메뉴 건너뛰기




Volumn 71, Issue 4, 2013, Pages 999-1011

Therapeutic targeting malignant mesothelioma with a novel 6-substituted pyrrolo[2,3-d]pyrimidine thienoyl antifolate via its selective uptake by the proton-coupled folate transporter

Author keywords

Antifolate; Folate; Mesothelioma; Pemetrexed; Proton coupled folate transporter

Indexed keywords

ANTINEOPLASTIC AGENT; CISPLATIN; GEMCITABINE; PEMETREXED; PHOSPHORIBOSYLGLYCINAMIDE FORMYLTRANSFERASE; PROTON COUPLED FOLATE TRANSPORTER; PYRROLO[2,3 D]PYRIMIDINE THIENOYL ANTIFOLATE DERIVATIVE; UNCLASSIFIED DRUG; FOLIC ACID ANTAGONIST; POLYGLUTAMIC ACID; PYRIMIDINE DERIVATIVE; PYRROLE DERIVATIVE;

EID: 84878840411     PISSN: 03445704     EISSN: 14320843     Source Type: Journal    
DOI: 10.1007/s00280-013-2094-0     Document Type: Article
Times cited : (22)

References (40)
  • 1
    • 0024499104 scopus 로고
    • A new folate antimetabolite, 5,10-dideaza-5,6,7,8-tetrahydrofolate is a potent inhibitor of de novo purine synthesis
    • Beardsley GP, Moroson BA, Taylor EC, Moran RG (1989) A new folate antimetabolite, 5,10-dideaza-5,6,7,8-tetrahydrofolate is a potent inhibitor of de novo purine synthesis. J Biol Chem 264:328-333 (Pubitemid 19027608)
    • (1989) Journal of Biological Chemistry , vol.264 , Issue.1 , pp. 328-333
    • Beardsley, G.P.1    Moroson, B.A.2    Taylor, E.C.3    Moran, R.G.4
  • 2
    • 33847364471 scopus 로고    scopus 로고
    • Pemetrexed: Biochemical and cellular pharmacology, mechanisms, and clinical applications
    • DOI 10.1158/1535-7163.MCT-06-0343
    • Chattopadhyay S, Moran RG, Goldman ID (2007) Pemetrexed: biochemical and cellular pharmacology, mechanisms, and clinical applications. Mol Cancer Ther 6:404-417 (Pubitemid 46332443)
    • (2007) Molecular Cancer Therapeutics , vol.6 , Issue.2 , pp. 404-417
    • Chattopadhyay, S.1    Moran, R.G.2    Goldman, I.D.3
  • 4
    • 1642362408 scopus 로고    scopus 로고
    • Asbestos and the pleura: A review
    • DOI 10.1378/chest.125.3.1103
    • Cugell DW, Kamp DW (2004) Asbestos and the pleura: a review. Chest 125:1103-1117 (Pubitemid 38367306)
    • (2004) Chest , vol.125 , Issue.3 , pp. 1103-1117
    • Cugell, D.W.1    Kamp, D.W.2
  • 5
    • 50249144557 scopus 로고    scopus 로고
    • Synthesis and discovery of high affinity folate receptor-specific glycinamide ribonucleotide formyltransferase inhibitors with antitumor activity
    • 18680275 10.1021/jm8003366 1:CAS:528:DC%2BD1cXptl2gtLo%3D
    • Deng Y, Wang Y, Cherian C, Hou Z, Buck SA, Matherly LH, Gangjee A (2008) Synthesis and discovery of high affinity folate receptor-specific glycinamide ribonucleotide formyltransferase inhibitors with antitumor activity. J Med Chem 51:5052-5063
    • (2008) J Med Chem , vol.51 , pp. 5052-5063
    • Deng, Y.1    Wang, Y.2    Cherian, C.3    Hou, Z.4    Buck, S.A.5    Matherly, L.H.6    Gangjee, A.7
  • 6
    • 65649129763 scopus 로고    scopus 로고
    • Synthesis and biological activity of a novel series of 6-substituted thieno[2,3-d]pyrimidine antifolate inhibitors of purine biosynthesis with selectivity for high affinity folate receptors over the reduced folate carrier and proton-coupled folate transporter for cellular entry
    • 19371039 10.1021/jm8011323 1:CAS:528:DC%2BD1MXks1OgtL4%3D
    • Deng Y, Zhou X, Kugel Desmoulin S, Wu J, Cherian C, Hou Z, Matherly LH, Gangjee A (2009) Synthesis and biological activity of a novel series of 6-substituted thieno[2,3-d]pyrimidine antifolate inhibitors of purine biosynthesis with selectivity for high affinity folate receptors over the reduced folate carrier and proton-coupled folate transporter for cellular entry. J Med Chem 52:2940-2951
