메뉴 건너뛰기




Volumn 3, Issue 4, 2012, Pages 268-272

Ribonuclease-activated cancer prodrug

Author keywords

4 hydroxytamoxifen; human pancreatic ribonuclease; pharmacokinetics; plasma; tamoxifen; timed release

Indexed keywords

AFIMOXIFENE; PANCREATIC RIBONUCLEASE; PRODRUG; UNCLASSIFIED DRUG; URIDINE 3' (4 HYDROXYTAMOXIFEN PHOSPHATE);

EID: 84859773889     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml2002554     Document Type: Article
Times cited : (17)

References (61)
  • 5
    • 0025047522 scopus 로고
    • New methods of drug delivery
    • Langer, R. New methods of drug delivery Science 1990, 249, 1527-1533
    • (1990) Science , vol.249 , pp. 1527-1533
    • Langer, R.1
  • 8
    • 77952950532 scopus 로고    scopus 로고
    • The eight human "canonical" ribonucleases: Molecular diversity, catalytic properties, and special biological actions of the enzyme proteins
    • Sorrentino, S. The eight human "canonical" ribonucleases: Molecular diversity, catalytic properties, and special biological actions of the enzyme proteins FEBS Lett. 2010, 584, 2194-2200
    • (2010) FEBS Lett. , vol.584 , pp. 2194-2200
    • Sorrentino, S.1
  • 10
    • 0021247192 scopus 로고
    • Immunological assay of pancreatic ribonuclease in serum as an indicator of pancreatic cancer
    • The ribonucleolytic activity in serum is attributable to RNase 1. Its concentration there is 156 units/mL with 1 unit of activity arising from 2.6 ng of enzyme. Weickmann, J. L.; Olson, E. M.; Glitz, D. G. Immunological assay of pancreatic ribonuclease in serum as an indicator of pancreatic cancer Cancer Res. 1984, 44, 1682-1687 (Pubitemid 14125864)
    • (1984) Cancer Research , vol.44 , Issue.4 , pp. 1682-1687
    • Weickmann, J.L.1    Olson, E.M.2    Glitz, D.G.3
  • 12
    • 0001005285 scopus 로고    scopus 로고
    • Ribonuclease A
    • Raines, R. T. Ribonuclease A. Chem. Rev. 1998, 98, 1045-1065 (Pubitemid 128632236)
    • (1998) Chemical Reviews , vol.98 , Issue.3 , pp. 1045-1065
    • Raines, R.T.1
  • 13
    • 80052710778 scopus 로고    scopus 로고
    • Bovine pancreatic ribonuclease: Fifty years of the first enzymatic reaction mechanism
    • Cuchillo, C. M.; Nogués, M. V.; Raines, R. T. Bovine pancreatic ribonuclease: Fifty years of the first enzymatic reaction mechanism Biochemistry 2011, 50, 7835-7841
    • (2011) Biochemistry , vol.50 , pp. 7835-7841
    • Cuchillo, C.M.1    Nogués, M.V.2    Raines, R.T.3
  • 14
    • 77049141059 scopus 로고
    • The structure of ribonucleic acids. 1. Cyclic nucleotides produced by ribonuclease and by alkaline hydrolysis
    • Markham, R.; Smith, J. D. The structure of ribonucleic acids. 1. Cyclic nucleotides produced by ribonuclease and by alkaline hydrolysis Biochem. J. 1952, 52, 552-557
    • (1952) Biochem. J. , vol.52 , pp. 552-557
    • Markham, R.1    Smith, J.D.2
  • 15
    • 0027430772 scopus 로고
    • The role of 2',3'-cyclic phosphodiesters in the bovine pancreatic ribonuclease A catalysed cleavage of RNA: Intermediates or products?
