Overview of Biologically Active Nucleoside Phosphonates

被引：43
作者：
Groaz, Elisabetta [1 ]
De Jonghe, Steven [2 ]
机构：
[1] Katholieke Univ Leuven, Rega Inst Med Res, Med Chem, Leuven, Belgium
[2] Katholieke Univ Leuven, Rega Inst Med Res, Lab Virol & Chemotherapy, Leuven, Belgium
来源：
FRONTIERS IN CHEMISTRY | 2021年 / 8卷
关键词：
nucleoside phosphonate; antivirals; anticancer drugs; antibacterials; antiparasitic agents; purinergic signaling; HEPATITIS-B-VIRUS; TENOFOVIR DISOPROXIL FUMARATE; HYPOXANTHINE-GUANINE PHOSPHORIBOSYLTRANSFERASE; REVERSE-TRANSCRIPTASE INHIBITOR; ACYCLIC NUCLEOTIDE ANALOGS; DNA-POLYMERASES ALPHA; ANTIVIRAL ACTIVITY; PLASMODIUM-FALCIPARUM; IN-VITRO; SELECTIVE INHIBITORS;
D O I：
10.3389/fchem.2020.616863
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The use of the phosphonate motif featuring a carbon-phosphorous bond as bioisosteric replacement of the labile P-O bond is widely recognized as an attractive structural concept in different areas of medicinal chemistry, since it addresses the very fundamental principles of enzymatic stability and minimized metabolic activation. This review discusses the most influential successes in drug design with special emphasis on nucleoside phosphonates and their prodrugs as antiviral and cancer treatment agents. A description of structurally related analogs able to interfere with the transmission of other infectious diseases caused by pathogens like bacteria and parasites will then follow. Finally, molecules acting as agonists/antagonists of P2X and P2Y receptors along with nucleotidase inhibitors will also be covered. This review aims to guide readers through the fundamentals of nucleoside phosphonate therapeutics in order to inspire the future design of molecules to target infections that are refractory to currently available therapeutic options.
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页数：29
相关论文
共 189 条
[1]   Efficacy and Safety of Besifovir Dipivoxil Maleate Compared With Tenofovir Disoproxil Fumarate in Treatment of Chronic Hepatitis B Virus Infection [J].
Ahn, Sang Hoon ;
Kim, Won ;
Jung, Young Kul ;
Yang, Jin Mo ;
Jang, Jae Young ;
Kweon, Yong Oh ;
Cho, Yong Kyun ;
Kim, Yoon Jun ;
Hong, Gun Young ;
Kim, Dong Joon ;
Um, Soon Ho ;
Sohn, Joo Hyun ;
Lee, Jin Woo ;
Park, Sung Jae ;
Lee, Byung Seok ;
Kim, Ju Hyun ;
Kim, Hong Soo ;
Yoon, Seung Kew ;
Kim, Moon Young ;
Yim, Hyung Joon ;
Lee, Kwan Sik ;
Lim, Young Suk ;
Lee, Wan Sik ;
Park, Neung Hwa ;
Jin, So Young ;
Kim, Kyun-Hwan ;
Choi, Won ;
Han, Kwang-Hyub .
CLINICAL GASTROENTEROLOGY AND HEPATOLOGY, 2019, 17 (09) :1850-+
[2]   Increased antiviral activity of 1-O-hexadecyloxypropyl-[ 2-14C] cidofovir in MRC-5 human lung fibroblasts is explained by unique cellular uptake and metabolism [J].
Aldern, KA ;
Ciesla, SL ;
Winegarden, KL ;
Hostetler, KY .
MOLECULAR PHARMACOLOGY, 2003, 63 (03) :678-681
[3]  
Andrei G, 1998, ONCOL RES, V10, P523
[4]   COMPARATIVE ACTIVITY OF SELECTED ANTIVIRAL COMPOUNDS AGAINST CLINICAL ISOLATES OF HUMAN CYTOMEGALOVIRUS [J].
ANDREI, G ;
SNOECK, R ;
SCHOLS, D ;
GOUBAU, P ;
DESMYTER, J ;
DECLERCQ, E .
EUROPEAN JOURNAL OF CLINICAL MICROBIOLOGY & INFECTIOUS DISEASES, 1991, 10 (12) :1026-1033
[5]  
Andrei G, 1998, ONCOL RES, V10, P533
[6]   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
[7]   6-[2-phosphonomethoxy)alkoxy]-2,4-diaminopyrimidines:: A new class of acyclic pyrimidine nucleoside phosphonates with antiviral activity [J].
Balzarini, J ;
Pannecouque, C ;
Naesens, L ;
Andrei, G ;
Snoeck, R ;
De Clercq, E ;
Hocková, D ;
Holy, A .
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2004, 23 (8-9) :1321-1327
[8]   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
[9]   Pronounced in vitro and in vivo antiretroviral activity of 5-substituted 2,4-diamino-6-[2-(phosphonomethoxy)ethoxy] pyrimidines [J].
Balzarini, Jan ;
Schols, Dominique ;
Van Laethem, Kristel ;
De Clercq, Erik ;
Hockova, Dana ;
Masojidkova, Milina ;
Holy, Antonin .
JOURNAL OF ANTIMICROBIAL CHEMOTHERAPY, 2007, 59 (01) :80-86
[10]   Guanine α-carboxy nucleoside phosphonate (G-α-CNP) shows a different inhibitory kinetic profile against the DNA polymerases of human immunodeficiency virus (HIV) and herpes viruses [J].
Balzarini, Jan ;
Menni, Michael ;
Das, Kalyan ;
van Berckelaer, Lizette ;
Ford, Alan ;
Maguire, Nuala M. ;
Liekens, Sandra ;
Boehmer, Paul E. ;
Arnold, Eddy ;
Gotte, Matthias ;
Maguire, Anita R. .
BIOCHEMICAL PHARMACOLOGY, 2017, 136 :51-61
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