Inhibitory effect of phenothiazine- and phenoxazine-derived chloroacetamides on Leishmania major growth and Trypanosoma brucei trypanothione reductase

European Journal of Medicinal Chemistry

Volumn 108, Issue , 2016, Pages 436-443

  Marcu, Ana ^b   Schurigt, Uta ^b   Müller, Klaus ^a   Moll, Heidrun ^b   Krauth Siegel, R Luise ^c   Prinz, Helge ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

^b UNIVERSITY OF WÜRZBURG   (Germany)

^c UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

Antileishmanial activity; Chloroacetamides; Phenothiazines; Phenoxazines; Trypanothione reductase

Indexed keywords

1 (2 CHLORO 10H PHENOXAZIN 10 YL)ETHAN 1 ONE; 1 (9H CARBAZOL 9 YL) 2 CHLOROETHAN 1 ONE; 2 BROMO 1 (2 CHLORO 10H PHENOXAZIN 10 YL)ETHAN 1 ONE; 2 CHLORO 1 (10,11 DIHYDRO 5H DIBENZO[B,F]AZEPIN 5 YL)ETHAN 1 ONE; 2 CHLORO 1 (10H PHENOTHIAZIN 10 YL)ETHAN 1 ONE; 2 CHLORO 1 (10H PHENOXAZIN 10 YL)PROPAN 1 ONE; 2 CHLORO 1 (2 CHLORO 10H PHENOTHIAZIN 10 YL)ETHAN 1 ONE; 2 CHLORO 1 (2 CHLORO 10H PHENOXAZIN 10 YL)ETHAN 1 ONE; 2 CHLORO 1 (2,8 DICHLORO 10H PHENOXAZIN 10 YL)ETHAN 1 ONE; 2 CHLORO 1 (5H DIBENZO[B,F]AZEPIN 5 YL)ETHAN 1 ONE; 2 CHLORO 1 (7 CHLORODIBENZO[B,E] [1,4]OXAZEPIN 5(11H) YL)ETHAN 1 ONE; 2 CHLORO 1 [2 (TRIFLUOROMETHYL) 10H PHENOXAZIN 10 YL]ETHAN 1 ONE; 2 CHLORO 10 (2 CHLOROETHYL) 10H PHENOXAZINE; 2 CHLORO 10H PHENOXAZINE; 2 CHLORO N (5 CHLORO 2 PHENOXYPHENYL)ACETAMIDE; 2 CHLORO N,N DIPHENYLACETAMIDE; 2,3 DICHLORO 1 (10H PHENOXAZIN 10 YL)PROPAN 1 ONE; 3 CHLORO 1 (10H PHENOXAZIN 10 YL)PROPAN 1 ONE; 3 CHLORO 1 (2 CHLORO 10H PHENOXAZIN 10 YL)PROPAN 1 ONE; 3 OXO 3 (10H PHENOXAZIN 10 YL)PROPANENITRILE; 3,3 DICHLORO 1 (10H PHENOXAZIN 10 YL)PROPAN 1 ONE; 4 CHLORO 1 (2 CHLORO 10H PHENOXAZIN 10 YL)BUTAN 1 ONE; CHLOROACETAMIDE; MILTEFOSINE; PAROMOMYCIN; PENTAMIDINE; PHENOTHIAZINE DERIVATIVE; PHENOXAZINE DERIVATIVE; TRYPANOTHIONE REDUCTASE; UNCLASSIFIED DRUG; ACETAMIDE DERIVATIVE; ANTIPROTOZOAL AGENT; ENZYME INHIBITOR; OXAZINE DERIVATIVE; OXIDOREDUCTASE; PHENOTHIAZINE; PHENOXAZINE;

ANTIPROTOZOAL ACTIVITY; ARTICLE; CLINICAL EVALUATION; COMPETITIVE INHIBITION; CYTOTOXICITY; DRUG MECHANISM; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; FUNGUS GROWTH; GROWTH INHIBITION; HUMAN; HUMAN CELL; IC50; IN VITRO STUDY; K562 CELL LINE; LEISHMANIA MAJOR; NONHUMAN; STRUCTURE ACTIVITY RELATION; TIME-DEPENDENT INHIBITION; TRYPANOSOMA BRUCEI; ANTAGONISTS AND INHIBITORS; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; DRUG SENSITIVITY; ENZYMOLOGY; GROWTH, DEVELOPMENT AND AGING; METABOLISM; SYNTHESIS; TRYPANOSOMA BRUCEI BRUCEI;