    • (2009) J Med Chem , vol.52 , pp. 2940-2951
    • Deng, Y.1    Zhou, X.2    Kugel Desmoulin, S.3    Wu, J.4    Cherian, C.5    Hou, Z.6    Matherly, L.H.7    Gangjee, A.8
  • 7
    • 0021356277 scopus 로고
    • Synthesis and properties of 7-hydroxymethotrexate polyglutamyl derivatives in Ehrlich ascites tumor cells in vitro
    • Fabre G, Fabre I, Matherly LH, Cano JP, Goldman ID (1984) Synthesis and properties of 7-hydroxymethotrexate polyglutamyl derivatives in Ehrlich ascites tumor cells in vitro. J Biol Chem 259:5066-5072 (Pubitemid 14140609)
    • (1984) Journal of Biological Chemistry , vol.259 , Issue.8 , pp. 5066-5072
    • Fabre, G.1    Fabre, I.2    Matherly, L.H.3
  • 9
    • 79958044918 scopus 로고    scopus 로고
    • Chemotherapy for malignant pleural mesothelioma
    • 21468683 10.1007/s11864-011-0152-6
    • Garland LL (2011) Chemotherapy for malignant pleural mesothelioma. Curr Treat Options Oncol 12:181-188
    • (2011) Curr Treat Options Oncol , vol.12 , pp. 181-188
    • Garland, L.L.1
  • 11
    • 0021838288 scopus 로고
    • The cellular pharmacology of methotrexate
    • DOI 10.1016/0163-7258(85)90083-X
    • Goldman ID, Matherly LH (1985) The cellular pharmacology of methotrexate. Pharmacol Ther 28:77-102 (Pubitemid 15015465)
    • (1985) Pharmacology and Therapeutics , vol.28 , Issue.1 , pp. 77-102
    • Goldman, I.D.1    Matherly, L.H.2
  • 12
    • 4944251014 scopus 로고    scopus 로고
    • FDA drug approval summaries: Pemetrexed (Alimta®)
    • DOI 10.1634/theoncologist.9-5-482
    • Hazarika M, White RM, Johnson JR, Pazdur R (2004) FDA drug approval summaries: pemetrexed (Alimta). Oncologist 9:482-488 (Pubitemid 39332311)
    • (2004) Oncologist , vol.9 , Issue.5 , pp. 482-488
    • Hazarika, M.1    White, R.M.2    Johnson, J.R.3    Pazdur, R.4
  • 13
    • 0030614893 scopus 로고    scopus 로고
    • 2 gradients in solid tumors in vivo: High-resolution measurements reveal a lack of correlation
    • DOI 10.1038/nm0297-177
    • Helmlinger G, Yuan F, Dellian M, Jain RK (1997) Interstitial pH and pO2 gradients in solid tumors in vivo: high-resolution measurements reveal a lack of correlation. Nat Med 3:177-182 (Pubitemid 27064702)
    • (1997) Nature Medicine , vol.3 , Issue.2 , pp. 177-182
    • Helmlinger, G.1    Yuan, F.2    Dellian, M.3    Jain, R.K.4
  • 14
    • 0020618105 scopus 로고
    • Use of non-physiological buffer systems in the analysis of methotrexate transport in L1210 cells
    • Henderson GB, Zevely EM (1983) Use of non-physiological buffer systems in the analysis of methotrexate transport in L1210 cells. Biochem Int 6:507-515 (Pubitemid 13107303)
    • (1983) Biochemistry International , vol.6 , Issue.4 , pp. 507-515
    • Henderson, G.B.1    Zevely, E.M.2
  • 17
    • 84870710332 scopus 로고    scopus 로고
    • The human proton-coupled folate transporter: Biology and therapeutic applications to cancer
    • 10.4161/cbt.22020
    • Kugel Desmoulin S, Hou Z, Gangjee A, Matherly LH (2012) The human proton-coupled folate transporter: biology and therapeutic applications to cancer. Cancer Biol Ther 13:1355-1373
    • (2012) Cancer Biol Ther , vol.13 , pp. 1355-1373
    • Kugel Desmoulin, S.1    Hou, Z.2    Gangjee, A.3    Matherly, L.H.4
  • 18
    • 81555195479 scopus 로고    scopus 로고
    • Therapeutic targeting of a novel 6-substituted pyrrolo [2,3-d]pyrimidine thienoyl antifolate to human solid tumors based on selective uptake by the proton-coupled folate transporter
    • 21940787 10.1124/mol.111.073833
    • Kugel Desmoulin S, Wang L, Hales E, Polin L, White K, Kushner J, Stout M, Hou Z, Cherian C, Gangjee A, Matherly LH (2011) Therapeutic targeting of a novel 6-substituted pyrrolo [2,3-d]pyrimidine thienoyl antifolate to human solid tumors based on selective uptake by the proton-coupled folate transporter. Mol Pharmacol 80:1096-1107
