Mechanism of the melanogenesis stimulation activity of (-)-cubebin in murine B16 melanoma cells.

Abstract:

:(-)-Cubebin showed a melanogenesis stimulation activity in a concentration-dependent manner in murine B16 melanoma cells without any significant effects on cell proliferation. Tyrosinase activity was increased at 24-72 h after addition of cubebin to B16 cells, and then intracellular melanin amount was increased at 48-96 h after the treatment. The expression levels of tyrosinase were time-dependently enhanced after the treatment with cubebin. At the same time, the expression levels of tyrosinase mRNA were also increased after addition of cubebin. Furthermore Western blot analysis revealed that cubebin elevated the level of phosphorylation of p38 mitogen-activated protein kinase (MAPK). SB203580, a selective inhibitor of p38 MAPK, completely blocked cubebin-induced expression of tyrosinase mRNA in B16 cells. These results suggested that cubebin increased melanogenesis in B16 cells through the enhancement of tyrosinase expression mediated by activation of p38 MAPK.

journal_name

Bioorg Med Chem

authors

Hirata N,Naruto S,Ohguchi K,Akao Y,Nozawa Y,Iinuma M,Matsuda H

doi

10.1016/j.bmc.2007.04.046

subject

Has Abstract

pub_date

2007-07-15 00:00:00

pages

4897-902

issue

14

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(07)00373-2

journal_volume

15

pub_type

杂志文章
  • 3-D-QSAR analysis of N-(3-acyloxy-2-benzylpropyl)-N'-dihydroxytetrahydrobenzazepine and tetrahydroisoquinoline and N-(3-acyloxy-2-benzylpropyl)-N'-(4-hydroxy-3-methoxybenzyl) thioureas analogues as potent vanilloid receptor ligands.

    abstract::3-D-Quantitative structure--activity relationships of N-(3-acyloxy-2-benzylpropyl)-N'-dihydroxytetrahydro-benzazepine and tetrahydroisoquinoline and N-(3-acyloxy-2-benzylpropyl)-N'-(4-hydroxy-3-methoxybenzyl) thiourea analogues as potent vanilloid receptor ligands were investigated using the CoMFA and the COMSIA metho...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(01)00404-7

    authors: Kim KH

    更新日期:2002-05-01 00:00:00

  • DNA double helix destabilizing properties of cyclobisintercaland compounds and competition with a single strand binding protein.

    abstract::The DNA helix destabilizing activity of a series of cyclobisintercaland compounds (CBIs) has been evaluated by measuring their ability to displace a 32P-labelled oligonucleotide primer (17-mer) hybridized to the single stranded DNA of M13. This destabilizing activity appears to be strongly dependent on the cyclic stru...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(99)00283-7

    authors: Teulade-Fichou MP,Fauquet M,Baudoin O,Vigneron JP,Lehn JM

    更新日期:2000-01-01 00:00:00

  • Synthesis and phosphodiesterase 5 inhibitory activity of novel phenyl ring modified sildenafil analogues.

    abstract::New sildenafil analogues containing an ether ring fused into the phenyl moiety, 6a--d and 7a--d, were efficiently synthesized from the readily available starting materials, 1a--d and 2, in five steps. Ab initio calculations indicated that introduction of a cyclic ether to the phenyl group might enhance the co-planarit...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(01)00055-4

    authors: Kim DK,Lee N,Lee JY,Ryu DH,Kim JS,Lee SH,Choi JY,Chang K,Kim YW,Im GJ,Choi WS,Kim TK,Ryu JH,Kim NH,Lee K

    更新日期:2001-06-01 00:00:00

  • Bisquaternary caracurine V and iso-caracurine V salts as ligands for the muscle type of nicotinic acetylcholine receptors: SAR and QSAR studies.

    abstract::The binding constants (K(i) values) of 24 caracurine V and 6 iso-caracurine V analogues for the muscle type of nicotinic ACh receptors (nAChR) from Torpedo californica were determined in a binding assay using (+/-)-[(3)H]epibatidine as a radioligand. The allyl alcohol group present in the iso-caracurine V ring system ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2004.08.053

    authors: Zlotos DP,Gündisch D,Ferraro S,Tilotta MC,Stiefl N,Baumann K

    更新日期:2004-12-01 00:00:00

  • Synthesis and dopamine receptor binding of sulfur-containing aporphines.

