Prodrugs of Phosphates and Phosphonates

Adefovir Dipivoxil for the Treatment of Hepatitis B e Antigen–Positive Chronic Hepatitis B

Marcellin, P., Chang, T.-T., Lim, S. G., Tong, M. J., Sievert, W., Shiffman, M. L., Jeffers, L., Goodman, Z., Wulfsohn, M. S., Xiong, S., et al. (2003) · New England Journal of Medicine · doi:10.1056/nejmoa020681 · Cited by 1,336

Enzymes involved in the bioconversion of ester-based prodrugs

Liederer, B. M., & Borchardt, R. T. (2006) · Journal of Pharmaceutical Sciences · doi:10.1002/jps.20542 · Cited by 377

Selective Intracellular Activation of a Novel Prodrug of the Human Immunodeficiency Virus Reverse Transcriptase Inhibitor Tenofovir Leads to Preferential Distribution and Accumulation in Lymphatic Tissue

Lee, W. A., He, G.-X., Eisenberg, E., Cihlar, T., Swaminathan, S., Mulato, A., & Cundy, K. C. (2005) · Antimicrobial Agents and Chemotherapy · doi:10.1128/aac.49.5.1898-1906.2005 · Cited by 338

Targeting thyroid hormone receptor-β agonists to the liver reduces cholesterol and triglycerides and improves the therapeutic index

Erion, M. D., Cable, E. E., Ito, B. R., Jiang, H., Fujitaki, J. M., Finn, P. D., Zhang, B.-H., Hou, J., Boyer, S. H., van Poelje, P. D., et al. (2007) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0702759104 · Cited by 271

Pronucleotides: Toward thein vivo delivery of antiviral and anticancer nucleotides

Wagner, C. R., Iyer, V. V., & McIntee, E. J. (2000) · Medicinal Research Reviews · doi:10.1002/1098-1128(200011)20:6<417::aid-med1>3.0.co;2-z · Cited by 265

Prodrugs of biologically active phosphate esters

Schultz, C. (2003) · Bioorganic & Medicinal Chemistry · doi:10.1016/s0968-0896(02)00552-7 · Cited by 216

Cathepsin A Is the Major Hydrolase Catalyzing the Intracellular Hydrolysis of the Antiretroviral Nucleotide Phosphonoamidate Prodrugs GS-7340 and GS-9131

Birkus, G., Wang, R., Liu, X., Kutty, N., MacArthur, H., Cihlar, T., Gibbs, C., Swaminathan, S., Lee, W., & McDermott, M. (2007) · Antimicrobial Agents and Chemotherapy · doi:10.1128/aac.00968-06 · Cited by 172

Design, Synthesis, and Characterization of a Series of Cytochrome P4503A-Activated Prodrugs (HepDirect Prodrugs) Useful for Targeting Phosph(on)ate-Based Drugs to the Liver§

Erion, M. D., Reddy, K. R., Boyer, S. H., Matelich, M. C., Gomez-Galeno, J., Lemus, R. H., Ugarkar, B. G., Colby, T. J., Schanzer, J., & van Poelje, P. D. (2004) · Journal of the American Chemical Society · doi:10.1021/ja031818y · Cited by 165

MB06322 (CS-917): A potent and selective inhibitor of fructose 1,6-bisphosphatase for controlling gluconeogenesis in type 2 diabetes

Erion, M. D., van Poelje, P. D., Dang, Q., Kasibhatla, S. R., Potter, S. C., Reddy, M. R., Reddy, K. R., Jiang, T., & Lipscomb, W. N. (2005) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0502983102 · Cited by 162

Prodrugs : challenges and rewards

Stella, V. J. (2007) · Cited by 153

Theory and practice of site-specific drug delivery

Tomlinson, E. (1987) · Advanced Drug Delivery Reviews · doi:10.1016/0169-409x(87)90001-9 · Cited by 148

Pivalate-Generating Prodrugs and Carnitine Homeostasis in Man

Brass, E. P. (2002) · Pharmacological Reviews · doi:10.1124/pr.54.4.589 · Cited by 136

Liver-Targeted Drug Delivery Using HepDirect Prodrugs

Erion, M. D., van Poelje, P. D., MacKenna, D. A., Colby, T. J., Montag, A. C., Fujitaki, J. M., Linemeyer, D. L., & Bullough, D. A. (2005) · Journal of Pharmacology and Experimental Therapeutics · doi:10.1124/jpet.104.075903 · Cited by 119

Synthesis and antiretroviral activity of phospholipid analogs of azidothymidine and other antiviral nucleosides.

