메뉴 건너뛰기




Volumn 39, Issue 8, 1996, Pages 1619-1625

Lipophilic, acid-stable, adenosine deaminase-activated anti-HIV prodrugs for central nervous system delivery. 3. 6-amino prodrugs of 2′-β-fluoro-2′,3′-dideoxyinosine

Author keywords

[No Author keywords available]

Indexed keywords

2',3' DIDEOXY 2' FLUORO 6 N,N DIMETHYLADENOSINE; 2',3' DIDEOXY 2' FLUOROINOSINE; ADENOSINE DEAMINASE; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; PRODRUG; PURINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0029975891     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9509197     Document Type: Article
Times cited : (26)

References (41)
  • 1
    • 85033843836 scopus 로고    scopus 로고
    • note
    • 50, compound concentration inhibiting HIV cytopathogenic effects by 50%; NCI, National Cancer Institute; P, octanol/pH 7.4 buffer partition coefficient; PHA-PBM, phytohemagglutinin-stimulated peripheral blood mononuclear cells; PNP, purine nucleoside phosphorylase.
  • 2
    • 0027096948 scopus 로고
    • Pathogenesis and Therapy of HIV-1 Infection of the Central Nervous System
    • (a) Geleziunas, R.; Schipper, H. M.; Wainberg, M. A. Pathogenesis and Therapy of HIV-1 Infection of the Central Nervous System. AIDS 1992, 6, 1411-1426.
    • (1992) AIDS , vol.6 , pp. 1411-1426
    • Geleziunas, R.1    Schipper, H.M.2    Wainberg, M.A.3
  • 4
    • 0028941196 scopus 로고
    • Antiviral Therapy for Human Immunodeficiency Virus Infections
    • De Clercq, E. Antiviral Therapy for Human Immunodeficiency Virus Infections. Clin. Microbiol. Rev. 1995, 8, 200-239.
    • (1995) Clin. Microbiol. Rev. , vol.8 , pp. 200-239
    • De Clercq, E.1
  • 5
    • 0027195154 scopus 로고
    • Challenges in the therapy of HIV Infection
    • (a) Yarchoan, Y.; Mitsuya, H.; Broder, S. Challenges in the therapy of HIV Infection. Immunol. Today 1993, 14, 303-309.
    • (1993) Immunol. Today , vol.14 , pp. 303-309
    • Yarchoan, Y.1    Mitsuya, H.2    Broder, S.3
  • 6
    • 0028214975 scopus 로고
    • Enhanced Brain Delivery of an Anti-HIV Nucleoside 2′-F-ara-ddI by Xanthine Oxidase Mediated Biotransformation
    • (b) Shanmuganathan, K.; Koudriakova, T.; Nampalli, S.; Du, J.; Gallo, J. M.; Schinazi, R. F.; Chu, C. K Enhanced Brain Delivery of an Anti-HIV Nucleoside 2′-F-ara-ddI by Xanthine Oxidase Mediated Biotransformation. J. Med. Chem. 1994, 37, 821-827.
    • (1994) J. Med. Chem. , vol.37 , pp. 821-827
    • Shanmuganathan, K.1    Koudriakova, T.2    Nampalli, S.3    Du, J.4    Gallo, J.M.5    Schinazi, R.F.6    Chu, C.K.7
  • 7
    • 0028905177 scopus 로고
    • Lipophilic, Acid-Stable Adenosine Deaminase-Activated Anti-HIV Prodrugs for Central Nervous System Delivery, 2. 6-Halo and 6-Alkoxy Prodrugs of 2′-β-Fluoro-2′,3′-dideoxyinosine
    • (a) Ford, H.; Siddiqui, M. A.; Driscoll, J. S.; Marquez, V. E.; Kelley, J. A.; Mitsuya, H.; Shirasaka, T. Lipophilic, Acid-Stable Adenosine Deaminase-Activated Anti-HIV Prodrugs for Central Nervous System Delivery, 2. 6-Halo and 6-Alkoxy Prodrugs of 2′-β-Fluoro-2′,3′-dideoxyinosine. J. Med. Chem. 1995, 38, 1189-1195.
