Computer modeling of blood brain barrier permeability of physiologically active compounds Raevsky O.A.1 1 2 2 1. Institute of Physiologically Active Compounds, Russian Academy of Science2. Orekhovich Institute of Biomedical Chemistry of Russian Academy of Medical Sciences Section: Review DOI: 10.18097/PBMC20146002161 PubMed Id: 24837308
Year: 2014 Volume: 60 Issue : 2 Pages: 161-181Download PDF: Keywords: blood brain barrier, QSAR, passive diffusion, active transport, descriptors, P-gp, permeability
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Raevsky O.A., Solodova S.L., Lagunin A.A., Poroikov V.V. (2014) Computer modeling of blood brain barrier permeability of physiologically active compounds. Biomeditsinskaya Khimiya, 60 (2), 161-181.
Raevsky O.A. et al. Computer modeling of blood brain barrier permeability of physiologically active compounds // Biomeditsinskaya Khimiya. - 2014. - V. 60. -N 2. - P. 161-181.
Raevsky O.A. et al., "Computer modeling of blood brain barrier permeability of physiologically active compounds." Biomeditsinskaya Khimiya 60.2 (2014): 161-181.
Raevsky, O. A., Solodova, S. L., Lagunin, A. A., Poroikov, V. V. (2014). Computer modeling of blood brain barrier permeability of physiologically active compounds. Biomeditsinskaya Khimiya , 60(2), 161-181.
This paper is also available as the English translation: 10.1134/S199075081302008X
References Show Bredberi M. (1983) Kontseptsiya gematoehntsefalicheskogo bar'era (per. s angl.), Meditsina, M. Scholar google search Pokrovskij V.M., Korot'ko G.F., Kobrin V.I. et al. (1997) Fiziologiya cheloveka: Uchebnik, Meditsina, M. Scholar google search Wolf S., Seehaus B., Minol K. (1996) Naturwissenschaften., 83, 302-311. CrossRef Scholar google search Risau W., Engelhardt B., Wekerle H. (1990) J. Cell Biol., 110, 1757-1766. CrossRef Scholar google search Abbott N.J., Rönnbäck L., Hansson E. (2006) Nat. Rev. Neurosci. 7, 41-53. CrossRef Scholar google search Lee J. (1971) Progress in neuropathology, 1, 84-145. Scholar google search Hawkins B.T., Davis T.P. (2005) Pharmacol. Rev., 57, 173-185. CrossRef Scholar google search Yu A.S., McCarthy K.M., Francis S.A., McCormack J.M., Lai J., Roger R.A., Lynch R.D., Schneeberger E.E. (2005) Am. J. Physiol. Cell Physiol., 288, 1231-1241. CrossRef Scholar google search Wolburg H., Lippoldt A. (2002) Vasc. Pharmacol., 38, 323-337. CrossRef Scholar google search Lee G., Dallas S., Hong M., Bendayan R. (2001) Pharmacol. Rev., 53, 569-596. CrossRef Scholar google search Banks W.A. (2009) BMC Neurol., 9 (Suppl 1), S1-S3. CrossRef Scholar google search Bernacki J. (2008) Pharmacol. Reports, 60, 600-622. Scholar google search Roberts L.M., Black D.S., Raman C. et al. (2008) Neuroscience, 155, 423-438. CrossRef Scholar google search Tsuji A. (2005) NeuroRx., 2, 54-62. CrossRef Scholar google search Dahlin A., Royall J., Hohmann J.G., Wang J. (2009) J. Pharmacol. Exp. Ther., 329, 558-570. CrossRef Scholar google search Kanai Y., Segawa H., Miyamoto K., Uchino H., Takeda E., Endou H. (1998) J. Biol. Chem., 273, 23629-23632. CrossRef Scholar google search Mastroberardino L., Spindler B., Pfeiffer R., Skelly P.J., Loffing J. (1998) Nature, 395, 288-291. CrossRef Scholar google search Pineda M., Fernandez