    • (2011) Mol Pharmacol , vol.80 , pp. 1096-1107
    • Kugel Desmoulin, S.1    Wang, L.2    Hales, E.3    Polin, L.4    White, K.5    Kushner, J.6    Stout, M.7    Hou, Z.8    Cherian, C.9    Gangjee, A.10    Matherly, L.H.11
  • 19
    • 84866844783 scopus 로고    scopus 로고
    • Functional loss of the reduced folate carrier enhances the antitumor activities of novel antifolates with selective uptake by the proton-coupled folate transporter
    • 10.1124/mol.112.079004
    • Kugel Desmoulin S, Wang L, Polin L, White K, Kushner J, Stout M, Hou Z, Cherian C, Gangjee A, Matherly LH (2012) Functional loss of the reduced folate carrier enhances the antitumor activities of novel antifolates with selective uptake by the proton-coupled folate transporter. Mol Pharmacol 82:591-600
    • (2012) Mol Pharmacol , vol.82 , pp. 591-600
    • Kugel Desmoulin, S.1    Wang, L.2    Polin, L.3    White, K.4    Kushner, J.5    Stout, M.6    Hou, Z.7    Cherian, C.8    Gangjee, A.9    Matherly, L.H.10
  • 20
    • 77957224999 scopus 로고    scopus 로고
    • Targeting the proton-coupled folate transporter for selective delivery of 6-substituted pyrrolo[2,3-d]pyrimidine antifolate inhibitors of de novo purine biosynthesis in the chemotherapy of solid tumors
    • 10.1124/mol.110.065896
    • Kugel Desmoulin S, Wang Y, Wu J, Stout M, Hou Z, Fulterer A, Chang MH, Romero MF, Cherian C, Gangjee A, Matherly LH (2010) Targeting the proton-coupled folate transporter for selective delivery of 6-substituted pyrrolo[2,3-d] pyrimidine antifolate inhibitors of de novo purine biosynthesis in the chemotherapy of solid tumors. Mol Pharmacol 78:577-587
    • (2010) Mol Pharmacol , vol.78 , pp. 577-587
    • Kugel Desmoulin, S.1    Wang, Y.2    Wu, J.3    Stout, M.4    Hou, Z.5    Fulterer, A.6    Chang, M.H.7    Romero, M.F.8    Cherian, C.9    Gangjee, A.10    Matherly, L.H.11
  • 21
    • 71849104860 scopus 로고
    • Protein measurement with the Folin phenol reagent
    • 14907713 1:CAS:528:DyaG38XhsVyrsw%3D%3D
    • Lowry OH, Rosebrough NJ, Farr AL, Randall RJ (1951) Protein measurement with the Folin phenol reagent. J Biol Chem 193:265-275
    • (1951) J Biol Chem , vol.193 , pp. 265-275
    • Lowry, O.H.1    Rosebrough, N.J.2    Farr, A.L.3    Randall, R.J.4
  • 22
    • 33947424386 scopus 로고    scopus 로고
    • Human reduced folate carrier: Translation of basic biology to cancer etiology and therapy
    • DOI 10.1007/s10555-007-9046-2, Special Issue on Transporters in Cancer
    • Matherly LH, Hou Z, Deng Y (2007) Human reduced folate carrier: translation of basic biology to cancer etiology and therapy. Cancer Metastasis Rev 26:111-128 (Pubitemid 46452186)
    • (2007) Cancer and Metastasis Reviews , vol.26 , Issue.1 , pp. 111-128
    • Matherly, L.H.1    Hou, Z.2    Deng, Y.3
  • 23
    • 76349104827 scopus 로고    scopus 로고
    • The role of folate receptor alpha (FRalpha) in the response of malignant pleural mesothelioma to pemetrexed-containing chemotherapy
    • 20051956 10.1038/sj.bjc.6605501 1:CAS:528:DC%2BC3cXhsVSrs7g%3D
    • Nutt JE, Razak AR, O'Toole K, Black F, Quinn AE, Calvert AH, Plummer ER, Lunec J (2010) The role of folate receptor alpha (FRalpha) in the response of malignant pleural mesothelioma to pemetrexed-containing chemotherapy. Br J Cancer 102:553-560
    • (2010) Br J Cancer , vol.102 , pp. 553-560
    • Nutt, J.E.1    Razak, A.R.2    O'Toole, K.3    Black, F.4    Quinn, A.E.5    Calvert, A.H.6    Plummer, E.R.7    Lunec, J.8
  • 28
    • 33751244559 scopus 로고    scopus 로고
