Synthesis of mevalonate-and fluorinated mevalonate prodrugs and their in vitro human plasma stability

European Journal of Medicinal Chemistry

Volumn 90, Issue , 2015, Pages 448-461

  Kang, Soosung ^a   Watanabe, Mizuki ^a   Jacobs, J C ^a   Yamaguchi, Masaya ^b   Dahesh, Samira ^b   Nizet, Victor ^b   Leyh, Thomas S ^c   Silverman, Richard B ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

^b UNIVERSITY OF CALIFORNIA SAN DIEGO   (United States)

^c ALBERT EINSTEIN COLLEGE OF MEDICINE   (United States)

Author keywords

6 6 6 Trifluoromevalonate; 6 Fluoromevalonate; Mevalonate; Plasma stability; Prodrugs

Indexed keywords

2 (4 METHYL 2 OXO 1,3 DIOXAN 4 YL) N PHENYLACETAMIDE; 2 (4 METHYL 2 OXO 1,3 DIOXAN 4 YL)ACETIC ACID; 2 [2 OXO 4 (TRIFLUOROMETHYL) 1,3 DIOXAN 4 YL]ACETIC ACID; 2 [4 (FLUOROMETHYL) 2 OXO 1,3 DIOXAN 4 YL]ACETIC ACID; 2,4 DIFLUOROBENZYL 2 [2 OXO 4 (TRI FL UOROMETHYL) 1,3 DIOXAN 4 YL]ACETATE; 3,5 DIHYDROXY 3 (TRI FL UOROMETHYL)PENTANOIC ACID; 3,5 DIHYDROXY 3 METHYLPENTANOATE; 4 FLUOROBENZYL 2 [2 OXO 4 (TRIFLUOROMETHYL) 1,3 DIOXAN 4YL]ACETATE; 4 FLUOROBENZYL 2 [4 ( FLUOROMETHYL) 2 OXO 1,3 DIOXAN 4 YL] ACETATE; 4 FLUOROPHENYL 2 (4 METHYL 2 OXO 1,3 DIOXAN 4 YL)ACETATE; 4 HYDROXY 4 (TRIFLUOROMETHYL)TETRAHYDRO 2H PYRAN 2 ONE; 4 MONOFLUOROMETHYL DERIVATIVE; 4 [(TERT BUTYLDIMETHYLSILYL)OXY]BUTAN 2 ONE; ACETAL DERIVATIVE; AMIDE; BENZYL 2 (4 METHYL 2 OXO 1,3 DIOXAN 4 YL)ACETATE; BENZYL 2 [2 OXO 4 (TRIFLUOROMETHYL) 1,3 DIOXAN 4 YL]ACETATE; BENZYL 2 [4(FLUOROMETHYL) 2 OXO 1,3 DIOXAN 4 YL]ACETATE; BENZYL 4,4,4 TRIFLUORO 3 FORMYL 3 HYDROXYBUTANOATE; BENZYL 5 ETHOXY 3 HYDROXY 3 (TRIFLUOROMETHYL)PENT 4 ENOATE; BENZYL 5 [(TERT BUTYLDIMETHYLSILYL)OXY] 3 HYDROXY 3 METHYPENTANOATE; CARBONIC ACID DERIVATIVE; DIBENZYL 3 (FLUOROMETHYL) 3 HYDROXYPENTANEDIOATE; ESTER; FLUORINATED MEVALONATE PRODRUG; MEVALONIC ACID; N BENZYL 2 (4 METHYL 2 OXO 1,3 DIOXAN 4 YL)ACETAMIDE; PHENYL 2 (4 METHYL 2 OXO 1,3 DIOXAN 4 YL)ACETATE; PRODRUG; UNCLASSIFIED DRUG; UNINDEXED DRUG; ANTIINFECTIVE AGENT; FLUORINATED HYDROCARBON;

