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Volumn 2011, Issue 1, 2011, Pages

Inhibitory effect of phthalic acid on tyrosinase: The mixed-type inhibition and docking simulations

Author keywords

[No Author keywords available]

Indexed keywords

LEUCINE; LEVODOPA; MONOPHENOL MONOOXYGENASE; PHTHALIC ACID;

EID: 84868217197     PISSN: 20900406     EISSN: 20900414     Source Type: Journal    
DOI: 10.4061/2011/294724     Document Type: Article
Times cited : (39)

References (34)
  • 1
    • 70350102888 scopus 로고    scopus 로고
    • New insights into the active site structure and catalytic mechanism of tyrosinase and its related proteins
    • 2-s2.0-70350102888 10.1111/j.1755-148X.2009.00636.x
    • Olivares C., Solano F., New insights into the active site structure and catalytic mechanism of tyrosinase and its related proteins. Pigment Cell and Melanoma Research 2009 22 6 750 760 2-s2.0-70350102888 10.1111/j.1755-148X.2009. 00636.x
    • (2009) Pigment Cell and Melanoma Research , vol.22 , Issue.6 , pp. 750-760
    • Olivares, C.1    Solano, F.2
  • 2
    • 37349053743 scopus 로고    scopus 로고
    • A review on spectrophotometric methods for measuring the monophenolase and diphenolase activities of tyrosinase
    • DOI 10.1021/jf0712301
    • García-Molina F., Muoz J. L., Varón R., Rodríguez-López J. N., García-Cánovas F., Tudela J., A review on spectrophotometric methods for measuring the monophenolase and diphenolase activities of tyrosinase. Journal of Agricultural and Food Chemistry 2007 55 24 9739 9749 2-s2.0-37349053743 10.1021/jf0712301 (Pubitemid 350305154)
    • (2007) Journal of Agricultural and Food Chemistry , vol.55 , Issue.24 , pp. 9739-9749
    • Garcia-Molina, F.1    Munoz, J.L.2    Varon, R.3    Rodriguez-Lopez, J.N.4    Garcia-Canovas, F.5    Tudela, J.6
  • 3
    • 0033854292 scopus 로고    scopus 로고
    • Assembly, target-signaling and intracellular transport of tyrosinase gene family proteins in the initial stage of melanosome biogenesis
    • DOI 10.1034/j.1600-0749.2000.130403.x
    • Jimbow K., Park J. S., Kato F., Hirosaki K., Toyofuku K., Hua C., Yamashita T., Assembly, target-signaling and intracellular transport of tyrosinase gene family proteins in the initial stage of melanosome biogenesis. Pigment Cell Research 2000 13 4 222 229 2-s2.0-0033854292 10.1034/j.1600-0749. 2000.130403.x (Pubitemid 30610798)
    • (2000) Pigment Cell Research , vol.13 , Issue.4 , pp. 222-229
    • Jimbow, K.1    Park, J.S.2    Kato, F.3    Hirosaki, K.4    Toyofuku, K.5    Hua, C.6    Yamashita, T.7
  • 4
    • 43549122572 scopus 로고    scopus 로고
    • Parkin protects against tyrosinase-mediated dopamine neurotoxicity by suppressing stress-activated protein kinase pathways
    • DOI 10.1111/j.1471-4159.2008.05277.x
    • Hasegawa T., Treis A., Patenge N., Fiesel F. C., Springer W., Kahle P. J., Parkin protects against tyrosinase-mediated dopamine neurotoxicity by suppressing stress-activated protein kinase pathways. Journal of Neurochemistry 2008 105 5 1700 1715 2-s2.0-43549122572 10.1111/j.1471-4159.2008.05277.x (Pubitemid 351678502)
    • (2008) Journal of Neurochemistry , vol.105 , Issue.5 , pp. 1700-1715
