메뉴 건너뛰기




Volumn 54, Issue 6, 2011, Pages 1847-1859

Nucleoside transport inhibitors: Structure-activity relationships for pyrimido[5,4-d ]pyrimidine derivatives that potentiate pemetrexed cytotoxicity in the presence of α-1-acid glycoprotein

Author keywords

[No Author keywords available]

Indexed keywords

1 [[4 [(3,4 DIMETHOXYBENZYL)AMINO] 6 [(2 HYDROXYPROPYL)AMINO] 8 [[3 METHOXY 4 (3 MORPHOLINOETHOXY)BENZYL]AMINO]PYRIMIDO[5,4 D]PYRIMIDINE 2 YL]AMINO]PROPAN 2 YL PHENYLCARBAMATE; 1 [[4 [(3,4 DIMETHOXYBENZYL)AMINO] 8 [(4 HYDROXY 3 METHOXYBENZYL)AMINO] 6 [(2 HYDROXYPROPYL)AMINO]PYRIMIDO[5,4 D]PYRIMIDINE 2 YL]AMINO]PROPAN 2 YL PHENYLCARBAMATE; 1 [[4,8 BIS[(3,4 DIMETHOXYBENZYL)AMINO] 6 [(2 HYDROXYPROPYL)AMINO]PYRIMIDO[5,4 D ]PYRIMIDINE 2 YL]AMINO]PROPAN 2 YL 2 [(TERT BUTOXYCARBONYL)AMINO] 3 METHYLBUTANOATE; 1 [[4,8 BIS[(3,4 DIMETHOXYBENZYL)AMINO] 6 [(2 HYDROXYPROPYL)AMINO]PYRIMIDO[5,4 D ]PYRIMIDINE 2 YL]AMINO]PROPAN 2 YL 2 AMINO 3 METHYLBUTANOATE; 1 [[4,8 BIS[(3,4 DIMETHOXYBENZYL)AMINO] 6 [(2 HYDROXYPROPYL)AMINO]PYRIMIDO[5,4 D]PYRIMIDINE 2 YL]AMINO]PROPAN 2 YL PHENYLCARBAMATE; 1 [[4,8 BIS[(3,4 DIMETHOXYBENZYL)AMINO] 6 [[2 (PHOSPHONOOXY)PROPYL]AMINO]PYRIMIDO[5,4 D]PYRIMIDINE 2 YL]AMINO]PROPAN 2 YL PHENYLCARBAMATE; 1 [[6 [(2,3 DIHYDROXYPROPYL)AMINO] 4,8 BIS[(3,4 DIMETHOXYBENZYL)AMINO]PYRIMIDO[5,4 D]PYRIMIDINE 2 YL]AMINO]PROPAN 2 YL PHENYLCARBAMATE; 1 [[6 [[2 [(2 AMINO 3 METHYLBUTANOYL)OXY]PROPYL]AMINO] 4,8 BIS[(3,4 DIMETHOXYBENZYL)AMINO]PYRIMIDO[5,4 D]PYRIMIDINE 2 YL]AMINO]PROPAN 2YL 2 AMINO 3 METHYLBUTANOATE; 1 [[6 [[2 [(DI TERT BUTOXYPHOSPHORYL)OXY]PROPYL]AMINO] 4,8 BIS[(3,4 DIMETHOXYBENZYL)AMINO]PYRIMIDO[5,4 D]PYRIMIDINE 2 YL]AMINO]PROPAN 2 YL PHENYLCARBAMATE; 4 [[1 [[4,8 BIS[(3,4 DIMETHOXYBENZYL)AMINO] 6 [(2 HYDROXYPROPYL)AMINO]PYRIMIDO[5,4 D]PYRIMIDINE 2 YL]AMINO]PROPAN 2 YL]OXY] 4 OXOBUTANOIC ACID; 4,4' [[[[4,8 BIS[(3,4 DIMETHOXYBENZYL)AMINO]PYRIMIDO[5,4 D]PYRIMIDINE 2,6 DIYL]BIS(AZANEDIYL)]BIS(PROPANE 2,1 DIYL)]BIS(OXY)]BIS(4 OXOBUTANOIC ACID); 4,8 BIS[(3,4 DIMETHOXYBENZYL)AMINO] 2,6 BIS[(2 HYDROXYPROPYL)AMINO]PYRIMIDO[5,4 D]PYRIMIDINE; [[4,8 BIS[(3,4 DIMETHOXYBENZYL)AMINO]PYRIMIDO[5,4 D]PYRIMIDINE 2,6 DIYL]BIS(AZANEDIYL)]BIS(PROPANE 2,1 DIYL)BIS(PHENYLCARBAMATE); [[4,8 BIS[(3,4 DIMETHOXYBENZYL)AMINO]PYRIMIDO[5,4 D]PYRIMIDINE 2,6 DIYL]BIS(AZANEDIYL)]BIS(PROPANE 2,1 DIYL)BIS[2 [(TERT BUTOXYCARBONYL)AMINO] 3 METHYLBUTANOATE]; DIPYRIDAMOLE; NU 3108; OROSOMUCOID; PEMETREXED; PYRIMIDO[5,4 D]PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 79952785674     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm101493z     Document Type: Article
Times cited : (17)

References (40)
  • 1
    • 0034995844 scopus 로고    scopus 로고