    • (1995) J. Med. Chem. , vol.38 , pp. 1189-1195
    • Ford, H.1    Siddiqui, M.A.2    Driscoll, J.S.3    Marquez, V.E.4    Kelley, J.A.5    Mitsuya, H.6    Shirasaka, T.7
  • 10
    • 0023203860 scopus 로고
    • 2′,3′-Dideoxy-2′-Fluoro-Ara-A. An Acid-Stable Purine Nucleoside Active Against Human Immunodeficiency Virus (HIV)
    • (a) Marquez, V. E.; Tseng, C. K.-H.; Kelley, J. A.; Mitsuya, H.; Broder, S.; Roth, J. S.; Driscoll, J. S. 2′,3′-Dideoxy-2′-Fluoro-Ara-A. An Acid-Stable Purine Nucleoside Active Against Human Immunodeficiency Virus (HIV). Biochem. Pharmacol. 1987, 36, 2719-2722.
    • (1987) Biochem. Pharmacol. , vol.36 , pp. 2719-2722
    • Marquez, V.E.1    Tseng, C.K.-H.2    Kelley, J.A.3    Mitsuya, H.4    Broder, S.5    Roth, J.S.6    Driscoll, J.S.7
  • 11
    • 0023551961 scopus 로고
    • Synthesis and Anti-HIV Activity of Various 2′-and 3′-Substituted 2′,3′-Dideoxyadenosines: A Structure-Activity Analysis
    • (b) Herdewijn, P.; Pauwels, R.; Baba, M.; Balzarini, J.; De Clercq, E. Synthesis and Anti-HIV Activity of Various 2′-and 3′-Substituted 2′,3′-Dideoxyadenosines: A Structure-Activity Analysis. J. Med. Chem. 1987, 30, 2131-2137.
    • (1987) J. Med. Chem. , vol.30 , pp. 2131-2137
    • Herdewijn, P.1    Pauwels, R.2    Baba, M.3    Balzarini, J.4    De Clercq, E.5
  • 14
    • 0026055397 scopus 로고
    • A More Expedient Approach to the Synthesis of the Anti-HIV-Active 2,3-Dideoxy-2-fluoro-β-D-thero-pentofuranosyl Nucleosides
    • (a) Wysocki, R. J.; Siddiqui, M. A.; Barchi, J. J.; Driscoll, J. S.; Marquez, V. E. A More Expedient Approach to the Synthesis of the Anti-HIV-Active 2,3-Dideoxy-2-fluoro-β-D-thero-pentofuranosyl Nucleosides. Synthesis 1991, 1005-1008.
    • (1991) Synthesis , pp. 1005-1008
    • Wysocki, R.J.1    Siddiqui, M.A.2    Barchi, J.J.3    Driscoll, J.S.4    Marquez, V.E.5
  • 15
    • 0028229018 scopus 로고
    • A Diasteroselective Synthesis of (S,S)-α-Fluoro-2,2-Dimethyl-1,3-Dioxolane-4-Propanoic Acid Methyl Ester, a Key Intermediate for the Preparation of Anti-HIV Effective Fluorodideoxynucleosides
    • (b) Siddiqui, M. A.; Marquez, V. E.; Driscoll, J. S.; Barchi, J. J. A Diasteroselective Synthesis of (S,S)-α-Fluoro-2,2-Dimethyl-1,3-Dioxolane-4-Propanoic Acid Methyl Ester, a Key Intermediate for the Preparation of Anti-HIV Effective Fluorodideoxynucleosides. Tetrahedron Lett. 1994, 35, 3263-3266.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 3263-3266
    • Siddiqui, M.A.1    Marquez, V.E.2    Driscoll, J.S.3    Barchi, J.J.4
  • 16
    • 0014216947 scopus 로고
    • Adenosine Aminohydrolase. Binding and Hydrolysis of 2- and 6-Substituted Purine Ribonucleosides and 9-Substituted Adenine Nucleosides
    • Chassy, B. M.; Suhadolnik, R. J. Adenosine Aminohydrolase. Binding and Hydrolysis of 2- and 6-Substituted Purine Ribonucleosides and 9-Substituted Adenine Nucleosides. J. Biol. Chem. 1967, 242, 3655-3658.