    • DOI 10.1016/0014-5793(93)80654-D
    • Cuchillo, C. M.; Parés, X.; Guasch, A.; Barman, T.; Travers, F.; Nogués, M. V. The role of 2′,3′-cyclic phosphodiesters in the bovine pancreatic ribonuclease A catalysed cleavage of RNA: Intermediates or products? FEBS Lett. 1993, 333, 207-210 (Pubitemid 23323983)
    • (1993) FEBS Letters , vol.333 , Issue.3 , pp. 207-210
    • Cuchillo, C.M.1    Pares, X.2    Guasch, A.3    Barman, T.4    Travers, F.5    Nogues, M.V.6
  • 16
    • 0028364742 scopus 로고
    • Energetics of catalysis by ribonucleases: Fate of the 2',3'-cyclic phosphodiester intermediate
    • DOI 10.1021/bi00189a047
    • Thompson, J. E.; Venegas, F. D.; Raines, R. T. Energetics of catalysis by ribonucleases: Fate of the 2′,3′-cyclic phosphodiester intermediate Biochemistry 1994, 33, 7408-7414 (Pubitemid 24208781)
    • (1994) Biochemistry , vol.33 , Issue.23 , pp. 7408-7414
    • Thompson, J.E.1    Venegas, F.D.2    Raines, R.T.3
  • 17
    • 0024285806 scopus 로고
    • Experimental charge measurement at leaving oxygen in the bovine ribonuclease A catalyzed cyclization of uridine 3′-phosphate aryl esters
    • Davis, A. M.; Regan, A. C.; Williams, A. Experimental charge measurement at leaving oxygen in the bovine ribonuclease A catalyzed cyclization of uridine 3′-phosphate aryl esters Biochemistry 1988, 27, 9042-9047
    • (1988) Biochemistry , vol.27 , pp. 9042-9047
    • Davis, A.M.1    Regan, A.C.2    Williams, A.3
  • 18
    • 0025971502 scopus 로고
    • U-3′-BCIP: A chromogenic substrate for the detection of RNase a in recombinant DNA expression systems
    • Witmer, M. R.; Falcomer, C. M.; Weiner, M. P.; Kay, M. S.; Begley, T. P.; Ganem, B.; Scheraga, H. A. U-3′-BCIP: A chromogenic substrate for the detection of RNase A in recombinant DNA expression systems Nucleic Acids Res. 1991, 19, 1-4 (Pubitemid 21912646)
    • (1991) Nucleic Acids Research , vol.19 , Issue.1 , pp. 1-4
    • Witmer, M.R.1    Falcomer, C.M.2    Weiner, M.P.3    Kay, M.S.4    Begley, T.P.5    Ganem, B.6    Scheraga, H.A.7
  • 19
    • 0027949817 scopus 로고
    • Value of general acid-base catalysis to Ribonuclease A
    • Thompson, J. E.; Raines, R. T. Value of general acid-base catalysis to Ribonuclease A J. Am. Chem. Soc. 1994, 116, 5467-5468
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 5467-5468
    • Thompson, J.E.1    Raines, R.T.2
  • 22
    • 49149135789 scopus 로고
    • Deoxynucleoside phosphoramidites-A new class of key intermediates for deoxypolynucleotide synthesis
    • Beaucage, S. L.; Caruthers, M. H. Deoxynucleoside phosphoramidites-A new class of key intermediates for deoxypolynucleotide synthesis Tetrahedron Lett. 1981, 22, 1859-1862
    • (1981) Tetrahedron Lett. , vol.22 , pp. 1859-1862
    • Beaucage, S.L.1    Caruthers, M.H.2
  • 23
    • 79953169546 scopus 로고    scopus 로고
    • A brief review of DNA and RNA chemical synthesis
    • Caruthers, M. H. A brief review of DNA and RNA chemical synthesis Biochem. Soc. Trans. 2011, 39, 575-580
    • (2011) Biochem. Soc. Trans. , vol.39 , pp. 575-580
    • Caruthers, M.H.1
  • 24
    • 34548024418 scopus 로고    scopus 로고
    • Prodrug strategies to overcome poor water solubility
    • DOI 10.1016/j.addr.2007.05.013, PII S0169409X07000865
    • Stella, V. J.; Nti-Addae, K. W. Prodrug strategies to overcome poor water solubility Adv. Drug Delivery Rev. 2007, 59, 677-94 (Pubitemid 47285410)