    • Hasegawa, T.1    Treis, A.2    Patenge, N.3    Fiesel, F.C.4    Springer, W.5    Kahle, P.J.6
  • 5
    • 2642539089 scopus 로고    scopus 로고
    • On the etiology of contact/occupational vitiligo
    • DOI 10.1111/j.1600-0749.2004.00130.x
    • Boissy R. E., Manga P., On the etiology of contact/occupational vitiligo. Pigment Cell Research 2004 17 3 208 214 2-s2.0-2642539089 10.1111/j.1600-0749. 2004.00130.x (Pubitemid 38724550)
    • (2004) Pigment Cell Research , vol.17 , Issue.3 , pp. 208-214
    • Boissy, R.E.1    Manga, P.2
  • 6
    • 0032697226 scopus 로고    scopus 로고
    • Expression of tyrosinase, TRP-1 and TRP-2 in ultraviolet-irradiated human melanomas and melanocytes: TRP-2 protects melanoma cells from ultraviolet B induced apoptosis
    • Nishioka E., Funasaka Y., Kondoh H., Chakraborty A. K., Mishima Y., Ichihashi M., Expression of tyrosinase, TRP-1 and TRP-2 in ultraviolet- irradiated human melanomas and melanocytes: TRP-2 protects melanoma cells from ultraviolet B induced apoptosis. Melanoma Research 1999 9 5 433 443 2-s2.0-0032697226 (Pubitemid 29494108)
    • (1999) Melanoma Research , vol.9 , Issue.5 , pp. 433-443
    • Nishioka, E.1    Funasaka, Y.2    Kondoh, H.3    Chakraborty, A.K.4    Mishima, Y.5    Ichihashi, M.6
  • 7
    • 0030112276 scopus 로고    scopus 로고
    • Induction of melanogenesis during the various melanoma growth phases and the role of tyrosinase, lysosome-associated membrane proteins, and p90 calnexin in the melanogenesis cascade
    • Salopek T. G., Jimbow K., Induction of melanogenesis during the various melanoma growth phases and the role of tyrosinase, lysosome-associated membrane proteins, and p90 calnexin in the melanogenesis cascade. Journal of Investigative Dermatology Symposium Proceedings 1996 1 2 195 202 2-s2.0-0030112276 (Pubitemid 126759365)
    • (1996) Journal of Investigative Dermatology Symposium Proceedings , vol.1 , Issue.2 , pp. 195-202
    • Salopek, T.G.1
  • 9
    • 33745237195 scopus 로고    scopus 로고
    • Prognostic significance of molecular staging study of sentinel lymph nodes by reverse transcriptase-polymerase chain reaction for tyrosinase in melanoma patients
    • 2-s2.0-33745237195 10.1245/ASO.2006.12.010
    • Mangas C., Hilari J. M., Paradelo C., Rex J., Fernández-Figueras M. T., Fraile M., Alastrue A., Ferrándiz C., Prognostic significance of molecular staging study of sentinel lymph nodes by reverse transcriptase- polymerase chain reaction for tyrosinase in melanoma patients. Annals of Surgical Oncology 2006 13 7 910 918 2-s2.0-33745237195 10.1245/ASO.2006.12.010
    • (2006) Annals of Surgical Oncology , vol.13 , Issue.7 , pp. 910-918
    • Mangas, C.1    Hilari, J.M.2    Paradelo, C.3    Rex, J.4    Fernández-Figueras, M.T.5    Fraile, M.6    Alastrue, A.7    Ferrándiz, C.8
  • 10
    • 0027417524 scopus 로고
    • Tyrosinase gene mutations causing oculocutaneous albinisms
    • Tomita Y., Tyrosinase gene mutations causing oculocutaneous albinisms. Journal of Investigative Dermatology 1993 100 supplement 2 186S 190S 2-s2.0-0027417524 (Pubitemid 23051696)
    • (1993) Journal of Investigative Dermatology , vol.100 , Issue.2 SUPPL.
