bioluminescence£cf chemiluminescence - gbv · mastroianni n, foti m, bovolenta s, stucchi m,...
TRANSCRIPT
Pacifico Yokohama, Yokohama, Japan2 - 6 August 2004
ISBC 2004
Bioluminescence£cfChemiluminescence
Progress and Perspectives
edited by
Akio TsujiShowa University, Japan
Masakatsu MatsumotoKanagawa University, Japan
Masako MaedaShowa University, Japan
Larry J KrickaUniversity of Pennsylvania School of Medicine, USA
Philip E StanleyCambridge Research & Technology Transfer Ltd, UK
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'World ScientificNEW JERSEY • LONDON • SINGAPORE • BEIJING • SHANGHAI • HONG KONG • TAIPEI • CHENNAI
CONTENTS
Preface vii
PART 1. BIOLUMEVESCENCE
Bioluminescence and mating behaviour in pony fish,Leiognathus nuchalis 3
Azuma N, Furubayashi Q Shichiri T, Wada M, Mizuno Nand Suzuki Y
Studies on the bioluminescent mechanism of symplectin photoprotein 7Isobe M, Matsuda T, Kuse M, Mori H, Fujii T, Kondo N andKageyama Y
Chemical studies on bioluminescence of Acorn worm, Ptychodera flava:isolation and characterization of luminous substances 11
Kanakubo A, Koga K and Isobe M
pH regulation of luciferase activity in dinoflagellates involves a novelenzymatic mechanism 15
Liu L, Schultz W and Hastings JW
Bioluminescence in Ophiuroids (Echinodermata): a minreview 19Mallefet J
Luminescent behaviour in the New Zealand Glowworm, Arachnocampaluminosa (Insecta; Diptera; Mycetophilidae) 23
Ohba N and Meyer-Rochow VB
Aequorin and GFP: an historical account 27Shimomura O
Bioluminescence reaction in the firefly squid Watasenia scintillans 35Tsuji FI
Pharmacological and electrophysiological studies of light emission in3 ophiuroid species: preliminary results 39
Vanderlinden C, Vanhemelen M, Nilius B, Gailly P and Mallefet J
xv
xvi Contents
PART 2. BEETLE BIOLUMINESCENCE
Importance of firefly luciferase C-terminal domain in binding ofluciferyl-adenylate 45
Ayabe K, Zako T and Veda H
Comparison of kinetic properties of firefly luciferase from Photinuspyralis and Luciola mingrelica 49
Brovko LY, Gandelman OA, Kershengolz IB and Ugarova NN
Firefly luciferase and Drosophila CG6178 gene product are fattyacyl-CoA synthetases 53
Oba Y, Ojika M and Inouye S
Solvent effect on the NMR and absorption spectra of firefly luciferin intetrahydrofuran 57
Odai K, Nishiyama S, Shibata R, Yoshida Y and Wada N
An evolutionary history of the Japanese aquatic fireflies inferred frommitochondrial DNA sequences 61
Suzuki H, Sato Y and Ohba N
Bioluminescence spectra of native and mutant firefly luciferases as afunction of pH 65
Ugarova NN, Maloshenok LG and Uporov IV
Interaction of oxyluciferin analogs, dimethyl oxyluciferin andmonomethyl oxyluciferin, with firefly luciferase 69
Vlasova 77V, Leontieva OV and Ugarova NN
PART 3. MARINE BACTERIA BIOLUMINESCENCE
Effect of oxygen and hydrogen ion on the modulation of thebioluminescence from luminous bacteria 75
Karatani H, Yoshizawa S and Hirayama S
Kinetic investigation of bacterial luciferase 79Mezhevikin W, Sukovataya IE and Tyulkova NA
A MND0-PM5 study of the enzyme-free NADH generation from NAD+
in the presence of electron-transfer mediator and an evaluation of theprocess based on bacterial bioluminescence 83
Sugimoto T, Wada N and Karatani H
Contents xvii
Effects of organic solvents on bioluminescence emission spectra ofbacterial luciferase from Photobacterium leiognathi 87
Sukovataya IE and Tyulkova NA
Formation of H2O2 in bacterial bioluminescence reaction withflavinmononucleotide activated with N-methylimidazole on the phosphategroup without addition of the exogenous aldehyde 91
Tyulkova NA and Krasnova 01
Luminous bacteria: biotechnological aspects 95Vydryakova GA, Chugaeva YuV, Tyulkova NA, Medvedeva SE,Kuznetsov AM andRodicheva EK