    • The ENT family of eukaryote nucleoside and nucleobase transporters: Recent advances in the investigation of structure/function relationships and the identification of novel isoforms
    • Hyde, R. J.; Cass, C. E.; Young, D. A.; Baldwin, A. E. The ENT family of eukaryotic nucleoside and nucleobase transporters; recent advances in the investigation of structure-function relationships and the identification of novel isoforms Mol. Membr. Biol. 2001, 18, 53-63 (Pubitemid 32521597)
    • (2001) Molecular Membrane Biology , vol.18 , Issue.1 , pp. 53-63
    • Hyde, R.J.1    Cass, C.E.2    Young, J.D.3    Baldwin, S.A.4
  • 2
    • 33745889935 scopus 로고    scopus 로고
    • Nucleoside transporters: from scavengers to novel therapeutic targets
    • DOI 10.1016/j.tips.2006.06.004, PII S0165614706001520
    • King, A. E.; Ackley, M. A.; Cass, C. E.; Young, J. D.; Baldwin, S. A. Nucleoside transporters: from scavengers to novel therapeutic targets Trends Pharmacol. Sci. 2006, 27, 416-425 (Pubitemid 44051567)
    • (2006) Trends in Pharmacological Sciences , vol.27 , Issue.8 , pp. 416-425
    • King, A.E.1    Ackley, M.A.2    Cass, C.E.3    Young, J.D.4    Baldwin, S.A.5
  • 3
    • 40349098206 scopus 로고    scopus 로고
    • Physiology of nucleoside transporters: Back to the future
    • Rose, J. B.; Coe, I. R. Physiology of nucleoside transporters: back to the future Physioloy 2008, 23, 41-48
    • (2008) Physiology , vol.23 , pp. 41-48
    • Rose, J.B.1    Coe, I.R.2
  • 4
    • 0030907430 scopus 로고    scopus 로고
    • Nucleoside transport inhibitors: Structure-activity relationships and potential therapeutic applications
    • Buolamwini, J. K. Nucleoside transport inhibitors: structure-activity relationships and potential therapeutic applications Curr. Med. Chem. 1997, 4, 35-66 (Pubitemid 27154393)
    • (1997) Current Medicinal Chemistry , vol.4 , Issue.1 , pp. 35-66
    • Buolamwini, J.K.1
  • 5
    • 31644436321 scopus 로고    scopus 로고
    • From methotrexate to pemetrexed and beyond. A review of the pharmacodynamic and clinical properties of antifolates
    • DOI 10.1007/s10637-005-4541-1
    • Walling, J. From methotrexate to pemetrexid and beyond. A review of the pharmacodynamics and clinical properties of antifolates Invest. New Drugs 2006, 24, 37-77 (Pubitemid 43168187)
    • (2006) Investigational New Drugs , vol.24 , Issue.1 , pp. 37-77
    • Walling, J.1
  • 6
    • 0020955571 scopus 로고
    • Biochemical strategy of cancer cells and the design of chemotherapy
    • Weber, G. Biochemical strategy of cancer cells and the design of chemotherapy Cancer Res. 1983, 43, 3466-3492
    • (1983) Cancer Res. , vol.43 , pp. 3466-3492
    • Weber, G.1
  • 7
    • 0025908157 scopus 로고
