Latest QSAR study of adenosine A2B receptor affinity of xanthines and deazaxanthines

Molecular Diversity

Volumn 19, Issue 4, 2015, Pages 975-989

  Pérez Garrido, Alfonso ^a   Rivero Buceta, Virginia ^b   Cano, Gaspar ^c   Kumar, Sanjay ^d   Pérez Sánchez, Horacio ^a   Bautista, Marta Teijeira ^b  

^a CATHOLIC UNIVERSITY OF MURCIA   (Spain)

^b UNIVERSITY OF VIGO   (Spain)

^c UNIVERSITY OF ALICANTE   (Spain)

^d Bioinformatics Centre   (India)

Author keywords

Adenosine A2B; Antagonist; Ensemble; QSAR; Xanthine

Indexed keywords

ADENOSINE A2 RECEPTOR ANTAGONIST; ADENOSINE A2B RECEPTOR; DEAZAXANTHINE DERIVATIVE; UNCLASSIFIED DRUG; XANTHINE DERIVATIVE;

ARTICLE; BINDING AFFINITY; CLASSIFIER; DRUG STRUCTURE; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; CHEMICAL STRUCTURE; CHEMISTRY; DRUG DESIGN; HUMAN;

ADENOSINE A2 RECEPTOR ANTAGONISTS; DRUG DESIGN; HUMANS; MOLECULAR STRUCTURE; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; XANTHINES;

EID: 84942888268     PISSN: 13811991     EISSN: 1573501X     Source Type: Journal    
DOI: 10.1007/s11030-015-9608-0     Document Type: Article

References (68)

