用户名: 密码: 验证码:
New insights into PDE4B inhibitor selectivity: CoMFA analyses and molecular docking studies
详细信息    查看全文
  • 作者:Sara Guariento ; Olga Bruno ; Paola Fossa ; Elena Cichero
  • 关键词:Phosphodiesterases ; PDE4B inhibitors ; PDE4D ; Molecular docking ; Selectivity ; CoMFA
  • 刊名:Molecular Diversity
  • 出版年:2016
  • 出版时间:February 2016
  • 年:2016
  • 卷:20
  • 期:1
  • 页码:77-92
  • 全文大小:2,193 KB
  • 参考文献:1.Li L, Yee C, Beavo JA (1999) CD3- and CD28-dependent induction of PDE7 required for T cell activation. Science 283:848–851. doi:10.​1126/​science.​283.​5403.​848 CrossRef PubMed
    2.Dousa TP (1999) Cyclic-3\(^\prime \) ,5\(^\prime \) -nucleotide phosphodiesterases isoenzyme in cell biology and pathophysiology of the kidney. Kidney Int 55:29–62. doi:10.​1046/​j.​1523-1755.​1999.​00233.​x CrossRef PubMed
    3.Pfister C, Bennett N, Bruckert F, Catty P, Clerc A, Pages F, Deterre P (1993) Interactions of a G-protein with its effector: transducin and cGMP phosphodiesterase in retinal rods. Cell Signal 5:235–241. doi:10.​1016/​0898-6568(93)90015-E CrossRef PubMed
    4.Jin SL, Richard FJ, Kuo WP, D’Ercole AJ, Conti M (1999) Impaired growth and fertility of c-AMP-specific phosphodiesterase PDE4D-deficient mice. Proc Natl Acad Sci USA 96:11998–12003. doi:10.​1073/​pnas.​96.​21.​11998 CrossRef PubMed PubMedCentral
    5.Bender AT, Beavo JA (2006) Cyclic nucleotide phosphodiesterases: molecular regulation to clinical use. Pharmacol Rev 58:488–520. doi:10.​1124/​pr.​58.​3.​5 CrossRef PubMed
    6.Manganiello VC, Murata T, Taira M, Belfrage P, Degerman E (1995) Diversity in cyclic nucleotide phosphodiesterase isoenzyme families. Arch Biochem Biophys 322:1–13. doi:10.​1006/​abbi.​1995.​1429 CrossRef PubMed
    7.Lugnier C (2006) Cyclic nucleotide phosphodiesterase (PDE) superfamily: a new target for the development of specific therapeutic agents. Pharmacol Ther 109:366–398. doi:10.​1016/​j.​pharmthera.​2005.​07.​003 CrossRef PubMed
    8.Omori K, Kotera J (2007) Overview of PDEs and their regulation. Circ Res 100:309–327. doi:10.​1161/​01.​RES.​0000256354.​95791.​f1 CrossRef PubMed
    9.Conti M, Beavo J (2007) Biochemistry and physiology of cyclic nucleotide phosphodiesterases: essential components in cyclic nucleotide signaling. Annu Rev Biochem 76:481–511. doi:10.​1146/​annurev.​biochem.​76.​060305.​150444 CrossRef PubMed
    10.Houslay MD, Baillie GS, Maurice DH (2007) cAMP-Specific phosphodiesterase-4 enzymes in the cardiovascular system: a molecular toolbox for generating compartmentalized cAMP signaling. Circ Res 100:950–966. doi:10.​1161/​01.​RES.​0000261934.​56938.​38 CrossRef PubMed
    11.Houslay MD, Adams RD (2003) PDE4 cAMP phosphodiesterases: modular enzymes that orchestrate signalling cross-talk, desensitization and compartmentalization. Biochem J 370:1–18. doi:10.​1042/​BJ20021698 CrossRef PubMed PubMedCentral