    • Decreasing sensitivity to cytotoxic agents agents parallels increasing tumorigenicity in human fibroblasts
    • Kinsella, A.; Harran, M. S. Decreasing sensitivity to cytotoxic agents agents parallels increasing tumorigenicity in human fibroblasts Cancer Res. 1991, 51, 1855-1859
    • (1991) Cancer Res. , vol.51 , pp. 1855-1859
    • Kinsella, A.1    Harran, M.S.2
  • 9
    • 0031730802 scopus 로고    scopus 로고
    • Role of folic acid in modulating the toxicity and efficacy of the multitargeted antifolate LY23514
    • Worzalla, J. F.; Shih, C.; Schultz, R. M. Role of folic acid in modulating the toxicity and efficacy of the multitargeted antifolate LY23514 Anticancer Res. 1998, 18, 3235-3240
    • (1998) Anticancer Res. , vol.18 , pp. 3235-3240
    • Worzalla, J.F.1    Shih, C.2    Schultz, R.M.3
  • 10
    • 0032898580 scopus 로고
    • Role of thymidylate synthase in the antitumor activity of the multitargeted antifolate LY23514
    • Schultz, R. M.; Patel, V. F.; Worzalla, J. F.; Shih, C. Role of thymidylate synthase in the antitumor activity of the multitargeted antifolate LY23514 Anticancer Res. 1989, 19, 437-444
    • (1989) Anticancer Res. , vol.19 , pp. 437-444
    • Schultz, R.M.1    Patel, V.F.2    Worzalla, J.F.3    Shih, C.4
  • 12
    • 29744448378 scopus 로고    scopus 로고
    • Dipyridamole, an underestimated vascular protective drug
    • DOI 10.1007/s10557-005-4659-6
    • Schaper, W. Dipyridamole, an underestimated vascular protective drug Cardiovasc. Drugs Ther. 2005, 19, 357-363 (Pubitemid 43029821)
    • (2005) Cardiovascular Drugs and Therapy , vol.19 , Issue.5 , pp. 357-363
    • Schaper, W.1
  • 13
    • 0023132212 scopus 로고
    • Augmentation of methotrexate cytotoxicity in human colonic cancer cells achieved through inhibition of thymidine salvage by dipyridamole
    • DOI 10.1016/0006-2952(87)90168-7
    • Van Mouwerik, T. J.; Pangallo, C. A.; Willson, J. K. V.; Fischer, P. H. Augmentation of methotrexate cyttoxicity in human colon cancer cells achieved through inhibition of thymidine salvage by dipyridamole Biochem. Pharmacol. 1987, 36, 809-814 (Pubitemid 17038023)
    • (1987) Biochemical Pharmacology , vol.36 , Issue.6 , pp. 809-814
    • Van Mouwerik, T.J.1    Pangallo, C.A.2    Willson, J.K.V.3    Fischer, P.H.4
  • 14
    • 0026267822 scopus 로고
    • Modulation of the activity of cancer chemotherapeutic agents by dipyridamole
    • Muggia, F. M., Ed.; Kluwer Academic Publishers: Boston
    • Goel, R; Howell, S. B. Modulation of the activity of cancer chemotherapeutic agents by dipyridamole. In New Drugs Concepts and Results in Cancer Chemotherapy; Muggia, F. M., Ed.; Kluwer Academic Publishers: Boston, 1992; pp 19 - 44.
