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

doi:10.1016/j.bmcl.2015.05.099

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 journal › Article › peer-review

23 Scopus citations

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 language	English (US)
Article number	22789
Pages (from-to)	3168-3171
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	25
Issue number	16
DOIs	https://doi.org/10.1016/j.bmcl.2015.05.099
State	Published - Jul 3 2015
Externally published	Yes

Bibliographical note

Funding Information:
HZ acknowledges support by the Henry Dreyfus Teacher-Scholar Award (2012), NIH MBRS-RISE grant ( 1R25GM096956 ), NIH NIBIB contract award ( HHSN268201200011C ), and National Natural Science Foundation of China – China ( 21328601 ). RJV acknowledges the support of Mercer University School of Medicine.

Publisher Copyright:
© 2015 Elsevier Ltd.

Keywords

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

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.bmcl.2015.05.099

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

Research output: Contribution to journal › Article › peer-review

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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.",

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AU - Zhang, Xiugen

AU - Arumugam, Sri Ranjini

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

Abstract

Bibliographical note

Keywords

UN SDGs

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