1. Mohamed T, Osman W, Tin G, Rao P (2013) Selective inhibition of human acetylcholinesterase by xanthine derivatives: in vitro inhibition and molecular modeling investigations. Bioorg Med Chem Lett 23:4336–4341. doi:10.1016/j.bmcl.2013.05.092
2. Salhiyyah K, Senanayake E, Abdel-Hadi M, Booth A, Michaels JA (2012) Pentoxifylline for intermittent claudication. Cochrane Database Syst Rev CD005262. doi:10.1002/14651858.CD005262.pub2
3. Czechtizky W, Dedio J, Desai B, Dixon K, Farrant E, Feng QX, Morgan T, Parry D (2013) Integrated synthesis and testing of substituted xanthine based DPP4 inhibitors: application to drug discovery. ACS Med Chem Lett 4:768–772. doi:10.1021/ml400171b
4. Cazzola M, Page C, Calzetta L, Matera M (2012) Pharmacology and therapeutics of bronchodilators. Pharmacol Rev 64:450–504. doi:10.1124/pr.111.004580
5. Diniz C, Borges F, Santana L, Uriarte E, Oliveira J, Goncalves J, Fresco P (2008) Ligands and therapeutic perspectives of adenosine A(2A) receptors. Curr Pharm Design 14:1698–1722. doi:10.2174/138161208784746842
6. Ratheesh A, Jain M, Gude P (2010) Antimetastatic action of pentoxifylline, a methyl xanthine derivative, through its effect on PKC mediated integrin transport in B16F10 melanoma cells. World J Oncol 1:194–203
7. Pacher P, Nivorozhkin A, Szabó C (2006) Therapeutic effects of xanthine oxidase inhibitors: Renaissance half a century after the discovery of allopurinol. Pharmacol Rev 58:87–114. doi:10.1124/pr.58.1.6
8. Francis SH, Sekhar KR, Ke H, Corbin JD (2011) Inhibition of cyclic nucleotide phosphodiesterases by methylxanthines and related compounds. Handb Exp Pharmacol 200:93–133. doi: 10.1007/978-3-642-13443-2_4
9. Gu Y, Wang W, Zhu X, Dong K (2014) Molecular dynamic simulations reveal the mechanism of binding between xanthine inhibitors and DPP-4. J Mol Model 20:1–12. doi:10.1007/s00894-014-2075-1
10. Mueller C, Jacobson K (2011) Xanthines as adenosine receptor antagonists. In: Fredholm BB (ed) Methylxanthines, handbook of experimental pharmacology. Springer, Berlin, pp 151–199
11. Fredholm BB, Ijzerman AP, Jacobson KA, Linden J, Muller CE (2011) International union of pharmacology XXV Nomenclature and classification of adenosine receptors. Pharmacol Rev 63:1–34
12. Wilson C, Mustafa S (2009) Adenosine receptors in health and disease. Springer, New York
13. Zhong H, Wu Y, Belardinelli L, Zeng D (2006) \rm {A}_{{\rm 2B}}A2B adenosine receptors induce IL-19 from bronchial epithelial cells, resulting in TNF-alpha increase. Am J Respir Cell Mol Biol 35:587–592. doi: 10.1165/rcmb.2005-04760C
14. Feoktistov I, Ryzhov S, Zhong H, Goldstein A, Matafonov A, Zeng D, Biaggioni I (2004) Hypoxia modulates adenosine receptors in human endothelial and smooth muscle cells toward an \rm {A}_{{\rm 2B}}A2B angiogenic phenotype. Hypertension 44:649–654. doi: 10.1161/01.HYP.0000144800.21037.a5
15. Feoktistov I, Ryzhov S, Goldstein A, Biaggioni I (2003) Mast cell-mediated stimulation of angiogenesis: cooperative interaction between \rm {A}_{{\rm 2B}}A2B and A3 adenosine receptors. Circ Res 92:485–492. doi: 10.1161/01.RES.0000061572.10929.2D
16. Kalla R, Elzein E, Perry T, Li X, Gimbel A, Yang M, Zeng D, Zablocki J (2008) Selective, high affinity \rm {A}_{{\rm 2B}}A2B adenosine receptor antagonist: N-1 monosubstituted 8-(pyrazol-4-yl)xanthines. Bioorg Med Chem Lett 18:1397–1401. doi: 10.1016/j.bmcl.2008.01.008
17. Ryzhov S, Novitskiy SV, Zaynagetdinov R, Goldstein AE, Carbone DP, Biaggioni I, Dikov MM, Feoktistov I (2008) Host \rm {A}_{{\rm 2B}}A2B adenosine receptors promote carcinoma growth. Neoplasia 10:987–995. doi: 10.1593/neo.08478
18. Beukers M, Meurs I, IJzerman A (2006) Structure-afinity relationships of adenosine \rm {A}_{{\rm 2B}}A2B receptor ligands. Med Res Rev 26:667–698. doi: 10.1002/med.20069