    abstract::We investigated acid-catalyzed rearrangement of thebaine 14 and its N-propyl analog 15 with methanesulfonic acid in the presence of the nucleophiles methanethiol and hydrogen sulfide. R(-)-2-methylthioapocodeine 16, R(-)-2-methylthioapomorphine 18, and their N-n-propyl analogs 17, 19 were obtained by rearrangement in ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2005.10.049

    authors: Tóth M,Berényi S,Csutorás C,Kula NS,Zhang K,Baldessarini RJ,Neumeyer JL

    更新日期:2006-03-15 00:00:00

  • Phenylimidazole derivatives as specific inhibitors of bacterial enoyl-acyl carrier protein reductase FabK.

    abstract::Bacterial enoyl-acyl carrier protein (ACP) reductases (FabI and FabK) catalyze the final step in each cycle of bacterial fatty acid biosynthesis and are attractive targets for the development of new antibacterial agents. Here, we report the development of novel FabK inhibitors with antibacterial activity against Strep...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2007.08.050

    authors: Ozawa T,Kitagawa H,Yamamoto Y,Takahata S,Iida M,Osaki Y,Yamada K

    更新日期:2007-12-01 00:00:00

  • Synthesis and evaluation of novel modified γ-lactam prostanoids as EP4 subtype-selective agonists.

    abstract::To identify chemically and metabolically stable subtype-selective EP4 agonists, design and synthesis of a series of modified γ-lactam prostanoids has been continued. Prostanoids bearing 2-oxo-1,3-oxazolidine, 2-oxo-1,3-thiazolidine and 5-thioxopyrrolidine as a surrogate for the γ-hydroxycyclopentanone without a troubl...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2011.12.009

    authors: Kambe T,Maruyama T,Nagase T,Ogawa S,Minamoto C,Sakata K,Maruyama T,Nakai H,Toda M

    更新日期:2012-01-15 00:00:00

  • Structural interrogation of benzosuberene-based inhibitors of tubulin polymerization.

    abstract::The discovery of 3-methoxy-9-(30,40,50-trimethoxyphenyl)-6,7-dihydro-5H-benzo[7]annulen-4-ol (a benzosuberene-based analogue referred to as KGP18) was originally inspired by the natural products colchicine and combretastatin A-4 (CA4). The relative structural simplicity and ease of synthesis of KGP18, coupled with its...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2015.10.012

    authors: Herdman CA,Devkota L,Lin CM,Niu H,Strecker TE,Lopez R,Liu L,George CS,Tanpure RP,Hamel E,Chaplin DJ,Mason RP,Trawick ML,Pinney KG

    更新日期:2015-12-15 00:00:00

  • A synthesis of (R)-recifeiolide by the aid of biochemical reaction as the key-step.

    abstract::(R)-Recifeiolide, a naturally occurring macrolactone, was synthesized in optically pure form by the aid of biocatalysts. Lipase-catalyzed lactonization of the racemic precursor afforded the desired compound with a concomitant kinetic resolution. The optically active acyclic precursor could be synthesized by the reduct...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(00)82105-7

    authors: Mochizuki N,Yamada H,Sugai T,Ohta H

    更新日期:1993-07-01 00:00:00

  • Optimization and bioevaluation of Cdc37-derived peptides: An insight into Hsp90-Cdc37 protein-protein interaction modulators.

    abstract::Targeting Hsp90-Cdc37 protein-protein interaction (PPI) is becoming an alternative approach for future anti-cancer drug development. We previously reported the discovery of an eleven-residue peptide (Pep-1) with micromolar activity for the disruption of Hsp90-Cdc37 PPI. Efforts to improve upon the Pep-1 led to the dis...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2016.10.028

    authors: Wang L,Li L,Fu WT,Jiang ZY,You QD,Xu XL

    更新日期:2017-01-01 00:00:00

  • Antiproliferative and apoptosis-inducing activities of novel naphthalimide-cyclam conjugates through dual topoisomerase (topo) I/II inhibition.