    • Tomita, Y.1
  • 11
    • 0033815395 scopus 로고    scopus 로고
    • The tyrosinase gene and oculocutaneous albinism type 1 (OCA1): A model for understanding the molecular biology of melanin formation
    • 2-s2.0-0033815395 10.1034/j.1600-0749.2000.130503.x
    • Oetting W. S., The tyrosinase gene and oculocutaneous albinism type 1 (OCA1): a model for understanding the molecular biology of melanin formation. Pigment Cell Research 2000 13 5 320 325 2-s2.0-0033815395 10.1034/j.1600-0749. 2000.130503.x
    • (2000) Pigment Cell Research , vol.13 , Issue.5 , pp. 320-325
    • Oetting, W.S.1
  • 12
    • 42749097427 scopus 로고    scopus 로고
    • Recent advances in genetic analyses of oculocutaneous albinism types 2 and 4
    • 2-s2.0-42749097427 10.1016/j.jdermsci.2007.12.008
    • Suzuki T., Tomita Y., Recent advances in genetic analyses of oculocutaneous albinism types 2 and 4. Journal of Dermatological Science 2008 51 1 1 9 2-s2.0-42749097427 10.1016/j.jdermsci.2007.12.008
    • (2008) Journal of Dermatological Science , vol.51 , Issue.1 , pp. 1-9
    • Suzuki, T.1    Tomita, Y.2
  • 13
    • 79952353515 scopus 로고    scopus 로고
    • Dimeric cinnamoylamide derivatives as inhibitors of melanogenesis
    • veronique.lemellay-hamon@mayoly-spindler.fr 10.1248/bpb.34.420
    • Criton M., Le Mellay-Hamon V., veronique.lemellay-hamon@mayoly-spindler. fr Dimeric cinnamoylamide derivatives as inhibitors of melanogenesis. Biological and Pharmaceutical Bulletin 2011 34 3 420 425 10.1248/bpb.34.420
    • (2011) Biological and Pharmaceutical Bulletin , vol.34 , Issue.3 , pp. 420-425
    • Criton, M.1    Le Mellay-Hamon, V.2
  • 14
    • 79951593821 scopus 로고    scopus 로고
    • Identifying melanogenesis inhibitors from cinnamomum subavenium with in vitro and in vivo screening systems by targeting the human tyrosinase
    • davidw@kmu.edu.tw 10.1111/j.1600-0625.2010.01161.x
    • Wang H. M., davidw@kmu.edu.tw Chen C. Y., Wen Z. H., Identifying melanogenesis inhibitors from cinnamomum subavenium with in vitro and in vivo screening systems by targeting the human tyrosinase. Experimental Dermatology 2011 20 3 242 248 10.1111/j.1600-0625.2010.01161.x
    • (2011) Experimental Dermatology , vol.20 , Issue.3 , pp. 242-248
    • Wang, H.M.1    Chen, C.Y.2    Wen, Z.H.3
  • 15
    • 77954788070 scopus 로고    scopus 로고
    • Quasi-drugs developed in Japan for the prevention or treatment of hyperpigmentary disorders
    • hideyaando@aol.com mmatsui@Estee.com mmichihashi@hotmail.com 10.3390/ijms11062566
    • Ando H., hideyaando@aol.com Matsui M. S., mmatsui@Estee.com Ichihashi M., mmichihashi@hotmail.com Quasi-drugs developed in Japan for the prevention or treatment of hyperpigmentary disorders. International Journal of Molecular Sciences 2010 11 6 2566 2575 10.3390/ijms11062566
    • (2010) International Journal of Molecular Sciences , vol.11 , Issue.6 , pp. 2566-2575
    • Ando, H.1    Matsui, M.S.2    Ichihashi, M.3
  • 16
    • 0034255667 scopus 로고    scopus 로고
    • Tyrosinase/catecholoxidase activity of hemocyanins: Structural basis and molecular mechanism
