메뉴 건너뛰기




Volumn 42, Issue 9, 1999, Pages 1604-1614

cycloSal-pronucleotides of 2',3'-dideoxyadenosine and 2',3'-dideoxy- 2',3'-didehydroadenosine: Synthesis and antiviral evaluation of a highly efficient nucleotide delivery system

Author keywords

[No Author keywords available]

Indexed keywords

2',3' DIDEHYDRO 2',3' DIDEOXYADENOSINE; 2',3' DIDEOXYADENOSINE; 2',3' DIDEOXYNUCLEOSIDE DERIVATIVE; ADENOSINE DEAMINASE; ADENOSINE MONOPHOSPHATE DEAMINASE; CYCLO(3 METHYLSALIGENYL) 5' O (2',3' DIDEHYDROADENOSINYL)PHOSPHATE; CYCLO(3,5 DIMETHYLSALIGENYL) 5' O (2',3' DIDEOXY 2',3' DIDEHYDROADENOSINYL)PHOSPHATE; CYCLO(3,5 DIMETHYLSALIGENYL) 5' O (2',3' DIDEOXYADENOSINYL)PHOSPHATE; CYCLOSALIGENYL 5' O (2',3' DIDEOXY 2',3' DIDEOXY 2',3' DIDEHYDROADENOSINYL)PHOSPHATE; UNCLASSIFIED DRUG;

EID: 0033529048     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm981096z     Document Type: Article
Times cited : (91)

References (44)
  • 1
    • 0022552064 scopus 로고
    • Chemotherapeutic approaches of the treatment of the acquired immunodeficiency syndrome
    • (a) De Clercq, E. Chemotherapeutic Approaches of the Treatment of the Acquired Immunodeficiency Syndrome. J. Med. Chem. 1986, 29, 1561-1569.
    • (1986) J. Med. Chem. , vol.29 , pp. 1561-1569
    • De Clercq, E.1
  • 2
    • 0029011730 scopus 로고
    • Towards improved anti-HIV chemotherapy: Therapeutic strategies for intervention with HIV infections
    • (b) De Clercq, E. Towards improved Anti-HIV Chemotherapy: Therapeutic Strategies for Intervention with HIV Infections. J. Med. Chem. 1995, 38, 2491-2517.
    • (1995) J. Med. Chem. , vol.38 , pp. 2491-2517
    • De Clercq, E.1
  • 3
    • 0028205185 scopus 로고
    • Metabolism and mechanism of antiretroviral action of purine and pyrimidine derivatives
    • (a) Balzarini, J. Metabolism and Mechanism of Antiretroviral Action of Purine and Pyrimidine Derivatives. Pharm. World Sci. 1994, 16, 113-126.
    • (1994) Pharm. World Sci. , vol.16 , pp. 113-126
    • Balzarini, J.1
  • 4
    • 0001720586 scopus 로고
    • 2′,3′-Dideoxynucleoside analogues as anti-HIV agents
    • De Clercq, E., Ed.; JAI Press Inc.: Greenwich, London
    • (b) Herdewijn, P.; Balzarini, J.; De Clercq, E. 2′,3′-Dideoxynucleoside Analogues as Anti-HIV Agents. In Advances in Antiviral Drug Design; De Clercq, E., Ed.; JAI Press Inc.: Greenwich, London, 1993; Vol. 1, pp 233-318.
    • (1993) Advances in Antiviral Drug Design , vol.1 , pp. 233-318
    • Herdewijn, P.1    Balzarini, J.2    De Clercq, E.3
  • 5
    • 0023265911 scopus 로고
    • The anti-HTLV-III (anti-HIV) and cytotoxic activity of 2′,3′-didehydro-2′,3′-dideoxyribonucleosides: A comparison with their parental 2′,3′-dideoxyribonucleosides
    • (c) Balzarini, J.; Kang, G.-J.; Dalal, M.; Herdewijn, P.; De Clercq, E.; Broder, S.; Johns, D. G. The Anti-HTLV-III (Anti-HIV) and Cytotoxic Activity of 2′,3′-Didehydro-2′,3′-dideoxyribonucleosides: A Comparison with their Parental 2′,3′-Dideoxyribonucleosides. Mol. Pharmacol. 1987, 32, 162-167.
