Repurposing human PDE4 inhibitors for neglected tropical diseases. evaluation of analogs of the human PDE4 inhibitor GSK-256066 as inhibitors of pdeb1 of trypanosoma brucei

Chemical Biology and Drug Design

Volumn 85, Issue 5, 2015, Pages 549-564

  Ochiana, Stefan O ^a   Bland, Nicholas D ^b   Settimo, Luca ^a   Campbell, Robert K ^b   Pollastri, Michael P ^a  

^a NORTHEASTERN UNIVERSITY   (United States)

^b MARINE BIOLOGICAL LABORATORY   (United States)

Author keywords

GSK 256066; phosphodiesterase inhibitors; TbrPDEB1; TbrPDEB2; Trypanosoma brucei

Indexed keywords

3 [3 CARBAMOYL 4 (3 METHOXYPHENYLAMINO) 8 METHYLQUINOLIN 6 YLSULFONYL]BENZOIC ACID; 3 [3 CARBAMOYL 4 [(3 METHOXYPHENYL)AMINO] 8METHYLQUINOLIN 6 YL] 5 (METHOXYCARBONYL)BENZOIC ACID; 4 (3 METHOXYPHENYLAMINO) 8 METHYL 6 [3 (METHYLCARBAMOYL)PHENYLSULFONYL]QUINOLINE 3 CARBOXAMIDE; 4 (CYCLOPENTYLAMINO) 8 METHYL 6 [3 (OXAZOL 2 YL) PHENYL]QUINOLINE 3 CARBOXAMIDE; 4 CHLORO 6 IODO 8 METHYLQUINOLINE 3 CARBOXAMIDE; 4 CHLORO 6 IODO N,8 DIMETHYLQUINOLINE 3 CARBOXAMIDE; 4 CHLORO 6 IODO N,N,8 TRIMETHYLQUINOLINE 3 CARBOXAMIDE; 4 [(3 METHOXYPHENYL)AMINO] 8 METHYL 6 (PHENYLSULFONYL)QUINOLINE 3 CARBOXAMIDE; 4 [(3 METHOXYPHENYL)AMINO] 8 METHYL 6 (PHENYLTHIO)QUINOLINE 3 CARBOXAMIDE; 4 [(3 METHOXYPHENYL)AMINO] N,8 DIMETHYL 6 (1 METHYL 1H INDAZOL 6 YL)QUINOLINE 3 CARBOXAMIDE; 4 [(3 METHOXYPHENYL)AMINO] N,N,8 TRIMETHYL 6 (1 METHYL 1H INDAZOL 6 YL)QUINOLINE 3 CARBOXAMIDE FORMIC ACID; 5 [3 CARBAMOYL 4 [(3 METHOXYPHENYL)AMINO] 8 METHYLQUINOLIN 6 YL]ISOPHTHALIC AICD; 6 (3 CARBAMOYLPHENYLSULFONYL) 4 (3 METHOXYPHENYLAMINO) 8 METHYLQUINOLINE 3 CARBOXAMIDE; 6 IODO 4 (3 METHOXYPHENYLAMINO) 8 METHYLQUINOLINE 3 CARBOXAMIDE; 6 IODO 4 [(3 METHOXYPHENYL)AMINO] N,8 DIMETHYLQUINOLINE 3 CARBOXAMIDE; 6 IODO 4 [(3 METHOXYPHENYL)AMINO] N,N,8 TRIMETHYLQUINOLINE 3 CARBOXAMIDE; 8 ETHYL 6 IODO 4 [(3 METHOXYPHENYL)AMINO]QUINOLINE 3 CARBOXAMIDE; ANTITRYPANOSOMAL AGENT; DIMETHYL 3,3' (3 CARBAMOYL 8 METHYLQUINOLINE 4,6 DIYL)DIBENZOATE; ETHYL 6 IODO 8 METHYL 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXYLATE; GSK 256066; METHYL 3 (3 CARBAMOYL 4 CHLORO 8 METHYLQUINOLIN 6 YL)BENZOATE; METHYL 3 (3 CARBAMOYL 8 METHYLQUINOLIN 6 YL)BENZOATE; METHYL 3 [3 CARBAMOYL 4 (3 METHOXYPHENYLAMINO) 8 METHYLQUINOLIN 6 YLAMINO)BENZOATE; METHYL 3 [3 CARBAMOYL 4 (3 METHOXYPHENYLAMINO) 8 METHYLQUINOLIN 6 YLSULFONYL]BENZOATE; METHYL 3 [3 CARBAMOYL 4 (3 METHOXYPHENYLAMINO) 8 METHYLQUINOLIN 6 YLTHIO]BENZOATE; PDEB1 PROTEIN; PHOSPHODIESTERASE; PHOSPHODIESTERASE IV; UNCLASSIFIED DRUG; 6-((3-((DIMETHYLAMINO)CARBONYL)PHENYL)SULFONYL)-8-METHYL-4-((3-METHYLOXYPHENYL)AMINO)-3-QUINOLINECARBOXAMIDE; AMINOQUINOLINE DERIVATIVE; CYCLIC AMP PHOSPHODIESTERASE; PDEB1 PROTEIN, TRYPANOSOMA BRUCEI; PHOSPHODIESTERASE IV INHIBITOR; PROTOZOAL PROTEIN; QUINOLINE; QUINOLINE DERIVATIVE; SULFONE;