    • DOI 10.1016/S0968-0004(00)01602-9, PII S0968000400016029
    • Decker H., Tuczek F., Tyrosinase/catecholoxidase activity of hemocyanins: structural basis and molecular mechanism. Trends in Biochemical Sciences 2000 25 8 392 397 2-s2.0-0034255667 10.1016/S0968-0004(00)01602-9 (Pubitemid 30497251)
    • (2000) Trends in Biochemical Sciences , vol.25 , Issue.8 , pp. 392-397
    • Decker, H.1    Tuczek, F.2
  • 17
    • 57749179740 scopus 로고    scopus 로고
    • The effect of histidine residue modification on tyrosinase activity and conformation: Inhibition kinetics and computational prediction
    • 2-s2.0-57749179740
    • Gou L., Lü Z. R., Park D., Sang HO. O., Shi L., Seong J. P., Bhak J., Park Y. D., Ren Z. L., Zou F., The effect of histidine residue modification on tyrosinase activity and conformation: inhibition kinetics and computational prediction. Journal of Biomolecular Structure and Dynamics 2008 26 3 395 402 2-s2.0-57749179740
    • (2008) Journal of Biomolecular Structure and Dynamics , vol.26 , Issue.3 , pp. 395-402
    • Gou, L.1    Lü, Z.R.2    Park, D.3    Sang, H.O.O.4    Shi, L.5    Seong, J.P.6    Bhak, J.7    Park, Y.D.8    Ren, Z.L.9    Zou, F.10
  • 18
    • 77949914143 scopus 로고    scopus 로고
    • The effect of trifluoroethanol on tyrosinase activity and conformation: Inhibition kinetics and computational simulations
    • 2-s2.0-77949914143 10.1007/s12010-009-8730-9
    • Lü Z. R., Shi L., Wang J., Park D., Bhak J., Yang J. M., Park Y. D., Zhou H. W., Zou F., The effect of trifluoroethanol on tyrosinase activity and conformation: inhibition kinetics and computational simulations. Applied Biochemistry and Biotechnology 2010 160 7 1896 1908 2-s2.0-77949914143 10.1007/s12010-009-8730-9
    • (2010) Applied Biochemistry and Biotechnology , vol.160 , Issue.7 , pp. 1896-1908
    • Lü, Z.R.1    Shi, L.2    Wang, J.3    Park, D.4    Bhak, J.5    Yang, J.M.6    Park, Y.D.7    Zhou, H.W.8    Zou, F.9
  • 19
    • 0037394181 scopus 로고    scopus 로고
    • Synthesis and tyrosinase inhibitory activity of novel N-hydroxybenzyl-N-nitrosohydroxylamines
    • DOI 10.1016/S0045-2068(03)00026-9
    • Shiino M., Watanabe Y., Umezawa K., Synthesis and tyrosinase inhibitory activity of novel N-hydroxybenzyl-N-nitrosohydroxylamines. Bioorganic Chemistry 2003 31 2 129 135 2-s2.0-0037394181 10.1016/S0045-2068(03)00026-9 (Pubitemid 36506835)
    • (2003) Bioorganic Chemistry , vol.31 , Issue.2 , pp. 129-135
    • Shiino, M.1    Watanabe, Y.2    Umezawa, K.3
  • 20
    • 33244460034 scopus 로고    scopus 로고
    • Flavonoids as mushroom tyrosinase inhibitors: A fluorescence quenching study
    • DOI 10.1021/jf0521855
    • Kim D., Park J., Kim J., Han C., Yoon J., Kim N., Seo J., Lee C., Flavonoids as mushroom tyrosinase inhibitors: a fluorescence quenching study. Journal of Agricultural and Food Chemistry 2006 54 3 935 941 2-s2.0-33244460034 10.1021/jf0521855 (Pubitemid 43274134)
    • (2006) Journal of Agricultural and Food Chemistry , vol.54 , Issue.3 , pp. 935-941
    • Kim, D.1    Park, J.2    Kim, J.3    Han, C.4    Yoon, J.5    Kim, N.6    Seo, J.7    Lee, C.8