    • (1987) Mol. Pharmacol. , vol.32 , pp. 162-167
    • Balzarini, J.1    Kang, G.-J.2    Dalal, M.3    Herdewijn, P.4    De Clercq, E.5    Broder, S.6    Johns, D.G.7
  • 6
    • 0023808097 scopus 로고
    • Metabolic pathways for the activation of the antiretroviral agent 2′,3′-dideoxyadenosine in human lymphoid cells
    • Johnson, M. A.; Ahluwalia, G.; Conelly, M. C.; Cooney, D. A.; Broder, S.; Johns, D. G.; Fridland, A. Metabolic Pathways for the Activation of the Antiretroviral Agent 2′,3′-Dideoxyadenosine in Human Lymphoid Cells. J. Biol. Chem. 1988, 263, 15354-15357.
    • (1988) J. Biol. Chem. , vol.263 , pp. 15354-15357
    • Johnson, M.A.1    Ahluwalia, G.2    Conelly, M.C.3    Cooney, D.A.4    Broder, S.5    Johns, D.G.6    Fridland, A.7
  • 9
    • 0023928448 scopus 로고
    • Biochemical genetic analysis of 2′,3′-dideoxyadenosine metabolism in human T lymphocytes
    • Carson, D. A.; Haertle, T.; Wasson, D. B.; Richman, D. D. Biochemical Genetic Analysis of 2′,3′-Dideoxyadenosine Metabolism in Human T Lymphocytes. Biochem. Biophys. Res. Commun. 1988, 151, 788-793.
    • (1988) Biochem. Biophys. Res. Commun. , vol.151 , pp. 788-793
    • Carson, D.A.1    Haertle, T.2    Wasson, D.B.3    Richman, D.D.4
  • 15
    • 0024435381 scopus 로고
    • Phosphorylation of 2′,3′-dideoxyinosine by cytosolic 5′-nucleotidase of human lymphoid cells
    • Johnson, M. A.; Fridland, A. Phosphorylation of 2′,3′-Dideoxyinosine by Cytosolic 5′-Nucleotidase of Human Lymphoid Cells. Mol. Pharmacol. 1989, 36, 291-295.
    • (1989) Mol. Pharmacol. , vol.36 , pp. 291-295
    • Johnson, M.A.1    Fridland, A.2
  • 16
    • 0027407484 scopus 로고
    • Nucleoside analogues: Similarities and differences
    • Sommadossi, J. P. Nucleoside Analogues: Similarities and Differences. Clin. Infect. Dis. 1993, 16, S7-S15.
    • (1993) Clin. Infect. Dis. , vol.16
    • Sommadossi, J.P.1
  • 17
    • 0027287973 scopus 로고
    • Differential phosphorylation of azidothymidine, dideoxycytidine, and dideoxyinosine in resting and activated peripheral blood mononuclear cells
    • Gao, W. Y.; Shirasaka, T.; Johns, D. G.; Broder, S.; Mitsuya, H. Differential Phosphorylation of Azidothymidine, Dideoxycytidine, and Dideoxyinosine in Resting and Activated Peripheral Blood Mononuclear Cells. J. Clin. Invest. 1993, 91, 2326-2333.
    • (1993) J. Clin. Invest. , vol.91 , pp. 2326-2333
    • Gao, W.Y.1    Shirasaka, T.2    Johns, D.G.3    Broder, S.4    Mitsuya, H.5
  • 18
    • 0026561089 scopus 로고
    • Interpretation of the roles of adenylosuccinate lyase and of AMP deaminase in the anti-HIV activity of 2′,3′-dideoxyadenosine and 2′,3′-dideoxyinosine
    • Nair, V.; Sells, T. B. Interpretation of the Roles of Adenylosuccinate Lyase and of AMP Deaminase in the Anti-HIV Activity of 2′,3′-Dideoxyadenosine and 2′,3′-Dideoxyinosine. Biochim. Biophys. Acta 1992, 1119, 201-204.
    • (1992) Biochim. Biophys. Acta , vol.1119 , pp. 201-204
    • Nair, V.1    Sells, T.B.2
  • 19
    • 0030575614 scopus 로고
    • Phosphoramidate derivatives of 2′,3′-didehydro-2′,3′-dideoxyadenosine (d4A) have markedly improved potency and selectivity
    • McGuigan, C.; Wedgwood, O.; De Clercq, E.; Balzarini, J. Phosphoramidate Derivatives of 2′,3′-Didehydro-2′,3′-dideoxyadenosine (d4A) Have Markedly Improved Potency and Selectivity. Bioorg. Med. Chem. Lett. 1969, 6, 2359-2362.
