The clinical potential of the acyclic (and cyclic) nucleoside phosphonates. The magic of the phosphonate bond

被引:102
作者
De Clercq, Erik [1 ]
机构
[1] Katholieke Univ Leuven, Dept Microbiol & Immunol, Rega Inst Med Res, B-3000 Louvain, Belgium
关键词
Antiviral; Phosphonate; Nucleotide; HEPATITIS-B-VIRUS; ANTIVIRAL ACTIVITY; IN-VITRO; INTRACELLULAR METABOLISM; NUCLEOTIDE ANALOG; DNA-POLYMERASE; SELECTIVE INHIBITOR; ADEFOVIR DIPIVOXIL; ESTER PRODRUGS; HIV-INFECTION;
D O I
10.1016/j.bcp.2011.03.027
中图分类号
R9 [药学];
学科分类号
1007 ;
摘要
The use of the acyclic nucleoside phosphonates, starting with (S)-HPMPA as the prototype, yielded three clinically approved antiviral drugs, cidofovir for the treatment of CMV retinitis in AIDS patients, adefovir dipivoxil for the treatment of chronic hepatitis B and tenofovir disoproxil fumarate for the treatment of HIV infections (AIDS) and HBV infections. This era has now grown to many more acyclic (and cyclic) nucleoside phosphonates (such as the "open ring" DAPy and Fd4A phosphonates) and alkoxyalkyl and phosphonoamidate prodrugs thereof, as well as new clinical applications, including new drug combination regimens for the treatment of AIDS, the chemoprophylaxis of HIV infections, and the anticancer potential against some malignant disorders. (C) 2011 Elsevier Inc. All rights reserved.
引用
收藏
页码:99 / 109
页数:11
相关论文
共 76 条
[1]   Antiretrovirus activity of a novel class of acyclic pyrimidine nucleoside phosphonates [J].
Balzarini, J ;
Pannecouque, C ;
De Clercq, E ;
Aquaro, S ;
Perno, CF ;
Egberink, H ;
Holy, A .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 2002, 46 (07) :2185-2193
[2]   INTRACELLULAR METABOLISM AND MECHANISM OF ANTIRETROVIRUS ACTION OF 9-(2-PHOSPHONYLMETHOXYETHYL)ADENINE, A POTENT ANTI-HUMAN-IMMUNODEFICIENCY-VIRUS COMPOUND [J].
BALZARINI, J ;
ZHANG, H ;
HERDEWIJN, P ;
JOHNS, DG ;
DECLERCQ, E .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1991, 88 (04) :1499-1503
[3]   DIFFERENTIAL ANTIHERPESVIRUS AND ANTIRETROVIRUS EFFECTS OF THE (S) AND (R) ENANTIOMERS OF ACYCLIC NUCLEOSIDE PHOSPHONATES - POTENT AND SELECTIVE INVITRO AND INVIVO ANTIRETROVIRUS ACTIVITIES OF (R)-9-(2-PHOSPHONOMETHOXYPROPYL)-2,6-DIAMINOPURINE [J].
BALZARINI, J ;
HOLY, A ;
JINDRICH, J ;
NAESENS, L ;
SNOECK, R ;
SCHOLS, D ;
DECLERCQ, E .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1993, 37 (02) :332-338
[4]   9-[(2RS)-3-FLUORO-2-PHOSPHONYLMETHOXYPROPYL] DERIVATIVES OF PURINES - A CLASS OF HIGHLY SELECTIVE ANTIRETROVIRAL AGENTS INVITRO AND INVIVO [J].
BALZARINI, J ;
HOLY, A ;
JINDRICH, J ;
DVORAKOVA, H ;
HAO, Z ;
SNOECK, R ;
HERDEWIJN, P ;
JOHNS, DG ;
DECLERCQ, E .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1991, 88 (11) :4961-4965
[5]   Synthesis and antiviral evaluation of alkoxyalkyl derivatives of 9-(S)-(3-hydroxy-2-phosphonomethoxypropyl)adenine against cytomegalovirus and orthopoxviruses [J].
Beadle, JR ;
Wan, WB ;
Ciesla, SL ;
Keith, KA ;
Hartline, C ;
Kern, ER ;
Hostetler, KY .
JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (06) :2010-2015
[6]   Design and profiling of GS-9148, a novel nucleotide analog active against nucleoside-resistant variants of human immunodeficiency virus type 1, and its orally bioavailable phosphonoamidate prodrug, GS-9131 [J].
Cihlar, Tomas ;
Ray, Adrian S. ;
Boojamra, Constantine G. ;
Zhang, Lijun ;
Hui, Hon ;
Laflamme, Genevieve ;
Vela, Jennifer E. ;
Grant, Deborah ;
Chen, James ;
Myrick, Florence ;
White, Kirsten L. ;
Gao, Ying ;
Lin, Kuei-Ying ;
Douglas, Janet L. ;
Parkin, Neil T. ;
Carey, Anne ;
Pakdaman, Rowchanak ;
Mackman, Richard L. .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 2008, 52 (02) :655-665
[7]   Nucleoside and nucleotide HIV reverse transcriptase inhibitors: 25 years after zidovudine [J].
Cihlar, Tomas ;
Ray, Adrian S. .
ANTIVIRAL RESEARCH, 2010, 85 (01) :39-58
[8]   Novel Nucleotide Human Immunodeficiency Virus Reverse Transcriptase Inhibitor GS-9148 with a Low Nephrotoxic Potential: Characterization of Renal Transport and Accumulation [J].
Cihlar, Tomas ;
LaFlamme, Genevieve ;
Fisher, Robyn ;
Carey, Anne C. ;
Vela, Jennifer E. ;
Mackman, Richard ;
Ray, Adrian S. .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 2009, 53 (01) :150-156
[9]   ORAL BIOAVAILABILITY OF THE ANTIRETROVIRAL AGENT 9-(2-PHOSPHONYLMETHOXYETHYL)ADENINE (PMEA) FROM 3-FORMULATIONS OF THE PRODRUG BIS(PIVALOYLOXYMETHYL)-PMEA IN FASTED MALE CYNOMOLGUS MONKEYS [J].
CUNDY, KC ;
FISHBACK, JA ;
SHAW, JP ;
LEE, ML ;
SOIKE, KF ;
VISOR, GC ;
LEE, WA .
PHARMACEUTICAL RESEARCH, 1994, 11 (06) :839-843
[10]   Large plantar wart caused by human papillomavirus-66 and resolution by topical cidofovir therapy [J].
Davis, MDP ;
Gostout, BS ;
McGovern, RM ;
Persing, DH ;
Schut, RL ;
Pittelkow, MR .
JOURNAL OF THE AMERICAN ACADEMY OF DERMATOLOGY, 2000, 43 (02) :340-343