AFRICAN TRYPANOSOMIASIS; ARTICLE; CELL GROWTH; CHEMICAL ANALYSIS; CLINICAL EVALUATION; CRYSTAL STRUCTURE; DRUG DETERMINATION; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; MOLECULAR DOCKING; NEGLECTED DISEASE; NEGLECTED TROPICAL DISEASE; NONHUMAN; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; TRYPANOSOMA BRUCEI BRUCEI; ANTAGONISTS AND INHIBITORS; BINDING SITE; CHEMISTRY; DRUG EFFECTS; DRUG REPOSITIONING; ENZYMOLOGY; METABOLISM; NEGLECTED DISEASES; PROTEIN TERTIARY STRUCTURE; TRYPANOSOMIASIS, AFRICAN;

TRYPANOSOMA BRUCEI;

3',5'-CYCLIC-AMP PHOSPHODIESTERASES; AMINOQUINOLINES; BINDING SITES; CYCLIC NUCLEOTIDE PHOSPHODIESTERASES, TYPE 4; DRUG REPOSITIONING; HUMANS; MOLECULAR DOCKING SIMULATION; NEGLECTED DISEASES; PHOSPHODIESTERASE 4 INHIBITORS; PROTEIN STRUCTURE, TERTIARY; PROTOZOAN PROTEINS; QUINOLINES; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONES; TRYPANOSOMA BRUCEI BRUCEI; TRYPANOSOMIASIS, AFRICAN;

EID: 84926624864     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/cbdd.12443     Document Type: Article

References (32)

