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Volumn 79, Issue 3, 2010, Pages 307-320

Interaction of benzopyranone derivatives and related compounds with human concentrative nucleoside transporters 1, 2 and 3 heterologously expressed in porcine PK15 nucleoside transporter deficient cells. Structure-activity relationships and determinants of transporter affinity and selectivity

Author keywords

Benzopyranone derivatives; CoMFA; CoMSIA; Concentrative nucleoside transporters; Structure activity relationships

Indexed keywords

3',4' DIHYDROXYFLAVONE; 3',4' DIMETHOXYFLAVONE; 3,4' DIHYDROXYFLAVONE; 3,5 DIHYDROXYFLAVONE; 3,6 DIHYDROXYFLAVONE; 3,7 DIHYDROXYFLAVONE; 4',6 DIHYDROXYFLAVONE; 5,6 DIHYDROXYFLAVONE; 6 HYDROXY 7 METHOXYFLAVONE; 6,7 DIHYDROXYFLAVONE; 7,2' DIHYDROXYFLAVONE; 7,4' DIHYDROXYFLAVONE; 7,8 DIHYDROXYFLAVONE; 7,8 DIMETHOXYFLAVONE; ALPHA NAPHTHOFLAVONE; BENZOPYRONE DERIVATIVE; BETA NAPHTHOFLAVONE; CHALCONE DERIVATIVE; CHRYSIN; COUMARIN DERIVATIVE; FLAVONE DERIVATIVE; ISOFLAVONE DERIVATIVE; NUCLEOSIDE TRANSPORTER; NUCLEOSIDE TRANSPORTER 1; NUCLEOSIDE TRANSPORTER 2; NUCLEOSIDE TRANSPORTER 3; NUCLEOSIDE TRANSPORTER INHIBITOR; PHLORIZIN; PROTEIN INHIBITOR; UNCLASSIFIED DRUG; UNINDEXED DRUG;

EID: 70449687880     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bcp.2009.08.028     Document Type: Article
Times cited : (23)

References (39)
  • 1
    • 0030606020 scopus 로고    scopus 로고
    • Nucleoside and nucleobase transport systems of mammalian cells
    • Griffith D.A., and Jarvis S.M. Nucleoside and nucleobase transport systems of mammalian cells. Biochim Biophys Acta 1286 (1996) 153-181
    • (1996) Biochim Biophys Acta , vol.1286 , pp. 153-181
    • Griffith, D.A.1    Jarvis, S.M.2
  • 3
    • 0035054188 scopus 로고    scopus 로고
    • Distinct regional distribution of human equilibrative nucleoside transporter proteins 1 and 2 (hENT1 and hENT2) in the central nervous system
    • Jennings L.L., Hao C., Cabrita M.A., Vickers M.F., Baldwin S.A., Young J.D., et al. Distinct regional distribution of human equilibrative nucleoside transporter proteins 1 and 2 (hENT1 and hENT2) in the central nervous system. Neuropharmacology 40 (2001) 722-731
    • (2001) Neuropharmacology , vol.40 , pp. 722-731
    • Jennings, L.L.1    Hao, C.2    Cabrita, M.A.3    Vickers, M.F.4    Baldwin, S.A.5    Young, J.D.6
  • 4
    • 0034765853 scopus 로고    scopus 로고
    • Adenosine in the central nervous system: release mechanisms and extracellular concentrations
    • Latini S., and Pedata F. Adenosine in the central nervous system: release mechanisms and extracellular concentrations. J Neurochem 79 (2001) 463-484
    • (2001) J Neurochem , vol.79 , pp. 463-484
    • Latini, S.1    Pedata, F.2
  • 5
    • 0345688175 scopus 로고    scopus 로고
    • Nucleoside anticancer drugs: the role of nucleoside transporters in resistance to cancer chemotherapy
    • Damaraju V.L., Damaraju S., Young J.D., Baldwin S.A., Mackey J., Sawyer M.B., et al. Nucleoside anticancer drugs: the role of nucleoside transporters in resistance to cancer chemotherapy. Oncogene 22 (2003) 7524-7536
    • (2003) Oncogene , vol.22 , pp. 7524-7536
    • Damaraju, V.L.1    Damaraju, S.2    Young, J.D.3    Baldwin, S.A.4    Mackey, J.5    Sawyer, M.B.6
  • 10
    • 0028362987 scopus 로고
    • Cloning and functional expression of a complementary DNA encoding a mammalian nucleoside transport protein
    • Huang Q.Q., Yao S.Y., Ritzel M.W., Paterson A.R., Cass C.E., and Young J.D. Cloning and functional expression of a complementary DNA encoding a mammalian nucleoside transport protein. J Biol Chem 269 (1994) 17757-17760
    • (1994) J Biol Chem , vol.269 , pp. 17757-17760