    • (1992) New Drugs Concepts and Results in Cancer Chemotherapy , pp. 19-44
    • Goel, R.1    Howell, S.B.2    Muggia, F.M.3
  • 15
    • 0033965553 scopus 로고    scopus 로고
    • Dipyridamole potentiates the in vitro activity of MTA (LY231514) by inhibition of thymidine transport
    • Smith, P. J.; Marshman, E.; Newell, D. R.; Curtin, N. J. Dipyridamole potentiates the in vitro activity of MTA (LY231514) by inhibition of thymidine transport Br. J. Cancer 2000, 82, 924-930 (Pubitemid 30085247)
    • (2000) British Journal of Cancer , vol.82 , Issue.4 , pp. 924-930
    • Smith, P.G.1    Marshman, E.2    Newell, D.R.3    Curtin, N.J.4
  • 16
    • 0030657927 scopus 로고    scopus 로고
    • Selective potentiation of lometrexol growth inhibition by dipyridamole through cell-specific inhibition of hypoxanthine salvage
    • Turner, R. N.; Aherne, G. W.; Curtin, N. J. Selective potentiation of lomotrexol growth inhibition by dipyridamole through cell-specific inhibition of hypoxanthine salvage Br. J. Cancer 1997, 76, 1300-1307 (Pubitemid 27474971)
    • (1997) British Journal of Cancer , vol.76 , Issue.10 , pp. 1300-1307
    • Turner, R.N.1    Aherne, G.W.2    Curtin, N.J.3
  • 17
    • 0031724435 scopus 로고    scopus 로고
    • Dipyridamole potentiates antipurine antifolate activity in the presence of hypoxanthine in tumor cells but not in normal tissues in vitro
    • Marshman, E.; Newell, D. R.; Calvert, A. H.; Dickinson, A. M.; Patel, H. R. H.; Campbell, F. C.; Curtin, N. J. Dipyridamole potentiates antipurine antifolate activity in the presence of hypoxanthine in tumor cells but not in normal tissues in vitro Clin. Cancer Res. 1998, 11, 2895-2902 (Pubitemid 28523521)
    • (1998) Clinical Cancer Research , vol.4 , Issue.11 , pp. 2895-2902
    • Marshman, E.1    Newell, D.R.2    Calvert, A.H.3    Dickinson, A.M.4    Patel, H.R.H.5    Campbell, F.C.6    Curtin, N.J.7
  • 18
    • 0024832231 scopus 로고
    • Potentiation of some anticancer agents by dipyridamole against drug-sensitive and drug-resistant cancer cell lines
    • Asoh, K.-I.; Yoshio, S.; Sato, S.-I.; Nogae, I.; Kohno, K.; Kuwano, M. Potentiation of some anticancer agents by dipyridamole against drug-sensitive and drug-resistant cancer cell lines Jpn. J. Cancer Res. 1990, 80, 475-481 (Pubitemid 20038139)
    • (1989) Japanese Journal of Cancer Research , vol.80 , Issue.5 , pp. 475-481
    • Asoh, K.-I.1    Saburi, Y.2    Sato, S.-I.3    Nogae, I.4    Kohno, K.5    Kuwano, M.6
  • 19
    • 0025832444 scopus 로고
    • Mechanism of cell death following thymidylate synthase inhibition: 2-deoxyuridine-5-triphosphate accumulation, DNA damage and growth inhibition following exposure to CB3717 and dipyridamole
    • Curtin, N. J.; Harris, A. L.; Aherne, G. W. Mechanism of cell death following thymidylate synthase inhibition: 2-deoxyuridine-5-triphosphate accumulation, DNA damage and growth inhibition following exposure to CB3717 and dipyridamole Cancer Res. 1991, 51, 2346-2352
    • (1991) Cancer Res. , vol.51 , pp. 2346-2352
    • Curtin, N.J.1    Harris, A.L.2    Aherne, G.W.3
  • 22
    • 0018233766 scopus 로고
    • Evaluation of the relationships of prealbumin components in sera of patients with cancer
    • Hollinshead, A. C.; Chuang, C.-Y. Evaluation of the relationships of prealbumin components in sera of patients with cancer Natl. Cancer Inst. Monogr. 1978, 49, 187-192 (Pubitemid 9141831)
    • (1978) National Cancer Institute Monograph , pp. 187-192
    • Hollinshead, A.C.1    Chuang, C.Y.2
  • 23
    • 0024454962 scopus 로고
