Carbon nanotubes supported tyrosinase in the synthesis of lipophilic hydroxytyrosol and dihydrocaffeoyl catechols with antiviral activity against DNA and RNA viruses

Giorgia Botta, Bruno Mattia Bizzarri, Adriana Garozzo, Rossella Timpanaro, Benedetta Bisignano, Donatella Amatore, Anna Teresa Palamara, Lucia Nencioni, Raffaele Saladino

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

Hydroxytyrosol and dihydrocaffeoyl catechols with lipophilic properties have been synthesized in high yield using tyrosinase immobilized on multi-walled carbon nanotubes by the Layer-by-Layer technique. All synthesized catechols were evaluated against a large panel of DNA and RNA viruses, including Poliovirus type 1, Echovirus type 9, Herpes simplex virus type 1 (HSV-1), Herpes simplex virus type 2 (HSV-2), Coxsackievirus type B3 (Cox B3), Adenovirus type 2 and type 5 and Cytomegalovirus (CMV). A significant antiviral activity was observed in the inhibition of HSV-1, HSV-2, Cox B3 and CMV. The mechanism of action of the most active dihydrocaffeoyl derivative was investigated against a model of HSV-1 infection.

Original languageEnglish
Pages (from-to)5345-5351
Number of pages7
JournalBioorganic and Medicinal Chemistry
Volume23
Issue number17
DOIs
Publication statusPublished - Sep 1 2015

Fingerprint

Catechols
Carbon Nanotubes
DNA Viruses
Monophenol Monooxygenase
RNA Viruses
Human Herpesvirus 1
Viruses
Antiviral Agents
Human Herpesvirus 2
Enterovirus
RNA
Cytomegalovirus
Echovirus 9
DNA
Poliovirus
Virus Diseases
Adenoviridae
3,4-dihydroxyphenylethanol
Derivatives

Keywords

  • Antiviral activity
  • Catechols
  • Dihydrocaffeoyl derivatives
  • DNA and RNA viruses
  • Hydroxytyrosol derivatives

ASJC Scopus subject areas

  • Biochemistry
  • Clinical Biochemistry
  • Molecular Biology
  • Molecular Medicine
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science

Cite this

Carbon nanotubes supported tyrosinase in the synthesis of lipophilic hydroxytyrosol and dihydrocaffeoyl catechols with antiviral activity against DNA and RNA viruses. / Botta, Giorgia; Bizzarri, Bruno Mattia; Garozzo, Adriana; Timpanaro, Rossella; Bisignano, Benedetta; Amatore, Donatella; Palamara, Anna Teresa; Nencioni, Lucia; Saladino, Raffaele.

In: Bioorganic and Medicinal Chemistry, Vol. 23, No. 17, 01.09.2015, p. 5345-5351.