    12.Page GP, Spina D (2011) Phosphodiesterase inhibitors in the treatment of inflammatory diseases. Handb Exp Pharmacol 204:391–414. doi:10.​1007/​978-3-642-17969-3_​17
    13.Conti M, Iona S, Cuomo M, Swinnen JV, Odeh J, Svoboda ME (1995) Characterization of a hormone-inducible, high affinity adenosine 3\(^\prime \) -5\(^\prime \) -cyclic monophosphate phosphodiesterase from the rat Sertoli cell. Biochemistry 34:7979–7987. doi:10.​1021/​bi00025a003 CrossRef PubMed
    14.Houslay MD (2001) PDE4 cAMP-specific phosphodiesterases. Prog Nucleic Acid Res Mol Biol 69:249–315. doi:10.​1016/​S0079-6603(01)69049-4 CrossRef PubMed
    15.Beard MB, Olsen AE, Jones RE, Erdogan S, Houslayan MD, Bolger GB (2000) UCR1 and UCR2 domains unique to the cAMP-specific phosphodiesterase family form a discrete module via electrostatic interactions. J Biol Chem 275:10349–10358. doi:10.​1074/​jbc.​275.​14.​10349 CrossRef PubMed
    16.Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE (2000) The Protein Data Bank. Nucleic Acids Res 28:235–242. doi:10.​1093/​nar/​28.​1.​235 CrossRef PubMed PubMedCentral
    17.Wang H, Liu Y, Hou J, Zheng M, Robinson H, Ke H (2007) Structural insight into substrate specificity of phosphodiestererase 10. Proc Natl Acad Sci USA 104:5782–5787. doi:10.​1073/​pnas.​0700279104 CrossRef PubMed PubMedCentral
    18.Card GL, England BP, Suzuki Y, Fong D, Powell B, Lee B, Luu C, Tabrizizad M, Gillette S, Ibrahim PN, Artis DR, Bollag G, Milburn MV, Kim SH, Sclessinger J, Zhang KY (2004) Structural basis for the activity of drugs that inhibit phosphodiesterases. Structure 12:2233–2247. doi:10.​1016/​j.​str.​2004.​10.​004 CrossRef PubMed
    19.Burgin AB, Magnusson OT, Singh J, Witte P, Staker BL, Bjornsson JM, Thorsteinsdottir M, Hrafnsdottir S, Hagen T, Kiselyov AS, Stewart LJ, Gurney ME (2010) Design of phosphodiesterase 4D (PDE4D) allosteric modulators for enhancing cognition with improved safety. Nat Biotechnol 28:63–70. doi:10.​1038/​nbt.​1598 CrossRef PubMed
    20.Fox D, Burgin AB, Gurney ME (2014) Structural basis for the design of selective phosphodiesterase 4B inhibitors. Cell Signal 26:657–663. doi:10.​1016/​j.​cellsig.​2013.​12.​003 CrossRef PubMed PubMedCentral
    21.Gurney ME, Burgin AB, Magnusson OT, Stewart LJ (2011) Small molecule allosteric modulators of phosphodiesterase 4. Handb Exp Pharmacol 204:167–192. doi:10.​1007/​978-3-642-17969-3_​7
    22.Lipworth BJ (2005) Phosphodiesterase 4 inhibitors for asthma and chronic obstructive pulmonary disease. Lancet 365:167–175. doi:10.​1016/​S0140-6736(05)17708-3 CrossRef PubMed
    23.Houslay MD, Schafer P, Zhang KYJ (2005) Phosphodiesterase-4 as a therapeutic target. Drug Discov Today 10:1503–1519. doi:10.​1016/​S1359-6446(05)03622-6 CrossRef PubMed
    24.Lerner A, Epstein PM (2006) Cyclic nucleotide phosphodiesterases as targets for treatment of haematological malignancies. Biochem J 393:21–41. doi:10.​1042/​BJ20051368 CrossRef PubMed PubMedCentral
