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Derivatization of honokiol by integrated acetylation and methylation for improved cutaneous delivery and anti-inflammatory potency.
Fang, Jia-You; Huang, Tse-Hung; Hung, Chi-Feng; Huang, Yu-Ling; Aljuffali, Ibrahim A; Liao, Wei-Chun; Lin, Chwan-Fwu.
Afiliación
  • Fang JY; Pharmaceutics Laboratory, Graduate Institute of Natural Products, Chang Gung University, Kweishan, Taoyuan, Taiwan; Research Center for Food and Cosmetic Safety and Research Center for Chinese Herbal Medicine, Chang Gung University of Science and Technology, Taoyuan, Taiwan; Department of Anesthesio
  • Huang TH; Department of Traditional Chinese Medicine, Chang Gung Memorial Hospital, Keelung, Taiwan; School of Traditional Chinese Medicine, Chang Gung University, Taoyuan, Taiwan; School of Nursing, National Taipei University of Nursing and Health Sciences, Taipei, Taiwan.
  • Hung CF; School of Medicine, Fu Jen Catholic University, Hsinchuang, New Taipei City, Taiwan.
  • Huang YL; National Research Institute of Chinese Medicine, Ministry of Health and Welfare, Taipei, Taiwan; Department of Cosmetic Science, Chang Gung University of Science and Technology, Kweishan, Taoyuan, Taiwan.
  • Aljuffali IA; Department of Pharmaceutics, College of Pharmacy, King Saud University, Riyadh, Saudi Arabia.
  • Liao WC; Pharmaceutics Laboratory, Graduate Institute of Natural Products, Chang Gung University, Kweishan, Taoyuan, Taiwan.
  • Lin CF; Research Center for Food and Cosmetic Safety and Research Center for Chinese Herbal Medicine, Chang Gung University of Science and Technology, Taoyuan, Taiwan; Department of Anesthesiology, Chang Gung Memorial Hospital, Linkou, Taoyuan, Taiwan; Department of Cosmetic Science, Chang Gung University o
Eur J Pharm Sci ; 114: 189-198, 2018 Mar 01.
Article en En | MEDLINE | ID: mdl-29241737
A set of honokiol derivatives was synthesized to evaluate skin permeation and bioactivity. The reaction for derivatization included acetylation and methylation. The anti-inflammatory activity against neutrophils and macrophages was examined. The experimental setup for the assessment of cutaneous absorption was the in vitro Franz diffusion assembly. Honokiol and its derivatives significantly downregulated superoxide anion and elastase production in neutrophils, with honokiol showing the greatest inhibition. All derivatives could be completely hydrolyzed to the parent compounds after passing into the skin. The skin deposition of honokiol at an infinite dose (3mM) was 0.33nmol/mg 4'-O-acetylhonokiol (AH), and 2,4'-diacetylhonokiol (DAH) exhibited comparable or less absorption than honokiol. The integrated acetylation and methylation (2-O-acetyl-4'-O-methylhonokiol, AMH) led to a 10.5-fold improvement of absorption compared to honokiol. AMH was advantageous for the targeted cutaneous treatment due to the high skin deposition and minimal penetration across the skin (8.40nmol/cm2 compared to 93.49nmol/cm2 for honokiol). The predicted therapeutic index for superoxide and interleukin (IL)-6 inhibition was much higher for topically applied AMH than for the other penetrants tested. The total polarity surface and hydrogen bond acceptor number calculated by molecular modeling were the parameters used to anticipate the cutaneous absorption. Our data suggest that AMH is a potent and safe candidate for cutaneous inflammation therapy.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Absorción Cutánea / Compuestos de Bifenilo / Sistemas de Liberación de Medicamentos / Lignanos / Antiinflamatorios Tipo de estudio: Prognostic_studies Límite: Animals / Female / Humans Idioma: En Revista: Eur J Pharm Sci Asunto de la revista: FARMACIA / FARMACOLOGIA / QUIMICA Año: 2018 Tipo del documento: Article Pais de publicación: Países Bajos
Texto completo
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Absorción Cutánea / Compuestos de Bifenilo / Sistemas de Liberación de Medicamentos / Lignanos / Antiinflamatorios Tipo de estudio: Prognostic_studies Límite: Animals / Female / Humans Idioma: En Revista: Eur J Pharm Sci Asunto de la revista: FARMACIA / FARMACOLOGIA / QUIMICA Año: 2018 Tipo del documento: Article Pais de publicación: Países Bajos