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Bioorganic and Medicinal Chemistry Letters
Volumn 23, Issue 4, 2013, Pages 1136-1142
Synthesis and dual biological effects of hydroxycinnamoyl phenylalanyl/prolyl hydroxamic acid derivatives as tyrosinase inhibitor and antioxidant
Author keywords

Antioxidant; Hydroxamic acid; Hydroxycinnamic acid; Hypo pigmenting effect; Tyrosinase inhibitor
Indexed keywords

ANTIOXIDANT; CAFFEIC ACID DERIVATIVE; COUMARIC ACID; ENZYME INHIBITOR; FERULIC ACID; HYDROXAMIC ACID DERIVATIVE; HYDROXYCINNAMOYLPHENYLALANYLPROLYLHYDROXAMIC ACID DERIVATIVE; MELANIN; MONOPHENOL MONOOXYGENASE; SINAPIC ACID DERIVATIVE; TROLOX C; UNCLASSIFIED DRUG;
EID: 84872930234     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2012.10.107     Document Type: Article
Times cited : (45)
References (38)
  • 17
    • 0038428272 scopus 로고
    • T.B. Fitzpatrick, A.Z. Eisen, K. Wolff, I.M. Freedberg, K.F. Austen, McGraw-Hill Press New York
    • D.B. Mosher, M.A. Pathak, and T.B. Fitzpatrick T.B. Fitzpatrick, A.Z. Eisen, K. Wolff, I.M. Freedberg, K.F. Austen, Dermatology in General Medicine 1983 McGraw-Hill Press New York 205 225
    • (1983) Dermatology in General Medicine , pp. 205-225
    • Mosher, D.B.1    Pathak, M.A.2    Fitzpatrick, T.B.3
  • 27
    • 84872945661 scopus 로고    scopus 로고
    • f= 0.4). After the water layer was removed, the organic layer was washed with saturated aqueous potassium hydrogen sulfate and brine. This organic extract was concentrated in high vacuum, and then N-Fmoc protected hydroxylamine (Fmoc-NHOH) was obtained as a white crystalline solid after trituration in hexane and stored overnight (80% yield)
    • +; found: 337.1). Their purities were analyzed by RP-HPLC (Thermo Scientific Spectra System AS300; Thermo-Fisher, Waltham, MA, USA) using C18 reverse phase column (120 Å, 5 μm, 4.6 × 250 mm; AAPPTec, Louisville, KY, USA) using the following conditions: gradient elution with A: 0.1% TFA/water, B: 0.1% TFA/acetonitrile; from 10% to 90% over 30 min, a flow rate: 1.0 mL/min; detection: UV, 280 or 326 nm. HCA-Phe-NHOH were purified by a semi-preparative RP-HPLC column using an A to B gradient (A: 0.1% TFA in water, B: 0.1% TFA in acetonitrile; from 10% to 90% B over 30 min, at a flow rate of 4.0 mL/min) and freeze-dried.
  • 28
    • 84872976765 scopus 로고    scopus 로고
    • 29 to measure free radical scavenging activity of HCA-Phe-NHOH and HCA-Pro-NHOH. Methanolic DPPH solution (0.1 mM, 1480 μL) was mixed with 20 μL of 1.85 mM or 3.70 mM sample dissolved in methanol. The absorbance was measured at 516 nm after 10 min by UV/visible spectrophotometer (Optizen 2120 UV, Mecasys Co. Ltd, Korea). The percentage of DPPH radical scavenging activity (RSA) was calculated as % RSA = (1-A/B) × 100, where A represented the absorbance of reaction mixture containing antioxidant sample, and B represented the absorbance of reference solution containing methanol instead of sample
    • 29 to measure free radical scavenging activity of HCA-Phe-NHOH and HCA-Pro-NHOH. Methanolic DPPH solution (0.1 mM, 1480 μL) was mixed with 20 μL of 1.85 mM or 3.70 mM sample dissolved in methanol. The absorbance was measured at 516 nm after 10 min by UV/visible spectrophotometer (Optizen 2120 UV, Mecasys Co. Ltd, Korea). The percentage of DPPH radical scavenging activity (RSA) was calculated as % RSA = (1-A/B) × 100, where A represented the absorbance of reaction mixture containing antioxidant sample, and B represented the absorbance of reference solution containing methanol instead of sample.