ACETAMIDES; ANTIPROTOZOAL AGENTS; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME INHIBITORS; LEISHMANIA MAJOR; MOLECULAR STRUCTURE; NADH, NADPH OXIDOREDUCTASES; OXAZINES; PARASITIC SENSITIVITY TESTS; PHENOTHIAZINES; STRUCTURE-ACTIVITY RELATIONSHIP; TRYPANOSOMA BRUCEI BRUCEI;

EID: 84950152686     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2015.11.023     Document Type: Article

References (28)

1. R.J. Baldessarini L.L. Brunton, J.S. Lazo, K.L. Parker, Goodman & Gilman's the Pharmacological Basis of Therapeutics 2006 McGraw-Hill New York 429 459
2. M.J. Ohlow, and B. Moosmann Phenothiazine: the seven lives of pharmacology's first lead structure Drug Discov. Today 16 2011 119 131
3. J.W. Harvey, and A.S. Keitt Studies of the efficacy and potential hazards of methylene blue therapy in aniline-induced methaemoglobinaemia Br. J. Haematol. 54 1983 29 41
4. R.D. Pearson, A.A. Manian, D. Hall, J.L. Harcus, and E.L. Hewlett Antileishmanial activity of chlorpromazine Antimicrob. Agents Chemother. 25 1984 571 574
5. T. Seebeck, and P. Gehr Trypanocidal action of neuroleptic phenothiazines in Trypanosoma brucei Mol. Biochem. Parasit. 9 1983 197 208
6. R. Fauro, S. Lo Presti, C. Bazan, A. Baez, M. Strauss, F. Triquell, D. Cremonezzi, O.S. Negrete, G.C. Willhuber, P. Paglini-Oliva, and H.W. Rivarola Use of clomipramine as chemotherapy of the chronic phase of Chagas disease Parasitology 140 2013 917 927
7. A.T. Evans, and S.L. Croft Antileishmanial actions of tricyclic neuroleptics appear to lack structural specificity Biochem. Pharmacol. 48 1994 613 616
8. G.P. Sarmiento, R.G. Vitale, J. Afeltra, G.Y. Moltrasio, and A.G. Moglioni Synthesis and antifungal activity of some substituted phenothiazines and related compounds Eur. J. Med. Chem. 46 2011 101 105
9. H. Prinz, B. Chamasmani, K. Vogel, K.J. Böhm, B. Aicher, M. Gerlach, E.G. Günther, P. Amon, I. Ivanov, and K. Müller N-benzoylated phenoxazines and phenothiazines: synthesis, antiproliferative activity, and inhibition of tubulin polymerization J. Med. Chem. 54 2011 4247 4263
10. T.J. Benson, J.H. Mckie, J. Garforth, A. Borges, A.H. Fairlamb, and K.T. Douglas Rationally designed selective inhibitors of trypanothione reductase - phenothiazines and related tricyclics as lead structures Biochem. J. 286 1992 9 11
11. C. Chan, H. Yin, J. Garforth, J.H. McKie, R. Jaouhari, P. Speers, K.T. Douglas, P.J. Rock, V. Yardley, S.L. Croft, and A.H. Fairlamb Phenothiazine inhibitors of trypanothione reductase as potential antitrypanosomal and antileishmanial drugs J. Med. Chem. 41 1998 148 156
12. E.M. Jacoby, I. Schlichting, C.B. Lantwin, W. Kabsch, and R.L. Krauth-Siegel Crystal structure of the Trypanosoma cruzi trypanothione reductase-mepacrine complex Proteins 24 1996 73 80
13. K.N. Thimmaiah, J.B. Easton, G.S. Germain, C.L. Morton, S. Kamath, J.K. Buolamwini, and P.J. Houghton Identification of N10-substituted phenoxazines as potent and specific inhibitors of Akt signaling J. Biol. Chem. 280 2005 31924 31935
14. G. De Muylder, K.K.H. Ang, S. Chen, M.R. Arkin, J.C. Engel, and J.H. McKerrow A screen against Leishmania intracellular amastigotes: comparison to a promastigote screen and identification of a host cell-specific hit PLoS Negl. Trop. Dis. 5 2011 e1253
