A multi-targeted drug candidate with dual anti-HIV and anti-HSV activity

PLoS Pathog. 2013;9(7):e1003456. doi: 10.1371/journal.ppat.1003456. Epub 2013 Jul 25.

Abstract

Human immunodeficiency virus (HIV) infection is often accompanied by infection with other pathogens, in particular herpes simplex virus type 2 (HSV-2). The resulting coinfection is involved in a vicious circle of mutual facilitations. Therefore, an important task is to develop a compound that is highly potent against both viruses to suppress their transmission and replication. Here, we report on the discovery of such a compound, designated PMEO-DAPym. We compared its properties with those of the structurally related and clinically used acyclic nucleoside phosphonates (ANPs) tenofovir and adefovir. We demonstrated the potent anti-HIV and -HSV activity of this drug in a diverse set of clinically relevant in vitro, ex vivo, and in vivo systems including (i) CD4⁺ T-lymphocyte (CEM) cell cultures, (ii) embryonic lung (HEL) cell cultures, (iii) organotypic epithelial raft cultures of primary human keratinocytes (PHKs), (iv) primary human monocyte/macrophage (M/M) cell cultures, (v) human ex vivo lymphoid tissue, and (vi) athymic nude mice. Upon conversion to its diphosphate metabolite, PMEO-DAPym markedly inhibits both HIV-1 reverse transcriptase (RT) and HSV DNA polymerase. However, in striking contrast to tenofovir and adefovir, it also acts as an efficient immunomodulator, inducing β-chemokines in PBMC cultures, in particular the CCR5 agonists MIP-1β, MIP-1α and RANTES but not the CXCR4 agonist SDF-1, without the need to be intracellularly metabolized. Such specific β-chemokine upregulation required new mRNA synthesis. The upregulation of β-chemokines was shown to be associated with a pronounced downmodulation of the HIV-1 coreceptor CCR5 which may result in prevention of HIV entry. PMEO-DAPym belongs conceptually to a new class of efficient multitargeted antivirals for concomitant dual-viral (HSV/HIV) infection therapy through inhibition of virus-specific pathways (i.e. the viral polymerases) and HIV transmission prevention through interference with host pathways (i.e. CCR5 receptor down regulation).

Publication types

  • Research Support, N.I.H., Intramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-HIV Agents / pharmacology
  • Anti-HIV Agents / therapeutic use
  • Antiviral Agents / pharmacology*
  • Antiviral Agents / therapeutic use
  • CD4-Positive T-Lymphocytes / drug effects
  • CD4-Positive T-Lymphocytes / immunology
  • CD4-Positive T-Lymphocytes / virology
  • Cells, Cultured
  • Female
  • HIV / drug effects*
  • HIV / enzymology
  • HIV / immunology
  • Herpes Simplex / drug therapy
  • Herpes Simplex / immunology
  • Herpes Simplex / metabolism
  • Herpes Simplex / virology
  • Herpesvirus 1, Human / drug effects*
  • Herpesvirus 1, Human / enzymology
  • Herpesvirus 1, Human / immunology
  • Herpesvirus 2, Human / drug effects*
  • Herpesvirus 2, Human / enzymology
  • Herpesvirus 2, Human / immunology
  • Humans
  • Immunologic Factors / pharmacology
  • Immunologic Factors / therapeutic use
  • Leukocytes, Mononuclear / cytology
  • Leukocytes, Mononuclear / drug effects
  • Leukocytes, Mononuclear / immunology
  • Leukocytes, Mononuclear / virology
  • Lymphoid Tissue / drug effects
  • Lymphoid Tissue / immunology
  • Lymphoid Tissue / metabolism
  • Lymphoid Tissue / virology
  • Mice
  • Mice, Hairless
  • Mice, Nude
  • Nucleic Acid Synthesis Inhibitors / pharmacology*
  • Nucleic Acid Synthesis Inhibitors / therapeutic use
  • Organophosphonates / pharmacology*
  • Organophosphonates / therapeutic use
  • Prodrugs / pharmacology
  • Prodrugs / therapeutic use
  • Pyrimidines / pharmacology*
  • Pyrimidines / therapeutic use
  • Reverse Transcriptase Inhibitors / pharmacology
  • Reverse Transcriptase Inhibitors / therapeutic use
  • Tissue Culture Techniques

Substances

  • 6-phosphonylmethoxyethoxy-2,4-diaminopyrimidine
  • Anti-HIV Agents
  • Antiviral Agents
  • Immunologic Factors
  • Nucleic Acid Synthesis Inhibitors
  • Organophosphonates
  • Prodrugs
  • Pyrimidines
  • Reverse Transcriptase Inhibitors