Lipoxin A4

Names

[ Name ]:
Lipoxin A4

[Synonym ]:
LIPOXIN A
Lipoxin A4
LXA
(5S,6R,7E,9E,11Z,13E,15S)-5,6,15-Trihydroxy-7,9,11,13-icosatetraenoic acid
LXA4
5S,6R,15S-trihydroxy-7,9,13-trans-11-cis-eicosatetraenoic acid
7,9,11,13-Eicosatetraenoic acid, 5,6,15-trihydroxy-, (5S,6R,7E,9E,11Z,13E,15S)-

Biological Activity

[Description]:

Lipoxin A4 (LXA4), an endogenous lipoxygenase-derived eicosanoid mediator, has potent dual pro-resolving and anti-inflammatory properties[1]. Lipoxin A4 inhibits proliferation and inflammatory cytokine/chemokine production of human epidermal keratinocytes (NHEKs) associated with the ERK1/2 and NF-kB pathways[2]. Lipoxin A4 inhibits serum amyloid A (SAA)-mediated IL-8 release with an IC50 value of 25.74 nM[3].

[Related Catalog]:

Signaling Pathways >> Immunology/Inflammation >> Interleukin Related

Research Areas >> Inflammation/Immunology

[In Vitro]

Lipoxin A4 (LXA4) inhibits the expression of IL-6 and IL-8 in NHEKs[2]. Lipoxin A4 downregulates the expression of cyclin D1[2]. Lipoxin A4 also suppresses the ERK1/2 phosphorylation and NF-kB-p65 nuclear translocation of NHEKs[2]. LXA4 (100 nM; preincubation for 30 minutes)inhibits the proliferation of NHEKs with or without stimulating by LPS (10 μg/mL)[2]. LXA4 pretreatment (100 nM for 30 minutes) downregulates the LPS-induced secretion and expression of HMGB1 in keratinocytes[1]. Cell Proliferation Assay[2] Cell Line: Normal human epidermal keratinocytes (NHEKs) Concentration: 100 nM Incubation Time: 30 minutes Result: A significant increase in proliferation of NHEKs after 7 days of stimulation with LPS (10 μg/mL) was seen. However, there was a significant decrease in the proliferation of NHEKs when pretreated with LXA4 for 30 min. Western Blot Analysis[1] Cell Line: Normal human epidermal keratinocytes (NHEKs) Concentration: 100 nM Incubation Time: 30 minutes. Result: HMGB1 protein levels in the cytoplasm of NHEKs were induced by LPS, which were decreased after preincubation with LXA4 but decreased in the nucleus after stimulation with LPS.

[References]

[1]. Feng Hu, et al. Lipoxin A4 inhibits proliferation and inflammatory cytokine/chemokine production of human epidermal keratinocytes associated with the ERK1/2 and NF-κB pathways. J Dermatol Sci. 2015 Jun;78(3):181-8.

[2]. Steven Bozinovski, et al. Serum amyloid A opposes lipoxin A₄ to mediate glucocorticoid refractory lung inflammation in chronic obstructive pulmonary disease. Proc Natl Acad Sci U S A. 2012 Jan 17;109(3):935-40.

[3]. Xinxin Liu, et al. Lipoxin A4 and its analog suppress inflammation by modulating HMGB1 translocation and expression in psoriasis.Sci Rep. 2017 Aug 2;7(1):7100.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
589.4±50.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₀H₃₂O₅

[ Molecular Weight ]:
352.47

[ Flash Point ]:
324.3±26.6 °C

[ Exact Mass ]:
352.224976

[ PSA ]:
97.99000

[ LogP ]:
2.43

[ Vapour Pressure ]:
0.0±3.8 mmHg at 25°C

[ Index of Refraction ]:
1.541

Safety Information

[ Symbol ]:

GHS02, GHS07

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H225-H319

[ Precautionary Statements ]:
P210-P280-P305 + P351 + P338-P337 + P313-P403 + P235

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face respirator (US);Gloves;multi-purpose combination respirator cartridge (US);type ABEK (EN14387) respirator filter

[ Hazard Codes ]:
F: Flammable;

[ Risk Phrases ]:
11

[ Safety Phrases ]:
7-16

[ RIDADR ]:
UN 1170 3/PG 2

[ HS Code ]:
2918199090

Customs

[ HS Code ]: 2918199090

[ Summary ]:
2918199090 other carboxylic acids with alcohol function but without other oxygen function, their anhydrides, halides, peroxides, peroxyacids and their derivatives。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:6.5%。General tariff:30.0%

Articles

HMDB: a knowledgebase for the human metabolome.

Nucleic Acids Res. 37(Database issue) , D603-10, (2009)

The Human Metabolome Database (HMDB, http://www.hmdb.ca) is a richly annotated resource that is designed to address the broad needs of biochemists, clinical chemists, physicians, medical geneticists, ...

The human serum metabolome.

PLoS ONE 6(2) , e16957, (2011)

Continuing improvements in analytical technology along with an increased interest in performing comprehensive, quantitative metabolic profiling, is leading to increased interest pressures within the m...

Protective effects of n-6 fatty acids-enriched diet on intestinal ischaemia/reperfusion injury involve lipoxin A4 and its receptor.

Br. J. Pharmacol. 172(3) , 910-23, (2015)

Long-term intake of dietary fatty acids is known to predispose to chronic inflammation, but their effects on acute intestinal ischaemia/reperfusion (I/R) injury is unknown. The aim of this study was t...

Related Compounds

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