    • (1969) Bioorg. Med. Chem. Lett. , vol.6 , pp. 2359-2362
    • McGuigan, C.1    Wedgwood, O.2    De Clercq, E.3    Balzarini, J.4
  • 20
    • 0027980948 scopus 로고
    • Equal inhibition of the replication of human immunodeficiency virus in human T-cell culture by ddA bis(sate)phosphotriester and 3′-azido-2′,3′-dideoxythymidine
    • Perigaud, C.; Aubertin, A.-M.; Benzaria, S.; Pelicano, H.; Giradet, J.-L.; Maury, G.; Gosselin, G.; Kirn, A.; Imbach, J.-L. Equal Inhibition of the Replication of Human Immunodeficiency Virus in Human T-Cell Culture by ddA Bis(Sate)phosphotriester and 3′-Azido-2′,3′-dideoxythymidine. Biochem. Pharmacol. 1994, 48, 11-14.
    • (1994) Biochem. Pharmacol. , vol.48 , pp. 11-14
    • Perigaud, C.1    Aubertin, A.-M.2    Benzaria, S.3    Pelicano, H.4    Giradet, J.-L.5    Maury, G.6    Gosselin, G.7    Kirn, A.8    Imbach, J.-L.9
  • 21
    • 0030786410 scopus 로고    scopus 로고
    • Conversion of 2′,3′-dideoxyadenosine (ddA) and 2′,3′-didehydro-2′,3′-dideoxyadenosine (d4A) to their activity against human immunodeficiency virus and hepatitis B virus
    • Balzarini, J.; Kruining, J.; Wedgwood, O.; Pannecouque, C.; Aquaro, A.; Perno, C.-F.; Naesens, L.; Witrouw, M.; Heijtink, R.; De Clercq, E.; McGuigan, C. Conversion of 2′,3′-Dideoxyadenosine (ddA) and 2′,3′-Didehydro-2′,3′-dideoxyadenosine (d4A) to their Activity against Human Immunodeficiency Virus and Hepatitis B Virus. FEBS Lett. 1997, 410, 324-328.
    • (1997) FEBS Lett. , vol.410 , pp. 324-328
    • Balzarini, J.1    Kruining, J.2    Wedgwood, O.3    Pannecouque, C.4    Aquaro, A.5    Perno, C.-F.6    Naesens, L.7    Witrouw, M.8    Heijtink, R.9    De Clercq, E.10    McGuigan, C.11
  • 22
    • 26844445742 scopus 로고    scopus 로고
    • Pro-nucleotides - Recent advances in the design of efficient tools for the delivery of biologically active nucleoaide monophosphates
    • (a) Meier, C. Pro-Nucleotides - Recent Advances in the Design of Efficient Tools for the Delivery of Biologically Active Nucleoaide Monophosphates. Synlett 1998, 233-242.
    • (1998) Synlett , pp. 233-242
    • Meier, C.1
  • 23
    • 77956802548 scopus 로고    scopus 로고
    • Comments on nucleotide delivery forms
    • De Clercq, E., Ed.; JAI Press Inc.: Greenwich, London
    • (b) Périgaud, C.; Giradet, J.-L.; Gosselin, G.; Imbach, J.-L. Comments on Nucleotide Delivery Forms. In Advances in Antiviral Drug Design; De Clercq, E., Ed.; JAI Press Inc.: Greenwich, London, 1996; Vol. 2, pp 147-172.
    • (1996) Advances in Antiviral Drug Design , vol.2 , pp. 147-172
    • Périgaud, C.1    Giradet, J.-L.2    Gosselin, G.3    Imbach, J.-L.4
  • 24
    • 0002451023 scopus 로고    scopus 로고
    • 4H-1.3.2-benzodioxaphosphorin-2-nucleosyl-2-oxide - A new concept for lipophilic, potential prodrugs of biologically active nucleoside monophosphates
    • Meier, C. 4H-1.3.2-Benzodioxaphosphorin-2-nucleosyl-2-oxide - A New Concept for Lipophilic, Potential Prodrugs of Biologically Active Nucleoside Monophosphates. Angew. Chem. 1996, 108, 77-79; Angew. Chem., Int. Ed. Engl. 1996, 35, 70-72.
