0000000000141412

AUTHOR

Maria Amigó

showing 6 related works from this author

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

2007

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-kappaB 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-kappaB activation with a mild antioxidant pharmacological profile.

AntioxidantMagnetic Resonance SpectroscopyNeutrophilsPhotochemistryUltraviolet Raysmedicine.medical_treatmentChemistry PharmaceuticalClinical BiochemistryMolecular ConformationPharmaceutical ScienceThio-BiochemistryChemical synthesisAntioxidantsCell Line TumorDrug DiscoverymedicineHumansCytotoxicityMolecular Biologyintegumentary systemChemistryTumor Necrosis Factor-alphaOrganic ChemistryNF-kappa BSemisynthesisIn vitroHaCaTmedicine.anatomical_structureBiochemistryModels ChemicalDrug DesignMolecular MedicineKeratinocyteReactive Oxygen SpeciesSesquiterpenesBioorganicmedicinal chemistry letters
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Synthesis of potentially anti-inflammatory IPL576,092-contignasterol and IPL576,092-manoalide hybrids

2004

The synthesis of two potentially anti-inflammatory steroidal hybrid compounds has been accomplished through a 16- and 17-step sequence, respectively, starting from commercially available androst-5-en-3β-ol-17-one. The synthetic strategies are based both on stereoselective side chains elaboration and high yielding functional group transformations.

Contignasterolmedicine.drug_classStereochemistryOrganic ChemistryBiochemistryHigh yieldingCombinatorial chemistryAnti-inflammatoryManoalidechemistry.chemical_compoundchemistryDrug DiscoverymedicineStereoselectivityTetrahedron
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Antipsoriatic effects of avarol-3′-thiosalicylate are mediated by inhibition of TNF-αgeneration and NF-κB activation in mouse skin

2007

Background and purpose: Avarol is a marine sesquiterpenoid hydroquinone with anti-inflammatory and antipsoriatic properties. The aim of this study was to evaluate the in vitro and in vivo pharmacological behaviour of the derivative avarol-3′-thiosalicylate (TA) on some inflammatory parameters related to the pathogenesis of psoriasis. Experimental approach: Human neutrophils and monocytes as well as the human keratinocyte cell line HaCaT were used to study the effect of TA on oxidative stress, the arachidonic acid pathway, tumour necrosis factor-α (TNF-α) release and nuclear factor-κB (NF-κB) activation. All these parameters were also determined in vivo using the zymosan induced mouse air po…

Pharmacologymedicine.medical_specialtyLeukotriene B4ZymosanPharmacologyBiologyNFKB1HaCaTchemistry.chemical_compoundmedicine.anatomical_structureEndocrinologyEicosanoidchemistryIn vivoInternal medicinemedicineTumor necrosis factor alphaKeratinocyteBritish Journal of Pharmacology
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Identification of avarol derivatives as potential antipsoriatic drugs using an in vitro model for keratinocyte growth and differentiation.

2006

Contains fulltext : 49512schalkwijk.pdf (Publisher’s version ) (Closed access) Avarol, a marine sesquiterpenoid hydroquinone, and 14 avarol derivatives have shown interesting anti-inflammatory properties in previous studies. In this study, avarol and derivatives were evaluated in high-throughput keratinocyte culture models using cytokeratin 10 and SKALP/Elafin expression as markers for respectively normal and psoriatic differentiation. Avarol and five of its derivatives (5, 10, 13, 14 and 15) were selected for further study. Only 10, 13, 14 and 15 were able to inhibit keratinocyte cell growth. Changes in expression levels of 22 genes were assessed by quantitative real time PCR (qPCR). From …

