CAMP-binding site of PKA as a molecular target of bisabolangelone against melanocyte-specific hyperpigmented disorder

Journal of Investigative Dermatology

Volumn 133, Issue 4, 2013, Pages 1072-1079

  Roh, Eunmiri ^a   Yun, Cheong Yong ^a   Yun, Ji Young ^a   Park, Dongsun ^a   Doo Kim, Nam ^b   Yeon Hwang, Bang ^a   Jung, Sang Hun ^c   Park, Sun Ki ^d   Kim, Yun Bae ^a   Han, Sang Bae ^a   Kim, Youngsoo ^a  

^a Chungbuk National University   (South Korea)

^b Daegu Gyeongbuk Medical Innovation Foundation   (South Korea)

^c Chungnam National University   (South Korea)

^d Cosmecca Korea ^*  (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ADENOSINE 3',5' PHOSPHOROTHIOATE; BISABOLANGELONE; CYCLIC AMP; CYCLIC AMP DEPENDENT PROTEIN KINASE; CYCLIC AMP RESPONSIVE ELEMENT BINDING PROTEIN; MICROPHTHALMIA ASSOCIATED TRANSCRIPTION FACTOR; RP ADENOSINE 3',5' CYCLIC MONOPHOSPHOROTHIOATE; SESQUITERPENE DERIVATIVE; TRANSCRIPTION FACTOR SOX9; UNCLASSIFIED DRUG;

ANGELICA; ANGELICAL KOREANA; ARTICLE; BINDING SITE; CONTROLLED STUDY; CRYSTAL STRUCTURE; DOWN REGULATION; ENZYME ACTIVATION; GENE EXPRESSION; HYPERPIGMENTATION; MELANOCYTE; PLANT ROOT; PRIORITY JOURNAL; PROTEIN PHOSPHORYLATION;

EID: 84875225174     PISSN: 0022202X     EISSN: 15231747     Source Type: Journal    
DOI: 10.1038/jid.2012.425     Document Type: Article

References (47)

