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NTIS 바로가기Journal of applied biological chemistry, v.54 no.1, 2011년, pp.56 - 62
박준호 (카나다 퀸스대학교 생물학과) , 성낙도 (충남대학교 농업생명과학대학 응용생물화학과)
Molecular docking of polyhydroxy substituted flavone analogues (1-25) as substrate molecules to the active site of tyrosinase (PDB ID: Deoxy-form (2ZMX) & Oxy-form (1WX2)) and Free-Wilson analysis were studied to understand the roles of hydroxyl substituents (
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핵심어 | 질문 | 논문에서 추출한 답변 |
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kojic acid의 저해반응성은 어떠한가? | 잘 알려진 tyrosinase 저해제로서 kojic acid는 tyrosinase의 반응점 내 구리 원자와의 배위결합으로 비경쟁적인 저해반응성[Tokiwa 등, 2007; Neeley 등, 2009]을 나타낸다. 반면에, azelaic acid는 구리 원자와 결합하지 못하고 반응점 주변 아미노산 잔기들과의 수소결합으로 인한 경쟁적인 저해반응성을 나타낸다[Mercedes 등, 2000]. | |
tyrosinase 저해제 중에서 구리 원자와 결합하지 못하는 것은 무엇인가? | 잘 알려진 tyrosinase 저해제로서 kojic acid는 tyrosinase의 반응점 내 구리 원자와의 배위결합으로 비경쟁적인 저해반응성[Tokiwa 등, 2007; Neeley 등, 2009]을 나타낸다. 반면에, azelaic acid는 구리 원자와 결합하지 못하고 반응점 주변 아미노산 잔기들과의 수소결합으로 인한 경쟁적인 저해반응성을 나타낸다[Mercedes 등, 2000]. 근래, tyrosinase의 X-ray 결정구조[Matoba 등, 2006]에 기초한 활성화 메카니즘은 물론[Kim과 Uyama, 2005], tyrosinase 저해제에 관련한 천연물 유래의 연구[Choi 등, 2008; Chen 등, 2009; Wang 등, 2010], 유기합성적인 연구[Chung 등, 2009; Ghani 과 Ullah, 2010], QSAR 연구[Xue 등, 2008; Sawant 등, 2010] 및 분자설계[Khan, 2007]와 분자도킹[Lam 등, 2010; Sun 등, 2010]] 등에 대한 연구들과 총설[Rendon과 Gaviria, 2005; Solano 등, 2006; Chang, 2009]이 다양하게 보고되고 있다. | |
flavone이란 무엇인가? | 식물의 2차 대사산물로서 페놀성 화합물인 flavone은 2-phenylchromone 분자의 골격으로 구성된 flavonoid 유도체(flavone, flavonol, isoflavone, chalcone, aurone, flavan-3-ol, anthocyanidin 및 leucoanthocyanidin)이며 고등 식물계에 널리 분포하는 색소 물질로서 꽃, 잎 및 뿌리에 많이 함유되어 있을뿐 아니라, 다양한 생물활성으로 인하여 기능성 식품, 천연물 농약 및 의약품, 등의 용도로 개발 가능성이 잠재된 매우 유용한 화합물이다[Andersen 및 Markham, 2006]. 이들 화합물 중에서 flavone 유도체들의 tyrosinase (EC. |
Andersen QM and Markham KR (2006) Flavonoids: Chemistry, Biochemistry and Applications. CRC Press. Taylor & Francis Group, Boca Raton, FL.
Arung ET, Shimizu K, and Kondo R (2006) Inhibitory effect of artocarpanone from Artocarpus heterophyllus on melanin biosynthesis. Biol Pharm Bull 29, 1966-1969.
Chang TS (2009) An updated review of tyrosinase inhibitors. Int J Mol Sci 10, 2440-2475.
Chen YR, Chiou RY, Lin TY, Huang CP, Tang WC, Chen ST, and Lin SB (2009) Identification of an alkylhydroquinone from Rhus succedanea as an inhibitor of tyrosinase and melanogenesis. J Agri Food Chem 57, 2200-2205.
Deeth RJ and Diedrich C (2010) Structural and mechanistic insights into the oxy form of tyrosinase from molecular dynamics simulations. J Biol Inorg Chem 5, 117-129.
Etter MC (1990) Encoding and decoding hydrogen-bond patterns of organic compounds. Acc Chem Res 23, 120-126.
Ghani U and Ullah N (2010) New potent inhibitors of tyrosinase: Novel clues to binding of 1,3,4-thiadiazole-2(3H)-thiones, 1,3,4- oxadiazole-2(3H)-thiones, 4-amino- 1,2,4-triazole-5(4H)thiones, and substituted hydrazides to the dicopper active site. Bioorg Med Chem 18, 4042-4048.
Itoh K, Hirata N, Masuda M, Naruto S, Murato K, Wakabayashi K, and Matsuda H (2009) Inhibitory effects of Citrus hassaku extract and its flavanone glycosides on melanogenesis. Biol Pharm Bull 32, 410-415.