    • (1996) Angew. Chem. , vol.108 , pp. 77-79
    • Meier, C.1
  • 25
    • 0003876666 scopus 로고    scopus 로고
    • Meier, C. 4H-1.3.2-Benzodioxaphosphorin-2-nucleosyl-2-oxide - A New Concept for Lipophilic, Potential Prodrugs of Biologically Active Nucleoside Monophosphates. Angew. Chem. 1996, 108, 77-79; Angew. Chem., Int. Ed. Engl. 1996, 35, 70-72.
    • (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 70-72
  • 26
    • 0030707857 scopus 로고    scopus 로고
    • CycloSal-pro-nucleotides: The design and biological evaluation of a new class of lipophilic nucleotide prodrugs
    • Meier, C.; Knispel, T.; Lorey, M.; Balzarini, J. CycloSal-Pro-Nucleotides: The Design and Biological Evaluation of a New Class of Lipophilic Nucleotide Prodrugs. Int. Antiviral News 1997, 5, 183-186.
    • (1997) Int. Antiviral News , vol.5 , pp. 183-186
    • Meier, C.1    Knispel, T.2    Lorey, M.3    Balzarini, J.4
  • 27
    • 0032560234 scopus 로고    scopus 로고
    • Cyclosal-d4TMP: Synthesis and antiviral evaluation of a new d4TMP delivery system
    • (a) Meier, C.; Lorey, M.; De Clercq, E.; Balzarini, J. cycloSal-d4TMP: Synthesis and Antiviral Evaluation of a New d4TMP Delivery System. J. Med. Chem. 1998, 41, 1417-1427.
    • (1998) J. Med. Chem. , vol.41 , pp. 1417-1427
    • Meier, C.1    Lorey, M.2    De Clercq, E.3    Balzarini, J.4
  • 28
    • 0031013734 scopus 로고    scopus 로고
    • Cyclic saligenyl phosphotriesters of 2′,3′-dideoxy-2′,3′-didehydrothymidine (d4T) - A new pro-nucleotide approach
    • (b) Meier, C.; Lorey, M.; De Clercq, E.; Balzarini, J. Cyclic Saligenyl Phosphotriesters of 2′,3′-Dideoxy-2′,3′-didehydrothymidine (d4T) - A New Pro-Nucleotide Approach. Bioorg. Med. Chem. Lett. 1997, 7, 99-104.
    • (1997) Bioorg. Med. Chem. Lett. , vol.7 , pp. 99-104
    • Meier, C.1    Lorey, M.2    De Clercq, E.3    Balzarini, J.4
  • 29
    • 0030927126 scopus 로고    scopus 로고
    • ADA-bypass by lipophilic CycloSal-ddAMP pro-nucleotides. A second example of the efficiency of the cycloSal-concept
    • Meier, C.; Knispel, T.; De Clercq, E.; Balzarini, J. ADA-Bypass by Lipophilic CycloSal-ddAMP Pro-Nucleotides. A Second Example of the Efficiency of the cycloSal-Concept. Bioorg. Med. Chem. Lett. 1997, 7, 1577-1582.
    • (1997) Bioorg. Med. Chem. Lett. , vol.7 , pp. 1577-1582
    • Meier, C.1    Knispel, T.2    De Clercq, E.3    Balzarini, J.4
  • 30
    • 0023742322 scopus 로고
    • Regioselective 5′-O-benzoylation of deoxyadenosine with benzoic acid catalyzed by N′,N′-bis-(2-oxo-oxazolidin-3-yl)phosphordiamidic chloride (BOPDC)
    • Liguori, A.; Perri, E.; Sidona, G.; Uccella, N. Regioselective 5′-O-Benzoylation of Deoxyadenosine with Benzoic Acid Catalyzed by N′,N′-Bis-(2-oxo-oxazolidin-3-yl)phosphordiamidic chloride (BOPDC). Tetrahedron 1988, 44, 229-234.
