Role of Superoxide in Bioluminescence†

doi:10.7503/cjcu20140804

Abstract

Abstract:

Following the introduction on reactive oxygen species and superoxide, this review summarized the role of supe-roxide in bioluminescence, and elaborated theoretical and experimental research progress of superoxide reaction in several different bioluminescent systems. The role of superoxide in bioluminescence was described in firefly, bacteria, fungi and dinoflagellate bioluminescent processes. The production, function and reaction of superoxide in bacteria bioluminescence was explained in details according to our recent study.

Key words: Superoxide, Bioluminescence, Electron transfer, Reactive oxygen species, Redox reaction

CLC Number:

O644

TrendMD:

LUO Yanling, LIU Yajun. Role of Superoxide in Bioluminescence^†[J]. Chem. J. Chinese Universities, 2015, 36(1): 24.

Figures/Tables 8

Fig.1 Routes to the formation and consumption of superoxide in the ocean

Fig.2 Molecular structures of luciferin in different organisms

Fig.3 Reactions of firefly bioluminescence

Fig.4 Possible reaction pathway for firefly bioluminescence participated by superoxide

Fig.5 Reaction of Cypridina bioluminescence

Fig.6 Diagram about bacterial bioluminescence process and the structure of several molecules involved in the process

Fig.7 Potential energy curve along the addition of O2 to FMNH-[87]