19. Moro S, Gao Z-G, Jacobson K, Spalluto G (2006) Progress in the pursuit of therapeutic adenosine receptor antagonists. Med Res Rev 26:131–159. doi:10.1002/med.20048
20. Burnet M, Stohr T, Donsbach M (2014) Patente \text{ no }no 20140142113 A1 20140522 US
21. Teijeira M, Gonzalez MP, Saiz-Urra L, Teran C, Rivero V, Lopez-Romero JM (2011) Topological descriptors for predicting affinity of xanthine derivates to \rm {A}_{{\rm 2B}}A2B adenosine receptors. In: Putz M (ed) Advances in chemical modeling. Nova Press, Burleigh Heads, pp 267–280
22. Paz O, Brito C, Castilho M (2014) Quantitative insights towards the design of potent deazaxanthine antagonists of adenosine 2B receptors. J Enzym Inhib Med Chem 29:590–598
23. Bonet I, Franco-Montero P, Rivero V, Teijeira M, Borges F (2013) Classifier ensemble based on feature selection and diversity measures for predicting the affinity of \rm {A}_{{\rm 2B}}A2B adenosine receptor antagonists. J Chem Inf Model 53:3140–3155. doi: 10.1021/ci300516w
24. Mansourian M, Fassihi A, Saghaie L, Madadkar-Sobhani A, Mahnam K, Abbasi M (2015) QSAR and docking analysis of \rm {A}_{{\rm 2B}}A2B adenosine receptor antagonists based on non-xanthine scaffold. Med Chem Res 24:394–407. doi: 10.1007/s00044-014-1133-7
25. Joseph TB, Kumar BVSS, Santhosh B, Kriti S, Pramod AB, Ravikumar M, Kishore M (2008) Quantitative structure activity relationship and pharmacophore studies of adenosine receptor \rm {A}_{{\rm 2B}}A2B inhibitors. Chem Biol Drug Des 72:395–408. doi: 10.1111/j.1747-0285.2008.00714.x
26. Song Y, Coupar IM, Iskander MN (2001) Structural predictions of adenosine 2B antagonist affinity using molecular field analysis. Quant Struct Act Relat 20:23–30. doi: 10.1002/1521-3838(200105)20:1.;23:AID-QSAR23.;3.0.CO;2-I
27. Ivanov AA, Wang B, Klutz AM, Chen VL, Gao ZG, Jacobson KA (2008) Probing distal regions of the \rm {A}_{{\rm 2B}}A2B adenosine receptor by quantitative structure-activity relationship modeling of known and novel agonists. J Med Chem 51:2088–2099. doi: 10.1021/jm701442d
28. Carotti A, Stefanachi A, Ravina E, Sotelo E, Loza MI, Cadavid MI, Centeno NB, Nicolotti O (2004) 8-substituted-9-deazaxanthines as adenosine receptor ligands: design, synthesis and structure-affinity relationships at A(2B). Eur J Med Chem 39:879–887. doi:10.1016/j.ejmech.2004.07.008
29. Stefanachi A, Brea JM, Cadavid MI, Centeno NB, Esteve C, Loza MI, Martinez A, Nieto R, Ravina E, Sanz F, Segarra V, Sotelo E, Vidal B, Carotti A (2008) 1-, 3- and 8-substituted-9-deazaxanthines as potent and selective antagonists at the human A(2B) adenosine receptor. Bioorg Med Chem 16:2852–2869. doi:10.1016/j.bmc.2008.01.002
30. Stefanachi A, Nicolotti O, Leonetti F, Cellamare S, Campagna F, Loza MI, Brea JM, Mazza F, Gavuzzo E, Carotti A (2008) 1,3-Dialkyl-8-(hetero)aryl-9-OH-9-deazaxanthines as potent \text{ A }_{\rm 2B}A2B adenosine receptor antagonists: Design, synthesis, structure-affinity and structure-selectivity relationships. Bioorg Med Chem 16:9780–9789. doi:10.1016/j.bmc.2008.09.067
31. Nieto MI, Balo MC, Brea J, Caamano O, Fernandez F, Garcia-Mera X, Lopez C (2010) Synthesis and pharmacological evaluation of novel substituted 9-deazaxanthines as A(2B) receptor antagonists. Eur J Med Chem 45:2884–2892. doi:10.1016/j.ejmech.2010.03.011
32. Fernandez F, Caamano O, Nieto MI, Lopez C, Garcia-Mera X, Stefanachi A, Nicolotti O, Loza MI, Brea J, Esteve C, Segarra V, Vidal B, Carotti A (2009) 1,3-Dialkyl-8-N-substituted benzyloxycarbonylamino-9-deazaxanthines as potent adenosine receptor ligands: Design, synthesis, structure-affinity and structure-selectivity relationships. Bioorg Med Chem 17:3618. doi:10.1016/j.bmc.2009.03.062