Expulsion of symbiotic luminous bacteria from pony fish,Leiognathus nuchalis 99
Wada M, Barbara G, Mizuno N, Azuma N, Kogure K and Suzuki Y
RFLP analysis of the Lux A genes of Photobacterium leiognathi isolatesderived from the symbiotic light organ of Leiognathid fish,Leiognathus rivulatus 103
Wada M, Kamiya A, Kita-Tsukamoto K, Ikejima K, Nishida M andKogure K
Supplements for Photobacterium phosphoreum RL-1 culture medium toenhance the luminescence activity 107
Yu R, Imada C, Wada M, Kobayashi T, Hamada-Sato N andWatanabe E
PART 4. CYPRIDINA (VARGULA) BIOLUMINESCENCE
Superoxide or singlet oxygen: the chemiluminescence of Cypridinaluciferin analogues in photodynamic solutions 113
Bancirovd M and Snyrychovd I
Development of the chemistry of the imidazopyrazionone-bioluminescence system: From the bio- and chemiluminescencemechanism to a design of sensor molecules 117
Hirano T, Nakai S, Sekiguchi T, Fujio S, Maki S and Niwa H
Biosynthesis of Cypridina luciferin from free amino acids in Cypridina(Vargula) hilgendorfii 121
Kato S, Oba Y, Ojika M andlnouye S
xviii Contents
Studies on the chemiluminescence mechanism of Cypridina luciferinanalogues: dissociation constants of the singlet-excited Cypridinaoxyluciferin analogues 125
Saito R, Iwasa E and Katoh A
Biosynthesis of Vargula hilgendorfii luciferin, arisen from L-arginine,L-tryptophan, and L-isoleucine 129
ToyaY
PART 5. CHEMILUMINESCENCE
On the role of the singlet-oxygen dimol chemiluminescence indioxirane reactions 135
Adam W, Kazakov VP, Kazakov DV, Latypova RR, Maistrenko GY,Mal'zev DV and Safarov FE
Solvent effects on the chemiluminescence of TCPO in presence of7-amino-4-trifluoromethylcoumarin 139
ChaichiMJ, Shamsipur M, KaramiA, Alizadeh KandNazari O
Chemiluminescence in the reactions of uranium and lanthanides 143Kazakov VP, Ostakhov SS, Kazakov DV, Mamikin AV, Antipin VA,Klimina SN, Khazimullina LN and Kochneva OA
Green luminescence emitted from adsorbed oxygen — Aurora hasappeared on the surface of materials? 147
Kimura J-I
Thermo- and photo-luminescence from a photocatalyst titaniumdioxide (TiO2) 151
Kimura J-I
Relationship between heat of reaction and chemiluminescence efficiencyof chemiluminescent reactions 155
Kimura M, Iga H, Araki H and Matsumoto M
The high energy key intermediates in the peroxyoxalate chemiluminescenceof 2,4,6-trichlorophenyl Af-aryl-N-tosyloxamates 159
Koike R, Motoyoshiya J and Aoyama H
Chemiluminescence studies on the photochemical production of hydrogenperoxide from porphyrins and their aggregates 163
Komagoe K, Osada S, Shindo Tand Tamagake K
Contents xix
Excited states of dioxins as studied by ab initio quantum chemicalcomputations: anomalous luminescence characteristics 167
Koto T, Toyota K, Sato K, Shiomi D and Takui T
Chemiluminescence reaction of 4-styrylphthalhydrazides. Remarkablesubstituent effect on the emitting species and chemiluminescence efficiency 171
Motoyoshiya J, Yokota K, Hotta M, Nishii YandAoyama H
Fluorescence and chemiluminescence characteristics of bisindoles 175Nakazono M, Asechi M andZaitsu K
Photosensitive luminol releasing compound, luminol-0-4,5-dimethoxy-2-nitrobenzylate 179
Nakazono M and Zaitsu K
Preparation of a crown-ether-modified isoluminol derivative and itschemiluminescence properties in an organic medium 183
Okamoto H and Kimura M
Chemiluminescent study on oxidation of mono-, di-, and poly-saccharides 187Tamefusa T, Kimura J, ho R, Inoue K, Yoshimura Y and Nakazawa H
Solid surface enhancement effects on chemiluminescence: investigation ofhigh performance solid media and its application to analytical chemistry 191
Yoshinaga T, Ichimura T and Hiratsuka H
PART 6. 1,2-DIOXETANES