Fig.8 Reaction pathways of superoxide and flavin semiquinone radical pair

References 104

[1]	Valentine J.S., Foote C. S., Greenberg A., Liebman J. F., Active Oxygen in Biochemistry, Blackie Academic & Professional, New York, 1995
[2]	Takeshita K., Okazaki S., Itoda A., Anal. Chem., 2013, 85(14), 6833—6839
[3]	Turro N.J.,Ramamurthy V., Scaiano J., Modern Molecular Photochemistry of Organic Molecules, University Science Books, Sausalito Calif, 2010
[4]	Premkumar L. S., Pabbidi R. M., Cell Biochem. Biophys., 2013, 67(2), 373—383
[5]	Murale D. P., Kim H., Choi W. S., Churchill D. G., Org. Lett., 2013, 15(15), 3946—3949
[6]	Simon H. U., Haj-Yehia A., Levi-Schaffer F., Apoptosis , 2000, 5(5), 415—418
[7]	Burns J. M., Cooper W. J., Ferry J. L., King D. W., DiMento B. P., McNeill K., Miller C. J., Miller W. L., Peake B. M., Rusak S. A., Aquat. Sci., 2012, 74(4), 683—734
[8]	Fleury C., Mignotte B., Vayssiere J. L., Biochimie , 2002, 84(2/3), 131—141
[9]	Alfadda A. A., Sallam R. M., J. Biomed. Biotechnol., 2012, 2012, 1—14
[10]	Halliwell B.,Encyclo. Life Sci., 2001, 1—7
[11]	Cross C. E., Halliwell B., Borish E. T., Pryor W. A., Ames B. N., Saul R. L., McCord J. M., Harman D., Ann. Intern. Med., 1987, 107(4), 526—545
[12]	Halliwell B., Gutteridge J. M. C., Cross C. E., J. Lab. Clin. Med., 1992, 119(6), 598—620
[13]	Finkel T., Curr. Opin. Cell Biol., 1998, 10(2), 248—253
[14]	Rhee S. G., Exp. Mol. Med., 1999, 31(2), 53—59
[15]	Bancirova M., Luminescence , 2011, 26(6), 685—688
[16]	Brezonik P. L., Fulkerson-Brekken J., Environ. Sci. Technol., 1998, 32(19), 3004—3010
[17]	Canonica S., Kohn T., Mac M., Real F. J., Wirz J., Von Gunten U., Environ. Sci. Technol., 2005, 39(23), 9182—9188
[18]	Westerhoff P., Mezyk S. P., Cooper W. J., Minakata D., Environ. Sci. Technol., 2007, 41(13), 4640—4646
[19]	Khan A. U., Wilson T., Chem. Biol., 1995, 2(7), 437—445
[20]	Babior B., Woodman R., Semin. Hematol., 1990, 27(3), 247—259
[21]	Maly F. E., Free Radical Res., 1990, 8(3), 143—148
[22]	Meier B., Radeke H. H., Selle S., Raspe H. H., Sies H., Resch K., Habermehl G. G., Free Radical Res., 1990, 8(3), 149—160
[23]	Murrell G. A., Francis M., Bromley L., Biochem. J., 1990, 265(3), 659—665
[24]	Britigan B. E., Roeder T. L., Shasby D. M., Blood , 1992, 79(3), 699—707
[25]	Kudin A. P., Bimpong-Buta N. Y. B., Vielhaber S., Elger C. E., Kunz W. S., J. Biol. Chem., 2004, 279(6), 4127—4135
[26]	Moncada S., Palmer R., Higgs E., Pharmacol. Rev., 1991, 43(2), 109—142
[27]	Laurindo F., da Luz P. L., Uint L., Rocha T., Jaeger R., Lopes E., Circulation , 1991, 83(5), 1705—1715
[28]	Gardner P. R., Fridovich I., J. Biol. Chem., 1992, 267(13), 8757—8763
[29]	Gardner P. R., Fridovich I., J. Biol. Chem., 1991, 266(3), 1478—1483
[30]	Marshall J. A., Hovenden M., Oda T., Hallegraeff G. M., J. Plankton Res., 2002, 24(11), 1231—1236
[31]	Kim D., Oda T., Ishimatsu A., Muramatsu T., Biosci. Biotechnol. Biochem., 2000, 64(4), 911—914
[32]	Heller M. I., Croot P. L., Environ. Sci. Technol., 2009, 44(1), 191—196
[33]	Zafiriou O. C., Voelker B. M., Sedlak D. L., J. Phys. Chem. A, 1998, 102(28), 5693—5700
[34]	Voelker B. M., Sedlak D. L., Zafiriou O. C., Environ. Sci. Technol., 2000, 34(6), 1036—1042