KeratinocytesDrug Evaluation PreclinicalAntineoplastic AgentsEnzyme-Linked Immunosorbent AssayIn Vitro TechniquesBiologyGeneral Biochemistry Genetics and Molecular BiologyDownregulation and upregulationTranslational research [ONCOL 3]DysideaGene expressionDithranolmedicineAnimalsHumansPsoriasisRNA MessengerGeneral Pharmacology Toxicology and PharmaceuticsCells CulturedCell ProliferationChronic inflammation and autoimmunity [UMCN 4.2]Messenger RNATumor Necrosis Factor-alphaCell growthInterleukin-8Membrane ProteinsCell DifferentiationGeneral MedicineMolecular biologyElafinPathogenesis and modulation of inflammation [N4i 1]medicine.anatomical_structureMechanism of actionCyclooxygenase 2KeratinsClinical Pharmacology and physiology [CTR 2]medicine.symptomKeratinocyteSesquiterpenesInfection and autoimmunity [NCMLS 1]Elafinmedicine.drug
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Potential Antipsoriatic Avarol Derivatives as Antioxidants and Inhibitors of PGE2 Generation and Proliferation in the HaCaT Cell Line

2004

The synthesis and structure-activity relationships for a series of 14 new avarol derivatives as antioxidants and inhibitors of cell proliferation and PGE(2) generation in human keratinocytes are described. Compound 6 (thiosalicylic derivative) was the most potent inhibitor of superoxide generation in human neutrophils and also potently inhibited PGE(2) generation in the human keratinocyte HaCaT cell line. Compound 7(3'-methylaminoavarone) presented the best antiproliferative profile, by the inhibition of (3)H-thymidine incorporation in HaCaT cells, with potency similar to the reference compound anthralin. None of the avarol derivatives showed any sign of cytotoxicity measured as LDH release…

KeratinocytesPharmaceutical ScienceAntioxidantsDinoprostoneAnalytical ChemistryInhibitory Concentration 50Structure-Activity Relationshipchemistry.chemical_compoundDrug DiscoverymedicineHumansStructure–activity relationshipCytotoxicityPharmacologyL-Lactate DehydrogenaseSuperoxideCell growthOrganic ChemistryFree Radical ScavengersSalicylatesIn vitroHaCaTmedicine.anatomical_structureItalyComplementary and alternative medicinechemistryBiochemistryCell cultureMolecular MedicineKeratinocyteSesquiterpenesJournal of Natural Products
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Avarol inhibits TNF-a generation and NF-kB activation in human cells and in animal models

2007

Avarol is a marine sesquiterpenoid hydroquinone with interesting pharmacological properties including anti-inflammatory and antipsoriatic effects. In the present study we evaluated the pharmacological effect of avarol on some inflammatory parameters related to the pathogenesis of psoriasis. Avarol inhibited tumor necrosis factor-alpha (TNF-alpha) generation in stimulated human monocytes (IC(50) 1 microM) and TNF-alpha-induced activation of nuclear factor-kappaB (NF-kappaB)-DNA binding in keratinocytes. In the mouse air pouch model, administration of avarol produced a dose-dependent reduction of TNF-alpha generation (ED(50) 9.2 nmol/pouch) as well as of interleukin (IL)-1beta, prostaglandin …

Keratinocytesmedicine.medical_specialtymedicine.medical_treatmentAnti-Inflammatory AgentsAntineoplastic AgentsBiologyPharmacologyMonocytesGeneral Biochemistry Genetics and Molecular BiologyCell LineMicechemistry.chemical_compoundDownregulation and upregulationIn vivoInternal medicinemedicineAnimalsHumansPsoriasisGeneral Pharmacology Toxicology and PharmaceuticsPeroxidaseInflammationHyperplasiaDose-Response Relationship DrugTumor Necrosis Factor-alphaNF-kappa B p50 SubunitInterleukinNF-κBGeneral MedicineDisease Models AnimalEndocrinologymedicine.anatomical_structureEicosanoidchemistryTetradecanoylphorbol AcetateFemaleTumor necrosis factor alphaEpidermisInflammation MediatorsKeratinocyteSesquiterpenesProstaglandin E
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