    • Identification of an Intestinal Folate Transporter and the Molecular Basis for Hereditary Folate Malabsorption
    • DOI 10.1016/j.cell.2006.09.041, PII S009286740601347X
    • Qiu A, Jansen M, Sakaris A, Min SH, Chattopadhyay S, Tsai E, Sandoval C, Zhao R, Akabas MH, Goldman ID (2006) Identification of an intestinal folate transporter and the molecular basis for hereditary folate malabsorption. Cell 127:917-928 (Pubitemid 44792250)
    • (2006) Cell , vol.127 , Issue.5 , pp. 917-928
    • Qiu, A.1    Jansen, M.2    Sakaris, A.3    Min, S.H.4    Chattopadhyay, S.5    Tsai, E.6    Sandoval, C.7    Zhao, R.8    Akabas, M.H.9    Goldman, I.D.10
  • 32
    • 0026597164 scopus 로고
    • Long-term folate deficiency alters folate content and distribution differentially in rat tissues
    • 1552373 1:CAS:528:DyaK38XitFensrw%3D
    • Varela-Moreiras G, Selhub J (1992) Long-term folate deficiency alters folate content and distribution differentially in rat tissues. J Nutr 122:986-991
    • (1992) J Nutr , vol.122 , pp. 986-991
    • Varela-Moreiras, G.1    Selhub, J.2
  • 33
    • 84863143908 scopus 로고    scopus 로고
    • Synthesis and biological activity of 6-substituted pyrrolo[2,3-d] pyrimidine thienoyl regioisomers as inhibitors of de novo purine biosynthesis with selectivity for cellular uptake by high affinity folate receptors and the proton-coupled folate transporter over the reduced folate carrier
    • 22243528 10.1021/jm201688n 1:CAS:528:DC%2BC38XntFGquw%3D%3D
    • Wang L, Cherian C, Kugel Desmoulin S, Mitchell-Ryan S, Hou Z, Matherly LH, Gangjee A (2012) Synthesis and biological activity of 6-substituted pyrrolo[2,3-d]pyrimidine thienoyl regioisomers as inhibitors of de novo purine biosynthesis with selectivity for cellular uptake by high affinity folate receptors and the proton-coupled folate transporter over the reduced folate carrier. J Med Chem 55:1758-1770
    • (2012) J Med Chem , vol.55 , pp. 1758-1770
    • Wang, L.1    Cherian, C.2    Kugel Desmoulin, S.3    Mitchell-Ryan, S.4    Hou, Z.5    Matherly, L.H.6    Gangjee, A.7
  • 34
    • 77249090272 scopus 로고    scopus 로고
    • Synthesis and antitumor activity of a novel series of 6-substituted pyrrolo[2,3-d]pyrimidine thienoyl antifolate inhibitors of purine biosynthesis with selectivity for high affinity folate receptors and the proton-coupled folate transporter over the reduced folate carrier for cellular entry
    • 20085328 10.1021/jm9015729 1:CAS:528:DC%2BC3cXnvFWntQ%3D%3D
    • Wang L, Cherian C, Kugel Desmoulin S, Polin L, Deng Y, Wu J, Hou Z, White K, Kushner J, Matherly LH, Gangjee A (2010) Synthesis and antitumor activity of a novel series of 6-substituted pyrrolo[2,3-d]pyrimidine thienoyl antifolate inhibitors of purine biosynthesis with selectivity for high affinity folate receptors and the proton-coupled folate transporter over the reduced folate carrier for cellular entry. J Med Chem 53:1306-1318
    • (2010) J Med Chem , vol.53 , pp. 1306-1318
    • Wang, L.1    Cherian, C.2    Kugel Desmoulin, S.3    Polin, L.4    Deng, Y.5    Wu, J.6    Hou, Z.7    White, K.8    Kushner, J.9    Matherly, L.H.10    Gangjee, A.11
  • 35
    • 80054932788 scopus 로고    scopus 로고
    • Synthesis, biological, and antitumor activity of a highly potent 6-substituted pyrrolo[2,3-d]pyrimidine thienoyl antifolate inhibitor with proton-coupled folate transporter and folate receptor selectivity over the reduced folate carrier that inhibits beta-glycinamide ribonucleotide formyltransferase
    • 21879757 10.1021/jm200739e 1:CAS:528:DC%2BC3MXht1Wks7jE
