlitzer M (2004a) Farnesyltransferase-Inhibitoren hemmen das Wachstum von Malaria-Erregern in vitro und in vivo. Angew Chem, 116: 254-257
26. Wiesner J, Kettler K, Sakowski J, Ortmann R, Katzin AM, Kimura EA, Silber K, Klebe G, Jomaa H, Schlitzer M (2004a) Farnesyltransferase inhibitors inhibit the growth of malaria parasites in vitro and in vivo. Angew Chem Int Ed 43: 251-254.
27. Wittinghofer A, Waldmann H (2000a) Ras - ein molekularer Schalter bei der Tumorentstehung. Angew Chem 112: 4360-4383
28. Wittinghofer A, Waldmann H (2000b) Ras - A moelecular switch involved in tumor formation. Angew Chem Int Ed 39: 4192-4214.
29. Yokoyama K, Trobridge P, Buckner FS, Van Voorhis WC, Stuart KD, Gelb MH (1998) The effects of protein farnesyltransferase inhibitors on trypanosomatids: inhibition of protein farnesylation and cell growth. J Biol Chem 273: 26497-26505.