当前位置： SCI文献检索 > BIOORGANIC & MEDICINAL CHEMISTRY期刊下所有文献 > Structural insights into the hot spot amino acid residues of mushroom tyrosinase for the bindings of thujaplicins.

Structural insights into the hot spot amino acid residues of mushroom tyrosinase for the bindings of thujaplicins.

Abstract：

:Tyrosinase inhibitors are important agents for cosmetic products. We examined here the inhibitory effects of three isomers of thujaplicins (α, β and γ) on mushroom tyrosinase and analyzed their binding modes using a homology model from the crystal structure of Streptomyces castaneoglobisporus tyrosinase (PDB ID: 1wx2). All the thujaplicins were found to be competitive inhibitors and γ-thujaplicin has the most potent inhibitory activity (IC(50)=0.07μM). It is noted that there are good correlations between their observed IC(50) values and their binding free energies calculated by MM-GB/SA. The binding modes of thujaplicins were predicted to be similar to that of Tyr98 of caddie protein (ORF378), which was co-crystallized with S. castaneoglobisporus tyrosinase. Furthermore, free energy decomposition analysis indicated that the potent inhibitory activity of γ-thujaplicin is due to the interactions with His242, Val243 and Pro257 (hot spot amino acid residues) at the active site of tyrosinase. These results provide a novel structural insight into the hot spot of mushroom tyrosinase for the specific binding of γ-thujaplicin.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Takahashi S,Kamiya T,Saeki K,Nezu T,Takeuchi S,Takasawa R,Sunaga S,Yoshimori A,Ebizuka S,Abe T,Tanuma S

doi

10.1016/j.bmc.2010.08.056

subject

Has Abstract

pub_date

2010-11-15 00:00:00

pages

8112-8

issue

22

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(10)00812-6

journal_volume

18

pub_type

杂志文章

相关文献

BIOORGANIC & MEDICINAL CHEMISTRY文献大全
  • Synthesis and structure-activity relationships of benzyloxyphenyl derivatives as a novel class of NCX inhibitors: effects on heart failure.

    abstract：:In the context of heart failure and myocardial ischemia reperfusion, the activity of the sodium-calcium exchanger can lead to calcium overload, which in turn can lead to contractile dysfunction and arrhythmia. Therefore, NCX is an attractive target for treatment of heart failure and myocardial ischemia reperfusion. We...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2004.10.048

    authors： Kuramochi T,Kakefuda A,Yamada H,Ogiyama T,Taguchi T,Sakamoto S

    更新日期：2005-02-01 00:00:00

  • Nucleosides with self-complementary hydrogen-bonding motifs: synthesis and base-pairing studies of two nucleosides containing the imidazo[4,5-d]pyridazine ring system.

    abstract：:Synthesis and base-pairing studies of two 2'-deoxyribonucleosides, containing a common heterocyclic base, 7(4)-amino-5(6)H-imidazo[4,5-d]pyridazin-4(7)one (1 and 2), have been reported. The synthesis was accomplished by base-promoted deoxyribosylation of ethyl 5(4)-cyanoimidazole-4(5)-carboxylate (6), followed by ring...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2006.05.043

    authors： Ujjinamatada RK,Paulman RL,Ptak RG,Hosmane RS

    更新日期：2006-09-15 00:00:00

  • Synthesis and fungicidal activity of enantiomerically pure (R)- and (S)-silicon-containing azole fungicides.

    abstract：:Enantiomerically pure (R)- and (S)-1-(1H-1,2,4-triazol-1-yl)-2-(4-fluorophenyl)-3-trimethylsilylpropan-2-ol 1 were prepared via an enantioselective Grignard reaction. The absolute stereochemistry of 1 was determined by X-ray analysis. In a comparison of in vitro antifungal activities of the enantiomers, the (-)-enanti...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2004.04.027

    authors： Itoh H,Furukawa Y,Tsuda M,Takeshiba H

    更新日期：2004-07-01 00:00:00

  • Catechol derivatives of aminopyrazine and cell protection against UVB-induced mortality.