    • (1988) Tetrahedron , vol.44 , pp. 229-234
    • Liguori, A.1    Perri, E.2    Sidona, G.3    Uccella, N.4
  • 31
    • 0027411541 scopus 로고
    • An efficient and general synthesis of 5′-Esters of 2′,3′-didehydro-2′,3′-dideoxynucleosides: A facile opening of 2′,3′-orthoacetates of ribonucleosides followed by reductive elimination of the halogeno-acetates
    • Ratnakar, R.; Talekar, P. L.; Coe, L.; Walker, R. T. An Efficient and General Synthesis of 5′-Esters of 2′,3′-Didehydro-2′,3′-Dideoxynucleosides: A Facile Opening of 2′,3′-Orthoacetates of Ribonucleosides Followed by Reductive Elimination of the Halogeno-acetates. Synthesis 1993, 303-306.
    • (1993) Synthesis , pp. 303-306
    • Ratnakar, R.1    Talekar, P.L.2    Coe, L.3    Walker, R.T.4
  • 33
    • 0026720613 scopus 로고
    • A highly stereoselective synthesis of anti-HIV 2′,3′-dideoxy- and 2′,3′-didehydro-2′,3′-dideoxynucleosides
    • Beach, J. W.; Kim, H. O.; Jeong, L. S.; Nampalli, S.; Islam, Q.; Ahn, S. K.; Babu, R.; Chu, C. K. A Highly Stereoselective Synthesis of Anti-HIV 2′,3′-Dideoxy- and 2′,3′-Didehydro-2′,3′-dideoxynucleosides. J. Org. Chem. 1992, 57, 3887-3894.
    • (1992) J. Org. Chem. , vol.57 , pp. 3887-3894
    • Beach, J.W.1    Kim, H.O.2    Jeong, L.S.3    Nampalli, S.4    Islam, Q.5    Ahn, S.K.6    Babu, R.7    Chu, C.K.8
  • 34
    • 0024554252 scopus 로고
    • General syntheses of 2′,3′-dideoxynucleosides and 2′,3′-didehydro-2′,3′-dideoxynucleosides
    • Chu, C. K.; Bhadti, V. S.; Doboszewski, B.; Gu, Z. P.; Kosugi, Y.; Pullaiah, K. C.; Van Roey, P. General Syntheses of 2′,3′-Dideoxynucleosides and 2′,3′-Didehydro-2′,3′-dideoxynucleosides. J. Org. Chem. 1989, 54, 2217-2225.
    • (1989) J. Org. Chem. , vol.54 , pp. 2217-2225
    • Chu, C.K.1    Bhadti, V.S.2    Doboszewski, B.3    Gu, Z.P.4    Kosugi, Y.5    Pullaiah, K.C.6    Van Roey, P.7
  • 35
    • 0003188936 scopus 로고    scopus 로고
    • Nucleotide delivery from cycloSaligenyl-3′-azido-3′-deoxythymidine monophosphates (cyctoSal-AZTMP)
    • Meier, C.; De Clercq, E.; Balzarini, J. Nucleotide Delivery from cycloSaligenyl-3′-Azido-3′-Deoxythymidine Monophosphates (cyctoSal-AZTMP). Eur. J. Org. Chem. 1998, 837-846.
    • (1998) Eur. J. Org. Chem. , pp. 837-846
    • Meier, C.1    De Clercq, E.2    Balzarini, J.3
  • 36
    • 0024520447 scopus 로고
    • Estimation of the lipophilicity of anti-HIV nucleoside analogues by determination of the partition coefficient and retention time on a LiChrosphere 60 RP-8 HPLC column
    • (a) Using a different methodology, a P value of 0.96 was determined for AZT: Balzarini, J.; Cools, J. M.; De Clercq, E. Estimation of the Lipophilicity of Anti-HIV Nucleoside Analogues by Determination of the Partition Coefficient and Retention Time on a LiChrosphere 60 RP-8 HPLC Column. Biochem. Biophys. Res. Commun. 1989, 158, 413-422.
    • (1989) Biochem. Biophys. Res. Commun. , vol.158 , pp. 413-422
    • Balzarini, J.1    Cools, J.M.2    De Clercq, E.3
  • 37
    • 0025774756 scopus 로고
    • Physical factors contributing to the partition coefficient and retention time of 2′,3′-dideoxynucleoside analogues
    • (b) Lien, E. J.; Gao, H.; Prabhakar, H. Physical Factors Contributing to the Partition Coefficient and Retention Time of 2′,3′-Dideoxynucleoside Analogues. J. Pharm. Sci. 1991, 80, 517-521.