    • (1967) J. Biol. Chem. , vol.242 , pp. 3655-3658
    • Chassy, B.M.1    Suhadolnik, R.J.2
  • 17
    • 0014238689 scopus 로고
    • Studies on the Specificity and Mechanism of Action of Adenosine Deaminase
    • Baer, H. P.; Drummond, G. I.; Gillis, J. Studies on the Specificity and Mechanism of Action of Adenosine Deaminase. Arch. Biochem. Biophys. 1968, 123, 172-178
    • (1968) Arch. Biochem. Biophys. , vol.123 , pp. 172-178
    • Baer, H.P.1    Drummond, G.I.2    Gillis, J.3
  • 18
    • 33947466108 scopus 로고
    • Synthesis of Potential Anticancer Agents. XIII. Ribosides of 6-Substituted Purines
    • (a) Johnson, J. A.; Thomas, H. J.; Schaeffer, H. J. Synthesis of Potential Anticancer Agents. XIII. Ribosides of 6-Substituted Purines. J. Am. Chem. Soc. 1958, 79, 699-702.
    • (1958) J. Am. Chem. Soc. , vol.79 , pp. 699-702
    • Johnson, J.A.1    Thomas, H.J.2    Schaeffer, H.J.3
  • 19
    • 0040774643 scopus 로고
    • Enzymatic Hydrolysis of 6-Substituents on Purine Ribosides
    • (b) Wolfenden, R. Enzymatic Hydrolysis of 6-Substituents on Purine Ribosides. J. Am. Chem. Soc. 1966, 88, 3157-3158.
    • (1966) J. Am. Chem. Soc. , vol.88 , pp. 3157-3158
    • Wolfenden, R.1
  • 20
    • 0025924002 scopus 로고
    • A Rapid Microscale Method for the Determination of Partition Coefficients by HPLC
    • Ford, H.; Merski, C. L.; Kelley, J. A. A Rapid Microscale Method for the Determination of Partition Coefficients by HPLC. J. Liquid Chromatogr. 1991, 14, 3365-3386.
    • (1991) J. Liquid Chromatogr. , vol.14 , pp. 3365-3386
    • Ford, H.1    Merski, C.L.2    Kelley, J.A.3
  • 21
    • 0015101125 scopus 로고
    • Interdepencence between Physical Parameters and Selection of Substitutent Groups for Correlation Studies
    • Craig, P. N. Interdepencence Between Physical Parameters and Selection of Substitutent Groups for Correlation Studies. J. Med. Chem. 1971, 14, 680-684.
    • (1971) J. Med. Chem. , vol.14 , pp. 680-684
    • Craig, P.N.1
  • 22
    • 0342549837 scopus 로고
    • Effect of the Structure of the Glycon on the Acid-Catalyzed Hydrolysis of Adenine Nucleosides
    • (a) 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
  • 23
    • 0026721305 scopus 로고
    • Didanosine. A Review of its Antiviral Activity, Pharmacokinetic Properties and Therapeutic Potential in Human Immunodeficiency Virus Infection
    • (b) Faulds, D.; Brogden, R. N. Didanosine. A Review of its Antiviral Activity, Pharmacokinetic Properties and Therapeutic Potential in Human Immunodeficiency Virus Infection. Drugs 1992, 1, 94-116.
    • (1992) Drugs , vol.1 , pp. 94-116
    • Faulds, D.1    Brogden, R.N.2
  • 24
    • 0014930807 scopus 로고
    • Calf Intestine Adenosine Deaminase. Substrate Specificity
    • (a) Simon, L. N.; Bauer, R. J.; Tolman, R. L.; Robins, R. K. Calf Intestine Adenosine Deaminase. Substrate Specificity. Biochemistry 1970, 9, 573-577.
    • (1970) Biochemistry , vol.9 , pp. 573-577
    • Simon, L.N.1    Bauer, R.J.2    Tolman, R.L.3    Robins, R.K.4
  • 25
    • 0013878432 scopus 로고
    • Specificity of Adenosine Deaminase Toward Adenosine and 2′-Deoxyadenosine Analogues
    • (b) Frederiksen, S. Specificity of Adenosine Deaminase Toward Adenosine and 2′-Deoxyadenosine Analogues. Arch. Biochem. Biophys. 1966, 113, 383-388.