    abstract：:A series of 5-aryl- and 3,5-bis-aryl-2-amino-1,4-pyrazine derivatives 4 and 6, and related imidazolopyrazinones 7, has been synthesized, the aryl groups of which are catechol and/or phenol substituents. These compounds, tested against human keratinocyte cells stressed by UVB irradiation, showed high antioxidative prop...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(00)00321-7

    authors： Cavalier JF,Burton M,Dussart F,Marchand C,Rees JF,Marchand-Brynaert J

    更新日期：2001-04-01 00:00:00

  • Tessaric acid derivatives induce G2/M cell cycle arrest in human solid tumor cell lines.

    abstract：:A series of analogs were synthesized in a straightforward manner from naturally available sesquiterpenes ilicic acid and tessaric acid. The in vitro antiproliferative activities were examined in the human solid tumor cell lines A2780, HBL-100, HeLa, SW1573, T-47D and WiDr. The most potent analog induced considerably g...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2009.07.053

    authors： León LG,Donadel OJ,Tonn CE,Padrón JM

    更新日期：2009-09-01 00:00:00

  • Structure-based design and synthesis of covalent-reversible inhibitors to overcome drug resistance in EGFR.

    abstract：:The clinical success of covalent kinase inhibitors in the treatment of EGFR-dependent non-small cell lung cancer (NSCLC) has rejuvenated the appreciation of reactive small molecules. Acquired drug resistance against first-line EGFR inhibitors remains the major bottleneck in NSCLC and is currently addressed by the appl...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2015.04.038

    authors： Basu D,Richters A,Rauh D

    更新日期：2015-06-15 00:00:00

  • Synthesis of chondroitin sulfate CC and DD tetrasaccharides and interactions with 2H6 and LY111.

    abstract：:We synthesized the biotinylated chondroitin sulfate tetrasaccharides CS-CC [-3)βGalNAc6S(1-4)βGlcA(1-]2 and CS-DD [-3)βGalNAc6S(1-4)βGlcA2S(1-]2 which possess sulfate groups at O-6 of GalNAc and an additional sulfate group at O-2 of GlcA, respectively. We also analyzed interactions among CS-CC and CS-DD and the antibo...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2018.01.011

    authors： Matsushita K,Nakata T,Takeda-Okuda N,Nadanaka S,Kitagawa H,Tamura JI

    更新日期：2018-03-01 00:00:00

  • Ensemble-based docking: From hit discovery to metabolism and toxicity predictions.

    abstract：:This paper describes and illustrates the use of ensemble-based docking, i.e., using a collection of protein structures in docking calculations for hit discovery, the exploration of biochemical pathways and toxicity prediction of drug candidates. We describe the computational engineering work necessary to enable large ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2016.07.064

    authors： Evangelista W,Weir RL,Ellingson SR,Harris JB,Kapoor K,Smith JC,Baudry J

    更新日期：2016-10-15 00:00:00

  • A convenient synthesis and hepatoprotective activity of imidazo[1,2-c]pyrimido[5,4-e]pyrimidine, tetraazaacenaphthene and tetraazaphenalene from cyclic ketene aminals through tandem addition-cyclization reactions.

    abstract：:A novel one-pot synthesis of imidazo[1,2-c]pyrimido[5,4-e]pyrimidinones (2), tetraazaacenaphthene-3,6-diones (4), tetarazaphenalene-1,7-dione (4d) is delineated from the reaction of cyclic ketene aminal (1) and alkyl or aryl isothiocyanate through tandem addition-cyclization reactions. However, reaction of ketene amin...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(01)00423-0

    authors： Ram VJ,Goel A,Sarkhel S,Maulik PR

    更新日期：2002-05-01 00:00:00

  • Novel and potent calcium-sensing receptor antagonists: discovery of (5R)-N-[1-ethyl-1-(4-ethylphenyl)propyl]-2,7,7-trimethyl-5-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxamide monotosylate (TAK-075) as an orally active bone anabolic agent.