    • Huang, Q.Q.1    Yao, S.Y.2    Ritzel, M.W.3    Paterson, A.R.4    Cass, C.E.5    Young, J.D.6
  • 11
    • 0029025787 scopus 로고
    • Primary structure and functional expression of a cDNA encoding the bile canalicular, purine-specific Na(+)-nucleoside cotransporter
    • Che M., Ortiz D.F., and Arias I.M. Primary structure and functional expression of a cDNA encoding the bile canalicular, purine-specific Na(+)-nucleoside cotransporter. J Biol Chem 270 (1995) 13596-13599
    • (1995) J Biol Chem , vol.270 , pp. 13596-13599
    • Che, M.1    Ortiz, D.F.2    Arias, I.M.3
  • 12
    • 0031409587 scopus 로고    scopus 로고
    • Na(+)-dependent purine nucleoside transporter from human kidney: cloning and functional characterization
    • Wang J., Su S.F., Dresser M.J., Schaner M.E., Washington C.B., and Giacomini K.M. Na(+)-dependent purine nucleoside transporter from human kidney: cloning and functional characterization. Am J Physiol 273 (1997) F1058-F1065
    • (1997) Am J Physiol , vol.273
    • Wang, J.1    Su, S.F.2    Dresser, M.J.3    Schaner, M.E.4    Washington, C.B.5    Giacomini, K.M.6
  • 13
    • 0030938889 scopus 로고    scopus 로고
    • Molecular cloning and functional expression of cDNAs encoding a human Na+-nucleoside cotransporter (hCNT1)
    • Ritzel M.W., Yao S.Y., Huang M.Y., Elliott J.F., Cass C.E., and Young J.D. Molecular cloning and functional expression of cDNAs encoding a human Na+-nucleoside cotransporter (hCNT1). Am J Physiol 272 (1997) C707-C714
    • (1997) Am J Physiol , vol.272
    • Ritzel, M.W.1    Yao, S.Y.2    Huang, M.Y.3    Elliott, J.F.4    Cass, C.E.5    Young, J.D.6
  • 15
    • 0035951808 scopus 로고    scopus 로고
    • +-nucleoside cotransporter (hCNT3 and mCNT3) broadly selective for purine and pyrimidine nucleoside (system cib)
    • +-nucleoside cotransporter (hCNT3 and mCNT3) broadly selective for purine and pyrimidine nucleoside (system cib). J Biol Chem 276 (2001) 2914-2927
    • (2001) J Biol Chem , vol.276 , pp. 2914-2927
    • Ritzel, M.W.1    Ng, A.M.2    Yao, S.Y.3    Graham, K.4    Leowen, S.K.5    Smith, K.M.6
  • 16
    • 35649019182 scopus 로고    scopus 로고
    • Conserved glutamate residues are critically involved in Na+/nucleoside cotransport by human concentrative nucleoside transporter 1 (hCNT1)
    • Yao S.Y., Ng A.M., Slugoski M.D., Smith K.M., Mulinta R., Karpinski E., et al. Conserved glutamate residues are critically involved in Na+/nucleoside cotransport by human concentrative nucleoside transporter 1 (hCNT1). J Biol Chem 282 (2007) 30607-30617
    • (2007) J Biol Chem , vol.282 , pp. 30607-30617
    • Yao, S.Y.1    Ng, A.M.2    Slugoski, M.D.3    Smith, K.M.4    Mulinta, R.5    Karpinski, E.6
  • 17
    • 34548048139 scopus 로고    scopus 로고
    • Localization of broadly selective equilibrative and concentrative nucleoside transporters, hENT1 and hCNT3, in human kidney
    • Damaraju V.L., Elwi A.N., Hunter C., Carpenter P., Santos C., Barron G.M., et al. Localization of broadly selective equilibrative and concentrative nucleoside transporters, hENT1 and hCNT3, in human kidney. Am J Physiol Renal Physiol 293 (2007) F200-F211
    • (2007) Am J Physiol Renal Physiol , vol.293
    • Damaraju, V.L.1    Elwi, A.N.2    Hunter, C.3    Carpenter, P.4    Santos, C.5    Barron, G.M.6
  • 19
    • 34547543603 scopus 로고    scopus 로고
    • Concentrative nucleoside transporters (CNTs) in epithelia: from absorption to cell signaling
    • Pastor-Anglada M., Errasti-Murugarren E., Aymerich I., and Casado F.J. Concentrative nucleoside transporters (CNTs) in epithelia: from absorption to cell signaling. J Physiol Biochem 63 (2007) 97-110
