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

被引:33
作者
Botta, Giorgia [1 ]
Bizzarri, Bruno Mattia [1 ]
Garozzo, Adriana [2 ]
Timpanaro, Rossella [2 ]
Bisignano, Benedetta [2 ]
Amatore, Donatella [3 ,4 ]
Palamara, Anna Teresa [3 ,4 ]
Nencioni, Lucia [3 ]
Saladino, Raffaele [1 ]
机构
[1] Univ Tuscia, Dept Ecol & Biol, I-01100 Viterbo, VT, Italy
[2] Univ Catania CT, Microbiol Sect, Dept Biomed & Biotechnol Sci, I-95124 Catania, Italy
[3] Univ Roma La Sapienza, Dept Publ Hlth & Infect Dis, I-00185 Rome, Italy
[4] Telemat Univ, IRCCS San Raffaele Pisana, I-00166 Rome, Italy
关键词
Antiviral activity; Catechols; Hydroxytyrosol derivatives; Dihydrocaffeoyl derivatives; DNA and RNA viruses; ROSMARINIC ACID; ANTIOXIDANT; DERIVATIVES; OIL; REPLICATION; INHIBITION; ACTIVATION; BEHAVIOR; SERIES;
D O I
10.1016/j.bmc.2015.07.061
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
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. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5345 / 5351
页数:7
相关论文
共 60 条
[1]  
[Anonymous], INT J PHARM BIO SCI
[2]   Naturally Occurring Hydroxytyrosol Derivatives: Hydroxytyrosyl Acetate and 3,4-Dihydroxyphenylglycol Modulate Inflammatory Response in Murine Peritoneal Macrophages. Potential Utility as New Dietary Supplements [J].
Aparicio-Soto, Marina ;
Sanchez-Fidalgo, Susana ;
Gonzalez-Benjumea, Alejandro ;
Maya, Ines ;
Fernandez-Bolanos, Jose G. ;
Alarcon-de-la-Lastra, Catalina .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2015, 63 (03) :836-846
[3]   Layer-by-layer Nanoarchitectonics: Invention, Innovation, and Evolution [J].
Ariga, Katsuhiko ;
Yamauchi, Yusuke ;
Rydzek, Gaulthier ;
Ji, Qingmin ;
Yonamine, Yusuke ;
Wu, Kevin C. -W. ;
Hill, Jonathan P. .
CHEMISTRY LETTERS, 2014, 43 (01) :36-68
[4]   Water-soluble carbon nanotube-enzyme conjugates as functional biocatalytic formulations [J].
Asuri, Prashanth ;
Karajanagi, Sandeep S. ;
Sellitto, Edward ;
Kim, Dae-Yun ;
Kane, Ravi S. ;
Dordick, Jonathan S. .
BIOTECHNOLOGY AND BIOENGINEERING, 2006, 95 (05) :804-811
[5]   Tyrosinase and Layer-by-Layer supported tyrosinases in the synthesis of lipophilic catechols with antiinfluenza activity [J].
Bozzini, Tiziana ;
Botta, Giorgia ;
Delfino, Michela ;
Onofri, Silvano ;
Saladino, Raffaele ;
Amatore, Donatella ;
Sgarbanti, Rossella ;
Nencioni, Lucia ;
Palamara, Anna Teresa .
BIOORGANIC & MEDICINAL CHEMISTRY, 2013, 21 (24) :7699-7708
[6]   In vitro inhibition of herpes simplex virus type 1 replication by Mentha suaveolens essential oil and its main component piperitenone oxide [J].
Civitelli, Livia ;
Panella, Simona ;
Marcocci, Maria Elena ;
De Petris, Alberto ;
Garzoli, Stefania ;
Pepi, Federico ;
Vavala, Elisabetta ;
Ragno, Rino ;
Nencioni, Lucia ;
Palamara, Anna Teresa ;
Angiolella, Letizia .
PHYTOMEDICINE, 2014, 21 (06) :857-865
[7]   Antiepileptogenic, antioxidant and genotoxic evaluation of rosmarinic acid and its metabolite caffeic acid in mice [J].
Coelho, Vanessa Rodrigues ;
Vieira, Caroline Goncalves ;
de Souza, Luana Pereira ;
Moyses, Felipe ;
Basso, Carla ;
Mausolff Papke, Debora Kuck ;
Pires, Thienne Rocha ;
Siqueira, Ionara Rodrigues ;
Picada, Jaqueline Nascimento ;
Pereira, Patricia .
LIFE SCIENCES, 2015, 122 :65-71
[8]   Polyelectrolyte multilayered assemblies in biomedical technologies [J].
Costa, Rui R. ;
Mano, Joao F. .
CHEMICAL SOCIETY REVIEWS, 2014, 43 (10) :3453-3479
[9]  
Cutrí CCC, 1998, BIOORGAN MED CHEM, V6, P2271, DOI 10.1016/S0968-0896(98)00179-5
[10]   Synthesis of new phenolic fatty acid esters and their evaluation as lipophilic antioxidants in an oil matrix [J].
de Pinedo, A. Torres ;
Penalver, P. ;
Perez-Victoria, I. ;
Rondon, D. ;
Morales, J. C. .
FOOD CHEMISTRY, 2007, 105 (02) :657-665