    abstract：:The calcium-sensing receptor antagonist (CaSR) has been recognized as a promising target of anabolic agents for treating osteoporosis. In the course of developing a new drug candidate for osteoporosis, we found tetrahydropyrazolopyrimidine derivative 1 to be an orally active CaSR antagonist that stimulated transient P...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2011.02.001

    authors： Yoshida M,Mori A,Morimoto S,Kotani E,Oka M,Notoya K,Makino H,Ono M,Shirasaki M,Tada N,Fujita H,Ban J,Ikeda Y,Kawamoto T,Goto M,Kimura H,Baba A,Yasuma T

    更新日期：2011-03-15 00:00:00

  • Novel azalides derived from 16-membered macrolides. Part II: Isolation of the linear 9-formylcarboxylic acid and its sequential macrocyclization with an amino alcohol or an azidoamine.

    abstract：:The design and synthesis of novel 14- to 16-membered 11-azalides starting from 16-membered macrolides are reported. A linear 9-formylcarboxylic acid was isolated via a mobile dialdehyde previously reported. Sequential macrocyclization of the formylcarboxylic acid with amino alcohol followed by deprotection afforded co...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2008.09.054

    authors： Miura T,Kanemoto K,Natsume S,Atsumi K,Fushimi H,Yoshida T,Ajito K

    更新日期：2008-12-01 00:00:00

  • Bioluminescence probe for γ-glutamyl transpeptidase detection in vivo.

    abstract：:To detect γ-Glutamyl Transpeptidase (GGT) activity in vitro and in vivo, a bioluminescence probe with high sensitivity and specificity was well designed and synthesized. This probe can be recognized by GGT and release strong bioluminescence with its further reaction with luciferase. The performance of this probe was d...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2017.11.025

    authors： Lin Y,Gao Y,Ma Z,Jiang T,Zhou X,Li Z,Qin X,Huang Y,Du L,Li M

    更新日期：2018-01-01 00:00:00

  • Concise syntheses of arabinogalactans with beta-(1-->6)-linked galactopyranose backbones and alpha-(1-->3)- and alpha-(1-->2)-linked arabinofuranose side chains.

    abstract：:4-methoxyphenyl glycosides of 2,3''-bis-alpha-L-arabinofuranosyl branched beta-D-(1-->6)-linked galactopyranosyl tetraose (16), 3',2''''-bis-alpha-L-arabinofuranosyl branched beta-D-(1-->6)-linked galactopyranosyl hexaose (27), and a twentyose (42) consisting of beta-(1-->6)-linked D-galactopyranosyl pentadecaoligosac...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2004.10.035

    authors： Li A,Kong F

    更新日期：2005-02-01 00:00:00

  • Synthesis and preliminary in vivo evaluation of new [18F]fluoro-inositols as Positron Emission Tomography radiotracers.

    abstract：:This study describes the synthesis and radiosynthesis of eight new [18F]fluoro-inositol-based radiotracers in myo- and scyllo-inositol configuration. These radiotracers are equipped with a propyl linker bearing fluorine-18. This fluorinated arm is either on a hydroxyl group, i.e. O-alkylated inositols, or on the cyclo...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2017.08.035

    authors： Collet C,Schmitt S,Maskali F,Clément A,Chrétien F,Karcher G,Marie PY,Poussier S,Lamandé-Langle S

    更新日期：2017-10-15 00:00:00

  • Use of enzyme penicillin acylase in selective amidation/amide hydrolysis to resolve ethyl 3-amino-4-pentynoate isomers.

    abstract：:The beta-amino acid, (S)-ethyl-3-amino-4-pentynoate, is a chiral synthon used in the synthesis of xemilofiban hydrochloride, an anti-platelet agent. A biocatalytic approach was developed to resolve (R)- and (S)-enantiomers of ethyl 3-amino-4-pentynoate in enantiomerically pure form employing the enzyme Penicillin acyl...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(99)00155-8

    authors： Topgi RS,Ng JS,Landis B,Wang P,Behling JR

    更新日期：1999-10-01 00:00:00

  • Studies of TAK1-centered polypharmacology with novel covalent TAK1 inhibitors.

    abstract：:Targeted polypharmacology provides an efficient method of treating diseases such as cancer with complex, multigenic causes provided that compounds with advantageous activity profiles can be discovered. Novel covalent TAK1 inhibitors were validated in cellular contexts for their ability to inhibit the TAK1 kinase and f...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2016.11.034

    authors： Tan L,Gurbani D,Weisberg EL,Jones DS,Rao S,Singer WD,Bernard FM,Mowafy S,Jenney A,Du G,Nonami A,Griffin JD,Lauffenburger DA,Westover KD,Sorger PK,Gray NS