15. A. Ponte-Sucre, R. Vicik, M. Schultheis, T. Schirmeister, and H. Moll Aziridine-2,3-dicarboxylates, peptidomimetic cysteine protease inhibitors with antileishmanial activity Antimicrob. Agents Chem. 50 2006 2439 2447
16. J.L. Richardson, I.R.E. Nett, D.C. Jones, M.H. Abdille, I.H. Gilbert, and A.H. Fairlamb Improved tricyclic inhibitors of trypanothione reductase by screening and chemical synthesis ChemMedChem 4 2009 1333 1340
17. C.B. Lozzio, and B.B. Lozzio Human chronic myelogenous leukemia cell-line with positive philadelphia chromosome Blood 45 1975 321 334
18. E. Persch, S. Bryson, N.K. Todoroff, C. Eberle, J. Thelemann, N. Dirdjaja, M. Kaiser, M. Weber, H. Derbani, R. Brun, G. Schneider, E.F. Pai, R.L. Krauth-Siegel, and F. Diederich Binding to large enzyme pockets: small-molecule inhibitors of trypanothione reductase ChemMedChem 9 2014 1880 1891
19. A.H. Fairlamb, P. Blackburn, P. Ulrich, B.T. Chait, and A. Cerami Trypanothione - a novel bis(Glutathionyl)spermidine cofactor for glutathione-reductase in trypanosomatids Science 227 1985 1485 1487
20. C. Eckermann, B. Matthes, M. Nimtz, V. Reiser, B. Lederer, P. Boger, and J. Schroder Covalent binding of chloroacetamide herbicides to the active site cysteine of plant type III polyketide synthases Phytochemistry 64 2003 1045 1054
21. C. Giordano, C. Gallina, V. Ottaviano, V. Consalvi, and R. Scandurra N-Haloacetyl-amino-acid amides as active-site-directed inhibitors of papain and cathepsin-B Eur. J. Med. Chem. 27 1992 865 873
22. M.C. Jockers-Scherübl, R.H. Schirmer, and R.L. Krauth-Siegel Trypanothione reductase from Trypanosoma cruzi. Catalytic properties of the enzyme and inhibition studies with trypanocidal compounds Eur. J. Biochem. FEBS 180 1989 267 272
23. A. Saravanamuthu, T.J. Vickers, C.S. Bond, M.R. Peterson, W.N. Hunter, and A.H. Fairlamb Two interacting binding sites for quinacrine derivatives in the active site of trypanothione reductase - a template for drug design J. Biol. Chem. 279 2004 29493 29500
24. F. Fueller, B. Jehle, K. Putzker, J.D. Lewis, and R.L. Krauth-Siegel High throughput screening against the peroxidase cascade of African trypanosomes identifies antiparasitic compounds that inactivate tryparedoxin J. Biol. Chem. 287 2012 8792 8802
25. D.C. Jones, A. Ariza, W.H.A. Chow, S.L. Oza, and A.H. Fairlamb Comparative structural, kinetic and inhibitor studies of Trypanosoma brucei trypanothione reductase with T-cruzi Mol. Biochem. Parasit. 169 2010 12 19
26. G.B. Eregowda, H.N. Kalpana, R. Hegde, and K.N. Thimmaiah Synthesis and analysis of structural features of phenoxazine analogues needed to reverse vinblastine resistance in multidrug resistant (MDR) cancer cells Indian J. Chem. 39B 2000 243 259
27. J. de Antoni Preparation of 2,8-disubstituted phenoxazines Bull. Soc. Chim. Fr. 12 1963 2874 2877
28. G.B. Eregowda, G. Krishnegowda, H.N. Kalpana, B.C. Channu, C. Dass, J.K. Horton, P.J. Houghton, and K.N. Thimmaiah Structural requirements for activity of phenoxazines for reversal of drug resistance in cancer cells Asian J. Chem. 11 1999 878 905