  • 30
    • 84872904775 scopus 로고    scopus 로고
    • 31 was used with a slight modification to evaluate antioxidant activity of test samples. Aliquots of the reaction mixture (25 μL) were taken out at specific intervals, and mixed with 1.175 mL of 75% ethanol, 25 μL of 20 mM ferrous chloride in 3.5% HCl, and 25 μL of 30% ammonium thiocyanate
    • 31 was used with a slight modification to evaluate antioxidant activity of test samples. Aliquots of the reaction mixture (25 μL) were taken out at specific intervals, and mixed with 1.175 mL of 75% ethanol, 25 μL of 20 mM ferrous chloride in 3.5% HCl, and 25 μL of 30% ammonium thiocyanate. The absorbance was measured at 500 nm after 3 min, when the color development by ferric thiocyanate complex reached maximum. Each experiment was performed in triplicate and averaged.
  • 33
    • 84872907411 scopus 로고    scopus 로고
    • Tyrosinase inhibition test: Tyrosinase inhibition activity was carried out with l-DOPA as a substrate. Two hundred fifty microliters of phosphate buffer (0.1 M, pH 6.8), 250 μL of 2.5 mM l-DOPA, 200 μL of water, and 25 μL of inhibitor dissolved in DMSO or DMSO alone were mixed together in an Eppendorf tube (1.5 mL-volume). The reaction mixture was incubated at 25 °C for 10 min after treating with 25 μL of aqueous mushroom tyrosinase solution (100 μg/mL), after which the UV absorbance was measured at 475 nm. The percentage of tyrosinase inhibition activity was calculated as% inhibition = (1-A/B) × 100, where A represents the absorbance of reaction mixture containing inhibitor, and B represents the absorbance of reference reaction mixture containing DMSO instead of inhibitor. Each experiment was performed in triplicate. The values are given as the mean ± standard error
    • Tyrosinase inhibition test: Tyrosinase inhibition activity was carried out with l-DOPA as a substrate. Two hundred fifty microliters of phosphate buffer (0.1 M, pH 6.8), 250 μL of 2.5 mM l-DOPA, 200 μL of water, and 25 μL of inhibitor dissolved in DMSO or DMSO alone were mixed together in an Eppendorf tube (1.5 mL-volume). The reaction mixture was incubated at 25 °C for 10 min after treating with 25 μL of aqueous mushroom tyrosinase solution (100 μg/mL), after which the UV absorbance was measured at 475 nm. The percentage of tyrosinase inhibition activity was calculated as% inhibition = (1-A/B) × 100, where A represents the absorbance of reaction mixture containing inhibitor, and B represents the absorbance of reference reaction mixture containing DMSO instead of inhibitor. Each experiment was performed in triplicate. The values are given as the mean ± standard error.
  • 37
    • 84872942166 scopus 로고    scopus 로고
    • 3 per well) were seeded into 96-well plates. Culture media were replaced with serum-free DMEM after 24 h, and incubated for another 24 h. Then, cells were treated with samples (100 μM) containing new serum-free media and incubated for 24 h. CCK-8 solution was added and cells were incubated for another 2 h at 37 °C. The amount of water-soluble formazan generated by the activity of dehydrogenase in cells was measured by optical density at 450 nm using SpectraMax Plus Microplate Reader (Molecular Devices, Sunnyvale, CA, USA)
    • 3 per well) were seeded into 96-well plates. Culture media were replaced with serum-free DMEM after 24 h, and incubated for another 24 h. Then, cells were treated with samples (100 μM) containing new serum-free media and incubated for 24 h. CCK-8 solution was added and cells were incubated for another 2 h at 37 °C. The amount of water-soluble formazan generated by the activity of dehydrogenase in cells was measured by optical density at 450 nm using SpectraMax Plus Microplate Reader (Molecular Devices, Sunnyvale, CA, USA).
  • 38
    • 84872924924 scopus 로고    scopus 로고
    • 2. Effects of the inhibitors on melanin formation in Mel-Ab cell line were estimated. When the samples were treated at the concentrations of 100 μM for 4 days, the inhibitors-treated cells produced less amount of melanin than the cells without inhibitors. The treated cells were then dissolved in 1 mL of 1 N NaOH at 100 °C for 30 min, and centrifuged for 20 min at 16,000g, after which the optical densities of the supernatants were measured at 400 nm. Each experiment was performed in triplicate and averaged
    • 2. Effects of the inhibitors on melanin formation in Mel-Ab cell line were estimated. When the samples were treated at the concentrations of 100 μM for 4 days, the inhibitors-treated cells produced less amount of melanin than the cells without inhibitors. The treated cells were then dissolved in 1 mL of 1 N NaOH at 100 °C for 30 min, and centrifuged for 20 min at 16,000g, after which the optical densities of the supernatants were measured at 400 nm. Each experiment was performed in triplicate and averaged.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.