Ionic derivatives of betulinic acid exhibit antiviral activity against herpes simplex virus type-2 (HSV-2), but not HIV-1 reverse transcriptase

Robert J. Visalli, Hannah Ziobrowski, Kameswara R. Badri, Johnny J. He, Xiugen Zhang, Sri Ranjini Arumugam, Hua Zhao

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Abstract Betulinic acid (1) has been modified to ionic derivatives (2-5) to improve its water solubility and biological activities. The binding properties of these derivatives with respect to human serum albumin (HSA) was examined and found to be similar to current anti-HIV drugs. These compounds did not inhibit HIV reverse transcriptase, however, 1, 2 and 5 inhibited herpes simplex type 2 (HSV-2) replication at concentrations similar to those reported for acyclovir (IC50 ∼0.1-10 μM) and with minimal cellular cytotoxicity. IC50 values for antiviral activity against HSV-2 186 were 1.6, 0.6, 0.9, 7.2, and 0.9 μM for compounds 1-5, respectively.

Original languageEnglish
Article number22789
Pages (from-to)3168-3171
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume25
Issue number16
DOIs
StatePublished - 3 Jul 2015

Fingerprint

Human Herpesvirus 2
Viruses
Inhibitory Concentration 50
Antiviral Agents
Derivatives
Anti-HIV Agents
Herpes Simplex
Acyclovir
Cytotoxicity
Virus Replication
Bioactivity
Serum Albumin
Solubility
Water
Human immunodeficiency virus 1 reverse transcriptase
betulinic acid
1-(2-(3-methoxyphenyl)ethyl)phenoxy-3-(dimethylamino)-2-propanol

Keywords

  • Betulinic acid
  • HIV-1 reverse transcriptase
  • Herpes simplex type 2 (HSV-2)
  • Inhibitor

Cite this

Visalli, Robert J. ; Ziobrowski, Hannah ; Badri, Kameswara R. ; He, Johnny J. ; Zhang, Xiugen ; Arumugam, Sri Ranjini ; Zhao, Hua. / Ionic derivatives of betulinic acid exhibit antiviral activity against herpes simplex virus type-2 (HSV-2), but not HIV-1 reverse transcriptase. In: Bioorganic and Medicinal Chemistry Letters. 2015 ; Vol. 25, No. 16. pp. 3168-3171.
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Ionic derivatives of betulinic acid exhibit antiviral activity against herpes simplex virus type-2 (HSV-2), but not HIV-1 reverse transcriptase. / Visalli, Robert J.; Ziobrowski, Hannah; Badri, Kameswara R.; He, Johnny J.; Zhang, Xiugen; Arumugam, Sri Ranjini; Zhao, Hua.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 25, No. 16, 22789, 03.07.2015, p. 3168-3171.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Ionic derivatives of betulinic acid exhibit antiviral activity against herpes simplex virus type-2 (HSV-2), but not HIV-1 reverse transcriptase

AU - Visalli, Robert J.

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AU - He, Johnny J.

AU - Zhang, Xiugen

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AU - Zhao, Hua

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N2 - Abstract Betulinic acid (1) has been modified to ionic derivatives (2-5) to improve its water solubility and biological activities. The binding properties of these derivatives with respect to human serum albumin (HSA) was examined and found to be similar to current anti-HIV drugs. These compounds did not inhibit HIV reverse transcriptase, however, 1, 2 and 5 inhibited herpes simplex type 2 (HSV-2) replication at concentrations similar to those reported for acyclovir (IC50 ∼0.1-10 μM) and with minimal cellular cytotoxicity. IC50 values for antiviral activity against HSV-2 186 were 1.6, 0.6, 0.9, 7.2, and 0.9 μM for compounds 1-5, respectively.

AB - Abstract Betulinic acid (1) has been modified to ionic derivatives (2-5) to improve its water solubility and biological activities. The binding properties of these derivatives with respect to human serum albumin (HSA) was examined and found to be similar to current anti-HIV drugs. These compounds did not inhibit HIV reverse transcriptase, however, 1, 2 and 5 inhibited herpes simplex type 2 (HSV-2) replication at concentrations similar to those reported for acyclovir (IC50 ∼0.1-10 μM) and with minimal cellular cytotoxicity. IC50 values for antiviral activity against HSV-2 186 were 1.6, 0.6, 0.9, 7.2, and 0.9 μM for compounds 1-5, respectively.

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