    • (1966) Arch. Biochem. Biophys. , vol.113 , pp. 383-388
    • Frederiksen, S.1
  • 26
    • 0008712511 scopus 로고
    • Structural Requirements of Nucleosides for Binding by Adenosine Deaminase
    • (c) Corey, J. G.; Suhadolnik, R. J. Structural Requirements of Nucleosides for Binding by Adenosine Deaminase. Biochemistry 1966, 4, 1729-1732, 1733-1735.
    • (1966) Biochemistry , vol.4 , pp. 1729-1732
    • Corey, J.G.1    Suhadolnik, R.J.2
  • 27
    • 0014749964 scopus 로고
    • Nucleosides. LXIV. Fluoro Sugar Analogs of Arabinosyl- and Xylosylcytosines
    • (d) Wright, J. A.; Wilson, D. P.; Fox, J. J. Nucleosides. LXIV. Fluoro Sugar Analogs of Arabinosyl- and Xylosylcytosines. J. Med. Chem. 1970, 13, 269-272.
    • (1970) J. Med. Chem. , vol.13 , pp. 269-272
    • Wright, J.A.1    Wilson, D.P.2    Fox, J.J.3
  • 28
    • 0025953066 scopus 로고
    • Selective Anabolism of 6-Methoxypurine Arabinoside in Varicella-Zoster Virus-Infected Cells
    • (e) Biron, K. K.; De Miranda, P.; Burnette, T. C.; Krenitsky, T. A. Selective Anabolism of 6-Methoxypurine Arabinoside in Varicella-Zoster Virus-Infected Cells. Antimicrob. Agents Chemother. 1991, 35, 2116-2120.
    • (1991) Antimicrob. Agents Chemother. , vol.35 , pp. 2116-2120
    • Biron, K.K.1    De Miranda, P.2    Burnette, T.C.3    Krenitsky, T.A.4
  • 29
    • 0023839773 scopus 로고
    • Investigations on the Anti-HIV Activity of 2′,3′-Dideoxyadenosine Analogues with Modifications in either the Pentose or Purine Moiety
    • (f) Pauwels, R.; Baba, M.; Balzarini, J.; Herdewijn, P.; Desmyther, J.; Robins, M. J.; Zou, R.; Madej, D.; De Clercq, E. Investigations on the Anti-HIV Activity of 2′,3′-Dideoxyadenosine Analogues with Modifications in either the Pentose or Purine Moiety. Biochem. Pharmacol. 1988, 37, 1317-1325.
    • (1988) Biochem. Pharmacol. , vol.37 , pp. 1317-1325
    • Pauwels, R.1    Baba, M.2    Balzarini, J.3    Herdewijn, P.4    Desmyther, J.5    Robins, M.J.6    Zou, R.7    Madej, D.8    De Clercq, E.9
  • 30
    • 0028300765 scopus 로고
    • Divergent Anti-human Immunodeficiency Virus Activity and Anabolic Phosphorylation of 2′,3′-Dideoxymicleoside Analogs in Resting and Activated Human Cells
    • Gao, W.-Y.; Agbaria, R.; Driscoll, J. S.; Mitsuya. H. Divergent Anti-human Immunodeficiency Virus Activity and Anabolic Phosphorylation of 2′,3′-Dideoxymicleoside Analogs in Resting and Activated Human Cells. J. Biol. Chem. 1994, 269, 12633-12638.
    • (1994) J. Biol. Chem. , vol.269 , pp. 12633-12638
    • Gao, W.-Y.1    Agbaria, R.2    Driscoll, J.S.3    Mitsuya, H.4
  • 34
    • 0028950543 scopus 로고
    • Prognostic Value of Adenosine Deaminase Compared to Other Markers for Progression to Acquired Immunodeficiency Syndrome among Intravenous Drug Users
    • Casoli, C.; Lisa, A.; Magnani, G.; Starcich, R.; Fiaccadori, F.; Bertazzoni, U.; Zei, G. Prognostic Value of Adenosine Deaminase Compared to Other Markers for Progression to Acquired Immunodeficiency Syndrome Among Intravenous Drug Users. J. Med. Virol. 1995, 45, 203-210.
