Synthesis and Protective Effects of Bis{4-[N,N-di-(carboxymethyl)amino]phenoxy}alkane Derivatives on UVA-Induced Production of MMP-1 in Human Skin Fibroblasts

UV-induced matrix metalloproteinase (MMP) production is considered a cause of skin aging. In this study, a number of novel bis{4-[N,N-di-(carboxymethyl)amino]phenoxy}alkane derivatives were synthesized and evaluated as UVA-protective agents. These compounds significantly protected human dermal fibro...

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Bibliographic Details
Published inChemical & pharmaceutical bulletin Vol. 62; no. 9; pp. 867 - 874
Main Authors Hsu, Ling-Yih, Nien, Chih-Ying, Huang, Wei-Ming, Hsu, Shou-Che, Chang, Tsu-Chung
Format Journal Article
LanguageEnglish
Japanese
Published TOKYO The Pharmaceutical Society of Japan 01.09.2014
Pharmaceutical Society of Japan
Pharmaceutical Soc Japan
Japan Science and Technology Agency
Subjects
Alkanes - pharmacology
Cells, Cultured
Chemistry
Chemistry, Medicinal
Chemistry, Multidisciplinary
dermal fibroblast
Humans
Life Sciences & Biomedicine
Matrix Metalloproteinase 1 - biosynthesis
metal chelating agent
Pharmacology & Pharmacy
Physical Sciences
Proton Magnetic Resonance Spectroscopy
Science & Technology
Skin - drug effects
Skin - enzymology
Skin - radiation effects
Spectrometry, Mass, Electrospray Ionization
ultraviolet irradiation
Ultraviolet Rays
UVA-protective agent
MATRIX METALLOPROTEINASES
CELLS
ACTIVATION
MEMBRANE
metal chelating agent
ultraviolet irradiation
UVA-protective agent
dermal fibroblast
ULTRAVIOLET-LIGHT
RADIATION
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Summary:UV-induced matrix metalloproteinase (MMP) production is considered a cause of skin aging. In this study, a number of novel bis{4-[N,N-di-(carboxymethyl)amino]phenoxy}alkane derivatives were synthesized and evaluated as UVA-protective agents. These compounds significantly protected human dermal fibroblast (HDF) cells from UVA-induced cytotoxicity and inhibited MMP-1 activation and expression with potency comparable to desferoxamine (DFO). Promoter activity assay indicated that they inhibited MMP-1 expression at the transcriptional level. Further studies revealed that the mechanism of these compounds may include blockage of the UVA-induced activation of the p38/mitogen-activated protein kinase (MAPK) and c-Jun N-terminal kinase (JNK) pathways. Together, these results suggest that further development of these compounds may be of interest.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.c14-00071