    • (2007) Advanced Drug Delivery Reviews , vol.59 , Issue.7 , pp. 677-694
    • Stella, V.J.1    Nti-Addae, K.W.2
  • 25
    • 0033736202 scopus 로고    scopus 로고
    • Pronucleotides: Toward the in vivo delivery of antiviral and anticancer nucleotides
    • Wagner, C. R.; Iyer, V. V.; McIntee, E. J. Pronucleotides: Toward the in vivo delivery of antiviral and anticancer nucleotides Med. Res. Rev. 2000, 20, 417-51
    • (2000) Med. Res. Rev. , vol.20 , pp. 417-451
    • Wagner, C.R.1    Iyer, V.V.2    McIntee, E.J.3
  • 26
    • 0034951870 scopus 로고    scopus 로고
    • Backbone modification of nucleic acids: Synthesis, structure and therapeutic applications
    • Micklefield, J. Backbone modification of nucleic acids: Synthesis, structure and therapeutic applications Curr. Med. Chem. 2001, 8, 1157-79 (Pubitemid 32655075)
    • (2001) Current Medicinal Chemistry , vol.8 , Issue.10 , pp. 1157-1179
    • Micklefield, J.1
  • 27
    • 0037333460 scopus 로고    scopus 로고
    • Prodrugs of biologically active phosphate esters
    • DOI 10.1016/S0968-0896(02)00552-7, PII S0968089602005527
    • Schultz, C. Prodrugs of biologically active phosphate esters Bioorg. Med. Chem. 2003, 11, 885-898 (Pubitemid 36287048)
    • (2003) Bioorganic and Medicinal Chemistry , vol.11 , Issue.6 , pp. 885-898
    • Schultz, C.1
  • 29
    • 15044362503 scopus 로고    scopus 로고
    • Ficoll and dextran vs. globular proteins as probes for testing glomerular permselectivity: Effects of molecular size, shape, charge, and deformability
    • DOI 10.1152/ajprenal.00171.2004
    • Venturoli, D.; Rippe, B. Ficoll and dextran vs. globular proteins as probes for testing glomerular permselectivity: Effects of molecular size, shape, charge, and deformability Am. J. Physiol.-Renal 2005, 288, F605-F613 (Pubitemid 40381726)
    • (2005) American Journal of Physiology - Renal Physiology , vol.288 , Issue.4
    • Venturoli, D.1    Rippe, B.2
  • 30
    • 28844488494 scopus 로고    scopus 로고
    • Opsonization, biodistribution, and pharmacokinetics of polymeric nanoparticles
    • DOI 10.1016/j.ijpharm.2005.10.010, PII S037851730500668X
    • Owens, D. E., 3rd; Peppas, N. A. Opsonization, biodistribution, and pharmacokinetics of polymeric nanoparticles Int. J. Pharm. 2006, 307, 93-102 (Pubitemid 41773257)
    • (2006) International Journal of Pharmaceutics , vol.307 , Issue.1 , pp. 93-102
    • Owens III, D.E.1    Peppas, N.A.2
  • 31
    • 43049112098 scopus 로고    scopus 로고
    • Prodrugs of phosphates and phosphonates
    • DOI 10.1021/jm701260b
    • Hecker, S. J.; Erion, M. D. Prodrugs of phosphates and phosphonates J. Med. Chem. 2008, 51, 2328-2345 (Pubitemid 351628494)
    • (2008) Journal of Medicinal Chemistry , vol.51 , Issue.8 , pp. 2328-2345
    • Hecker, S.J.1    Erion, M.D.2
  • 32
    • 77952518302 scopus 로고    scopus 로고
    • Anti-HIV therapy with AZT prodrugs: AZT phosphonate derivatives, current state and prospects
    • Khandazhinskaya, A.; Matyugina, E.; Shirokova, E. Anti-HIV therapy with AZT prodrugs: AZT phosphonate derivatives, current state and prospects Expert Opin. Drug Metab. Toxicol. 2011, 6, 701-714
    • (2011) Expert Opin. Drug Metab. Toxicol. , vol.6 , pp. 701-714
    • Khandazhinskaya, A.1    Matyugina, E.2    Shirokova, E.3
  • 33
    • 4243063941 scopus 로고    scopus 로고