On the CIEEL mechanism of triggerable dioxetanes: does the electronjump or is it charge transfer? 197
Adam Wand TrofitnovAV
Chemiluminescence involving the phosphorus chemistry. Phospha-1,2-dioxetanes as the most likely high-energy intermediates in autoxidation ofphosphonate carbanions 201
Motoyoshiya J and Aoyama H
Chemiluminescence of unsubstituted and phenoxide substituted1,2-dioxetanes 205
Tanaka J, Tanaka C and Matsumoto M
x x Contents
Intramolecular CIEEL mechanism on chemiluminescence of phenoxidesubstituted 1,2-dioxetanes 209
Tanaka C, Tanaka J and Matsumoto M
PART 7. INSTRUMENTATION & DEVICES
Single-molecule imaging of protein in living cells by pin-fibervideo-microscopy 215
Hirakawa Y, Hasegawa T, Masujima T, Tokunaga M, Tsuyama Nand Kawano M
Scanning near field optical/atomic force microscopy (SNOM/AFM) —novel imaging technique in nano-meter scale and DNA-nanoFISH method 219
Ohtani T, Kim JM, Yoshino T, Nakao H, Sasou M, Sugiyama S andMuramatsu H
A new instrument for automated luminescent assays 223Symonds WH, Squirrell DJ and Jackson RS
PART 8. APPLICATIONS OF LUMINESCENCE
Construction of a novel bioluminescence bacterial biosensor for real-timemonitoring of cytotoxic drugs activity 229
Alloush HM, Angell JE, Smith MA, Hill PJ and Salisbury VC
Method for implementing bioluminescence-based analytical assays innanoliter volumes 233
Bartholomeusz DA, Davis RH, Yang TSM andAndrade JD
Immobilization of bioluminescent systems and their applications 237Esimbekova EN and Kratasyuk VA
Determination of basic compounds with peroxyoxalatechemiluminescence detection 241
Kawanishi H, Tsumura M, Fukushima T, Kato M and Toyo'oka T
Determination of artemisinin by HPLC with on-line photoreactor andperoxyoxalate chemiluminescence detection 245
KurodaN, Amponsaa-Karikari A, KishikawaN, Ohba Y andNakashima K
Contents xxi
Photina™: an improved Ca2+-sensitive photoprotein 249Mastroianni N, Foti M, Bovolenta S, Stucchi M, Rossignoli A andCorazza S
Development of fluorescence probes for biological applications, based onphotoinduced electron transfer 253
NaganoT
HPLC with fluorescence detection of morphine in rat plasma using4-(4,5-diphenyl-l//-imidazol-2-yl)benzoyl chloride as a label 257
Nakashima K, Ogata Y, Nakashima MN and Wada M
Luminescence probes for sensitive and specific optical imaging 261Roda A, Guardigli M, Pasini P, Mirasoli M, Michelini E,Charbonniere L and Ziessel R
Modeling of the signal intensity in the various reaction chambers ofthe NO-O3 chemiluminescence nitrogen oxides monitor to obtainhigher sensitivity 265
Sawada H, Okitsu K, Takenaka N and Bandow H
Development of highly sensitive analysis of glycated protein in humanhair by luminol chemiluminescence 269
Yajima T, Ito K, Ito R, Inoue K, Masubuchi K, Yoshimura Y,Yamada S, Atsuda K, Kubo H and Nakazawa H
Fluorescence sensor peptide for protein phosphorylation 273Yokoyama K and Itoda K
PART 9. ANTIOXIDANTS, REACTIVE OXYGEN SPECIES &PHAGOCYTOSIS
The chemiluminescent measurement of the black and green teaantioxidant capacity and the comparison with their antimicrobial activity 279
Bancifovd M and Snyrychovd I
Universal chemiluminescent assay for oxidative and antioxidativeprocesses in chemical and biological media: fundamentals and applicationaspects 283
Belyakov VA, Fedorova GF, Naumov W, Trofimov AVandVasil'evRF
xxjj Contents
Effect of anaesthesia with propofol and remifentanil on whole bloodchemiluminescence: discriminant analysis of the data 287
De Sole P, Rossi C and Scatena R
Chemiluminescent microspheres for measuring reactive oxygen speciesin phagocytosis 291
Hosaka S, Hosaka Y and Ichimura K
Effects of caloric restriction and aging on the generation of reactiveoxygen species in rat liver mitochondria and peroxisomes 295