1. Savioli L., Daumerle D., Sustaining the drive to overcome the global impact of neglected tropical diseases. World Health Organization 2013. Available from: http://apps.who.int/iris/bitstream/10665/77950/1/9789241564540-eng.pdf.
2. Priotto G., Kasparian S., Mutombo W., Ngouama D., Ghorashian S., Arnold U., Ghabri S., et al,. (2009) Nifurtimox-eflornithine combination therapy for second-stage African Trypanosoma brucei gambiense trypanosomiasis: a multicentre, randomised, phase III, non-inferiority trial. Lancet; 374: 56-64.
3. Nok A.J., (2003) Arsenicals (melarsoprol), pentamidine and suramin in the treatment of human African trypanosomiasis. Parasitol Res; 90: 71-79.
4. Pollastri M.P., Campbell R.K., (2011) Target repurposing for neglected diseases. Future Med Chem; 3: 1307-1315.
5. Ochiana S.O., Pandarinath V., Wang Z., Kapoor R., Ondrechen M.J., Ruben L., Pollastri M.P., (2013) The human Aurora kinase inhibitor danusertib is a lead compound for anti-trypanosomal drug discovery via target repurposing. Eur J Med Chem; 62: 777-784.
6. Patel G., Karver C.E., Behera R., Guyett P.J., Sullenberger C., Edwards P., Roncal N.E., Mensa-Wilmot K., Pollastri M.P., (2013) Kinase scaffold repurposing for neglected disease drug discovery: discovery of an efficacious, lapatanib-derived lead compound for trypanosomiasis. J Med Chem; 56: 3820-3832.
7. Bland N.D., Wang C., Tallman C., Gustafson A.E., Wang Z., Ashton T.D., Ochiana S.O., et al,. (2011) Pharmacological validation of Trypanosoma brucei phosphodiesterases B1 and B2 as druggable targets for African sleeping sickness. J Med Chem; 54: 8188-8194.
8. Ochiana S.O., Gustafson A., Bland N.D., Wang C., Russo M.J., Campbell R.K., Pollastri M.P., (2012) Synthesis and evaluation of human phosphodiesterases (PDE) 5 inhibitor analogs as trypanosomal PDE inhibitors. Part 2. Tadalafil analogs. Bioorg Med Chem Lett; 22: 2582-2584.
9. Wang C., Ashton T.D., Gustafson A., Bland N.D., Ochiana S.O., Campbell R.K., Pollastri M.P., (2012) Synthesis and evaluation of human phosphodiesterases (PDE) 5 inhibitor analogs as trypanosomal PDE inhibitors. Part 1. Sildenafil analogs. Bioorg Med Chem Lett; 22: 2579-2581.
10. Woodring J.L., Bland N.D., Ochiana S.O., Campbell R.K., Pollastri M.P., (2013) Synthesis and assessment of catechol diether compounds as inhibitors of trypanosomal phosphodiesterase B1 (TbrPDEB1). Bioorg Med Chem Lett; 23: 5971-5974.
11. Setter S.M., Iltz J.L., Fincham J.E., Campbell R.K., Baker D.E., (2005) Phosphodiesterase 5 inhibitors for erectile dysfunction. Ann Pharmacother; 39: 1286-1295.
12. Greulich T., Koczulla A.R., Vogelmeier C., (2012) Chronic obstructive pulmonary disease: new pharmacotherapeutic options. Internist (Berl); 53: 1364-1370.
13. Maiga M., Agarwal N., Ammerman N.C., Gupta R., Guo H., Maiga M.C., Lun S., Bishai W.R., (2012) Successful shortening of tuberculosis treatment using adjuvant host-directed therapy with FDA-approved phosphodiesterase inhibitors in the mouse model. PLoS ONE; 7: e30749.
14. Yano M., Kohno M., Ohkusa T., Mochizuki M., Yamada J., Hisaoka T., Ono K., Tanigawa T., Kobayashi S., Matsuzaki M., (2000) Effect of milrinone on left ventricular relaxation and Ca(2 +) uptake function of cardiac sarcoplasmic reticulum. Am J Physiol Heart Circ Physiol; 279: H1898-H1905.
15. Oberholzer M., Marti G., Baresic M., Kunz S., Hemphill A., Seebeck T., (2007) The Trypanosoma brucei cAMP phosphodiesterases TbrPDEB1 and TbrPDEB2: flagellar enzymes that are essential for parasite virulence. FASEB J; 21: 720-731.
16. Woodrow M.D., Ballantine S.P., Barker M.D., Clarke B.J., Dawson J., Dean T.W., Delves C.J., et al,. (2009) Quinolines as a novel structural class of potent and selective PDE4 inhibitors. Optimisation for inhaled administration. Bioorg Med Chem Lett; 19: 5261-5265.