Hostetler, K. Y., Stuhmiller, L. M., Lenting, H. B. M., van den BOSCH, H., & Richman, D. D. (1990) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(19)39299-3 · Cited by 110

Diaryl ester prodrugs of fR900098 with improved in vivo antimalarial activity

Reichenberg, A., Wiesner, J., Weidemeyer, C., Dreiseidler, E., Sanderbrand, S., Altincicek, B., Beck, E., Schlitzer, M., & Jomaa, H. (2001) · Bioorganic & Medicinal Chemistry Letters · doi:10.1016/s0960-894x(01)00075-0 · Cited by 106

Mechanism of anti-HIV action of masked alaninyl d4T-MP derivatives.

Balzarini, J. M., Karlsson, A., Aquaro, S., Perno, C. F., Cahard, D., Naesens, L. M. J., Clercq, E. D., & McGuigan, C. (1996) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.93.14.7295 · Cited by 105

Discovery of Potent and Specific Fructose-1,6-Bisphosphatase Inhibitors and a Series of Orally-Bioavailable Phosphoramidase-Sensitive Prodrugs for the Treatment of Type 2 Diabetes

Dang, Q., Kasibhatla, S. R., Reddy, K. R., Jiang, T., Reddy, M. R., Potter, S. C., Fujitaki, J. M., van Poelje, P. D., Huang, J., Lipscomb, W. N., et al. (2007) · Journal of the American Chemical Society · doi:10.1021/ja074871l · Cited by 103

Application of Phosphoramidate Pronucleotide Technology to Abacavir Leads to a Significant Enhancement of Antiviral Potency

McGuigan, C., Harris, S., Daluge, S. M., Gudmundsson, K. S., McLean, E. W., Burnette, T. C., Marr, H. B., Hazen, R. J., Condreay, L. D., Johnson, L. C., et al. (2005) · Journal of Medicinal Chemistry · doi:10.1021/jm0491400 · Cited by 93

Phosphoramidate Pronucleotides: A Comparison of the Phosphoramidase Substrate Specificity of Human and Escherichia coli Histidine Triad Nucleotide Binding Proteins

Chou, T., Baraniak, J., Kaczmarek, R., Zhou, X. E., Cheng, J., Ghosh, B. K., & Wagner, C. R. (2007) · Molecular Pharmaceutics · doi:10.1021/mp060070y · Cited by 92

Synthesis and Cell-Based Activity of a Potent and Selective Protein Tyrosine Phosphatase 1B Inhibitor Prodrug

Boutselis, I. G., Yu, X., Zhang, Z., & Borch, R. F. (2007) · Journal of Medicinal Chemistry · doi:10.1021/jm061146x · Cited by 80

Addressing Metabolic Activation as an Integral Component of Drug Design

Doss, G. A., & Baillie, T. A. (2006) · Drug Metabolism Reviews · doi:10.1080/03602530600959466 · Cited by 72

Synthesis and Biological Studies of Novel Nucleoside Phosphoramidate Prodrugs

Tobias, S. C., & Borch, R. F. (2001) · Journal of Medicinal Chemistry · doi:10.1021/jm010337r · Cited by 69

Synthesis and anti-HIV activity of some haloalkyl phosphoramidate derivatives of 3′-azido-3′-deoxythymidine (AZT): potent activity of the trichloroethyl methoxyalaninyl compound

McGuigan, C., Devine, K. G., OʼConnor, T. J., & Kinchington, D. (1991) · Antiviral Research · doi:10.1016/0166-3542(91)90071-x · Cited by 62

Synthesis and Evaluation of Nitroheterocyclic Phosphoramidates as Hypoxia-Selective Alkylating Agents

Borch, R. F., Liu, J., Schmidt, J. P., Marakovits, J. T., Joswig, C., Gipp, J. J., & Mulcahy, R. T. (2000) · Journal of Medicinal Chemistry · doi:10.1021/jm0001020 · Cited by 61

