(+)-Usnic acid enamines with remarkable cicatrizing properties

Bruno M., Trucchi B., Burlando B., Ranzato E., Martinotti S., AKKOL E., ...Daha Fazla

BIOORGANIC & MEDICINAL CHEMISTRY, cilt.21, sa.7, ss.1834-1843, 2013 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 21 Sayı: 7
  • Basım Tarihi: 2013
  • Doi Numarası: 10.1016/j.bmc.2013.01.045
  • Dergi Adı: BIOORGANIC & MEDICINAL CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.1834-1843
  • Anahtar Kelimeler: (+)-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
  • Gazi Üniversitesi Adresli: Evet

Özet

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.