33. Carotti A, Cadavid MI, Centeno NB, Esteve C, Loza MI, Martinez A, Nieto R, Ravina E, Sanz F, Segarra V, Sotelo E, Stefanachi A, Vidal B (2006) Design, synthesis, and structure-activity relationships of 1-,3-,8-, and 9-substituted-9-deazaxanthines at the human A(2B) adenosine receptor. J Med Chem 49:282–299. doi:10.1021/jm0506221
34. Baraldi PG, Tabrizi MA, Preti D, Bovero A, Romagnoli R, Fruttarolo F, Naser Abdel M, Allan R, Varani K, Gessi S, Merighi S, Borea PA (2004) Design, synthesis, and biological evaluation of new 8-heterocyclic xanthine derivatives as highly potent and selective human \rm {A}_{{2B}}A2B adenosine receptor antagonists. J Med Chem 47:1434–1447. doi: 10.1021/jm0309654
35. Balo MC, Brea J, Caamano O, Fernandez F, Garcia-Mera X, Lopez C, Loza MI, Nieto MI, Rodriguez-Borges JE (2009) Synthesis and pharmacological evaluation of novel 1- and 8- substituted-3-furfutyl xanthines as adenosine receptor antagonists. Bioorg Med Chem 17:6755–6760. doi:10.1016/j.bmc.2009.07.034
36. Rodriguez-Borges JE, Garcia-Mera X, Balo MC, Brea J, Caamano O, Fernandez F, Lopez C, Loza MI, Nieto MI (2010) Synthesis and pharmacological evaluation of novel 1,3,8-and 1,3,7,8-substituted xanthines as adenosine receptor antagonists. Bioorg Med Chem 18:2001–2009. doi:10.1016/j.bmc.2010.01.028
37. Nieto MI, Balo MC, Brea J, Caamano O, Cadavid MI, Fernandez F, Mera XG, Lopez C, Rodriguez-Borges JE (2009) Synthesis of novel 1-alkyl-8-substituted-3-(3-methoxypropyl) xanthines as putative A(2B) receptor antagonists. Bioorg Med Chem 17:3426. doi:10.1016/j.bmc.2009.03.029
38. Talete, srl (2006) Dragon for windows (software for molecular descriptors calculation) version 54. Talete, srl, Milano
39. Chemical Computing Group (2008) Molecular operating environment (MOE). Chemical Computing Group, Montreal
40. Yasri A, Hartsough D (2001) Toward an optimal procedure for variable selection and QSAR model building. J Chem Inf Comput Sci 41:1218–27. doi:10.1021/ci010291a
41. Gore P (2000) Handbook of applied multivariate statistics and mathematical modelling. Academic Press, San Diego
42. Duchowicz PR, Castro EA, Fernndez FM (2006) Alternative algorithm for the search of an optimal set of descriptors in QSAR-QSPR studies. MATCH Commun Math Comput Chem 55:179–192
43. StatSoft Inc. (2002) StatSoft Statistica, version 8.0. StatSoft Inc., Tulsa
44. Pérez-Garrido A, Helguera AM, Borges F, Cordeiro MN, Rivero V, Escudero AG (2011) Two new parameters based on distances in a receiver operating characteristic chart for the selection of classification models. J Chem Inf Model 51:2746–2759. doi:10.1021/ci2003076
45. Olivares-Morales A, Hatley OJD, Turner D, Galetin A, Aarons L, Rostami-Hodjegan A (2014) The use of ROC analysis for the qualitative prediction of human oral bioavailability from animal data. Pharm Res 31:720–730. doi:10.1007/s11095-013-1193-2
46. Nandy A, Kar S, Roy K (2014) Development of classification- and regression-based QSAR models and in silico screening of skin sensitisation potential of diverse organic chemicals. Mol Simul 40:261–274. doi:10.1080/08927022.2013.801076
47. Pérez-Garrido A, Girón-Rodríguez F, Morales Helguera A, Borges F, Combes RD (2014) Topological structural alerts modulations of mammalian cell mutagenicity for halogenated derivatives. SAR QSAR Environ Res 25:17–33. doi:10.1080/1062936X.2013.820791
48. Morales Helguera A, Pérez-Garrido A, Gaspar A, Cagide F, Vina D, Cordeiro MNDS, Borges F (2013) Combining QSAR classification models for predictive modeling of human monoamine oxidase inhibitors. Eur J Med Chem 59:75–90. doi:10.1016/j.ejmech.2012.10.035
49. Wold S, Eriksson L, Clementi S (1995) Statistical validation of QSAR results. In: van de Waterbeemd H (ed) Chemometric methods in molecular design. Wiley-VCH, Berlin, pp 309–338. doi:10.1002/9783527615452.ch5