ALDOL REACTION; ANTIBACTERIAL ACTIVITY; ARTICLE; BLOOD; CHIRAL CHROMATOGRAPHY; CYTOTOXICITY; DECOMPOSITION; DRUG BIOAVAILABILITY; DRUG DECOMPOSITION; DRUG STABILITY; ESTERIFICATION; FREEZE DRYING; HUMAN; HYDROLYSIS; IN VITRO STUDY; MEMBRANE PERMEABILITY; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; STREPTOCOCCUS PNEUMONIAE; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; MICROBIAL SENSITIVITY TEST; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANTI-BACTERIAL AGENTS; DOSE-RESPONSE RELATIONSHIP, DRUG; HUMANS; HYDROCARBONS, FLUORINATED; MEVALONIC ACID; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; PRODRUGS; STREPTOCOCCUS PNEUMONIAE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84949116538     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.11.040     Document Type: Article

References (31)

1. E.I. Wilding J.R. Brown A.P. Bryant A.F. Chalker D.J. Holmes K.A. Ingraham S. Iordanescu C.Y. So M. Rosenberg M.N. Gwynn Identification, evolution, and essentiality of the mevalonate pathway for isopentenyl diphosphate biosynthesis in gram-positive cocci J. Bacteriol. 182 2000 4319 4327
2. E. Oldfield Targeting isoprenoid biosynthesis for drug discovery: bench to bedside Acc. Chem. Res. 43 2010 1216 1226
3. S.A. Holstein The isoprenoid biosynthetic pathway and statins Enzymes 30 2011 279 299
4. K. Ohno K. Mori M. Orita M. Takeuchi Computational insights into binding of bisphosphates to farnesyl pyrophosphate synthase Curr. Med. Chem. 18 2011 220 233 (b)
5. K.M. Swanson R.J. Hohl Anti-cancer therapy: targeting the mevalonate pathway Curr. Cancer Drug Targets 6 2006 15 37
6. W.R. Schafer R. Kim R. Sterne J. Thorner S.H. Kim J. Rine Genetic and pharmacological suppression of oncogenic mutations in ras genes of yeast and humans Science 245 1989 379 385
7. W.N. Hunter Isoprenoid precursor biosynthesis offers potential targets for drug discovery against diseases caused by apicomplexan parasites Curr. Top. Med. Chem. 11 2011 2048 2059
8. J.L. Andreassi K. Dabovic T.S. Leyh Streptococcus pneumoniae isoprenoid biosynthesis is downregulated by diphosphomevalonate: an antimicrobial target Biochemistry 43 2004 16461 16466
9. S.T. Lefurgy S.B. Rodriguez C.S. Park S. Cahill R.B. Silverman T.S. Leyh Probing ligand-binding pockets of the mevalonate pathway enzymes from streptococcus pneumonia J. Biol. Chem. 285 2010 20654 20663
10. D.D. Hinson K.L. Chambliss M.J. Toth R.D. Tanaka K.M. Gibson Post-translational regulation of mevalonate kinase by intermediates of the cholesterol and nonsterol isoprene biosynthetic pathways J. Lipid Res. 38 1997 2216 2223
11. N.E. Voynova S.E. Rios H.M. Miziorko Staphylococcus aureus mevalonate kinase: Isolation and characterization of an enzymeof the isoprenoid biosynthetic pathway J. Bacteriol. 186 2004 61 67
12. T. Kudoh C.S. Park S.T. Lefurgy M. Sun T. Michels T.S. Leyh R.B. Silverman Mevalonate analogues as substrates of enzymes in the isoprenoid biosynthetic pathway of Streptococcus pneumonia Bioorg. Med. Chem. 18 2010 1124 1143
13. J.E. Reardon R.H. Abeles Inhibition of cholesterol biosynthesis by fluorinated mevalonate analogs Biochemistry 26 1987 4717 4722
14. J.A. Cuthbert P.E. Lipsky Inhibition by 6-fluoromevalonate demonstrates that mevalonate or one of the mevalonate phosphates is necessary for lymphocyte proliferation J. Biol. Chem. 265 1990 18568 18575
15. G. Fritz Targeting the mevalonate pathway for improved anticancer therapy Curr. Cancer Drug Targets 9 2009 626 638