Application of Phosphoramidate ProTide Technology Significantly Improves Antiviral Potency of Carbocyclic Adenosine Derivatives

McGuigan, C., Hassan-Abdallah, A., Srinivasan, S., Wang, Y., Siddiqui, A. Q., Daluge, S. M., Gudmundsson, K. S., Zhou, H., McLean, E. W., Peckham, J., et al. (2006) · Journal of Medicinal Chemistry · doi:10.1021/jm060776w · Cited by 61

Effect of ER-27856, a novel squalene synthase inhibitor, on plasma cholesterol in rhesus monkeys: comparison with 3-hydroxy-3-methylglutaryl-CoA reductase inhibitors

Hiyoshi, H., Yanagimachi, M., Ito, M., Ohtsuka, I., Yoshida, I., Saeki, T., & TANAKA, H. L. (2000) · Journal of Lipid Research · doi:10.1016/s0022-2275(20)32020-4 · Cited by 61

Design and Synthesis of Lipophilic Phosphoramidate d4T-MP Prodrugs Expressing High Potency Against HIV in Cell Culture: Structural Determinants for in Vitro Activity and QSAR

Siddiqui, A. Q., McGuigan, C., Ballatore, C., Zuccotto, F., Gilbert, I. H., Clercq, E. D., & Balzarini, J. M. (1999) · Journal of Medicinal Chemistry · doi:10.1021/jm9807104 · Cited by 57

Synthesis and Biological Evaluation of a Cytarabine Phosphoramidate Prodrug

Tobias, S. C., & Borch, R. F. (2003) · Molecular Pharmaceutics · doi:10.1021/mp034019v · Cited by 45

Decomposition Pathways of the Mono- and Bis(Pivaloyloxymethyl) Esters of Azidothymidine 5′-Monophosphate in Cell Extract and in Tissue Culture Medium: An Application of the ‘on-line ISRP-Cleaning’ HPLC Technique

Pompon, A., Lefèbvre, I., Imbach, J., Kahn, S., & Farquhar, D. (1994) · Antiviral chemistry & chemotherapy · doi:10.1177/095632029400500205 · Cited by 45

Synthesis and Characterization of a Novel Liver-Targeted Prodrug of Cytosine-1-β- d -arabinofuranoside Monophosphate for the Treatment of Hepatocellular Carcinoma

Boyer, S. H., Sun, Z., Jiang, H., Esterbrook, J., Gomez‐Galeno, J., Craigo, W. A., Reddy, K. R., Ugarkar, B. G., MacKenna, D. A., & Erion, M. D. (2006) · Journal of Medicinal Chemistry · doi:10.1021/jm0607449 · Cited by 43

Metabolism of Stavudine-5′-[p-Bromophenyl Methoxyalaninyl Phosphate], Stampidine, in Mice, Dogs, and Cats

Chen, C., Yu, G., Venkatachalam, T. K., & Uckun, F. M. (2002) · Drug Metabolism and Disposition · doi:10.1124/dmd.30.12.1523 · Cited by 31

Phase II Placebo-Controlled Trial of Fozivudine Tidoxil for HIV Infection: Pharmacokinetics, Tolerability, and Efficacy

Girard, P., Pegram, P. S., Diquet, B., Anderson, R. D., Raffi, F., Tubiana, R., Séréni, D., & Boerner, D. (2000) · JAIDS Journal of Acquired Immune Deficiency Syndromes · doi:10.1097/00042560-200003010-00003 · Cited by 27

Synthesis and anti-HIV Activity of Some Novel Phosphorodiamidate Derivatives of 3′-azido-3′-deoxythymidine (AZT)

Jones, B. C. N. M., McGuigan, C., O'Connor, T. J., Jeffries, D. J., & Kinchington, D. (1991) · Antiviral chemistry & chemotherapy · doi:10.1177/095632029100200106 · Cited by 27

Participation of the peroxisomal β-oxidation system in the chain-shortening of PCA16, a metabolite of the cytosine arabinoside prodrug, YNKO1, in rat liver