50. de Cerqueira Lima P, Golbraikh A, Oloff S, Xiao Y, Tropsha A (2006) Combinatorial QSAR modeling of P-glycoprotein substrates. J Chem Inf Model 46:1245–1254. doi:10.1021/ci0504317
51. Todeschini R, Ballabio D, Consonni V, Manganaro W, Mauri A (2009) Canonical measure of correlation (CMC) and canonical measure of distance (CMD) between sets of data part 1 theory and simple chemometric applications. Anal Chim Acta 648:45–51. doi:10.1016/j.aca.2009.06.032
52. Krzanowski WJ (1988) Principles of multivariate analysis. Oxford University Press, New York
53. Kuncheva LI (2004) Combining pattern classifiers methods and algorithms. Wiley, New Jersey
54. Netzeva TI, Worth AP, Aldenberg T, Benigni R, Cronin MTD, Gramatica P, Jaworska JS, Kahn S, Klopman P, Marchant CA, Myatt G, Patlewicz GY, Perkins R, Roberts DW, Schultz TW, Stanton DT (2005) Current status of methods for defining the applicability domain of (quantitative) structure-activity relationships. ATLA 33:155–173
55. Gramatica P (2007) Principles of QSAR models validation: internal and external. QSAR Comb Sci 26:694–701. doi:10.1002/qsar.200610151
56. Pérez-Garrido A, Morales Helguera A, Caravaca G, Cordeiro MNDS, scudero AG (2010) A topological substructural molecular design approach for predicting mutagenesis end-points of \alpha, \beta α,β-unsaturated carbonyl compounds. Toxicology 268:64–77. doi:10.1016/j.tox.2009.11.023
57. Pérez-Garrido A, Morales Helguera A, Ruiz JMM, Rentero PZ (2012) Topological sub-structural molecular design approach: radical scavenging activity. Eur J Med Chem 49:86–94. doi:10.1016/j.ejmech.2011.12.030
58. Tropsha A, Gramatica P, Gombar V (2003) The importance of being earnest: validation is the absolute essential for successful application and interpretation of QSPR Models. QSAR Comb Sci 22:69–77. doi:10.1002/qsar.200390007
59. Polishchuk PG, Kuz’min VE, Artemenko AG, Muratov EN (2013) Universal approach for structural interpretation of QSAR/QSPR models. Mol Inf 32:843–853. doi:10.1002/minf.201300029
60. Instant Jchem version 6.2.1 (2014) Chemaxon Ltd, Budapest, https://www.chemaxon.com
61. Liu H, Gramatica P (2007) QSAR study of selective ligands for the thyroid hormone receptor beta. Bioorg Med Chem 15:5251–5261. doi:10.1016/j.bmc.2007.05.016
62. Helguera A, Combes R, González M, Cordeiro M (2008) Aplications of 2D descriptors in drug design: a DRAGON tale. Curr Top Med Chem 8:1628–1655. doi:10.2174/156802608786786598
63. Borghini A, Pietra D, Domenichellia P, Bianuccia A (2005) QSAR study on thiazole and thiadiazole analogues as antagonists for the adenosine A1 and A3 receptors. Bioorg Med Chem 13:5330–5337. doi:10.1016/j.bmc.2005.05.041
64. Bhattacharya P, Leonard J, Roy K (2005) Exploring QSAR of thiazole and thiadiazole derivatives as potent and selective human adenosine A3 receptor antagonists using FA and GFA techniques. Bioorg Med Chem 13:1159–1165. doi:10.1016/j.bmc.2004.11.022
65. Roy K, Leonard J, Sengupt C (2004) QSAR of adenosine receptor antagonists part 3: exploring physicochemical requirements for selective binding of 1,2,4-triazolo5,1-i.purine derivatives with human adenosine A3 receptor subtype. Bioorg Med Chem Lett 14:3705–3709. doi:10.1016/j.bmcl.2004.05.007
66. Bhattacharya P, Roy K (2005) QSAR of adenosine A3 receptor antagonist 1,2,4-triazolo4,3-a.quinoxalin-1-one derivatives using chemometric tools. Bioorg Med Chem Lett 15:3737–3743. doi:10.1016/j.bmcl.2005.05.051
67. Doichinova I, Natcheva R, Mihailova D (1994) QSAR studies of S-substituted xanthines as adenosine receptor antagonists. Eur J Med Chem 29:133–138. doi:10.1016/0223-5234(94)90210-0
68. Cheng F, Xu Z, Liu G, Tang Y (2010) Insights into binding modes of adenosine A_{2B}2B antagonists with ligand-based and receptor-based methods. Eur J Med Chem 45:3459–3471. doi:10.1016/j.ejmech.2010.04.039