Jain AN (2003) Surflex: fully automatic flexible molecular docking using molecular similarity-based search engine. J Med Chem. 46, 499-511.
Khan MTH (2007) Molecular design of tyrosinase inhibitors: A critical review of promising novel inhibitors from synthetic origins. Pure Appl Chem 79, 2277-2295.
Kim D, Park J, Kim J, Han C, Yoon J, Kim N, Seo J, and Lee C (2006) Flavonnoids as mushroom tyrosinase inhibitors: A fluorescence quenching study. J Agric Food Chem 54, 935-941.
Kim YJ and Uyama H (2005) Tyrosinase inhibitors from natural and synthetic sources: structure, inhibition mechanism and perspective for the fure. Cell Mol Life Sci 62, 1707-1723.
Kubinyi H (1993) In QASR: Hansch Analysis and Related Approaches. Applications of Free Wilson Analysis and Related Models. Mannhold R, Larsen K, and Timmerman H (eds), Methods and Principles in Medicinal Chemistry 1, 139-147. VCH Verlagsgeslschaft mbH, Weinheim, Germany.
Lam KW, Syahida A, Haq ZU, Rahman MBA, and Lajis NH (2010) Synthesis and biological activity of oxadiazole and triazolothiadiazole derivatives as tyrosinase inhibitors. Bioorg Med Chem Lett 20, 3755-3759.
Matoba Y, Kumagai T, Yamamoto A, Yoshitsu H, and Sugiyama M (2006) Crystallographic Evidence That the Dinuclear Copper Center of Tyrosinase is Flexible during Catalysis. J Biol Chem 281, 8981-8990.
Mercedes J, Soledad C, Josefa E, Juana C, and Francisco GC (2000) Competitive inhibition of mushroom tyrosinase by 4-substituted benzaldehydes. J Agric Food Chem 49, 4060-4063.
Natsch A, Emter R, and Ellis G (2009) Filling the concept with data: Integrating data from different in-vitro and in-silico assays on skin sensitizers to explore the battery approach for animal-free skin sensitization testing. Toxicol Sci 107, 106-121.
Neeley E, Fritch G, Fulle A, Wolfe J, Wright J, and Flurkey W (2009) Variations in IC50 values with purity of mushroom tyrosinase. Int J Mol Sci 10, 3811-3823.
Patrick AH, Jonathan BC, and John OT (2008) Molecular docking of interactions and groove-binders to nucleic acids using autodock and surflex. J Chem Inf Model 48, 1602-1615.
Rendon MI and Gaviria JI (2005) Review of skin-lightening agents. Dermatol Surg 31, 886-889.
Ryu YB, Ha TJ, Curtis-Long MJ, Ryu HW, Gal SW, and Park KH (2008) Inhibitory effects on mushroom tyrosinase by flavones from the stem barks of Morus lhou (S.) Koidz. J Enzyme Inhib Med Chem 23, 922-930.
Sawant R, Lanke P, Jadhav G, and Bhangale L (2010) QSAR analysis of structurally similar 1,3,4-oxadiazoles as enzyme tyrosinase inhibitors. Drug Invention Today 2, 169-172.
Solano F, Briganti S, Picardo M, and Ghanem G (2006) Hypopigmenting agents: An update review on biological, chemical and clinical aspects. Pigment Cell Res 19, 550-571.
Sun J, Cai S, Yan WN, and Mei H (2010) Docking and 3D-QSAR studies of influenza neuraminidase inhibitors using threedimensional holographic vector of atomic interaction field analysis. European J Med Chem 45, 1008-1014.
Sung ND, Jung HS, and Kim SJ (2004) Hydrolytic reactivity and holographic quantitative structure-activity relationship analyses on the melanogenesis inhibitory activities of alkyl-3,4-dihydroxylbenzoate and N-alkyl-3,4-dihydroxy benzamide derivatives. J Soc Cosmet Scientists Korea 30, 491-497.
Tokiwa Y, Kitagawa M, and Raku T (2007) Enzymatic synthesis of arbutin undecylenic acid ester and its inhibitory effect on mushroom tyrosinase. Biotechnol Lett 29, 481-486.
Wang HM, Chen CY, Ho ML, Chou YT, Chang HC, Lee CH, Wang CZ, and Chu IM (2010) (-)-N-Formylanonaine from Michelia alba as a human tyrosinase inhibitor and antioxidant, Bioorg Med Chem 18, 5241-5247.
Xue CB, Luo WC, Ding Q, Liu SZ, and Gao XX (2008) Quantitative structure-activity relationship studies of mushroom tyrosinase inhibitors. J Comput Aided Mol Des 22, 290-309.
Zhang C, Lu Y, Tao L, Tao X, Su X, and Wei D (2007) Tyrosinase inhibitory effects and inhibition mechanism of nobiletin and hesperidin from citrus peel crude extracts. J Enzyme Inhib Med Chem 22, 83-90.
Zheng ZP, Cheng KW, To JT, and Li H (2008) Isolation of tyrosinase inhibitors from Artocarpus heterophyllus and use of its extract as antibrowning agent. Mol Nutr Food Res 52, 1530-1538.
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