    • Comprehensive evaluation of tamoxifen sequential biotransformation by the human cytochrome P450 system in vitro: Prominent roles for CYP3A and CYP2D6
    • DOI 10.1124/jpet.104.065607
    • Desta, Z.; Ward, B. A.; Soukhova, N. V.; Flockhart, D. A. Comprehensive evaluation of tamoxifen sequential biotransformation by the human cytochrome P450 system in vitro: Prominent roles for CYP3A and CYP2D6 J. Pharmacol. Exp. Ther. 2004, 310, 1062-1075 (Pubitemid 39108928)
    • (2004) Journal of Pharmacology and Experimental Therapeutics , vol.310 , Issue.3 , pp. 1062-1075
    • Desta, Z.1    Ward, B.A.2    Soukhova, N.V.3    Flockhart, D.A.4
  • 34
    • 0020003085 scopus 로고
    • 7 cells: Correlation between binding to estrogen receptor and inhibition of cell growth
    • Coezy, E.; Borgna, J. L.; Rochefort, H. Tamoxifen and metabolites in MCF7 cells: Correlation between binding to estrogen receptor and inhibition of cell growth Cancer Res. 1982, 42, 317-323 (Pubitemid 12207285)
    • (1982) Cancer Research , vol.42 , Issue.1 , pp. 317-323
    • Coezy, E.1    Borgna, J.L.2    Rochefort, H.3
  • 35
    • 0036232065 scopus 로고    scopus 로고
    • The evolution of tamoxifen therapy in breast cancer: Selective oestrogen-receptor modulators and downregulators
    • DOI 10.1016/S1470-2045(02)00711-8
    • O'Regan, R. M.; Jordan, V. C. The evolution of tamoxifen therapy in breast cancer: Selective oestrogen-receptor modulators and downregulators Lancet Oncol. 2002, 3, 207-214 (Pubitemid 34441026)
    • (2002) Lancet Oncology , vol.3 , Issue.4 , pp. 207-214
    • O'Regan, R.M.1    Jordan, V.C.2
  • 36
    • 0037334073 scopus 로고    scopus 로고
    • Anti-oestrogenic chemoprevention of breast cancer - The need to progress
    • DOI 10.1016/S0959-8049(02)00771-2
    • Powles, T. J. Anti-oestrogenic chemoprevention of breast cancer-the need to progress Eur. J. Cancer 2003, 39, 572-579 (Pubitemid 36287368)
    • (2003) European Journal of Cancer , vol.39 , Issue.5 , pp. 572-579
    • Powles, T.J.1
  • 38
    • 0034626064 scopus 로고    scopus 로고
    • Risk and prognosis of endometrial cancer after tamoxifen for breast cancer. Comprehensive cancer centres' ALERT group. Assessment of liver and endometrial cancer risk following tamoxifen
    • Bergman, L.; Beelen, M. L.; Gallee, M. P.; Hollema, H.; Benraadt, J.; van Leeuwen, F. E. Risk and prognosis of endometrial cancer after tamoxifen for breast cancer. Comprehensive cancer centres' ALERT group. Assessment of liver and endometrial cancer risk following tamoxifen Lancet 2000, 356, 881-887
    • (2000) Lancet , vol.356 , pp. 881-887
    • Bergman, L.1    Beelen, M.L.2    Gallee, M.P.3    Hollema, H.4    Benraadt, J.5    Van Leeuwen, F.E.6
  • 40
  • 42
    • 77957377256 scopus 로고    scopus 로고
    • Tamoxifen citrate encapsulated sustained release liposomes: Preparation and evaluation of physicochemical properties
    • Layek, B.; Mukherjee, B. Tamoxifen citrate encapsulated sustained release liposomes: Preparation and evaluation of physicochemical properties Sci. Pharm. 2010, 78, 507-515
    • (2010) Sci. Pharm. , vol.78 , pp. 507-515
    • Layek, B.1    Mukherjee, B.2
  • 43
    • 14644399827 scopus 로고    scopus 로고
    • Advanced strategies in liposomal cancer therapy: Problems and prospects of active and tumor specific drug release
    • DOI 10.1016/j.plipres.2004.12.001