E., Torrents D., Estevez R. et al. (1999) J. Biol. Chem., 274, 19738-19744. CrossRef Scholar google search Segawa H., Fukasawa Y., Miyamoto K., Takeda E., Endou H. (1999) J. Biol. Chem., 274,19745-19751. CrossRef Scholar google search Kido Y., Tamai I., Uchino H., Sai Y., Suzuki F., Tsuji A. (2001) J. Pharm. Pharmacol., 53, 497-503. CrossRef Scholar google search Kumagai A.K., Dwyer K.J., Pardridge W.M. (1994) Biochem. Biophys. Acta., 91, 24-30. CrossRef Scholar google search Oldendolf W.H. (1971) Eur. Neurol., 6, 49-55. CrossRef Scholar google search Oldendolf W.H. (1973) Am. J. Physiol. (Lond), 224, 1450-1453. Scholar google search Nemoto E.M., Severinghaus J.W. (1997) Stroke, 5, 81-84. CrossRef Scholar google search Kang Y.S., Terasaki T., Tsuji A. (1990) J. Pharmacobiodyn., 13, 158-163. CrossRef Scholar google search Kusuhara H., Sekine T., Utsunomiya-Tate N., Tsuda M. et al. (1999) J. Biol. Chem., 274, 13675-13680. CrossRef Scholar google search Tamai I., Ohashi R., Nezu J., Yabuuchi H. et al. (1998) J. Biol. Chem., 273, 20378-20382. CrossRef Scholar google search Wu X., Kekuda R., Huang W., Fei Y.-J. et al. (1998) J. Biol. Chem., 273, 32776-32786. CrossRef Scholar google search Banks W.A., Audus K., Davis T.P. (1992) Peptides, 13, 1289-1294. CrossRef Scholar google search Begley D.J. (1996) J. Pharm. Pharmacol., 48, 136-146. CrossRef Scholar google search Molina-Arcas M., Casado F.J., Pastor-Anglada M. (2009) Curr. Vasc. Pharmacol., 7(4), 426-434. CrossRef Scholar google search Bhutia Y.D., Hung S.W., Patel B., Lovin D., Govindarajan R. (2011) Cancer Res., 71(5), 1825-35. CrossRef Scholar google search Nagai K., Nagasawa K., Fujimoto S. (2005) Cancer Chemother. Pharmacol., 55(3), 222-230. CrossRef Scholar google search Roninson I.B. (1991) Structure and evolution of P-glycoprotein. From, edited by I. Roninson, 189-209. Plenum Press, New York. Scholar google search Higgins C.F. (2001) Res. Microbiol., 152, 205-210. CrossRef Scholar google search Bakos E. (2007) Eur. J. Physiol., 453, 621-641. CrossRef Scholar google search Dean M., Hamon Y., Chimini G. (2001) J. Lipid. Res., 42, 1007-1017. Scholar google search Bakos E., Homolya L. (2007) Pflugers. Arch., 453(5), 621-41. CrossRef Scholar google search Ramachandra M., Ambudkar S.V., Chen D. et al. (1998) Biochemistry, 37(14), 5010-5019. CrossRef Scholar google search Lam F.C., Liu R., Lu P. et al. (2001) J. Neurochem. 76, 1121-1128. CrossRef Scholar google search Miller D.S., Bauer B., Hartz A.M.S. (2008) Pharmacol. Rev., 60, 196-209. CrossRef Scholar google search Bendayan R., Ronaldson P.T., Gingras D., Bendayan M. (2006) J. Histochem. Cytochem., 54, 1159-1167. CrossRef Scholar google search Higgins C.F., Linton K.J. (2004) Nat. Struct. Mol. Biol., 11(10), 918-926. CrossRef Scholar google search Aszalos A. (2007) Drug. Discov. Today, 12, 833-837. CrossRef Scholar google search Rosenberg M.F., Kamis A.B., Callaghan R., Higgins C.F., Ford R.C. (2003) J. Biol. Chem., 278, 8294-8299. CrossRef Scholar google search Rosenberg M.F., Callaghan R., Modok S., Higgins C.F., Ford R.C. (2005) J. Biol. Chem., 280, 2857-2862. CrossRef Scholar google search Aller S.G., Yu J., Ward A., Weng Y. et al.