    • (1995) J. Med. Virol. , vol.45 , pp. 203-210
    • Casoli, C.1    Lisa, A.2    Magnani, G.3    Starcich, R.4    Fiaccadori, F.5    Bertazzoni, U.6    Zei, G.7
  • 36
    • 0007960915 scopus 로고
    • Lipophilic 6-Halo-2′,3′-dideoxypurine Nucleosides: Potential Antiretroviral Agents Targeting HIV-Associated Neurologic Disorders
    • Kumar, A., Ed.; Plenum Press: New York
    • Shirasaka, T.; Watanabe, K.; Yoshioka, H.; Kojima, E.; Aoki, S.; Murakami, K.; Mitsuya, H. Lipophilic 6-Halo-2′,3′-dideoxypurine Nucleosides: Potential Antiretroviral Agents Targeting HIV-Associated Neurologic Disorders. In Advances in Molecular Biology and Targeted Treatment for AIDS; Kumar, A., Ed.; Plenum Press: New York, 1991; pp 323-333.
    • (1991) Advances in Molecular Biology and Targeted Treatment for AIDS , pp. 323-333
    • Shirasaka, T.1    Watanabe, K.2    Yoshioka, H.3    Kojima, E.4    Aoki, S.5    Murakami, K.6    Mitsuya, H.7
  • 37
    • 0026675554 scopus 로고
    • Central Nervous System Targeting of 2′,3′-Dideoxyinosine via Adenosine Deaminase-Activated 6-Halo-Dideoxypurine Prodrugs
    • Morgan, M. E.; Chi, S.-C.; Murakami, K.; Mitsuya, H.; Anderson, B. D. Central Nervous System Targeting of 2′,3′-Dideoxyinosine via Adenosine Deaminase-Activated 6-Halo-Dideoxypurine Prodrugs. Antimicrob. Agents Chemother. 1992, 36, 2156-2165.
    • (1992) Antimicrob. Agents Chemother. , vol.36 , pp. 2156-2165
    • Morgan, M.E.1    Chi, S.-C.2    Murakami, K.3    Mitsuya, H.4    Anderson, B.D.5
  • 38
    • 0028060211 scopus 로고
    • Brain Targeting of Anti-HIV Nucleosides: In Vitro and in Vivo Evaluation of 6-Chloro-2′,3′-dideoxypurine, a Lipophilic prodrug of 2′,3′-Dideoxyinosine
    • Doshi, K. J.; Boudinot, F. D.; Gallo, J. M.; Schinazi, R. F.; Chu, C. K. Brain Targeting of Anti-HIV Nucleosides: In Vitro and In Vivo Evaluation of 6-Chloro-2′,3′-dideoxypurine, a Lipophilic prodrug of 2′,3′-Dideoxyinosine. Antiviral Agents Chemother. 1994, 5, 304-311.
    • (1994) Antiviral Agents Chemother. , vol.5 , pp. 304-311
    • Doshi, K.J.1    Boudinot, F.D.2    Gallo, J.M.3    Schinazi, R.F.4    Chu, C.K.5
  • 39
    • 0029151512 scopus 로고
    • Enhanced Oral Bioavailability of ddI after Administration of 6-Cl-ddP, an Adenosine Deaminase-Activated Prodrug, to Chronically Catheterized Rats
    • Anderson, B. D.; Morgan, M. E.; Singhai, D. Enhanced Oral Bioavailability of ddI After Administration of 6-Cl-ddP, an Adenosine Deaminase-Activated Prodrug, to Chronically Catheterized Rats. Pharm. Res. 1995, 12, 1126-1133.
    • (1995) Pharm. Res. , vol.12 , pp. 1126-1133
    • Anderson, B.D.1    Morgan, M.E.2    Singhai, D.3
  • 40
    • 84989046002 scopus 로고
    • A Mechanism for Dehalogenation Reactions in Fast Atom Bombardment Mass Spectrometry
    • Musser, S. M.; Kelley, J. A. A Mechanism for Dehalogenation Reactions in Fast Atom Bombardment Mass Spectrometry. Org. Mass Spectrom. 1993, 28, 672-678.
    • (1993) Org. Mass Spectrom. , vol.28 , pp. 672-678
    • Musser, S.M.1    Kelley, J.A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.