    • (1991) J. Pharm. Sci. , vol.80 , pp. 517-521
    • Lien, E.J.1    Gao, H.2    Prabhakar, H.3
  • 38
    • 0025826715 scopus 로고
    • Potential anti-AIDS drugs. Lipophilic, adenosine deaminase-activated prodrugs
    • Also using a HPLC methodology, the log P values for AZT (0.05), ddA (-0.29), and ddI (-1.24) have been determined: Barchi, J. J.; Marquez, V. E.; Driscoll, J. S.; Ford, H., Jr.; Mitsuya, H.; Shirasaka, T.; Aoki, S.; Kelley, J. A. Potential Anti-AIDS Drugs. Lipophilic, Adenosine Deaminase-activated Prodrugs. J. Med. Chem. 1991, 34, 1647-1655.
    • (1991) J. Med. Chem. , vol.34 , pp. 1647-1655
    • Barchi, J.J.1    Marquez, V.E.2    Driscoll, J.S.3    Ford H., Jr.4    Mitsuya, H.5    Shirasaka, T.6    Aoki, S.7    Kelley, J.A.8
  • 39
    • 0023258934 scopus 로고
    • 3′-azido-3′-deoxythymidine, an unusual nucleoside analogue that permeates the membrane of human erythrocytes and lymphocytes by nonfacilitated diffusion
    • Zimmermann, T. P.; Mahony, W. B.; Prus, K. L. 3′-Azido-3′-deoxythymidine, an Unusual Nucleoside Analogue that Permeates the Membrane of Human Erythrocytes and Lymphocytes by Nonfacilitated Diffusion. J. Biol. Chem. 1987, 262, 5748-5754.
    • (1987) J. Biol. Chem. , vol.262 , pp. 5748-5754
    • Zimmermann, T.P.1    Mahony, W.B.2    Prus, K.L.3
  • 41
    • 0342549837 scopus 로고
    • Effect of the structure of the glycon on the acid-catalyzed hydrolysis of adenine nucleosides
    • York, J. L. Effect of the Structure of the Glycon on the Acid-Catalyzed Hydrolysis of Adenine Nucleosides. J. Org. Chem. 1981, 46, 2171-2173.
    • (1981) J. Org. Chem. , vol.46 , pp. 2171-2173
    • York, J.L.1
  • 42
    • 0014127726 scopus 로고
    • The role of the 5′-hydroxyl group of adenosine in determining substrate specificity for adenosine deaminase
    • Bloch, A.; Robins, M. J.; McCarthy, J. R., Jr. The Role of the 5′-Hydroxyl Group of Adenosine in Determining Substrate Specificity for Adenosine Deaminase. J. Med. Chem. 1967, 10, 908-912.
    • (1967) J. Med. Chem. , vol.10 , pp. 908-912
    • Bloch, A.1    Robins, M.J.2    McCarthy J.R., Jr.3
  • 43
    • 0021237243 scopus 로고
    • Detection, isolation, and continuous production of cytopathic retroviruses (HTLV-III) from patients with AIDS and pre-AIDS
    • Popovic, M.; Sarngadharan, M. G.; Read, E.; Gallo, R. C. Detection, Isolation, and Continuous Production of Cytopathic Retroviruses (HTLV-III) from Patients with AIDS and pre-AIDS. Science 1984, 224, 497-600.
    • (1984) Science , vol.224 , pp. 497-600
    • Popovic, M.1    Sarngadharan, M.G.2    Read, E.3    Gallo, R.C.4
  • 44
    • 0025979184 scopus 로고
    • 9-(2-phosphonylmethoxyethyl)adenine (PMEA) efficiently inhibits retrovirus replication in vitro and Simian immunodeficiency virus infection in rhesus monkeys
    • Balzarini, J.; Naesens, L.; Slachmuylders, J.; Niphuis, H.; Rosenberg, I.; Holy, A.; Schellekens, H.; De Clercq, E. 9-(2-Phosphonylmethoxyethyl)adenine (PMEA) Efficiently Inhibits Retrovirus Replication in vitro and Simian Immunodeficiency Virus Infection in Rhesus Monkeys. AIDS 1991, 5, 21-28.
    • (1991) AIDS , vol.5 , pp. 21-28
    • Balzarini, J.1    Naesens, L.2    Slachmuylders, J.3    Niphuis, H.4    Rosenberg, I.5    Holy, A.6    Schellekens, H.7    De Clercq, E.8


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.