(2009) Science, 323, 1718-1722. CrossRef Scholar google search Seelig A., Landwojtowicz E. (2000) Eur. J. Pharm. Sci., 12, 31-40. CrossRef Scholar google search Ecker G., Huber M., Schmid D., Chiba P. (1999) Mol Pharmacol., 56, 791-796. Scholar google search Lagunin A.A., Gloriozova T.A., Dmitriev A.V., Volgina N.E., Porojkov V.V. (2012) Bulletin of Experimental Biology and Medicine, 154(10), 520-524. Scholar google search Torshin N.A., Vlasova V.I. (2001) Osnovy fiziologii cheloveka - Uchebnik dlya studentov vuzov, obuchayushhikhsya po meditsinskim i biologicheskim spetsial'nostyam. 2-e izdanie, ispravlennoe. RUDN, M. Scholar google search Desai M.C., Thadeio P.F., Lipinski Chr.A., Liston D.R., Spencer R.W., Williams I.H. (1991) Bioorg. Med. Chem. Lett., 8, 411-414. CrossRef Scholar google search Abraham M.H., Lieb W.R., Franks N.P. (1991) J. Pharm. Sci., 80, 719-724. CrossRef Scholar google search Abraham M.H., Chadha H.S., Mitchell R.C. (1995) J. Pharm. Sci., 84, 1257-1268. Scholar google search Abraham M.H., Chadha H.S., Mitchell R.C. (1995) Drug Des. Discov., 13, 123-131. Scholar google search Abraham M.H., Takacs-Novak K., Mitchell R.C. (1997) J. Pharm. Sci., 86, 310-315. CrossRef Scholar google search Van de Waterbeemd H., Kansy M. (1992) Chimia, 46, 299-303. Scholar google search Seelig A., Gottschlich R., Devant R.M. (1994) Proc. Natl. Acad. Sci. USA, 91, 68-72. CrossRef Scholar google search Ter Laak A.M., Tsai R.S., Donne-Op den Kelder G.M., Carrupt P.A., Testa B. (1994) Eur. J. Pharm. Sci., 2, 373-384. CrossRef Scholar google search Chikhale E.G., Ng K.-Y., Burton Ph.S., Borchardt R.T. (1994) Pharm. Res., 3, 412-419. CrossRef Scholar google search Calder J.A., Ganellin C.R. (1994) Drug Des. Discov., 11, 259-268. Scholar google search Basak S.C., Gute B.D., Drewes L.R. (1996) Pharm. Res., 13,775-778. CrossRef Scholar google search Kai J., Nakamura K., Masuda T., Ueda I., Fujiwara H. (1996) J. Med. Chem., 39, 2621-2624. CrossRef Scholar google search Lombardo F., Blake J.F., Curatolo W.J. (1996) J. Med. Chem., 39, 4750-4755. CrossRef Scholar google search Young R.C., Mitchell R.C., Brown Th.H., Ganellin C.R. et al. (1988) J. Med. Chem., 31, 656-671. CrossRef Scholar google search N’Goka V., Schlewer G., Linget J.M. et al. (1991) J. Med. Chem., 34, 2547-2557. Scholar google search Testa B., Seiler P. (1981) Drug Res., 31, 1053-1058. Scholar google search Van de Waterbeemd H., Testa B. (1987) Adv. Drug Res., 16, 85-225. Scholar google search Tayar El., Tsai N., Testa R.-S., et al. (1991) J. Pharm. Sci., 80, 590-598. CrossRef Scholar google search Tayar El., Testa N., Carrupt P.-A. (1992) J. Phys. Chem., 96, 1455-1459. CrossRef Scholar google search Van de Waterbeemd H., Camenisch G., Folkers G., Chretien J.R., Raevsky O.A. (1998) J. Drug Targeting, 6, 151-165. CrossRef Scholar google search Leo A., Hansch C., Elkins D. (1971) Chem. Rev., 71, 525-616. CrossRef Scholar google search Camenisch G., Folkers G., Van de Waterbeemd H. (1996) Pharm. Acra Helv., 71, 309-327. CrossRef Scholar google search Van de Waterbeemd H., Kansy M., Wagner B., Fischer H. (l996) In: Lipophilicity in Drug Action and Toxicology (Pliska V., Testa B., Van de Waterbeemd H., eds.), Weinheim: VCH. Scholar google search Xiang T.X., Anderson B.D. (1994) J. Membr. Biol., 140, 111-122. CrossRef Scholar google search Abraham M.H. et al. (1994) J. Pharm. Sci., 83, 1257-1268. CrossRef Scholar google search Luco J.M. (1999) J. Chem. Inf. Comput. Sci., 39, 396-404. CrossRef Scholar google search Clark D.E. (1999) J. Pharm. Sci., 88, 815-821. CrossRef Scholar google search Abraham M.H., Ibrahim A., Zhao Y., Acree W. (2006) Eur. J. Pharm. Sci., 95, 2091-2100. CrossRef Scholar google search Subramanian G., Kitchen D.B. (2003) J. Comp.