1. Berman HM, Ten Eyck LF, Goodsell DS et al. (2005) The cAMP binding domain: an ancient signaling module. Proc Natl Acad Sci USA 102:45-50
2. Bertolotto C, Bille K, Ortonne JP et al. (1996) Regulation of tyrosinase gene expression by cAMP in B16 melanoma cells involves two CATGTG motifs surrounding the TATA box: implication of the microphthalmia gene product. J Cell Biol 134:747-55
3. Brandon EP, Idzerda RL, McKnight GS (1997) PKA isoforms, neural pathways, and behaviour: making the connection. Curr Opin Neurobiol 7:397-403
4. Busca R, Ballotti R (2000) Cyclic AMP a key messenger in the regulation of skin pigmentation. Pigment Cell Res 13:60-9
5. Cheli Y, Luciani F, Khaled M et al. (2009) a-MSH and cyclic AMP elevating agents control melanosome pH through a protein kinase A-independent mechanism. J Biol Chem 284:18699-706
6. Dorazio J, Fisher DE (2011) Central role for cAMP signaling in pigmentation and UV resistance. Cell Cycle 10:8-9
7. Davies SP, Reddy H, Caivano M et al. (2000) Specificity and mechanism of action of some commonly used protein kinase inhibitors. Biochem J 351:95-105
8. Diller TC, Madhusudan, Xuong NH et al. (2001) Molecular basis for regulatory subunit diversity in cAMP-dependent protein kinase: crystal structure of the type IIb regulatory subunit. Structure 9:73-82
9. Dostmann WR, Taylor SS, Genieser HG et al. (1990) Probing the cyclic nucleotide binding sites of cAMP-dependent protein kinases I and II with analogs of adenosine 30,50-cyclic phosphorothioates. J Biol Chem 265:10484-91
10. Engh RA, Girod A, Kinzel V et al. (1996) Crystal structures of catalytic subunit of cAMP-dependent protein kinase in complex with isoquinolinesulfonyl protein kinase inhibitors H7, H8, and H89: structural implications for selectivity. J Biol Chem 271:26157-64
11. Englaro W, Rezzonico R, Durand-Clement M et al. (1995) Mitogen-activated protein kinase pathway and AP-1 are activated during cAMP-induced melanogenesis in B-16 melanoma cells. J Biol Chem 270:24315-24320
12. Hummler E, Cole TJ, Blendy JA et al. (1994) Targeted mutation of the CREB gene: compensation within the CREB/ATF family of transcription factors. Proc Natl Acad Sci USA 91:5647-51
13. Jung HW, Mahesh R, Park JH et al. (2010) Bisabolangelone isolated from Ostericum koreanum inhibits the production of inflammatory mediators by down-regulation of NF-kB and ERK MAP kinase activity in LPS-stimulated RAW264.7 cells. Int Immunopharmacol 10:155-62
14. Kang SW, Kim HK, Lee WJ et al. (2006) Toxicity of bisabolangelone from Ostericum koreanum roots to Dermatophagoides farinae and Dermatophagoides pteronyssinus (Acari: Pyroglyphidae). J Agric Food Chem 54:3547-50
15. Khaled M, Larribere L, Bille K et al. (2002) Glycogen synthase kinase 3b is activated by cAMP and plays an active role in the regulation of melanogenesis. J Biol Chem 277:33690-7
16. Khaled M, Larribere L, Bille K et al. (2003) Microphthalmia associated transcription factor is a target of the phosphatidylinositol-3-kinase pathway. J Invest Dermatol 121:831-6
17. Kim C, Cheng CY, Saldanha SA et al. (2007) PKA-I holoenzyme structure reveals a mechanism for cAMP-dependent activation. Cell 130:1032-43
18. Kim S, Lee J, Jung E et al. (2008) Mechanisms of depigmentation by abisabolol. J Dermatol Sci 52:219-22
19. Knighton DR, Zheng JH, Ten Eyck LF et al. (1991) Structure of a peptide inhibitor bound to the catalytic subunit of cyclic adenosine monophosphate- dependent protein kinase. Science 253:414-20
20. Kondo T, Hearing VJ (2011) Update on the regulation of mammalian melanocyte function and skin pigmentation. Expert Rev Dermatol 6:97-108
21. Le Pape E, Wakamatsu K, Ito S et al. (2008) Regulation of eumelanin/pheomelanin synthesis and visible pigmentation in melanocytes by ligands of the melanocortin 1 receptor. Pigment Cell Melanoma Res 21:477-86
22. Lee J, Jun H, Jung E et al. (2010) Whitening effect of a-bisabolol in Asian women subjects. Int J Cosmet Sci 32:299-303
23. Liu JJ, Fisher DE (2010) Lighting a path to pigmentation: mechanisms of MITF induction by UV. Pigment Cell Melanoma Res 23:741-5
24. Lochner A, Moolman JA (2006) The many faces of H89: a review. Cardiovasc Drug Rev 24:261-74
25. Maeda K, Fukuda M (1996) Arbutin: mechanism of its depigmenting action in human melanocyte culture. J Pharmacol Exp Ther 276:765-9
26. Moll D, Prinz A, Brendel CM et al. (2008) Biochemical characterization and cellular imaging of a novel, membrane permeable fluorescent cAMP analog. BMC Biochem 9:18
27. Ohguchi K, Ito M, Yokoyama K et al. (2009) Effects of sesquiterpene lactones on melanogenesis in mouse B16 melanoma cells. Biol Pharm Bull 32:308-10
28. Olivares C, Solano F (2009) New insights into the active site structure and catalytic mechanism of tyrosinase and its related proteins. Pigment Cell Melanoma Res 22:750-60
29. Ortonne JP, Passeron T (2005) Melanin pigmentary disorders: treatment update. Dermatol Clin 23:209-26
30. Passeron T, Valencia JC, Bertolotto C et al. (2007) SOX9 is a key player in ultraviolet B-induced melanocyte differentiation and pigmentation. Proc Natl Acad Sci USA 104:13984-9
31. Piera-Velazquez S, Hawkins DF, Whitecavage MK et al. (2007) Regulation of the human SOX9 promoter by Sp1 and CREB. Exp Cell Res 313:1069-79
32. Roh E, Yun CY, Lee JW et al. (2011) Hypopigmenting activity of bisabolangelone isolated from Angelica koreana Maxim. in a-melanocyte stimulating hormone-activated B16 or melan-a cells. Planta Med 77:248-51
33. Sands WA, Palmer TM (2008) Regulating gene transcription in response to cyclic AMP elevation. Cell Signal 20:460-6
34. Skalhegg BS, Tasken K (2000) Specificity in the cAMP/PKA signaling pathway: differential expression, regulation, and subcellular localization of subunits of PKA. Front Biosci 5:D678-93
35. Slominski A, Tobin DJ, Shibahara S et al. (2004) Melanin pigmentation in mammalian skin and its hormonal regulation. Physiol Rev 84:1155-228
36. Solano F, Briganti S, Picardo M et al. (2006) Hypopigmenting agents: an updated review on biological, chemical and clinical aspects. Pigment Cell Res 19:550-71
37. Taylor SS, Kim C, Cheng CY et al. (2008) Signaling through cAMP and cAMPdependent protein kinase: diverse strategies for drug design. Biochim Biophys Acta 1784:16-26
38. Udono T, Yasumoto K, Takeda K et al. (2000) Structural organization of the human microphthalmia-associated transcription factor gene containing four alternative promoters. Biochim Biophys Acta 1491:205-19
39. Vachtenheim J, Borovansky J (2010) ''Transcription physiology'' of pigment formation in melanocytes: central role of MITF. Exp Dermatol 19:617-27
40. Wang J, Zhu L, Zou K et al. (2009) The anti-ulcer activities of bisabolangelone from Angelica polymorpha. J Ethnopharmacol 123:343-6
41. Wu J, Jones JM, Nguyen-Huu X et al. (2004) Crystal structures of RIa subunit of cyclic adenosine 50-monophosphate (cAMP)-dependent protein kinase complexed with (Rp)-adenosine 30,50-cyclic monophosphothioate and (Sp)-adenosine 30,50-cyclic monophosphothioate, the phosphothioate analogues of cAMP. Biochemistry 43:6620-9
42. Wu M, Hemesath TJ, Takemoto CM et al. (2000) c-Kit triggers dual phosphorylations, which couple activation and degradation of the essential melanocyte factor Mi. Genes Dev 14:301-12
43. Young Kang H, Ortonne JP (2009) Melasma update. Actas Dermosifiliogr 100(Suppl 2):110-3
44. Yun CY, Kim D, Lee WH et al. (2009) Torilin from Torilis japonica inhibits melanin production in a-melanocyte stimulating hormone-activated B16 melanoma cells. Planta Med 75:1505-8
45. Zawadzki KM, Taylor SS (2004) cAMP-dependent protein kinase regulatory subunit type IIb: active site mutations define an isoform-specific network for allosteric signaling by cAMP. J Biol Chem 279:7029-36
46. Zhang X, Odom DT, Koo SH et al. (2005) Genome-wide analysis of cAMPresponse element binding protein occupancy, phosphorylation, and target gene activation in human tissues. Proc Natl Acad Sci USA 102:4459-64
47. Zimmermann B, Schweinsberg S, Drewianka S et al. (2008) Effect of metal ions on high-affinity binding of pseudosubstrate inhibitors to PKA. Biochem J 413:93-101