    • (2007) J Physiol Biochem , vol.63 , pp. 97-110
    • Pastor-Anglada, M.1    Errasti-Murugarren, E.2    Aymerich, I.3    Casado, F.J.4
  • 20
    • 0030907430 scopus 로고    scopus 로고
    • Nucleoside transporter inhibitors: structure-activity relationships and potential therapeutic applications
    • Buolamwini J.K. Nucleoside transporter inhibitors: structure-activity relationships and potential therapeutic applications. Curr Med Chem 4 (1997) 35-66
    • (1997) Curr Med Chem , vol.4 , pp. 35-66
    • Buolamwini, J.K.1
  • 21
    • 33846803914 scopus 로고    scopus 로고
    • Inhibition of the intestinal glucose transporter GLUT2 by flavonoids
    • Kwon O., Eck P., Chen S., Corpe C.P., Lee J.H., Kruhlak M., et al. Inhibition of the intestinal glucose transporter GLUT2 by flavonoids. FASEB J 21 (2007) 366-377
    • (2007) FASEB J , vol.21 , pp. 366-377
    • Kwon, O.1    Eck, P.2    Chen, S.3    Corpe, C.P.4    Lee, J.H.5    Kruhlak, M.6
  • 22
    • 0034708596 scopus 로고    scopus 로고
    • Kinetic and pharmacological properties of cloned human equilibrative nucleoside transporters, ENT1 and ENT2, stably expressed in nucleoside transporter-deficient PK15 cells. ENT2 exhibits a low affinity for guanosine and cytidine but a high affinity for inosine
    • Ward J.L., Sherali A., Mo Z.P., and Tse C.M. Kinetic and pharmacological properties of cloned human equilibrative nucleoside transporters, ENT1 and ENT2, stably expressed in nucleoside transporter-deficient PK15 cells. ENT2 exhibits a low affinity for guanosine and cytidine but a high affinity for inosine. J Biol Chem 275 (2000) 8375-8381
    • (2000) J Biol Chem , vol.275 , pp. 8375-8381
    • Ward, J.L.1    Sherali, A.2    Mo, Z.P.3    Tse, C.M.4
  • 23
    • 0023751431 scopus 로고
    • comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins
    • Cramer III R.D., Patterson D.E., and Bunce J.D. comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins. J Am Chem Soc 110 (1988) 5959-5967
    • (1988) J Am Chem Soc , vol.110 , pp. 5959-5967
    • Cramer III, R.D.1    Patterson, D.E.2    Bunce, J.D.3
  • 24
    • 0027944195 scopus 로고
    • Molecular similarity indices in a comparative analysis (CoMSIA) of drug molecules to correlate and predict their biological activity
    • Klebe G., Abraham U., and Mietzner T. Molecular similarity indices in a comparative analysis (CoMSIA) of drug molecules to correlate and predict their biological activity. J Med Chem 37 (1994) 4130-4146
    • (1994) J Med Chem , vol.37 , pp. 4130-4146
    • Klebe, G.1    Abraham, U.2    Mietzner, T.3
  • 25
    • 0842287376 scopus 로고    scopus 로고
    • Genomic organization and functional characterization of the human concentrative nucleoside transporter-3 isoform (hCNT3) expressed in mammalian cells
    • Toan S., To K.K., Leung G.P., Souza M.O., Ward J.L., and Tse C. Genomic organization and functional characterization of the human concentrative nucleoside transporter-3 isoform (hCNT3) expressed in mammalian cells. Eur J physiol 447 (2003) 195-204
    • (2003) Eur J physiol , vol.447 , pp. 195-204
    • Toan, S.1    To, K.K.2    Leung, G.P.3    Souza, M.O.4    Ward, J.L.5    Tse, C.6
  • 26
    • 58549111373 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of Phloridzin analogs as human concentrative nucleoside transporter 3 (hCNT3) inhibitors
    • Gupte A., and Buolamwini J.K. Synthesis and biological evaluation of Phloridzin analogs as human concentrative nucleoside transporter 3 (hCNT3) inhibitors. Bioorg Med Chem Lett 19 (2009) 917-921
    • (2009) Bioorg Med Chem Lett , vol.19 , pp. 917-921
    • Gupte, A.1    Buolamwini, J.K.2
  • 27
    • 4444371568 scopus 로고    scopus 로고