    • 1acid glycoprotein. Reduced potentiation of quinazoline antifolate (CB3717) cytotoxicity by dipyridamole
    • DOI 10.1016/0006-2952(89)90626-6
    • 1-acid glycoprotein: reduced potentiation of quinazoline antifolate (CB3717) cytotoxicity by dipyridamole Biochem. Pharmacol. 1989, 38, 3281-3288 (Pubitemid 19254119)
    • (1989) Biochemical Pharmacology , vol.38 , Issue.19 , pp. 3281-3288
    • Curtin, N.J.1    Newell, D.R.2    Harris, A.L.3
  • 25
    • 0023153495 scopus 로고
    • Phase I trial of combination therapy of cancer with N-phosphonacetyl-L- aspartic acid and dipyridamole
    • DOI 10.1007/BF00296262
    • Marman, M.; Chan, T. C. K.; Cleary, S.; Howell, S. B. Phase I trial of combination therapy of cancer with. N-phosphonacetyl- l -aspartate and dipyridamole Cancer Chemother. Pharmacol. 1987, 19, 80-83 (Pubitemid 17017046)
    • (1987) Cancer Chemotherapy and Pharmacology , vol.19 , Issue.1 , pp. 80-83
    • Markman, M.1    Chan, T.C.K.2    Cleary, S.3    Howell, S.B.4
  • 29
    • 4243706184 scopus 로고
    • British Patent 807826
    • Thomae, K. G. (1959, British Patent 807826 (Chem. Abstr. 1959, 53, 12317e)
    • (1959) Chem. Abstr. , vol.53
    • Thomae, K.G.1
  • 30
    • 79952798247 scopus 로고
    • (, German Patent 1151806 (Chem. Abstr. 1964, 60).
    • Thomae, K. G. (1963, German Patent 1151806 (Chem. Abstr. 1964, 60, 2974a).
    • (1963)
    • Thomae, K.G.1
  • 31
    • 0013923502 scopus 로고
    • Some congeners and analogs of dipyridamole
    • Kaminsky, D.; Lutz, W. B.; Lazarus, S. Some congeners and analogs of dipyridamole J. Med. Chem. 1966, 9, 610-612
    • (1966) J. Med. Chem. , vol.9 , pp. 610-612
    • Kaminsky, D.1    Lutz, W.B.2    Lazarus, S.3
  • 32
    • 34548057625 scopus 로고    scopus 로고
    • Synthesis, flow cytometric evaluation, and identification of highly potent dipyridamole analogues as equilibrative nucleoside transporter 1 inhibitors
    • DOI 10.1021/jm070311l
    • Lin, W.; Buolamwini, J. K. Synthesis, flow cytometric evaluation, and identification of highly potent dipyridamole analogues as equilibrative nucleoside transporter 1 inhibitors J. Med. Chem. 2007, 50, 3906-3920 (Pubitemid 47292054)
    • (2007) Journal of Medicinal Chemistry , vol.50 , Issue.16 , pp. 3906-3920
    • Lin, W.1    Buolamwini, J.K.2
  • 35
    • 0034783030 scopus 로고    scopus 로고
    • In vitro and in vivo properties of novel nucleoside transport inhibitors with improved pharmacological properties that potentiate antifolate activity
    • Smith, P. G.; Thomas, H. D.; Barlow, H. C.; Griffin, R. J.; Golding, B. T.; Calvert, A. H.; Newell, D. R.; Curtin, N. J. In vitro and in vivo properties of novel nucleoside transport inhibitors with improved pharmacological properties that potentiate antifolate activity Clin. Cancer. Res. 2001, 7, 2105-2113 (Pubitemid 32994851)
    • (2001) Clinical Cancer Research , vol.7 , Issue.7 , pp. 2105-2113
    • Smith, P.G.1    Thomas, H.D.2    Barlow, H.C.3    Griffin, R.J.4    Golding, B.T.5    Calvert, A.H.6    Newell, D.R.7    Curtin, N.J.8
  • 40
    • 0035955602 scopus 로고    scopus 로고
    • Methylation-dependent silencing of the reduced folate carrier gene in inherently methotrexate-resistant human breast cancer cells
    • Worm, J.; Kirkin, A. F.; Dzhandzhugazyan, K. N.; Guldberg, P. Methylation-dependent silencing of the reduced folate carrier gene in inherently methotrexate-resistant human breast cancer cells J. Biol. Chem. 2001, 276, 39990-40000
    • (2001) J. Biol. Chem. , vol.276 , pp. 39990-40000
    • Worm, J.1    Kirkin, A.F.2    Dzhandzhugazyan, K.N.3    Guldberg, P.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.