[35]	Voelker B. M., Sedlak D. L., Mar. Chem., 1995, 50(1), 93—102
[36]	Rose A. L., Waite T. D., Geochim. Cosmochim. Acta, 2006, 70(15), 3869—3882
[37]	O’Sullivan D. W., Hanson A. K., Miller W. L., Kester D. R., Limnol. Oceanogr., 1991, 36(8), 1727—1741
[38]	Fan S. M., Mar. Chem., 2008, 109(1), 152—164
[39]	Weber L., Volker C., Schartau M., Wolf-Gladrow D., Global Biogeochem. Cycles, 2005, 19(1), 1—23
[40]	Tagliabue A., Bopp L., Aumont O., Arrigo K. R., Global Biogeochem. Cycles, 2009, 23(2), 1—12
[41]	Sawyer D. T., Int. Rev. Exp. Pathol., 1990, 31, 109—131
[42]	Fujii M., Ito H., Rose A. L., Waite T. D., Omura T., Geochim. Cosmochim. Acta, 2008, 72(24), 6079—6089
[43]	Mager H. I., Tu S., Photochem. Photobiol., 1995, 62(4), 607—614
[44]	Wilson T., Hastings J. W., Annu. Rev. Cell Dev. Biol. , 1998, 14(1), 197—230
[45]	Widder E. A., Falls B., Ieee J. Sel. Top. Quant. , 2014, 20(2), 1—10
[46]	Li Z.S., Theoretical Study of Multicolour Bioluminescence, Jilin University, Changchun, 2013(李作盛. 生物多色发光的理论研究, 长春, 吉林大学, 2013)
[47]	Shimomura O., Bioluminescence: Chemical Principles And Methods, World Scientific, Hackensack NJ, 2006
[48]	Herring P. J., J. Biolumin. Chemilumin., 1987, 1(3), 147—163
[49]	Badr C. E., Tannous B. A., Trends Biotechnol., 2011, 29(12), 624—633
[50]	Roda A., Guardigli M., Michelini E., Mirasoli M., Trac Trends Anal. Chem., 2009, 28(3), 307—322
[51]	Roda A., Guardigli M., Pasini P., Mirasoli M., Michelini E., Musiani M., Anal. Chim. Acta, 2005, 541(1), 25—35
[52]	Steinberg S. M., Poziomek E. J., Engelmann W. H., Rogers K. R., Chemosphere , 1995, 30(11), 2155—2197
[53]	Heller M., Croot P., Anal. Chim. Acta, 2010, 667(1), 1—13
[54]	Chen S. F., Liu Y. J., Navizet I., Ferre N., Fang W. H., Lindh R., J. Chem. Theory Comput., 2011, 7(3), 798—803
[55]	Yue L., Liu Y. J., Fang W. H., J. Am. Chem. Soc., 2012, 134(28), 11632—11639
[56]	Navizet I., Liu Y. J., Ferre N., Roca-Sanjuan D., Lindh R., Chemphyschem. , 2011, 12(17), 3064—3076
[57]	Vieira J., Pinto da Silva L., Esteves da Silva J. C., J. Photochem. Photobiol. B: Biol. , 2012, 117, 33—39
[58]	Fraga H., Photochem. Photobiol. Sci., 2008, 7(2), 146—158
[59]	Cheng Y. Y., Zhu J., Liu Y. J., Chem. Phys. Lett., 2014, 591, 156—160
[60]	Chen S. F., Yue L., Liu Y. J., Lindh R., Int. J. Quantum Chem., 2011, 111(13), 3371—3377
[61]	Navizet I., Liu Y. J., Ferre N., Xiao H. Y., Fang W. H., Lindh R., J. Am. Chem. Soc., 2010, 132(2), 706—712
[62]	Naumov P., Ozawa Y., Ohkubo K., Fukuzumi S., J. Am. Chem. Soc., 2009, 131(32), 11590—11605
[63]	Wada N., Mitsuta K., Kohno M., Suzuki N., J. Phys. Soc. Jpn., 1989, 58(10), 3501—3504
[64]	Wada N., Shibata R., Shibazaki M., Suzuki N., Photochem. Photobiol., 1989, 49(4), 513—518
[65]	Sundlov J. A., Fontaine D. M., Southworth T. L., Branchini B. R., Gulick A. M., Biochemistry , 2012, 51(33), 6493—6495
[66]	Da Silva L. P., Esteves da Silva J. C., Chem. Phys. Lett., 2013, 577, 127—130
[67]	Da Silva L. P., Esteves da Silva J. C., Chem. Phys. Lett., 2013, 590, 180—182
[68]	Johnson F. H., Shimomura O., Saiga Y., Gershman L. C., Reynolds G. T., Waters J. R., J. Cell. Comp. Physiol., 1962, 60(1), 85—103
[69]	Shimomura O., Johnson F. H., Photochem. Photobiol., 1970, 12(4), 291—295
