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Tyrosinase and Layer-by-Layer supported tyrosinases in the synthesis of lipophilic catechols with antiinfluenza activity.

Catechol derivatives with lipophilic properties have been selectively synthesized by tyrosinase in high yield avoiding long and tedious protection/deprotection steps usually required in traditional procedures. The synthesis was effective also with immobilized tyrosinase able to perform for more runs... Full description

Journal Title: Bioorganic & medicinal chemistry December 15, 2013, Vol.21(24), pp.7699-7708
Main Author: Bozzini, Tiziana
Other Authors: Botta, Giorgia , Delfino, Michela , Onofri, Silvano , Saladino, Raffaele , Amatore, Donatella , Sgarbanti, Rossella , Nencioni, Lucia , Palamara, Anna Teresa
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: E-ISSN: 1464-3391 ; DOI: 10.1016/j.bmc.2013.10.026
Link: http://search.proquest.com/docview/1464907332/?pq-origsite=primo
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title: Tyrosinase and Layer-by-Layer supported tyrosinases in the synthesis of lipophilic catechols with antiinfluenza activity.
format: Article
creator:
  • Bozzini, Tiziana
  • Botta, Giorgia
  • Delfino, Michela
  • Onofri, Silvano
  • Saladino, Raffaele
  • Amatore, Donatella
  • Sgarbanti, Rossella
  • Nencioni, Lucia
  • Palamara, Anna Teresa
subjects:
  • Animals–Chemistry
  • Antioxidants–Metabolism
  • Antiviral Agents–Pharmacology
  • Catechols–Chemistry
  • Chickens–Metabolism
  • Dogs–Pharmacology
  • Dose-Response Relationship, Drug–Chemistry
  • Epithelial Cells–Metabolism
  • Erythrocytes–Pharmacology
  • Humans–Drug Effects
  • Hydrophobic and Hydrophilic Interactions–Virology
  • Influenza A Virus–Drug Effects
  • Microbial Sensitivity Tests–Virology
  • Monophenol Monooxygenase–Drug Effects
  • Oxidation-Reduction–Metabolism
  • Structure-Activity Relationship–Metabolism
  • Antioxidants
  • Antiviral Agents
  • Catechols
  • Monophenol Monooxygenase
ispartof: Bioorganic & medicinal chemistry, December 15, 2013, Vol.21(24), pp.7699-7708
description: Catechol derivatives with lipophilic properties have been selectively synthesized by tyrosinase in high yield avoiding long and tedious protection/deprotection steps usually required in traditional procedures. The synthesis was effective also with immobilized tyrosinase able to perform for more runs. The novel catechols were evaluated against influenza A virus, that continue to represent a severe threat worldwide. A significant antiviral activity was observed in derivatives characterized by antioxidant activity and long carbon alkyl side-chains, suggesting the possibility of a new inhibition mechanism based on both redox and lipophilic properties. ; p. 7699-7708.
language: eng
source:
identifier: E-ISSN: 1464-3391 ; DOI: 10.1016/j.bmc.2013.10.026
fulltext: fulltext
issn:
  • 14643391
  • 1464-3391
url: Link


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titleTyrosinase and Layer-by-Layer supported tyrosinases in the synthesis of lipophilic catechols with antiinfluenza activity.
creatorBozzini, Tiziana ; Botta, Giorgia ; Delfino, Michela ; Onofri, Silvano ; Saladino, Raffaele ; Amatore, Donatella ; Sgarbanti, Rossella ; Nencioni, Lucia ; Palamara, Anna Teresa
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ispartofBioorganic & medicinal chemistry, December 15, 2013, Vol.21(24), pp.7699-7708
identifierE-ISSN: 1464-3391 ; DOI: 10.1016/j.bmc.2013.10.026
subjectAnimals–Chemistry ; Antioxidants–Metabolism ; Antiviral Agents–Pharmacology ; Catechols–Chemistry ; Chickens–Metabolism ; Dogs–Pharmacology ; Dose-Response Relationship, Drug–Chemistry ; Epithelial Cells–Metabolism ; Erythrocytes–Pharmacology ; Humans–Drug Effects ; Hydrophobic and Hydrophilic Interactions–Virology ; Influenza A Virus–Drug Effects ; Microbial Sensitivity Tests–Virology ; Monophenol Monooxygenase–Drug Effects ; Oxidation-Reduction–Metabolism ; Structure-Activity Relationship–Metabolism ; Antioxidants ; Antiviral Agents ; Catechols ; Monophenol Monooxygenase
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descriptionCatechol derivatives with lipophilic properties have been selectively synthesized by tyrosinase in high yield avoiding long and tedious protection/deprotection steps usually required in traditional procedures. The synthesis was effective also with immobilized tyrosinase able to perform for more runs. The novel catechols were evaluated against influenza A virus, that continue to represent a severe threat worldwide. A significant antiviral activity was observed in derivatives characterized by antioxidant activity and long carbon alkyl side-chains, suggesting the possibility of a new inhibition mechanism based on both redox and lipophilic properties. ; p. 7699-7708.
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