    更新日期：2017-02-15 00:00:00

  • A colormetric assay for catechol-O-methyltransferase.

    abstract：:A series of catechol diazo dyes were synthesized and tested as substrates for the enzyme catechol-O-methyltransferase (COMT) with the aim of developing a sensitive HPLC assay method using visible wavelength light detection. A method was developed which allowed for the determination of the two regioisomeric methylated ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2003.10.038

    authors： Bailey K,Cowling R,Tan EW,Webb D

    更新日期：2004-02-01 00:00:00

  • Indole and benzimidazole derivatives as steroid 5alpha-reductase inhibitors in the rat prostate.

    abstract：:A novel series of indole and benzimidazole derivatives were synthesized and evaluated for their inhibitory activity of rat prostatic 5alpha-reductase. Among these compounds, 4-¿2-[1-(4,4'-dipropylbenzhydryl)indole-5-carboxamido]phenoxy¿buty ric acid (15) and its benzimidazole analogue 25 showed potent inhibitory activ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(98)80018-7

    authors： Takami H,Kishibayashi N,Ishii A,Kumazawa T

    更新日期：1998-12-01 00:00:00

  • Synthesis and molecular modeling of some novel hexahydroindazole derivatives as potent monoamine oxidase inhibitors.

    abstract：:A novel series of 2-thiocarbamoyl-2,3,4,5,6,7-hexahydro-1H-indazole and 2-substituted thiocarbamoyl-3,3a,4,5,6,7-hexahydro-2H-indazoles derivatives were synthesized and investigated for the ability to inhibit the activity of the A and B isoforms of monoamine oxidase (MAO). The target molecules were identified on the b...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2009.07.033

    authors： Gökhan-Kelekçi N,Simşek OO,Ercan A,Yelekçi K,Sahin ZS,Işik S,Uçar G,Bilgin AA

    更新日期：2009-09-15 00:00:00

  • Extending SAR of bile acids as FXR ligands: discovery of 23-N-(carbocinnamyloxy)-3α,7α-dihydroxy-6α-ethyl-24-nor-5β-cholan-23-amine.

    abstract：:Within our efforts in the discovery of novel potent and selective ligands for the FXR receptor, 23-N-(carbocinnamyloxy)-3α,7α-dihydroxy-6α-ethyl-24-nor-5β-cholan-23-amine was synthesized and evaluated for its ability to activate and modulate the biological response of the receptor. Alphascreen and RT-PCR revealed that...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2011.03.004

    authors： Gioiello A,Macchiarulo A,Carotti A,Filipponi P,Costantino G,Rizzo G,Adorini L,Pellicciari R

    更新日期：2011-04-15 00:00:00

  • Synthesis and biological activity of a fluorescent schweinfurthin analogue.

    abstract：:Most of the natural schweinfurthins are potent and selective inhibitors of cell growth as measured by the National Cancer Institute's 60-cell line screen. Due to the limited supply of these natural products, we have initiated a program aimed at their synthesis. To date, this effort has led to the preparation of three ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2009.04.071

    authors： Kuder CH,Neighbors JD,Hohl RJ,Wiemer DF

    更新日期：2009-07-01 00:00:00

  • Synthesis and antimicrobial activity of dermaseptin S1 analogues.

    abstract：:Dermaseptins are peptides found in the skin secretions of Phyllomedusinae frogs. These peptides exert lytic action on some microorganisms without substantial haemolysis. In an attempt to understand the antimicrobial activity of these peptides we designed several dermaseptin S1 (ALWKTMLKKLGTMALHAGKAALGAAADTISQGTQ) (DS1...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2008.07.032

    authors： Savoia D,Guerrini R,Marzola E,Salvadori S

    更新日期：2008-09-01 00:00:00

  • Synthesis and in vitro evaluation of aspartate transcarbamoylase inhibitors.