    • Electrophysiological characterization of a recombinant human Na+-coupled nucleoside transporter (hCNT1) produced in Xenopus oocytes
    • Smith K.M., Ng A.M., Yao S.Y., Labedz K.A., Knaus E.E., Wiebe L.I., et al. Electrophysiological characterization of a recombinant human Na+-coupled nucleoside transporter (hCNT1) produced in Xenopus oocytes. J Physiol 558 (2004) 807-823
    • (2004) J Physiol , vol.558 , pp. 807-823
    • Smith, K.M.1    Ng, A.M.2    Yao, S.Y.3    Labedz, K.A.4    Knaus, E.E.5    Wiebe, L.I.6
  • 28
    • 23944467804 scopus 로고    scopus 로고
    • Uridine binding and transportability determinants of human concentrative nucleoside transporters
    • Zhang J., Smith K.M., Tackaberry T., Visser F., Robins M.J., Nielsen L.P., et al. Uridine binding and transportability determinants of human concentrative nucleoside transporters. Mol Pharmacol 68 (2005) 830-839
    • (2005) Mol Pharmacol , vol.68 , pp. 830-839
    • Zhang, J.1    Smith, K.M.2    Tackaberry, T.3    Visser, F.4    Robins, M.J.5    Nielsen, L.P.6
  • 29
    • 1842481060 scopus 로고    scopus 로고
    • Interactions of nucleoside analogs, caffeine, and nicotine with human-concentrative nucleoside transporters 1 and 2 stably produced in a transport-defective human cell line
    • Lang T.T., Young J.D., and Cass C.E. Interactions of nucleoside analogs, caffeine, and nicotine with human-concentrative nucleoside transporters 1 and 2 stably produced in a transport-defective human cell line. Mol Pharmacol 65 (2004) 925-933
    • (2004) Mol Pharmacol , vol.65 , pp. 925-933
    • Lang, T.T.1    Young, J.D.2    Cass, C.E.3
  • 30
    • 15744373314 scopus 로고    scopus 로고
    • Residue 33 of human equilibrative nucleoside transporter 2 is a functionally important component of both the dipyridamole and nucleoside-binding sites
    • Visser F., Zhang J., Raborn R.T., Baldwin S.A., Young J.D., and Cass C.E. Residue 33 of human equilibrative nucleoside transporter 2 is a functionally important component of both the dipyridamole and nucleoside-binding sites. Mol Pharmacol 67 (2005) 1291-1298
    • (2005) Mol Pharmacol , vol.67 , pp. 1291-1298
    • Visser, F.1    Zhang, J.2    Raborn, R.T.3    Baldwin, S.A.4    Young, J.D.5    Cass, C.E.6
  • 32
    • 1342308339 scopus 로고    scopus 로고
    • Molecular requirements of the human nucleoside transporters hCNT1, hCNT2, and hENT1
    • Chang C., Swaan P.W., Ngo L.Y., Lum P.Y., Patil S.D., and Unadkat J.D. Molecular requirements of the human nucleoside transporters hCNT1, hCNT2, and hENT1. Mol Pharmacol 65 (2004) 558-570
    • (2004) Mol Pharmacol , vol.65 , pp. 558-570
    • Chang, C.1    Swaan, P.W.2    Ngo, L.Y.3    Lum, P.Y.4    Patil, S.D.5    Unadkat, J.D.6
  • 33
    • 33645828207 scopus 로고    scopus 로고
    • Electrophysiological characterization and modeling of the structure activity relationship of the human concentrative nucleoside transporter 3 (hCNT3)
    • Hu H., Endres C.J., Chang C., Umapathy N.S., Lee E.W., Fei Y.J., et al. Electrophysiological characterization and modeling of the structure activity relationship of the human concentrative nucleoside transporter 3 (hCNT3). Mol Pharmacol 69 (2006) 1542-1553
    • (2006) Mol Pharmacol , vol.69 , pp. 1542-1553
    • Hu, H.1    Endres, C.J.2    Chang, C.3    Umapathy, N.S.4    Lee, E.W.5    Fei, Y.J.6
  • 34
    • 70449671429 scopus 로고    scopus 로고
    • Nonaka Y, Tatani K, Hiratochi M, Kuramochi Y, Isaji M. Preparation of 5'-modified nucleoside derivatives as CNT-2 inhibitors. WO 2004101593; 2004
    • Nonaka Y, Tatani K, Hiratochi M, Kuramochi Y, Isaji M. Preparation of 5'-modified nucleoside derivatives as CNT-2 inhibitors. WO 2004101593; 2004.