    abstract::A novel series of naphthalimide-cyclam conjugates were designed and synthesized. Among them, compounds 4c, 4d, 8c and 8d which bearing long lipophilic alkyl chains, displayed comparable or more potent cytotoxic activities against human tumor cell lines than amonafide. Furthermore, the four compounds were proved to pos...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2015.07.011

    authors: Tan S,Sun D,Lyu J,Sun X,Wu F,Li Q,Yang Y,Liu J,Wang X,Chen Z,Li H,Qian X,Xu Y

    更新日期:2015-09-01 00:00:00

  • A prenylbisabolane with NF-kappaB inhibiting properties from Cascarilla (Croton eluteria).

    abstract::Investigation of the bark of Croton eluteria Bennett for biologically active compounds has led to the isolation of the new prenylbisabolane 3, whose structure was assessed by spectroscopic methods. The corresponding known enone 4 and the eudesmane sesquiterpene 2 were also obtained. Compound 3 proved active in selecti...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2005.04.025

    authors: Campagnuolo C,Fattorusso E,Petrucci F,Taglialatela-Scafati O,Appendino G,Marquez N,Muñoz E

    更新日期:2005-07-01 00:00:00

  • [1,2,4]Triazole derivatives as 5-HT(1A) serotonin receptor ligands.

    abstract::A series of new 4-amino-3-[3-[4-(2-methoxy or nitro phenyl)-1-piperazinyl] propyl]thio]-5-(substitutedphenyl)[1,2,4]triazoles 11a-t was synthesized in order to obtain compounds with high affinity and selectivity for 5-HT(1A) receptor over the alpha(1)-adrenoceptor. A series of isomeric 4-amino-2-[3-[4-(2-methoxy or ni...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(01)00281-4

    authors: Sarvà MC,Romeo G,Guerrera F,Siracusa M,Salerno L,Russo F,Cagnotto A,Goegan M,Mennini T

    更新日期:2002-02-01 00:00:00

  • Conversion of iodine to fluorine-18 based on iodinated chalcone and evaluation for β-amyloid PET imaging.

    abstract::In the amyloid cascade hypothesis, β-amyloid (Aβ) plaques is one of the major pathological biomarkers in the Alzheimer's disease (AD) brain. We report the synthesis and evaluation of novel radiofluorinated chalcones, [18F]4-dimethylamino-4'-fluoro-chalcone ([18F]DMFC) and [18F]4'-fluoro-4-methylamino-chalcone ([18F]FM...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2018.05.001

    authors: Kaide S,Ono M,Watanabe H,Shimizu Y,Nakamoto Y,Togashi K,Yamaguchi A,Hanaoka H,Saji H

    更新日期:2018-07-23 00:00:00

  • Synthesis and biological evaluation of largazole zinc-binding group analogs.

    abstract::Histone acetylation is an extensively investigated post-translational modification that plays an important role as an epigenetic regulator. It is controlled by histone acetyl transferases (HATs) and histone deacetylases (HDACs). The overexpression of HDACs and consequent hypoacetylation of histones have been observed ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2017.03.071

    authors: Kim B,Ratnayake R,Lee H,Shi G,Zeller SL,Li C,Luesch H,Hong J

    更新日期:2017-06-15 00:00:00

  • Synthesis, X-ray molecular structure, biological evaluation and molecular docking studies of some N4-benzyl substituted 5-nitroisatin-3-thiosemicarbazones.

    abstract::A series of fifteen N4-benzyl substituted 5-nitroisatin-3-thiosemicarbazones 5a-o was synthesized and evaluated for urease inhibitory, phytotoxic and cytotoxic influences. All the compounds proved to be highly potent inhibitors of the enzyme, showing inhibitory activity (IC50=0.87±0.25-8.09±0.23μM) much better than th...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2016.12.012

    authors: Pervez H,Khan N,Zaib S,Yaqub M,Naseer MM,Tahir MN,Iqbal J

    更新日期:2017-02-01 00:00:00

  • Glycosyl bis-porphyrin conjugates: synthesis and potential application in PDT.

    abstract::Syntheses of new glycosylated neutral and cationic porphyrin dimers linked at the meso-position via a flexible hydrocarbon chain are described. A detailed 1H and 13C NMR study allows their complete structural elucidation. The UV-visible, fluorescence and MALDI mass spectra are also presented. Photocytotoxicities of th...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2006.08.004

    authors: Sol V,Chaleix V,Champavier Y,Granet R,Huang YM,Krausz P

    更新日期:2006-12-01 00:00:00

  • Stereoselective synthesis and anti-inflammatory activities of 6- and 7-membered dioxacycloalkanes.

