(+)-Usnic acid enamines with remarkable cicatrizing properties

被引：38

作者：

Bruno, Michela ^{[1
,2
]}

Trucchi, Beatrice ^{[1
,2
]}

Burlando, Bruno ^{[3
]}

Ranzato, Elia ^{[3
]}

Martinotti, Simona ^{[3
]}

Akkol, Esra Kupeli ^{[4
]}

Suntar, Ipek ^{[4
]}

Keles, Hikmet ^{[5
]}

Verotta, Luisella ^{[1
,2
]}

机构：

[1] Univ Milan, Dipartimento Chim, I-20133 Milan, Italy

[2] Consorzio Interuniv Nazl Metodol & Proc Innovat S, I-20133 Milan, Italy

[3] Univ Piemonte Orientale, Dipartimento Sci & Innovaz Tecnol, I-15121 Alessandria, Italy

[4] Gazi Univ, Fac Pharm, Dept Pharmacognosy, TR-06330 Ankara, Turkey

[5] Afyon Kocatepe Univ, Fac Vet Med, Dept Pathol, TR-03200 Afyon, Turkey

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2013年 / 21卷 / 07期

关键词：

(+)-Usnic acid; Mannich bases; Scratch wound assay; In vivo wound healing assays; Wound healing therapy; HUMAN DERMAL FIBROBLASTS; USNIC ACID; HACAT KERATINOCYTES; ELASTASE ACTIVITY; NATURAL-PRODUCTS; LICHEN; RATS; EXTRACT; AGENTS; MICE;

D O I：

10.1016/j.bmc.2013.01.045

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：

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. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：1834 / 1843

页数：10

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