  • 35
    • 70449658089 scopus 로고    scopus 로고
    • Preparation of ribofuranoside compounds having benzimidazole moiety as CNT2 inhibitors
    • Kikuchi N., Nonaka Y., Tatani K., Hiratochi M., Kuramochi Y., Isaji M., et al. Preparation of ribofuranoside compounds having benzimidazole moiety as CNT2 inhibitors. PCT Int Appl (2005) 141
    • (2005) PCT Int Appl , pp. 141
    • Kikuchi, N.1    Nonaka, Y.2    Tatani, K.3    Hiratochi, M.4    Kuramochi, Y.5    Isaji, M.6
  • 36
    • 70449640775 scopus 로고    scopus 로고
    • Preparation of purine nucleoside derivatives modified in 8-position as inhibitors of concentrative nucleoside transporter 2
    • WO 2006030803;
    • Tatani, K.N.Y., Kikuchi, N. Preparation of purine nucleoside derivatives modified in 8-position as inhibitors of concentrative nucleoside transporter 2. WO 2006030803; 2006.
    • (2006)
    • Tatani, K.N.Y.1    Kikuchi, N.2
  • 37
    • 0033520708 scopus 로고    scopus 로고
    • Gemcitabine transport in xenopus oocytes expressing recombinant plasma membrane mammalian nucleoside transporters
    • Mackey J.R., Yao S.Y., Smith K.M., Karpinski E., Baldwin S.A., Cass C.E., et al. Gemcitabine transport in xenopus oocytes expressing recombinant plasma membrane mammalian nucleoside transporters. J Natl Cancer Inst 91 (1999) 1876-1881
    • (1999) J Natl Cancer Inst , vol.91 , pp. 1876-1881
    • Mackey, J.R.1    Yao, S.Y.2    Smith, K.M.3    Karpinski, E.4    Baldwin, S.A.5    Cass, C.E.6
  • 38
    • 58149516930 scopus 로고    scopus 로고
    • Human concentrative nucleoside transporter 1-mediated uptake of 5-azacytidine enhances DNA demethylation
    • Rius M., Stresemann C., Keller D., Brom M., Schirrmacher E., Keppler D., et al. Human concentrative nucleoside transporter 1-mediated uptake of 5-azacytidine enhances DNA demethylation. Mol Cancer Ther 8 (2009) 225-231
    • (2009) Mol Cancer Ther , vol.8 , pp. 225-231
    • Rius, M.1    Stresemann, C.2    Keller, D.3    Brom, M.4    Schirrmacher, E.5    Keppler, D.6
  • 39
    • 34547113312 scopus 로고    scopus 로고
    • Role of CNT3 in the transepithelial flux of nucleosides and nucleoside-derived drugs
    • Errasti-Murugarren E., Pastor-Anglada M., and Casado F.J. Role of CNT3 in the transepithelial flux of nucleosides and nucleoside-derived drugs. J Physiol 582 (2007) 1249-1260
    • (2007) J Physiol , vol.582 , pp. 1249-1260
    • Errasti-Murugarren, E.1    Pastor-Anglada, M.2    Casado, F.J.3


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