17. de Koning H.P., Gould M.K., Sterk G.J., Tenor H., Kunz S., Luginbuehl E., Seebeck T., (2012) Pharmacological validation of Trypanosoma brucei phosphodiesterases as novel drug targets. J Infect Dis; 206: 229-237.
18. Orrling K.M., Jansen C., Vu X.L., Balmer V., Bregy P., Shanmugham A., England P., et al,. (2012) Catechol pyrazolinones as trypanocidals: fragment-based design, synthesis, and pharmacological evaluation of nanomolar inhibitors of trypanosomal phosphodiesterase B1. J Med Chem; 55: 8745-8756.
19. Lunniss C.J., Cooper A.W., Eldred C.D., Kranz M., Lindvall M., Lucas F.S., Neu M., Preston A.G., Ranshaw L.E., Redgrave A.J., Ed Robinson J., Shipley T.J., Solanke Y.E., Somers D.O., Wiseman J.O., (2009) Quinolines as a novel structural class of potent and selective PDE4 inhibitors: optimisation for oral administration. Bioorg Med Chem Lett; 19: 1380-1385.
20. Baldwin I.R., Barker M.D., Dean A.W., Eldred C.D., Evans B., Gough S.L., Guntrip S.B., et al,. (2004) Preparation of quinoline derivatives as phosphodiesterase inhibitors. WO2004103998A1.
21. Jansen C., Wang H., Kooistra A.J., de Graaf C., Orrling K.M., Tenor H., Seebeck T., Bailey D., de Esch I.J., Ke H., Leurs R., (2013) Discovery of novel Trypanosoma brucei phosphodiesterase B1 inhibitors by virtual screening against the unliganded TbrPDEB1 crystal structure. J Med Chem; 56: 2087-2096.
22. Surry D.S., Buchwald S.L., (2008) Biaryl phosphane ligands in palladium-catalyzed amination. Angew Chem; 47: 6338-6361.
23. Schopfer U., Schlapbach A., (2001) A general palladium-catalyzed synthesis of aromatic and heteroaromatic thioethers. Tetrahedron; 57: 3069-3073.
24. Buckman B., Nicholas J.B., Beigelman L., Serebryany V., Stoycheva A.D., Thrailkill T., Seiwert S.D., (2011) Preparation of macrocyclic peptides, especially proline-containing peptides, as inhibitors of hepatitis C virus replication for treating hepatitis C infection and liver fibrosis. WO2011038293A1.
25. Wu W.-L., Burnett D.A., Stamford A.W., Cumming J.N., Bennett C.E., Gilbert E.J., Peng X., Scott J.D., Yu Y., (2012) Preparation of 5-substituted iminothiazines and their mono- and dioxides as BACE inhibitors. WO2012139425A1.
26. Young J., Czako B., Altman M., Guerin D., Martinez M., Rivkin A., Wilson K., Lipford K., White C., Surdi L., Chichetti S., Daniels M.H., Ahearn S.P., Falcone D., Osimboni E., (2011) Pyridazinones as tyrosine kinase inhibitors and their preparation and use in the treatment of cancer. WO2011084402A1.
27. Wada A., (1976) The alpha-helix as an electric macro-dipole. Adv Biophys; 1-63.
28. Higman V.A., Boyd J., Smith L.J., Redfield C., (2004) Asparagine and glutamine side-chain conformation in solution and crystal: a comparison for hen egg-white lysozyme using residual dipolar couplings. J Biomol NMR; 30: 327-346.
29. Word J.M., Lovell S.C., Richardson J.S., Richardson D.C., (1999) Asparagine and glutamine: using hydrogen atom contacts in the choice of side-chain amide orientation. J Mol Biol; 285: 1735-1747.
30. Amata E., Bland N.D., Hoyt C.T., Settimo L., Campbell R.K., Pollastri M.P., (2014) Repurposing human phosphodiesterase 4 inhibitors for neglected tropical diseases. 1. Design, synthesis and evaluation of cilomilast analogues as Trypanosoma brucei phosphodiesterase B1 (TbrPDEB1) inhibitors. Bioorg Med Chem Lett; 24: 4084-4089.
31. Duplantier A.J., Bachert E.L., Cheng J.B., Cohan V.L., Jenkinson T.H., Kraus K.G., McKechney M.W., Pillar J.D., Watson J.W., (2007) SAR of a Series of 5,6-Dihydro-(9H)-pyrazolo[3,4-c]-1,2,4-triazolo[4,3-α]pyridines as Potent Inhibitors of Human Eosinophil Phosphodiesterase. J Med Chem; 50: 344-349.
32. Ehrman T.M., Barlow D.J., Hylands P.J., (2010) In silico search for multi-target anti-inflammatories in Chinese herbs and formulas. Bioorg Med Chem; 18: 2204-2218.