    25.Huang Z, Mancini JA (2006) Phosphodiesterase 4 inhibitors for the treatment of asthma and COPD. Curr Med Chem 13:3253–3263. doi:10.​2174/​0929867067787730​40 CrossRef PubMed
    26.Ariga M, Neitzert B, Nakae S, Mottin G, Bertrand C, Pruniaux MP, Jin SL, Conti M (2004) Nonredudant function of phosphodiesterases 4D and 4B in neutrophil recruitment to the site of inflammation. J Immunol 173:7531–7538. doi:10.​4049/​jimmunol.​173.​12.​7531 CrossRef PubMed
    27.Jin SL, Lan L, Zoudilova M, Conti M (2005) Specific role of phosphodiesterase 4B in lipopolysaccharide-induced signaling in mouse macrophages. J Immunol 175:1523–1531. doi:10.​4049/​jimmunol.​175.​3.​1523 CrossRef PubMed
    28.Gurney ME, D’Amato EC, Burgin AB (2015) Phosphodiesterase-4 (PDE4) molecular pharmacology and Alzheimer’s disease. Neurotherapeutics 12:49–56. doi:10.​1007/​s13311-014-0309-7 CrossRef PubMed PubMedCentral
    29.Brooks M (21 March 2014) FDA clears apremilast (Otezla) for psoriatic arthritis. Medscape Medical News (WebMD). http://​www.​medscape.​com . Retrieved 28 March 2014
    30.Peter D, Jin SL, Conti M, Hatzelmann A, Zitt C (2007) Differential expression and function of phosphodiesterase 4 (PDE4) subtypes in human primary CD4+ T cells: predominant role of PDE4D. J Immunol 178:4820–4831. doi:10.​4049/​jimmunol.​178.​8.​4820 CrossRef PubMed
    31.O’Donnell JM, Zhang HT (2004) Antidepressant effects of inhibitors of cAMP phosphodiesterase (PDE4). Trends Pharmacol Sci 25:158–163. doi:10.​1016/​j.​tips.​2004.​01.​003 CrossRef PubMed
    32.Kanes SJ, Tokarczyk SJ, Bilker W, Abel T, Kelly MP (2007) Rolipram: a specific phosphodiesterase 4 inhibitor with potential antipsychotic activity. Neuroscience 144:239–246. doi:10.​1016/​j.​neuroscience.​2006.​09.​026 CrossRef PubMed PubMedCentral
    33.Robichaud A, Stamatiou PB, Jin SL, Lachance N, MacDonald D, Laliberte F, Liu S, Huang Z (2002) Adrenoceptor-mediated anesthesia, a behavioral correlate of emesis. J Clin Invest 110:1045–1052. doi:10.​1172/​JCI15506 CrossRef PubMed PubMedCentral
    34.Li YF, Cheng YF, Huang Y, Conti M, Wilson SP, O’Donnell JM, Zhang HT (2011) Phosphodiesterase-4D knock-out and RNA interference-mediated knock-down enhance memory and increase hippocampal neurogenesis via increased cAMP signaling. J Neurosci 31:172–183. doi:10.​1523/​JNEUROSCI.​5236-10.​2011 CrossRef PubMed PubMedCentral
    35.Bruno O, Fedele E, Prickaerts J, Parker LA, Canepa E, Brullo C, Cavallero A, Gardella E, Balbi A, Domenicotti C, Bollen E, Gijselaers HJ, Vanmierlo T, Erb K, Limebeer CL, Argellati F, Marinari UM, Pronzato MA, Ricciarelli R (2011) GEBR-7b, a novel PDE4D selective inhibitor that improves memory in rodents at non-emetic doses. Br J Pharmacol 164:2054–2063. doi:10.​1111/​j.​1476-5381.​2011.​01524.​x CrossRef PubMed PubMedCentral