  • 21
    • 34547758423 scopus 로고    scopus 로고
    • Functional interaction of diphenols with polyphenol oxidase: Molecular determinants of substrate/inhibitor specificity
    • DOI 10.1111/j.1742-4658.2007.05944.x
    • Kanade S. R., Suhas V. L., Chandra N., Gowda L. R., Functional interaction of diphenols with polyphenol oxidase. Molecular determinants of substrate/inhibitor specificity. FEBS Journal 2007 274 16 4177 4187 2-s2.0-34547758423 10.1111/j.1742-4658.2007.05944.x (Pubitemid 47228634)
    • (2007) FEBS Journal , vol.274 , Issue.16 , pp. 4177-4187
    • Kanade, S.R.1    Suhas, V.L.2    Chandra, N.3    Gowda, L.R.4
  • 22
    • 67649909586 scopus 로고    scopus 로고
    • Synthesis and evaluation of 5-benzylidene(thio)barbiturate- β -D-glycosides as mushroom tyrosinase inhibitors
    • 2-s2.0-67649909586 10.1016/j.bmcl.2009.06.018
    • Yan Q., Cao R., Yi W., Yu L., Chen Z., Ma L., Song H., Synthesis and evaluation of 5-benzylidene(thio)barbiturate- β -D-glycosides as mushroom tyrosinase inhibitors. Bioorganic and Medicinal Chemistry Letters 2009 19 15 4055 4058 2-s2.0-67649909586 10.1016/j.bmcl.2009.06.018
    • (2009) Bioorganic and Medicinal Chemistry Letters , vol.19 , Issue.15 , pp. 4055-4058
    • Yan, Q.1    Cao, R.2    Yi, W.3    Yu, L.4    Chen, Z.5    Ma, L.6    Song, H.7
  • 23
    • 25444479368 scopus 로고    scopus 로고
    • - binding
    • DOI 10.1016/j.biochi.2005.06.006, PII S030090840500146X
    • Park Y. D., Kim S. Y., Lyou Y. J., Lee J. Y., Yang J. M., A new type of uncompetitive inhibition of tyrosinase induced by Cl- binding. Biochimie 2005 87 11 931 937 2-s2.0-25444479368 10.1016/j.biochi.2005.06.006 (Pubitemid 41377152)
    • (2005) Biochimie , vol.87 , Issue.11 , pp. 931-937
    • Park, Y.-D.1    Kim, S.-Y.2    Lyou, Y.-J.3    Lee, J.-Y.4    Yang, J.-M.5
  • 25
    • 20444413775 scopus 로고    scopus 로고
    • Interaction between hesperetin and human serum albumin revealed by spectroscopic methods
    • DOI 10.1016/j.bbagen.2005.04.009, PII S0304416505001054
    • Xie M. X., Xu X. Y., Wang Y. D., Interaction between hesperetin and human serum albumin revealed by spectroscopic methods. Biochimica et Biophysica Acta 2005 1724 1-2 215 224 2-s2.0-20444413775 10.1016/j.bbagen.2005.04.009 (Pubitemid 40799127)
    • (2005) Biochimica et Biophysica Acta - General Subjects , vol.1724 , Issue.1-2 , pp. 215-224
    • Xie, M.-X.1    Xu, X.-Y.2    Wang, Y.-D.3
  • 26
    • 32144432437 scopus 로고    scopus 로고
    • The SWISS-MODEL workspace: A web-based environment for protein structure homology modelling
    • DOI 10.1093/bioinformatics/bti770
    • Arnold K., Bordoli L., Kopp J., Schwede T., Trsten.Schwede@unibas.ch The SWISS-MODEL workspace: a web-based environment for protein structure homology modelling. Bioinformatics 2006 22 2 195 201 10.1093/bioinformatics/bti770 (Pubitemid 43205406)
    • (2006) Bioinformatics , vol.22 , Issue.2 , pp. 195-201
    • Arnold, K.1    Bordoli, L.2    Kopp, J.3    Schwede, T.4
  • 28
    • 33947716119 scopus 로고    scopus 로고