    • Andresen, T. L.; Jensen, S. S.; Jorgensen, K. Advanced strategies in liposomal cancer therapy: Problems and prospects of active and tumor specific drug release Prog. Lipid Res. 2005, 44, 68-97 (Pubitemid 40313220)
    • (2005) Progress in Lipid Research , vol.44 , Issue.1 , pp. 68-97
    • Andresen, T.L.1    Jensen, S.S.2    Jorgensen, K.3
  • 44
    • 0021872966 scopus 로고
    • Facile geometric isomerization of phenolic non-steroidal estrogens and antiestrogens: Limitations to the interpretation of experiments characterizing the activity of individual isomers
    • DOI 10.1016/0022-4731(85)90210-9
    • Katzenellenbogen, J. A.; Carlson, K. E.; Katzenellenbogen, B. S. Facile geometric isomerization of phenolic non-steroidal estrogens and antiestrogens: Limitations to the interpretation of experiments characterizing the activity of individual isomers J. Steroid Biochem. 1985, 22, 589-596 (Pubitemid 15003142)
    • (1985) Journal of Steroid Biochemistry , vol.22 , Issue.5 , pp. 589-596
    • Katzenellenbogen, J.A.1    Carlson, K.E.2    Katzenellenbogen, B.S.3
  • 45
    • 0025200665 scopus 로고
    • Structure-function relationships of hydroxylated metabolites of tamoxifen that control the proliferation of estrogen-responsive T47D breast cancer cells in vitro
    • Murphy, C. S.; Langan-Fahey, S. M.; McCague, R.; Jordan, V. C. Structure-function relationships of hydroxylated metabolites of tamoxifen that control the proliferation of estrogen-responsive T47D breast cancer cells in vitro Mol. Pharmacol. 1990, 38, 737-743
    • (1990) Mol. Pharmacol. , vol.38 , pp. 737-743
    • Murphy, C.S.1    Langan-Fahey, S.M.2    McCague, R.3    Jordan, V.C.4
  • 47
    • 84859738582 scopus 로고    scopus 로고
    • Calculator Plugins were used for structure property prediction and calculation
    • ChemAxon: Budapest, Hungary.
    • Calculator Plugins were used for structure property prediction and calculation. Marvin 5.4.1.1; ChemAxon: Budapest, Hungary, 2011.
    • (2011) Marvin 5.4.1.1
  • 49
    • 0038756863 scopus 로고    scopus 로고
    • Potent inhibition of ribonuclease A by oligo(vinylsulfonic acid)
    • DOI 10.1074/jbc.M301852200
    • Smith, B. D.; Soellner, M. B.; Raines, R. T. Potent inhibition of ribonuclease A by oligo(vinylsulfonic acid) J. Biol. Chem. 2003, 278, 20934-20938 (Pubitemid 36806401)
    • (2003) Journal of Biological Chemistry , vol.278 , Issue.23 , pp. 20934-20938
    • Smith, B.D.1    Soellner, M.B.2    Raines, R.T.3
  • 50
    • 33947598165 scopus 로고    scopus 로고
    • Inhibition of Human Pancreatic Ribonuclease by the Human Ribonuclease Inhibitor Protein
    • DOI 10.1016/j.jmb.2007.02.005, PII S0022283607001684
    • Johnson, R. J.; McCoy, J. G.; Bingman, C. A.; Phillips, G. N., Jr.; Raines, R. T.; Phillips, G. N. Inhibition of human pancreatic ribonuclease by the human ribonuclease inhibitor protein J. Mol. Biol. 2007, 368, 434-449 (Pubitemid 46483483)
    • (2007) Journal of Molecular Biology , vol.368 , Issue.2 , pp. 434-449
    • Johnson, R.J.1    McCoy, J.G.2    Bingman, C.A.3    Phillips Jr., G.N.4    Raines, R.T.5
  • 51
    • 79958032034 scopus 로고    scopus 로고
    • Binding of antitumor tamoxifen and its metabolites 4-hydroxytamoxifen and endoxifen to human serum albumin
    • Serum contains both contaminating ribonucleases and albumin, which binds and thus sequesters HT.