    36.Sierksma AS, Van den Hove DL, Pfau F, Philippens M, Bruno O, Fedele E, Ricciarelli R, Steinbusch HW, Van Mierlo T, Prickaerts J (2014) Improvement of spatial memory function in APPswe/PS1dE9 mice after chronic inhibition of phosphodiesterase type 4D. Neuropharmacology 77:120–130. doi:10.​1016/​j.​neuropharm.​2013.​09.​015 CrossRef PubMed
    37.Srivani P, Usharani D, Jemmis ED, Sastry GN (2008) Subtype selectivity in phosphodiesterase 4 (PDE4): a bottleneck in rational drug design. Curr Pharm Des 14:3854–3872. doi:10.​2174/​1381612087868986​53 CrossRef PubMed
    38.Cichero E, Cesarini S, Fossa P, Spallarossa A, Mosti L (2009) Thiocarbamates as non-nucleoside HIV-1 reverse transcriptase inhibitors: docking-based CoMFA and CoMSIA analyses. Eur J Med Chem 44:2059–2070. doi:10.​1016/​j.​ejmech.​2008.​10.​014 CrossRef PubMed
    39.Cichero E, Cesarini S, Fossa P, Spallarossa A, Mosti L (2009) Acylthiocarbamates as non-nucleoside HIV-1 reverse transcriptase inhibitors: docking studies and ligand-based CoMFA and CoMSIA analyses. J Mol Model 15:871–884. doi:10.​1007/​s00894-008-0441-6 CrossRef PubMed
    40.Cichero E, Fossa P (2012) Docking-based 3D-QSAR analyses of pyrazole derivatives as HIV-1 non-nucleoside reverse transcriptase inhibitors. J Mol Model 18:1153–1582. doi:10.​1007/​s00894-011-1190-5 CrossRef
    41.Cichero E, Bruno O, Fossa P (2011) Docking-based CoMFA and CoMSIA analyses of tetrahydro-\(\beta \) -carboline derivatives as type-5 phosphodiesterase inhibitors. J Enzyme Inhib Med Chem 27:730–743. doi:10.​3109/​14756366.​2011.​611136 CrossRef PubMed
    42.Bhansali SG, Kulkarni VM (2014) Combined 2D and 3D-QSAR, molecular modelling and docking studies of pyrazolodiazepinones as novel phosphodiesterase 2 inhibitors. SAR QSAR Environ Res 25:905–937. doi:10.​1080/​1062936X.​2014.​969309 CrossRef PubMed
    43.Patel SR, Gangwal R, Sangamwar AT, Jain R (2015) Synthesis, biological evaluation and 3D QSAR study of 2,4-disubstituted quinolines as anti-tuberculosis agents. Eur J Med Chem 93:511–522. doi:10.​1016/​j.​ejmech.​2015.​02.​034 CrossRef PubMed
    44.Mella-Raipán J, Hernández-Pino S, Morales-Verdejo C, Pessoa-Mahana D (2014) 3D-QSAR/CoMFA-based structure-affinity/selectivity relationships of aminoalkylindoles in the cannabinoid CB1 and CB2 receptors. Molecules 19:2842–2861. doi:10.​3390/​molecules1903284​2 CrossRef PubMed
    45.Naganuma K, Omura A, Maekawara N, Saitoh M, Ohkawa N, Kubota T, Nagumo H, Kodama T, Takemura M, Ohtsuka Y, Nakamura J, Tsujita R, Kawasaki K, Yokoi H, Kawanishi (2009) Discovery of selective PDE4B inhibitors. Bioorg Med Chem Lett 19:3174–3176. doi:10.​1016/​j.​bmcl.​2009.​04.​121 CrossRef PubMed
    46.Hagen TJ, Mo X, Burgin AB, Fox D 3rd, Zhang Z, Gurney ME (2014) Discovery of triazines as selective PDE4B versus PDE4D inhibitors. Bioorg Med Chem Lett 24:4031–4034. doi:10.​1016/​j.​bmcl.​2014.​06.​002 CrossRef PubMed PubMedCentral