    abstract：:The design, synthesis, and evaluation of a series of novel inhibitors of aspartate transcarbamoylase (ATCase) are reported. Several submicromolar phosphorus-containing inhibitors are described, but all-carboxylate compounds are inactive. Compounds were synthesized to probe the postulated cyclic transition-state of the...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2009.09.045

    authors： Coudray L,Pennebaker AF,Montchamp JL

    更新日期：2009-11-15 00:00:00

  • An approach to identifying novel substrates of bacterial arylamine N-acetyltransferases.

    abstract：:Arylamine N-acetyltransferases (NATs) catalyse the acetylation of arylamine, arylhydrazine and arylhydroxylamine substrates by acetyl Coenzyme A. NAT has been discovered in a wide range of eukaryotic and prokaryotic species. Although prokaryotic NATs have been implicated in xenobiotic metabolism, to date no endogenous...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(02)00642-9

    authors： Brooke EW,Davies SG,Mulvaney AW,Pompeo F,Sim E,Vickers RJ

    更新日期：2003-04-03 00:00:00

  • Analogs of iso-azepinomycin as potential transition-state analog inhibitors of guanase: synthesis, biochemical screening, and structure-activity correlations of various selectively substituted imidazo[4,5-e][1,4]diazepines.

    abstract：:Guanase is an important enzyme of the purine salvage pathway of nucleic acid metabolism and its inhibition has beneficial implications in viral, bacterial, and cancer therapy. The work described herein is based on a hypothesis that azepinomycin, a heterocyclic natural product and a purported transition state analog in...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2013.06.069

    authors： Tantravedi S,Chakraborty S,Shah NH,Fishbein JC,Hosmane RS

    更新日期：2013-09-01 00:00:00

  • Synthesis, binding, nuclease resistance and cellular uptake properties of 2'-O-acetalester-modified oligonucleotides containing cationic groups.

    abstract：:We report on the synthesis and properties of oligonucleotides (ONs) with 2'-O-acetalester modifications containing cationic side chains in a prodrug-like approach. In the aim to improve cell penetration and nuclease resistance, various different amino- or guanidino-acetalester were grafted to 2'-OH of uridine and the ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2015.07.054

    authors： Biscans A,Rouanet S,Bertrand JR,Vasseur JJ,Dupouy C,Debart F

    更新日期：2015-09-01 00:00:00

  • Stochastic-based descriptors studying peptides biological properties: modeling the bitter tasting threshold of dipeptides.

    abstract：:MARCH-INSIDE methodology was applied to the prediction of the bitter tasting threshold of 48 dipeptides by means of pattern recognition techniques, in this case linear discriminant analysis (LDA), and regression methods. The LDA models yielded a percentage of good classification higher than 80% with the two main famil...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2004.07.017

    authors： Ramos de Armas R,González Díaz H,Molina R,Pérez González M,Uriarte E

    更新日期：2004-09-15 00:00:00

  • KM-01, a brassinolide inhibitor, its production, isolation and structure from two fungi Drechslera avenae and Pycnoporus coccineus.

    abstract：:A new brassinolide inhibitor, named KM-01, was isolated from the culture filtrates of two fungal species, Drechslera avenae and Pycnoporus coccineus, and the structure with absolute stereochemistry was elucidated as the fatty acid ester of an eremophilane sesquiterpene, bipolaroxin, based on spectroscopic analysis, ch...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(98)00088-1

    authors： Kim SK,Hatori M,Ojika M,Sakagami Y,Marumo S

    更新日期：1998-11-01 00:00:00

  • Variations in the C-unit of bedaquiline provides analogues with improved biology and pharmacology.

    abstract：:Analogues of the anti-tuberculosis drug bedaquiline, bearing a 3,5-dimethoxy-4-pyridyl C-unit, retain high anti-bacterial potency yet exert less inhibition of the hERG potassium channel, in vitro, than the parent compound. Two of these analogues (TBAJ-587 and TBAJ-876) are now in preclinical development. The present s...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2019.115213

    authors： Sutherland HS,Tong AST,Choi PJ,Blaser A,Franzblau SG,Cooper CB,Upton AM,Lotlikar M,Denny WA,Palmer BD

    更新日期：2020-01-01 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