    • Serum contains both contaminating ribonucleases and albumin, which binds and thus sequesters HT. Bourassa, P.; Dubeau, S.; Maharvi, G. M.; Fauq, A. H.; Thomas, T. J.; Tajmir-Riahi, H. A. Binding of antitumor tamoxifen and its metabolites 4-hydroxytamoxifen and endoxifen to human serum albumin Biochimie 2011, 93, 1089-1101
    • (2011) Biochimie , vol.93 , pp. 1089-1101
    • Bourassa, P.1    Dubeau, S.2    Maharvi, G.M.3    Fauq, A.H.4    Thomas, T.J.5    Tajmir-Riahi, H.A.6
  • 53
    • 0028131158 scopus 로고
    • Human pancreatic-type and nonpancreatic-type ribonucleases: A direct side-by-side comparison of their catalytic properties
    • Sorrentino, S.; Libonati, M. Human pancreatic-type and nonpancreatic-type ribonucleases: A direct side-by-side comparison of their catalytic properties Arch. Biochem. Biophys. 1994, 312, 340-348
    • (1994) Arch. Biochem. Biophys. , vol.312 , pp. 340-348
    • Sorrentino, S.1    Libonati, M.2
  • 55
    • 0037090881 scopus 로고    scopus 로고
    • Efficient recombination in diverse tissues by a tamoxifen-inducible form of Cre: A tool for temporally regulated gene activation/inactivation in the mouse
    • DOI 10.1006/dbio.2002.0597
    • Hayashi, S.; McMahon, A. P. Efficient recombination in diverse tissues by a tamoxifen-inducible form of Cre: A tool for temporally regulated gene activiation/inactivation in the mouse Dev. Biol. 2002, 244, 305-318 (Pubitemid 34450645)
    • (2002) Developmental Biology , vol.244 , Issue.2 , pp. 305-318
    • Hayashi, S.1    McMahon, A.P.2
  • 56
    • 0021247192 scopus 로고
    • Immunological assay of pancreatic ribonuclease in serum as an indicator of pancreatic cancer
    • Weickmann, J. L.; Olson, E. M.; Glitz, D. G. Immunological assay of pancreatic ribonuclease in serum as an indicator of pancreatic cancer Cancer Res. 1984, 44, 1682-1687 (Pubitemid 14125864)
    • (1984) Cancer Research , vol.44 , Issue.4 , pp. 1682-1687
    • Weickmann, J.L.1    Olson, E.M.2    Glitz, D.G.3
  • 57
    • 33745150448 scopus 로고    scopus 로고
    • Hybridase activity of human ribonuclease-1 revealed by a real-time fluorometric assay
    • DOI 10.1093/nar/gkl368
    • Potenza, N.; Salvatore, V.; Migliozzi, A.; Martone, V.; Nobile, V.; Russo, A. Hybridase activity of human ribonuclease-1 revealed by a real-time fluorometric assay Nucleic Acids Res. 2006, 34, 2906-2913 (Pubitemid 44540418)
    • (2006) Nucleic Acids Research , vol.34 , Issue.10 , pp. 2906-2913
    • Potenza, N.1    Salvatore, V.2    Migliozzi, A.3    Martone, V.4    Nobile, V.5    Russo, A.6
  • 60
    • 33845966763 scopus 로고    scopus 로고
    • Eosinophilic granulocytes and damage-associated molecular pattern molecules (DAMPs): Role in the inflammatory response within tumors
    • DOI 10.1097/01.cji.0000211324.53396.f6, PII 0000237120070100000002
    • Lotfi, R.; Lee, J. J.; Lotze, M. T. Eosinophilic granulocytes and damage-associated molecular pattern molecules (DAMPs): Role in the inflammatory response within tumors J. Immunother. 2007, 30, 16-28 (Pubitemid 46052200)
    • (2007) Journal of Immunotherapy , vol.30 , Issue.1 , pp. 16-28
    • Lotfi, R.1    Lee, J.J.2    Lotze, M.T.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.