Synthesis and evaluation of diverse thio avarol derivatives as potential UVB photoprotective candidates

被引：10

作者：

Amigo, Maria

Terencio, Maria C.

Paya, Miguel

Iodice, Carmine

De Rosa, Salvatore

机构：

[1] Univ Valencia, Fac Farm, Dept Farmacol, E-46100 Burjassot, Spain

[2] CNR, Ist Chim Biomol, I-80078 Naples, Italy

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2007年 / 17卷 / 09期

关键词：

keratinocytes; TNF-alpha; NF-kappa B; UVB; thio avarol; derivatives;

D O I：

10.1016/j.bmcl.2007.02.007

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Semisynthesis of 13 new thio avarol derivatives (4-16) and in vitro evaluation on the photodamage response induced by UVB irradiation are described. Their ability to inhibit NF-kappa B activation and TNF-alpha generation in HaCaT cells as well as their antioxidant capacity in human neutrophils has also been studied. Among them we have identified two monophenyl thio avarol derivatives (4-5) lacking cytotoxicity which can be considered promising UVB photoprotective agents through the potent inhibition of NF-kappa B activation with a mild antioxidant pharmacological profile. (c) 2007 Elsevier Ltd. All rights reserved.

引用

收藏

页码：2561 / 2565

页数：5

相关论文

共 34 条

[11]

De Rosa S, 2002, PR PHYT SOC, V47, P441

[12]

deRosa S., 1976, J CHEM SOC P1, P1408

[13] AVAROL AND AVARONE, 2 NEW ANTIINFLAMMATORY AGENTS OF MARINE ORIGIN [J].

FERRANDIZ, ML ;

SANZ, MJ ;

BUSTOS, G ;

PAYA, M ;

ALCARAZ, MJ ;

DEROSA, S .

EUROPEAN JOURNAL OF PHARMACOLOGY, 1994, 253 (1-2) :75-82

[14] Molecular basis of sun-induced premature skin ageing and retinoid antagonism [J].

Fisher, GJ ;

Datta, SC ;

Talwar, HS ;

Wang, ZQ ;

Varani, J ;

Kang, S ;

Voorhees, JJ .

NATURE, 1996, 379 (6563) :335-339

[15] Inflammation, gene mutation and photoimmunosuppression in response to UVR-induced oxidative damage contributes to photocarcinogenesis [J].

Halliday, GA .

MUTATION RESEARCH-FUNDAMENTAL AND MOLECULAR MECHANISMS OF MUTAGENESIS, 2005, 571 (1-2) :107-120

[16] Ultraviolet radiation and skin cancer: molecular mechanisms [J].

Hussein, MR .

JOURNAL OF CUTANEOUS PATHOLOGY, 2005, 32 (03) :191-205

[17] EFFECT OF TOPICALLY APPLIED TOCOPHEROL ON ULTRAVIOLET RADIATION-MEDIATED FREE-RADICAL DAMAGE IN SKIN [J].

JURKIEWICZ, BA ;

BISSETT, DL ;

BUETTNER, GR .

JOURNAL OF INVESTIGATIVE DERMATOLOGY, 1995, 104 (04) :484-488

[18] Fraxetin inhibits the induction of anti-Fas IgM, tumor necrosis factor-α and interleukin-1β-mediated apoptosis by Fas pathway inhibition in human osteoblastic cell line MG-63 [J].

Kuo, PL ;

Huang, YT ;

Chang, CH ;

Chang, JK .

INTERNATIONAL IMMUNOPHARMACOLOGY, 2006, 6 (07) :1167-1175

[19] FK506 inhibits tumour necrosis factor-α secretion in human keratinocytes via regulation of nuclear factor-κB [J].

Lan, CCE ;

Yu, HS ;

Wu, CS ;

Kuo, HY ;

Chai, CY ;

Chen, GS .

BRITISH JOURNAL OF DERMATOLOGY, 2005, 153 (04) :725-732

[20] Ultraviolet (UV) A- and UVB-induced redox alterations and activation of nuclear factor-κB in human melanocytes-protective effects of α-tocopherol [J].

Larsson, P. ;

Ollinger, K. ;

Rosdahl, I. .

BRITISH JOURNAL OF DERMATOLOGY, 2006, 155 (02) :292-300

← 1 2 3 4 →