    • Software news and update a semiempirical free energy force field with charge-based desolvation
    • DOI 10.1002/jcc.20634
    • Huey R., Morris G. M., Olson A. J., Goodsell D. S., A semiempirical free energy force field with charge-based desolvation. Journal of Computational Chemistry 2007 28 6 1145 1152 2-s2.0-33947716119 10.1002/jcc.20634 (Pubitemid 46506716)
    • (2007) Journal of Computational Chemistry , vol.28 , Issue.6 , pp. 1145-1152
    • Huey, R.1    Morris, G.M.2    Olson, A.J.3    Goodsell, D.S.4
  • 31
    • 10444280081 scopus 로고    scopus 로고
    • Chalcones as potent tyrosinase inhibitors: The importance of a 2,4-substituted resorcinol moiety
    • DOI 10.1016/j.bmc.2004.10.010, PII S0968089604007849
    • Khatib S., Nerya O., Musa R., Shmuel M., Tamir S., Vaya J., Chalcones as potent tyrosinase inhibitors: the importance of a 2,4-substituted resorcinol moiety. Bioorganic and Medicinal Chemistry 2005 13 2 433 441 2-s2.0-10444280081 10.1016/j.bmc.2004.10.010 (Pubitemid 39642925)
    • (2005) Bioorganic and Medicinal Chemistry , vol.13 , Issue.2 , pp. 433-441
    • Khatib, S.1    Nerya, O.2    Musa, R.3    Shmuel, M.4    Tamir, S.5    Vaya, J.6
  • 32
    • 3242811929 scopus 로고    scopus 로고
    • Interaction of mushroom tyrosinase with aromatic amines, o-diamines and o-aminophenols
    • DOI 10.1016/j.bbagen.2004.04.013, PII S0304416504001096
    • Gasowska B., Kafarski P., Wojtasek H., Interaction of mushroom tyrosinase with aromatic amines, o-diamines and o-aminophenols. Biochimica et Biophysica Acta 2004 1673 3 170 177 2-s2.0-3242811929 10.1016/j.bbagen.2004.04.013 (Pubitemid 38981770)
    • (2004) Biochimica et Biophysica Acta - General Subjects , vol.1673 , Issue.3 , pp. 170-177
    • Gasowska, B.1    Kafarski, P.2    Wojtasek, H.3
  • 33
    • 33645394824 scopus 로고    scopus 로고
    • TXM13 human melanoma cells: A novel source for the inhibition kinetics of human tyrosinase and for screening whitening agents
    • 2-s2.0-33645394824 10.1139/o05-151
    • Park Y. D., Kim S. Y., Lyou Y. J., Lee D. Y., Yang J. M., TXM13 human melanoma cells: a novel source for the inhibition kinetics of human tyrosinase and for screening whitening agents. Biochemistry and Cell Biology 2006 84 1 112 116 2-s2.0-33645394824 10.1139/o05-151
    • (2006) Biochemistry and Cell Biology , vol.84 , Issue.1 , pp. 112-116
    • Park, Y.D.1    Kim, S.Y.2    Lyou, Y.J.3    Lee, D.Y.4    Yang, J.M.5
  • 34
    • 33749989366 scopus 로고    scopus 로고
    • Complex inhibition of tyrosinase by thiol-composed Cu2+ chelators: A clue for designing whitening agents
    • 2-s2.0-33749989366
    • Park Y. D., Lyou Y. J., Hahn H. S., Hahn M. J., Yang J. M., Complex inhibition of tyrosinase by thiol-composed Cu2+ chelators: a clue for designing whitening agents. Journal of Biomolecular Structure and Dynamics 2006 24 2 131 138 2-s2.0-33749989366
    • (2006) Journal of Biomolecular Structure and Dynamics , vol.24 , Issue.2 , pp. 131-138
    • Park, Y.D.1    Lyou, Y.J.2    Hahn, H.S.3    Hahn, M.J.4    Yang, J.M.5


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