Yoshida, Y., Yamada, J., Watanabe, T., et al. (1990) · Biochemical Pharmacology · doi:10.1016/0006-2952(90)90514-l · Cited by 26

Synthesis, Biochemical, and Cellular Evaluation of Farnesyl Monophosphate Prodrugs as Farnesyltransferase Inhibitors

Clark, M. K., Scott, S. A., Wojtkowiak, J. W., D'Angelo, R. C., Mathieu, P., Reiners, J. J., Mattingly, R. R., Borch, R. F., & Gibbs, R. A. (2007) · Journal of Medicinal Chemistry · doi:10.1021/jm0701829 · Cited by 24

Synthesis, Bioactivation and Anti-HIV Activity of 4-Acyloxybenzylbis(Nucleosid-5′-yl) Phosphates

Routledge, A., Walker, I., Freeman, S., Hay, A. J., & Mahmood, N. (1995) · Nucleosides and Nucleotides · doi:10.1080/15257779508009491 · Cited by 24

Kinase bypass: A new strategy for anti-HIV drug design

McGuigan, C., Kinchington, D., Nicholls, S. R., Nickson, C., & OʼConnor, T. J. (1993) · Bioorganic & Medicinal Chemistry Letters · doi:10.1016/s0960-894x(00)80316-9 · Cited by 20

Non-peptidic inhibitors of neutral endopeptidase 24.11 2. Design and pharmacology of orally active phosphonate prodrugs

Lombaer, S. D., Blanchard, L., Berry, C., Ghai, R., & Trapani, A. (1995) · Bioorganic & Medicinal Chemistry Letters · doi:10.1016/0960-894x(94)00475-u · Cited by 20

Human Immunodeficiency Virus Resistance to AZT in MOLT4/8 Cells is Associated with a Lack of AZT Phosphorylation and is Bypassed by AZT-Monophosphate SATE Prodrugs

Cinatl, J. J., Gröschel, B., Zehner, R., Cinatl, J. J., Périgaud, C., Gosselin, G., Imbach, J., & Hw, D. (1997) · Antiviral chemistry & chemotherapy · doi:10.1177/095632029700800407 · Cited by 18

DDC- and 3TC-bis(SATE) Monophosphate Prodrugs Overcome Cellular Resistance Mechanisms to HIV-1 Associated with Cytidine Kinase Deficiency

Gröschel, B., HIMMEL, N., Cinatl, J. J., Périgaud, C., Gosselin, G., Imbach, J., Doerr, H. W., & Cinatl, J. J. (1999) · Nucleosides and Nucleotides · doi:10.1080/15257779908041600 · Cited by 13

Prodrugs for Liver-targeted Drug Delivery

Erion, M. D. (2007) · Springer eBooks · doi:10.1007/978-0-387-49785-3_16 · Cited by 10

Therapeutic Targeting of Oncogenic K‐Ras by a Covalent Catalytic Site Inhibitor

Lim, S. M., Westover, K. D., Ficarro, S. B., Harrison, R. A., Choi, H. G., Pacold, M. E., Carrasco, M., Hunter, J., Kim, N. D., Xie, T., et al. (2014) · Angewandte Chemie International Edition · doi:10.1002/anie.201307387 · Cited by 300

The Role of the Phosphorus Atom in Drug Design

Rodriguez, J. B., & Gallo‐Rodriguez, C. (2019) · ChemMedChem · doi:10.1002/cmdc.201800693 · Cited by 267

A potent phosphodiester Keap1-Nrf2 protein-protein interaction inhibitor as the efficient treatment of Alzheimer's disease

Sun, Y., Xu, L., Zheng, D., Wang, J., Liu, G., Mo, Z., Liu, C., Zhang, W., Yu, J., Xing, C., et al. (2023) · Redox Biology · doi:10.1016/j.redox.2023.102793 · Cited by 54

PDE6D Inhibitors with a New Design Principle Selectively Block K-Ras Activity

Siddiqui, F. A., Alam, C., Rosenqvist, P., Ora, M., Sabt, A., Manoharan, G. B., Bindu, L., Okutachi, S., Catillon, M., Taylor, T., et al. (2020) · ACS Omega · doi:10.1021/acsomega.9b03639 · Cited by 46