Document Detail


(+)-Usnic acid enamines with remarkable cicatrizing properties.
MedLine Citation:
PMID:  23434134     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
Wound healing is a significant concern in many pathologies (post-surgeries, burns, scars) and the search for new chemical entities is advisable. The lichen compound (+)-usnic acid (1) has found application in dermatological and cosmetic preparations, due to its bacteriostatic and antioxidant activities. The compound has also been shown to stimulate the wound closure of keratinocyte monolayers at subtoxic doses. Here we describe the design and synthesis of usnic acid enamines (compounds 2-11), obtained through nucleophilic attack of amino acids or decarboxyamino acids at the acyl carbonyl of the enolized 1,3 diketone. The wound repair properties of these derivatives were evaluated using in vitro and in vivo assays. Compounds 8 and 9 combine low cytotoxicity with high wound healing performance, suggesting their possible use in wound healing-promoting or antiage skin preparations.
Authors:
Michela Bruno; Beatrice Trucchi; Bruno Burlando; Elia Ranzato; Simona Martinotti; Esra Küpeli Akkol; Ipek Süntar; Hikmet Keleş; Luisella Verotta
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2013-2-4
Journal Detail:
Title:  Bioorganic & medicinal chemistry     Volume:  -     ISSN:  1464-3391     ISO Abbreviation:  Bioorg. Med. Chem.     Publication Date:  2013 Feb 
Date Detail:
Created Date:  2013-2-25     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9413298     Medline TA:  Bioorg Med Chem     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Copyright Information:
Copyright © 2013 Elsevier Ltd. All rights reserved.
Affiliation:
Dipartimento di Chimica, Universita' degli Studi di Milano, via C. Golgi 19, 20133 Milano, Italy; Consorzio Interuniversitario Nazionale "Metodologie e Processi Innovativi di Sintesi", I-20133 Milano, Italy.
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