-Aided Mol. Design, 17, 643-664. CrossRef Scholar google search Sun H. (2004) J. Chem. Inf. Comput. Sci., 44, 748-757. CrossRef Scholar google search Adenot M., Lahana R. (2004) J. Chem. Inf. Comput. Sci., 44, 239-248. CrossRef Scholar google search Liu X., Ma P.X. (2004) Drug Metab. Dispos., 32, 132-139. CrossRef Scholar google search Cabrera M.A., Bermejo M., Perez M., Ramos R.J. (2004) Pharm. Sci., 93, 1701-1717. CrossRef Scholar google search Mensch J., Oyarzabal J., Mackie C., Augustijns P. (2009) J. Pharm. Sci., 98, 4429-4468. CrossRef Scholar google search Mehdipour A.R., Hamidi M. (2009) Drug Discovery Today, 14, 1030-1036. CrossRef Scholar google search Zhang L., Zhu H., Oprea T.I., Golbraikh A., Tropsha A. (2008) Pharm. Res., 25, 1902-1914. CrossRef Scholar google search Zhao Y.H., Abraham M.H. et al. (2007) J. Chem. Inf. Model., 47, 170-175. CrossRef Scholar google search Li H., Yap C. W., Ung C. Y., Xue Y. et al. (2005) J. Chem. Inf. Model., 45, 1376-1384. CrossRef Scholar google search Al-Fahemi J.H.A., Cooper D.L., Allan N.L. (2007) J. Molecular Graphics and Modelling, 26, 607-612. CrossRef Scholar google search Cuadrado M.U., Ruiz I.L., Angel M. (2007) J. Comput. Chem., 28, 1252-1260. CrossRef Scholar google search Wichmann K. et al. (2007) J. Chem. Inf. Model., 47, 228-233. CrossRef Scholar google search Konovalov D.A. et al. (2007) J. Chem. Inf. Model., 47, 1648-1656. CrossRef Scholar google search Obrezanova O, Csanyi G., Gola J.M.R., Segall M.D. (2007) J. Chem. Inf. Model., 47, 1847-1857. CrossRef Scholar google search Wan H. et al. (2007) J. Med Chem., 50, 4606-4615. CrossRef Scholar google search Obrezanova O. et al. (2008) J. Comput. Aided Mol., 22, 431-440. CrossRef Scholar google search Kortagere S., Chekmarev D., Welsh W.J., Ekins S (2008) Pharmaceutical Res., 25, 1836-1845. CrossRef Scholar google search Guerra A., Paez J.A., Campillo N.E. (2008) QSAR Comb. Sci., 27, 586-594. CrossRef Scholar google search Fu X.-C., Wang G.-P., Shan H.-L. et al. (2008) Eur. J. Pharm. Biopharmaceut., 70, 462-466. CrossRef Scholar google search Van Damme S., Langenaeker W., Bultinck P. (2008) J. Molecular Graphics and Modelling, 26, 1223-1236. CrossRef Scholar google search Shen J., Dub Y., Zhaoa Y., Liua G., Tanga Y. (2008) QSAR Comb. Sci., 27, No.6, 704-717. CrossRef Scholar google search Konovalov D.A., Sim N., Deconinck E. et al. (2008) J. Chem. Inf. Model., 48, 370-383. CrossRef Scholar google search Karelson M. et al. (2008) ARKIVOC, 38-60. Scholar google search Lanevskij K., Japertasa P., Didziapetrisa R., Petrauskasa A. (2009) Chemistry Biodiversity, 6, 2050-2054. CrossRef Scholar google search Guo Q., Brady M., Gunn R.N. (2009) J Nucl Med; 50, 1715-1723. CrossRef Scholar google search Chen Y., Zhub Q.-J., Pana J., Yanga Y., Wuc X.