    47.Goto T, Shiina A, Murata T, Tomii M, Yamazaki T, Yoshida K, Yoshino T, Suzuki O, Sogawa Y, Mizukami K, Takagi N, Yoshitomi T, Etori M, Tsuchida H, Mikkaichi T, Nakao N, Takahashi M, Takahashi H, Sasaki S (2014) Identification of the 5,5-dioxo-7,8-dihydro-6H-thiopyrano[3,2-d] pyrimidine derivatives as highly selective PDE4B inhibitors. Bioorg Med Chem Lett 24:893–899. doi:10.​1016/​j.​bmcl.​2013.​12.​076 CrossRef PubMed
    48.MOE: Chemical Computing Group Inc., Montreal. http://​www.​chemcomp.​com
    49.Cramer RD III, Patterson DE, Bunce JD (1988) Comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins. J Am Chem Soc 110:5959–5967. doi:10.​1021/​ja00226a005 CrossRef PubMed
    50.Sybyl-X 1.0. Tripos Inc., St. Louis
    51.Cichero E, Ligresti A, Allarà M, Di Marzo V, Lazzati Z, D’Ursi P, Marabotti A, Milanesi L, Spallarossa A, Ranise A, Fossa P (2011) Homology modeling in tandem with 3D-QSAR analyses: a computational approach to depict the agonist binding site of the human CB2 receptor. Eur J Med Chem 46:4489–4505. doi:10.​1016/​j.​ejmech.​2011.​07.​023 CrossRef PubMed
    52.Cichero E, Buffa L, Fossa P (2011) 3,4,5-Trisubstituted-1,2,4–4H-triazoles as WT and Y188L mutant HIV-1 non-nucleoside reverse transcriptase inhibitors: docking-based CoMFA and CoMSIA analyses. J Mol Model 7:1537–1550. doi:10.​1007/​s00894-010-0857-7 CrossRef
    53.Cichero E, Cesarini S, Mosti L, Fossa P (2010) CoMFA and CoMSIA analyses on 1,2,3,4-tetrahydropyrrolo[3,4-b]indole and benzimidazole derivatives as selective CB2 receptor agonists. J Mol Model 16:1481–1498. doi:10.​1007/​s00894-010-0664-1 CrossRef PubMed
    54.Cichero E, Cesarini S, Mosti L, Fossa P (2010) CoMFA and CoMSIA analyses on 4-oxo-1,4-dihydroquinoline and 4-oxo-1,4-dihydro-1,5-, -1,6- and -1,8-naphthyridine derivatives as selective CB2 receptor agonists. J Mol Model 16:677–691. doi:10.​1007/​s00894-009-0580-4 CrossRef PubMed
    55.Jain AN (1996) Scoring noncovalent protein-ligand interactions: a continuous differentiable function tuned to compute binding affinities. J Comput Aided Mol Des 10:427–440. doi:10.​1007/​BF00124474 CrossRef PubMed
    56.Aspiotis R, Deschenes D, Dubè D, Girard Y, Huang Z, Lalibertè F, Liu S, Pappa R, Nicholson DW, Young RN (2010) The discovery and synthesis of highly potent subtype selective phosphodiesterase 4D inhibitors. Bioorg Med Chem Lett 20:5502–5505. doi:10.​1016/​j.​bmcl.​2010.​07.​076 CrossRef PubMed
  • 作者单位:Sara Guariento (1)
    Olga Bruno (1)
    Paola Fossa (1)
    Elena Cichero (1)

    1. Department of Pharmacy, University of Genoa, Viale Benedetto XV, 3, 16132, Genoa, Italy
  • 刊物类别:Chemistry and Materials Science
  • 刊物主题:Chemistry
    Analytical Chemistry
    Polymer Sciences
    Organic Chemistry
    Pharmacy
  • 出版者:Springer Netherlands
  • ISSN:1573-501X
文摘

© 2004-2018 中国地质图书馆版权所有 京ICP备05064691号 京公网安备11010802017129号

地址:北京市海淀区学院路29号 邮编:100083

电话:办公室:(+86 10)66554848;文献借阅、咨询服务、科技查新:66554700