    • Wang L, Kugel Desmoulin S, Cherian C, Polin L, White K, Kushner J, Fulterer A, Chang MH, Mitchell-Ryan S, Stout M, Romero MF, Hou Z, Matherly LH, Gangjee A (2011) Synthesis, biological, and antitumor activity of a highly potent 6-substituted pyrrolo[2,3-d]pyrimidine thienoyl antifolate inhibitor with proton-coupled folate transporter and folate receptor selectivity over the reduced folate carrier that inhibits beta-glycinamide ribonucleotide formyltransferase. J Med Chem 54:7150-7164
    • (2011) J Med Chem , vol.54 , pp. 7150-7164
    • Wang, L.1    Kugel Desmoulin, S.2    Cherian, C.3    Polin, L.4    White, K.5    Kushner, J.6    Fulterer, A.7    Chang, M.H.8    Mitchell-Ryan, S.9    Stout, M.10    Romero, M.F.11    Hou, Z.12    Matherly, L.H.13    Gangjee, A.14
  • 36
    • 0021732164 scopus 로고
    • The relevance of tumour pH to the treatment of malignant disease
    • Wike-Hooley JL, Haveman J, Reinhold HS (1984) The relevance of tumour pH to the treatment of malignant disease. Radiother Oncol 2:343-366 (Pubitemid 15166545)
    • (1984) Radiotherapy and Oncology , vol.2 , Issue.4 , pp. 343-366
    • Wike-Hooley, J.L.1    Haveman, J.2    Reinhold, H.S.3
  • 37
    • 0842304934 scopus 로고    scopus 로고
    • A Prominent Low-pH Methotrexate Transport Activity in Human Solid Tumors: Contribution to the Preservation of Methotrexate Pharmacologic Activity in HeLa Cells Lacking the Reduced Folate Carrier
    • DOI 10.1158/1078-0432.CCR-1066-03
    • Zhao R, Gao F, Hanscom M, Goldman ID (2004) A prominent low-pH methotrexate transport activity in human solid tumors: contribution to the preservation of methotrexate pharmacologic activity in HeLa cells lacking the reduced folate carrier. Clin Cancer Res 10:718-727 (Pubitemid 38180440)
    • (2004) Clinical Cancer Research , vol.10 , Issue.2 , pp. 718-727
    • Zhao, R.1    Gao, F.2    Hanscom, M.3    Goldman, I.D.4
  • 38
    • 33947361166 scopus 로고    scopus 로고
    • The molecular identity and characterization of a Proton-Coupled Folate Transporter - PCFT; biological ramifications and impact on the activity of pemetrexed-12 06 06
    • DOI 10.1007/s10555-007-9047-1, Special Issue on Transporters in Cancer
    • Zhao R, Goldman ID (2007) The molecular identity and characterization of a proton-coupled folate transporter - PCFT; biological ramifications and impact on the activity of pemetrexed. Cancer Metastasis Rev 26:129-139 (Pubitemid 46452187)
    • (2007) Cancer and Metastasis Reviews , vol.26 , Issue.1 , pp. 129-139
    • Zhao, R.1    Goldman, I.D.2
  • 39
    • 59849093173 scopus 로고    scopus 로고
    • Membrane transporters and folate homeostasis: Intestinal absorption and transport into systemic compartments and tissues
    • 19173758 10.1017/S1462399409000969
    • Zhao R, Matherly LH, Goldman ID (2009) Membrane transporters and folate homeostasis: intestinal absorption and transport into systemic compartments and tissues. Expert Rev Mol Med 11:e4
    • (2009) Expert Rev Mol Med , vol.11 , pp. 4
    • Zhao, R.1    Matherly, L.H.2    Goldman, I.D.3
  • 40
    • 50549085728 scopus 로고    scopus 로고
    • The proton-coupled folate transporter: Impact on pemetrexed transport and on antifolates activities compared with the reduced folate carrier
    • 18524888 10.1124/mol.108.045443 1:CAS:528:DC%2BD1cXhtVClt7bI
    • Zhao R, Qiu A, Tsai E, Jansen M, Akabas MH, Goldman ID (2008) The proton-coupled folate transporter: impact on pemetrexed transport and on antifolates activities compared with the reduced folate carrier. Mol Pharmacol 74:854-862
    • (2008) Mol Pharmacol , vol.74 , pp. 854-862
    • Zhao, R.1    Qiu, A.2    Tsai, E.3    Jansen, M.4    Akabas, M.H.5    Goldman, I.D.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.