    abstract::A class of 5-trifluoroacetylamino-1,3-dioxacycloalkanes, 5-benzoylamino-1,3-dioxacycloalkanes, and 5-amino-1,3-dioxacycloalkane compounds were stereoselectively synthesized as potential anti-inflammatory drug candidates. The anti-inflammatory activities of these compounds were tested using the xylene-induced mouse ear...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2005.09.068

    authors: Gu K,Bi L,Zhao M,Wang C,Dolan C,Kao MC,Tok JB,Peng S

    更新日期:2006-03-01 00:00:00

  • Kinetic properties and affinities for sulfonamide inhibitors of an α-carbonic anhydrase (CruCA4) involved in coral biomineralization in the Mediterranean red coral Corallium rubrum.

    abstract::We report the kinetic properties and sulfonamide inhibition profile of an α-carbonic anhydrase (CA, EC 4.2.1.1), named CruCA4, identified in the red coral Corallium rubrum. This isoform is involved in the biomineralization process leading to the formation of a calcium carbonate skeleton. Experiments performed on the r...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2017.05.001

    authors: Del Prete S,Vullo D,Zoccola D,Tambutté S,Capasso C,Supuran CT

    更新日期:2017-07-01 00:00:00

  • Design and synthesis of 3-fluoro-2-oxo-3-phenylpropionic acid derivatives as potent inhibitors of 4-hydroxyphenylpyruvate dioxygenase from pig liver.

    abstract::Several rationally designed analogs of 3-fluoro-2-oxo-3-phenylpropionic acid were chemically synthesized, and the reactions of the hydrate form of these compounds with 4-hydroxyphenylpyruvate dioxygenase from pig liver as inhibitors were examined. Compounds 14a and 14b were found to be potent competitive inhibitors of...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(99)00062-0

    authors: Ling TS,Shiu S,Yang DY

    更新日期:1999-07-01 00:00:00

  • Synthesis and activity evaluation of the cyclic dipeptides arylidene N-alkoxydiketopiperazines.

    abstract::A series of arylidene N-alkoxydiketopiperazines was designed and stereoselectively synthesized via oxime-ether formation and intramolecular acylation. Possible cyclization and acid-catalyzed rearrangement-fragmentation mechanisms were discussed. The crystal structure of the novel diketopiperazine further confirmed the...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2016.08.038

    authors: Tian X,Feng J,Fan SM,Zhen XL,Han JR,Liu SX

    更新日期:2016-11-01 00:00:00

  • Alkaloids from Sri Lankan curry-leaf (Murraya koenigii) display melanogenesis inhibitory activity: structures of karapinchamines A and B.

    abstract::A methanolic extract and its ethyl acetate-soluble fraction from Sri Lankan curry-leaf, the leaves of Murraya koenigii, inhibited melanogenesis in theophylline-stimulated murine B16 melanoma 4A5 cells. Two new carbazole alkaloids, karapinchamines A and B, were isolated from the ethyl acetate-soluble fraction together ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2013.01.012

    authors: Nakamura S,Nakashima S,Oda Y,Yokota N,Fujimoto K,Matsumoto T,Ohta T,Ogawa K,Maeda S,Nishida S,Matsuda H,Yoshikawa M

    更新日期:2013-03-01 00:00:00

  • Programmable oligomers targeting 5'-GGGG-3' in the minor groove of DNA and NF-kappaB binding inhibition.

    abstract::A series of hairpin oligomers containing benzimidazole (Bi) and imidazopyridine (Ip) rings were synthesized and screened to target 5'-WGGGGW-3', a core sequence in the DNA-binding site of NF-kappaB, a prolific transcription factor important in biology and disease. Five Bi and Ip containing oligomers bound to the 5'-WG...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2006.10.051

    authors: Chenoweth DM,Poposki JA,Marques MA,Dervan PB

    更新日期:2007-01-15 00:00:00

  • Synthesis of pdCpAs and transfer RNAs activated with thiothreonine and derivatives.