-P. (2009) Computer methods and programs in biomedicine, 95, 280-287. CrossRef Scholar google search Wang Z., Yan A., Yuan Q. (2009) QSAR Comb. Sci., 28, 989-994. CrossRef Scholar google search Varnek A., Gaudin C., Marcou G. et al. (2009) J. Chem. Inf. Model., 49, 133-144. CrossRef Scholar google search Friden M., Winiwarter S., Jerndal G., Bengtsson O., Wan H. (2009) J. Med. Chem., 52, 6233-6243. CrossRef Scholar google search Di L., Kerns E. H., Bezar I. F., Petusky S. L., Huangdi Y. (2009) J. Pharm Sci., 98, 1980-1991. CrossRef Scholar google search Petereit A.C., Swinney K., Mensch J., Mackie C., Stokbroekx S., Brewster M., Dressman J.B. (2010) Eur. J. Pharm. Biopharm., 75, 405-410. CrossRef Scholar google search Sá M.M., Pasqualoto K.F.M., Rangel-Yagui C.O. (2010) Brazilian J. Pharm. Sci., 46, 741-751. Scholar google search Shen J., Cheng F., Xu Y., Li W., Tang Y. (2010) J. Chem. Inf. Model., 50(6), 1034-1041. CrossRef Scholar google search Obrezanova O., Segall M.D. (2010) J. Chem. Inf. Model., 50, 1053-1061. CrossRef Scholar google search Fan Y. (2010) J. Chem. Inf. Model., 50, 1123-1133. CrossRef Scholar google search Abraham M. et al. (2010) J. Pharm. Sci., 99, 2492-2501. CrossRef Scholar google search Mensch J. et al. (2010) Int. J. Pharm., 395, 182-197. CrossRef Scholar google search Mabondzo A., Bottlaender M., Guyot A.-C., Tsaouin K., Robert Deverre J., Balimane P. V. (2010) Mol. Pharm., 7, 1805-1815. CrossRef Scholar google search Tsinman O., Tsinman K., Sun N., Avdeef A. (2011) Pharm Res., 28, 337-363. CrossRef Scholar google search Chen H. et al. (2011) J. Mol. Graph. Model., 29, 985-995. CrossRef Scholar google search The H.P. et al. (2011) Mol. Inf., 30, 376-385. CrossRef Scholar google search Lacombe O., Videau O., Chevillon D., Guyot A.-C. et al. (2011) Mol. Pharm., 8, 651-663. CrossRef Scholar google search Raevsky O.A., Solodova S.L., Raevskaya O.E., Liplavskiy Y.V., Mannhold R. (2012) Biochemistry (Moscow) Supplement Series B: Biomedical Chemistry, 6, 31-38. Scholar google search Lipinski C.A. Drugs structure and properties, past and present. Can we design drugs with beautiful properties? http://www.iainm.demon.co.uk/spring99/lipins_n.pdf. Scholar google search Hughes J.D. et al. (2008) Bioorg. Med. Chem. Lett., 18, 4872-4875. CrossRef Scholar google search Zhang H. (2004) J. Pharm. Sci., 93, 1595-1604. CrossRef Scholar google search Crivori P., Reinach B., Pezzetta D., Poggesi I. (2006) Mol. Pharm., 3, 33-44. CrossRef Scholar google search Volsurf, version 4.0; available from Molecular Discovery Ltd., London, U.K. (www.moldiscovery.com). Scholar google search GRID, version 22; available from Molecular Discovery Ltd., London, U.K. (www.moldiscovery.com). Scholar google search Cianchetta G., Singleton R.W., Zhang M., Wildgoose M., Giesing D., Fravolini A., Cruciani G., Vaz R.J. (2005) J. Med. Chem.,48, 2927-2935. CrossRef Scholar google search CORINA, version 3.2; available from Molecular Networks, GmbH, Computerchemie, Erlangen, Germany (www.mol-net.de). Scholar google search Seelig A. (1998) Eur. J. Biochem., 251, 252-261. CrossRef Scholar google search Bikadi Z., Hazai I., Malik D., Jemnitz K., Veres Z. et al. (2011) PLoS ONE, 6(10), e25815. Scholar google search