[70]	Shimomura O., Goto T., Hirata Y., Bull. Chem. Soc. Jpn., 1957, 30(8), 929—933
[71]	Kishi T., Goto T., Hirata Y., Shimomura O., Johnson F. H., Tetrahedron Lett., 1966, 7(29), 3427—3436
[72]	Shimomura O., Johnson F. H., Masugi T., Science , 1969, 164(3885), 1299—1300
[73]	Teranishi K., Bioorg. Chem., 2007, 35(1), 82—111
[74]	Naumov P., Wu C., Liu Y. J., Ohmiya Y., Photochem. Photobiol. Sci., 2012, 11(7), 1151—1155
[75]	Goto T., Inoue S., Sugiura S., Tetrahedron Lett., 1968, 36, 3873—3876
[76]	Kondo H., Igarashi T., Maki S., Niwa H., Ikeda H., Hirano T., Tetrahedron Lett., 2005, 46(45), 7701—7704
[77]	Sun Y., Ren A. M., Min C. G., Zou L. Y., Ren X. F., Acta Phys. Chim. Sin., 2010, 26(10), 2779—2786
	(孙颖, 任爱民, 闵春刚, 邹陆一, 任雪峰. 物理化学学报, 2010, 26(10), 2779—2786)
[78]	Du Z. J., Wang X. H., Li H. F., Chi Z. M., High Technol. Lett., 2003, 13(12), 103—106
	(杜宗军, 王祥红, 李海峰, 池振明. 高技术通讯, 2003, 13(12), 103—106)
[79]	Ke D., Tu S., Photochem. Photobiol., 2011, 87(6), 1346—1353
[80]	Zhu W. J., He X. M., Yang Y. K., Chin. J. Lumin., 1986, 7(1), 127—131
	(朱文杰, 何学民, 杨颐康. 发光学报, 1986, 7(1), 127—131)
[81]	Wada N., Sugimoto T., Watanabe H., Tu S., Photochem. Photobiol., 1999, 70(1), 116—122
[82]	Baldwin T., Nicoli M., Becvar J., Hastings J., J. Biol. Chem., 1975, 250(8), 2763—2768
[83]	Tu S. C., Photochem. Photobiol. Sci., 2008, 7(2), 183—188
[84]	Nemtseva E. V., Kudryasheva N. S., Russ. Chem. Rev., 2007, 76(1), 91—100
[85]	Klinman J. P., Acc. Chem. Res., 2007, 40(5), 325—333
[86]	Andersson K., Malmqvist P. A., Roos B. O., J. Chem. Phys., 1992, 96(2), 1218—1226
[87]	Hou C., Liu Y. J., Ferre N., Fang W. H., Chem. Eur. J., 2014, 20(26), 7979—7986
[88]	Nanni E. J., Sawyer D. T., Ball S. S., Bruice T. C., J. Am. Chem. Soc., 1981, 103(10), 2797—2802
[89]	Kurfurst M., Ghisla S., Hastings J. W., Biochemistry , 1983, 22(7), 1521—1525
[90]	Pennati A., Gadda G., Biochemistry , 2011, 50(1), 1—3
[91]	Chaiyen P., Fraaije M. W., Mattevi A., Trends Biochem. Sci., 2012, 37(9), 373—380
[92]	Mori K., Kojima S., Maki S., Hirano T., Niwa H., Luminescence , 2011, 26(6), 604—610
[93]	Oliveira A. G., Desjardin D. E., Perry B. A., Stevani C. V., Photochem. Photobiol. Sci., 2012, 11(5), 848—852
[94]	Stevani C. V., Oliveira A. G., Mendes L. F., Ventura F. F., Waldenmaier H. E., Carvalho R. P., Pereira T. A., Photochem. Photobiol., 2013, 89(6), 1318—1326
[95]	Dubois R., C. R. Seances Soc. Biol. Paris , 1885, 2(37), 559—562
[96]	Oliveira A. G., Stevani C. V., Photochem. Photobiol. Sci., 2009, 8(10), 1416—1421
[97]	Airth R. L., McElroy W. D., J. Bacteriol., 1959, 77(2), 249—250
[98]	Airth R. L., Foerster G. E., Arch. Biochem. Biophys., 1962, 97(3), 567—573
[99]	Isobe M., Uyakul D., Goto T., J. Biolumin. Chemilumin., 1987, 1(3), 181—188
[100]	Isobe M., Uyakul D. C., Goto T., Tetrahedron Lett., 1988, 29(10), 1169—1172
[101]	Isobe M., Takahashi H., Usami K., Hattori M., Nishigohri Y., Pure Appl. Chem., 1994, 66(4), 765—772
[102]	Takahashi H., Isobe M., Goto T., Tetrahedron , 1991, 47(32), 6215—6222
[103]	Shimomura O., Satoh S., Kishi Y., J. Biolumin. Chemilumin., 1993, 8(4), 201—205
[104]	Cussatlegras A. S., Le Gal P., J. Exp. Mar. Biol. Ecol. , 2007, 343(1), 74—81