    abstract::N,S-diprotected L-thiothreonine and L-allo-thiothreonine derivatives were synthesized using a novel chemical strategy, and used for esterification of the dinucleotide pdCpA. The aminoacylated dinucleotides were then employed for the preparation of activated suppressor tRNA(CUA) transcripts. Thiothreonine and allo-thio...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2012.02.024

    authors: Chen S,Fahmi NE,Nangreave RC,Mehellou Y,Hecht SM

    更新日期:2012-04-15 00:00:00

  • Conformational studies of dithymidine boranomonophosphate diastereoisomers.

    abstract::The boranophosphate ester nucleotides are a new class of nucleic acid analogues that are isoelectronic and isostructural to normal phosphodiester nucleic acids and that maintain the anionic charge of the nucleic acid backbone. The two P-diastereoisomers of dithymidine boranomonophosphates were separated using reverse ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(96)00259-3

    authors: Li H,Huang F,Shaw BR

    更新日期:1997-05-01 00:00:00

  • Selective angiotensin II AT(2) receptor agonists devoid of the imidazole ring system.

    abstract::A versatile parallel synthetic method to obtain three series of non-cyclic analogues of the first drug-like selective angiotensin II AT(2) receptor agonist (1) has been developed. In analogy with the transformation of losartan to valsartan it was demonstrated that a non-cyclic moiety could be employed as an imidazole ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2007.07.026

    authors: Murugaiah AM,Wallinder C,Mahalingam AK,Wu X,Wan Y,Plouffe B,Botros M,Karlén A,Hallberg M,Gallo-Payet N,Alterman M

    更新日期:2007-11-15 00:00:00

  • Synthesis, semipreparative HPLC separation, biological evaluation, and 3D-QSAR of hydrazothiazole derivatives as human monoamine oxidase B inhibitors.

    abstract::The present study reports on synthesis in high yields (70-99%), HPLC enantioseparation, inhibitory activity against human monoamino oxidases, and molecular modeling including 3D-QSAR studies, of a large series of (4-aryl-thiazol-2-yl)hydrazones (1-45). Most of the synthesized compounds proved to be potent and selectiv...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2010.05.070

    authors: Chimenti F,Secci D,Bolasco A,Chimenti P,Granese A,Carradori S,Maccioni E,Cardia MC,Yáñez M,Orallo F,Alcaro S,Ortuso F,Cirilli R,Ferretti R,Distinto S,Kirchmair J,Langer T

    更新日期:2010-07-15 00:00:00

  • Conjugation of cell-penetrating peptides leads to identification of anti-HIV peptides from matrix proteins.

    abstract::Compounds which inhibit the HIV-1 replication cycle have been found amongst fragment peptides derived from an HIV-1 matrix (MA) protein. Overlapping peptide libraries covering the whole sequence of MA were designed and constructed with the addition of an octa-arginyl group to increase their cell membrane permeability....

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2011.12.055

    authors: Narumi T,Komoriya M,Hashimoto C,Wu H,Nomura W,Suzuki S,Tanaka T,Chiba J,Yamamoto N,Murakami T,Tamamura H

    更新日期:2012-02-15 00:00:00

  • New sensible method to quantize the intestinal absorption of receptor ligands.

    abstract::In recent years, special attention has been paid to the A3 adenosine receptor (A3AR) as a possible pharmacological target to treat intestinal inflammation. In this work, it was set up a novel method to quantify the concentration of a promising anti-inflammatory agent inside and outside of intestinal barrier using the ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2019.06.011

    authors: Buccioni M,Dal Ben D,Lambertucci C,Martí Navia A,Ricciutelli M,Spinaci A,Volpini R,Marucci G

    更新日期:2019-08-01 00:00:00

  • Analysis of the binding specificities of oligomannoside-binding proteins using methylated monosaccharides.

    abstract::The binding specificities of the closely related lectins from Canavalia ensiformis and Dioclea grandiflora were examined using specifically O-alkylated mono- and disaccharides. Both lectins accept any substitution at the monosaccharide C2 hydroxyl group. The binding energy of C2-alkylated ligands-concanavalin A comple...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(96)00178-2

    authors: Chervenak MC,Toone EJ

    更新日期:1996-11-01 00:00:00