16. A.J. Wiemer R.J. Hohl D.F. Wiemer The intermediate enzymes of isoprenoid metabolism as anticancer targets Anticancer Agents Med. Chem. 9 2009 526 542
17. H. Nikaido M. Vaara Molecular basis of bacterial Outer membrane permeability Microbiol. Rev. 1985 1 32
18. J. Rautio H. Kampulainen T. Heimbach R. Oliyai D. Oh T. Järvinen T. Savolainen Prodrugs: design and clinical applications J. Nat. Rev. Drug. Discov. 7 2008 255 270
19. L. Di E.H. Kerns Y. Hong H. Chen Development and application of high throughput plasma stability assay for drug discovery Int. J. Pharm. 297 2005 110 119
20. S.L. Graham S.J. deSolms E.A. Giuliani N.E. Kohl S.D. Mosser A.I. Oliff D.L. Pompliano E. Rands M.J. Breslin A.A. Deana V.M. Garsky T.H. Scholz J.B. Gibbs R.L. Smith Pseudopeptide inhibitors of Ras farnesyl-protein transferase J. Med. Chem. 37 1994 725 732
21. M. Gooyit M. Lee V.A. Schroeder M. Ikejiri M.A. Suckow S. Mobashery M. Chang Selective water-soluble gelatinase inhibitor prodrugs J. Med. Chem. 54 2011 6676 6690
22. P. Vlieghe F. Bihel T. Clerc C. Pannecouque M. Witvrouw E. De Clercq J.-P. Salles J.-C. Chermann J.L. Kraus New 3'-Azido-3'-deoxythymidin-5'-yl O-(ω-hydroxyalkyl) carbonate prodrugs 5'.Synthesis and anti-HIV evaluation J. Med. Chem. 44 2001 777 786
23. D.L. Soper J.X. Sheville S.V. O'Neil Y. Wang M.C. Laufersweiler K.A. Oppong J.A. Wos K.D. Ellis M.W. Baize J.C. Chen A.N. Fancher W. Lu M.K. Suchanek R.L. Wang W.P. Schwecke C.A. Cruze M. Buchalova M. Belkin F. Wireko A. Ritter B. De D. Wang T.P. Demuth Synthesis and evaluation of novel 8,5-fused bicyclic peptidomimetic compounds as interleukin-1b converting enzyme (ICE) inhibitors Bioorg. Med. Chem. 14 2006 7880 7892
24. A. Mattarei M. Azzolini M. Carraro N. Sassi M. Zoratti C. Paradisi L. Biasutto Acetal derivatives as prodrugs of resveratrol Mol. Pharm. 10 2013 2781 2792
25. M.J. Cho G.L. Bundy J.J. Biermacher Prostaglandin prodrugs. 5'. Prostaglandin Ez ethylene ketal J. Med. Chem. 20 1977 1525 1527
26. J.F. Nave H. d'Orchymont J.B. Ducep F. Piriou M.J. Jung Mechanism of the inhibition of cholesterol biosynthesis by 6-fluoromevalonate Biochem. J. 227 1985 247 254
27. See the plasma stability test protocols at the following web pages Rapid method development to study plasma stability of diverse pharmaceutical compounds using rapid resolution LC and triple quadrupole MS. Agilent application note Cyprotex; Cloe screen plasma stability flyer; March 2014 March 2014 http://www.cyprotex.com/assay-reports/Cloe-Screen-Plasma-Stability.pdf http://www.chem.agilent.com/Library/applications/5990-4603EN.pdf
28. S.-N. Lin L. Lamm T.F. Newton M.S. Reid D.E. Moody R.L. Foltz A liquid chromatography-electrospray ionization-tandem mass spectrometry method for quantitation of aripiprazole in human plasma reproduction (photocopying) of editorial content of this journal is prohibited without publisher's permission J. Anal. Toxicol. 33 2009 237 242
29. B. Li M. Sedlacek I. Manoharan R. Boopathy E.G. Duysen P. Masson O. Lockridge Butyrylcholinesterase, paraoxonase, and albumin esterase, but not carboxylesterase, are present in human plasma Biochem. Pharmacol. 70 2005 1673 1684
30. A.K. Kristian V. Datta C. Weidenmaier R. Kansal I. Fedtke A. Peschel R.L. Gallo V.D. Nizet Alanylation of teichoic acids promotes group a Streptococcus antimicrobial peptide resistance, neutrophil survival, and epithelial cell invasion J. Bacteriol. 2005 6719 6725
31. I.S. Kondratov I.I. Gerus V.P. Kukhar O.V. Manoilenko New synthetic approach to mevalonate and mevaldate fluoroanalogues Tet.: Asymm 18 2007 1918 1925