Research output: Contribution to journalArticle

Botta, Giorgia ; Bizzarri, Bruno Mattia ; Garozzo, Adriana ; Timpanaro, Rossella ; Bisignano, Benedetta ; Amatore, Donatella ; Palamara, Anna Teresa ; Nencioni, Lucia ; Saladino, Raffaele. / Carbon nanotubes supported tyrosinase in the synthesis of lipophilic hydroxytyrosol and dihydrocaffeoyl catechols with antiviral activity against DNA and RNA viruses. In: Bioorganic and Medicinal Chemistry. 2015 ; Vol. 23, No. 17. pp. 5345-5351.
@article{dd4a331efd884ffc9038835380c199da,
title = "Carbon nanotubes supported tyrosinase in the synthesis of lipophilic hydroxytyrosol and dihydrocaffeoyl catechols with antiviral activity against DNA and RNA viruses",
abstract = "Hydroxytyrosol and dihydrocaffeoyl catechols with lipophilic properties have been synthesized in high yield using tyrosinase immobilized on multi-walled carbon nanotubes by the Layer-by-Layer technique. All synthesized catechols were evaluated against a large panel of DNA and RNA viruses, including Poliovirus type 1, Echovirus type 9, Herpes simplex virus type 1 (HSV-1), Herpes simplex virus type 2 (HSV-2), Coxsackievirus type B3 (Cox B3), Adenovirus type 2 and type 5 and Cytomegalovirus (CMV). A significant antiviral activity was observed in the inhibition of HSV-1, HSV-2, Cox B3 and CMV. The mechanism of action of the most active dihydrocaffeoyl derivative was investigated against a model of HSV-1 infection.",
keywords = "Antiviral activity, Catechols, Dihydrocaffeoyl derivatives, DNA and RNA viruses, Hydroxytyrosol derivatives",
author = "Giorgia Botta and Bizzarri, {Bruno Mattia} and Adriana Garozzo and Rossella Timpanaro and Benedetta Bisignano and Donatella Amatore and Palamara, {Anna Teresa} and Lucia Nencioni and Raffaele Saladino",
year = "2015",
month = "9",
day = "1",
doi = "10.1016/j.bmc.2015.07.061",
language = "English",
volume = "23",
pages = "5345--5351",
journal = "Bioorganic and Medicinal Chemistry",
issn = "0968-0896",
publisher = "Elsevier Limited",
number = "17",

}

TY - JOUR

T1 - Carbon nanotubes supported tyrosinase in the synthesis of lipophilic hydroxytyrosol and dihydrocaffeoyl catechols with antiviral activity against DNA and RNA viruses

AU - Botta, Giorgia

AU - Bizzarri, Bruno Mattia

AU - Garozzo, Adriana

AU - Timpanaro, Rossella

AU - Bisignano, Benedetta

AU - Amatore, Donatella

AU - Palamara, Anna Teresa

AU - Nencioni, Lucia

AU - Saladino, Raffaele

PY - 2015/9/1

Y1 - 2015/9/1

N2 - Hydroxytyrosol and dihydrocaffeoyl catechols with lipophilic properties have been synthesized in high yield using tyrosinase immobilized on multi-walled carbon nanotubes by the Layer-by-Layer technique. All synthesized catechols were evaluated against a large panel of DNA and RNA viruses, including Poliovirus type 1, Echovirus type 9, Herpes simplex virus type 1 (HSV-1), Herpes simplex virus type 2 (HSV-2), Coxsackievirus type B3 (Cox B3), Adenovirus type 2 and type 5 and Cytomegalovirus (CMV). A significant antiviral activity was observed in the inhibition of HSV-1, HSV-2, Cox B3 and CMV. The mechanism of action of the most active dihydrocaffeoyl derivative was investigated against a model of HSV-1 infection.

AB - Hydroxytyrosol and dihydrocaffeoyl catechols with lipophilic properties have been synthesized in high yield using tyrosinase immobilized on multi-walled carbon nanotubes by the Layer-by-Layer technique. All synthesized catechols were evaluated against a large panel of DNA and RNA viruses, including Poliovirus type 1, Echovirus type 9, Herpes simplex virus type 1 (HSV-1), Herpes simplex virus type 2 (HSV-2), Coxsackievirus type B3 (Cox B3), Adenovirus type 2 and type 5 and Cytomegalovirus (CMV). A significant antiviral activity was observed in the inhibition of HSV-1, HSV-2, Cox B3 and CMV. The mechanism of action of the most active dihydrocaffeoyl derivative was investigated against a model of HSV-1 infection.

KW - Antiviral activity

KW - Catechols

KW - Dihydrocaffeoyl derivatives

KW - DNA and RNA viruses

KW - Hydroxytyrosol derivatives

UR - http://www.scopus.com/inward/record.url?scp=84946488941&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84946488941&partnerID=8YFLogxK

U2 - 10.1016/j.bmc.2015.07.061

DO - 10.1016/j.bmc.2015.07.061

M3 - Article

C2 - 26260341

AN - SCOPUS:84946488941

VL - 23

SP - 5345

EP - 5351

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

SN - 0968-0896

IS - 17

ER -