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

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2015年 / 23卷 / 17期

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

页码：5345 / 5351

页数：7

共 60 条

[11]

DECHER G, 1992, PROG COLL POL SCI S, V89, P160

[12] Fuzzy nanoassemblies: Toward layered polymeric multicomposites [J].

Decher, G .

SCIENCE, 1997, 277 (5330) :1232-1237

[13] RAPID COLORIMETRIC ASSAY FOR CELL-GROWTH AND SURVIVAL - MODIFICATIONS TO THE TETRAZOLIUM DYE PROCEDURE GIVING IMPROVED SENSITIVITY AND RELIABILITY [J].

DENIZOT, F ;

LANG, R .

JOURNAL OF IMMUNOLOGICAL METHODS, 1986, 89 (02) :271-277

[14] Effects of polyphenol compounds on influenza A virus replication and definition of their mechanism of action [J].

Fioravanti, Rossella ;

Celestino, Ignacio ;

Costi, Roberta ;

Crucitti, Giuliana Cuzzucoli ;

Pescatori, Luca ;

Mattiello, Leonardo ;

Novellino, Ettore ;

Checconi, Paola ;

Palamara, Anna Teresa ;

Nencioni, Lucia ;

Di Santo, Roberto .

BIOORGANIC & MEDICINAL CHEMISTRY, 2012, 20 (16) :5046-5052

[15] Structure-Based Evaluation of C5 Derivatives in the Catechol Diether Series Targeting HIV-1 Reverse Transcriptase [J].

Frey, Kathleen M. ;

Gray, William T. ;

Spasov, Krasimir A. ;

Bollini, Mariela ;

Gallardo-Macias, Ricardo ;

Jorgensen, William L. ;

Anderson, Karen S. .

CHEMICAL BIOLOGY & DRUG DESIGN, 2014, 83 (05) :541-549

[16] Antirhinovirus activity of 3-methylthio-5-aryl-4-isothiazolecarbonitrile derivatives [J].

Garozzo, A ;

Cutrì, CCC ;

Castro, A ;

Tempera, G ;

Guerrera, F ;

Sarvà, MC ;

Geremia, E .

ANTIVIRAL RESEARCH, 2000, 45 (03) :199-210

[17] Anti-tyrosinase, antioxidant and antimicrobial activities of hydroxycinnamoylamides [J].

Georgiev, Lyubomir ;

Chochkova, Maya ;

Totseva, Iskra ;

Seizova, Katya ;

Marinova, Emma ;

Ivanova, Galya ;

Ninova, Mariana ;

Najdenski, Hristo ;

Milkova, Tsenka .

MEDICINAL CHEMISTRY RESEARCH, 2013, 22 (09) :4173-4182

[18] Catechols from abietic acid:: Synthesis and evaluation as bioactive compounds [J].

Gigante, B ;

Santos, C ;

Silva, AM ;

Curto, MJM ;

Nascimento, MSJ ;

Pinto, E ;

Pedro, M ;

Cerqueira, F ;

Pinto, MM ;

Duarte, MP ;

Laires, A ;

Rueff, J ;

Gonçalves, J ;

Pegado, MI ;

Valdeira, ML .

BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (08) :1631-1638

[19]

Haslam E, 1993, Shikimic Acid: Metabolism and Metabolites

[20] Hispolon from Phellinus linteus possesses mediate caspases activation and induces human nasopharyngeal carcinomas cells apoptosis through ERK1/2, JNK1/2 and p38 MAPK pathway [J].

Hsieh, Ming-Ju ;

Chien, Su-Yu ;

Chou, Ying-Erh ;

Cheng, Chih-Jung ;

Chen, Judy ;

Chen, Mu-Kuan .

PHYTOMEDICINE, 2014, 21 (12) :1746-1752

← 1 2 3 4 5 6 →