Imada I, Sato EF, Konaka R, Nishikawa M, Kira Y, Park A-M, Li Qand Inoue M
Noncompetitive inhibition of lanthanide-induced oxidative burst by zincin tobacco BY-2 cells: a chemiluminescent analysis 299
Kawano T, Kadono T, Yang SC and Muto S
Lophine peroxides as an efficient organic source of singlet oxygen 303Kimura M, Lu G, Iga H and Nishikawa H
Effects of forced exercise started from different ages on chemiluminescentresponse and cytokine excretion of alveolar macrophage 307
Kumae TandArakawa H
Visualization of superoxide generated from colonies of Candida albicans 311Masui S, Majima T, Ito-Kuwa S, Nakamura Kand Aoki S
Effects of various antifungal agents on reactive oxygen species generationby Candida albicans 315
Masui S and Majima T
Chemiluminescent analysis of hydrogen peroxide generation from naturalantimicrobial materials 319
Matsuo N, Someya K, Ueda Y, Arakawa H and Maeda M
Induction of differentiation in HL-60 human leukemia cells by HEMA,TEGDMA and bis-GMA 323
Nocca G, De Sole P, Gambarini G, Chimenti C, De Palma F,Giardina B and Lupi A
Comparative study of ROS scavengers based on quenching ofMCLA-dependent chemiluminescence 327
Obuki M, Nakajima J, Suzuki M, Miyahara K and Hosaka S
Contents XX1U
Specific detection of singlet oxygen using vinylpyrene derivatives aschemiluminescent probe 331
Ohno K, Haryu Y, Nakano K, Lin J-M and Yamada M
6,8-Diarylimidazo[l,2-a]pyrazin-3(7//)-ones as potentialchemiluminescent pH/superoxide double sensors 335
Saito R, Suga N, Katoh A, Maki S, Hirano T and Niwa H
Simultaneous measurement of fluorescence and chemiluminescenceusing neutrophil-like culture cells 339
Satozono H, Kazumura K, Okazaki S and Hiramatsu M
Purification of environment by singlet oxygen 343SuzukiN
Study on chemiluminescent probes for superoxide anions: control ofchemiluminescence resonance energy transfer bycyclomaltooligosaccharide (cyclodextrin) 347
Teranishi K and Nishiguchi T
Luminol-dependent chemiluminescence of peripheral neutrophils fromworkers exposed to low frequency electromagnetic fields 351
Vuotto ML, Sannolo N, Miranda R, Liotti F, De Seta C, Spatuzzi D,Ruggiero G, Di Grazia M and De Sole P
Development of FIA-chemiluminescence methods to evaluate quenchingeffects against reactive oxygen species 355Wada M, Katoh M, Kido H, Nakashima MN, Kuroda N and Nakashima K
Syntheses and properties of cell-membrane permeable lucigeninderivatives for the assay of intracellular superoxide 359
Yamada S, Kohsaka N and Iwamura M
PART 10. APPLICATIONS IN MICROBIOLOGY, ECOLOGY,AND ENVIRONMENTAL & FOOD TESTING
Use of bioluminescent Salmonella typhimurium DT104 to monitor uptakeand intracellular survival within a human cell-line 365
Angell JE, Salisbury VC, Hill PJ andAlloush HM
xxiv Contents
Development of a range of bioluminescent food borne pathogens forassessing in-situ heat inactivation and recovery of bacteria during heattreatment of foods 369
Baldwin A, Nelson SM, Lewis RJ, Dowman A, Alloush HM andSalisbury VC
A novel method to enhance the subcutaneous detection of bioluminescencein the facultative anaerobe, Streptococcus pyogenes, by DMSO-assistedtransdermal oxygen delivery 373
Buxton DE, Childers BJ and Oberg KC
Development and testing of bacteriophage-based bioluminescentbioreporters for the monitoring of microbial pathogens in thespacecraft environment 377
Daumer KA, Ripp SA, Sayler GS and Garland JL
A single-step bioluminescent assay for rapid detection and quantitation ofviable microbial cells 381
Fan F, Butler B and Wood KV
Bioluminescent assay of total bacterial contamination (TBC) in force-meatusing Filtravette™ 385
Frundzhyan VG, Ugarova NN and Moroz NA
Bioluminescent assay of sterility or cleanliness in a hospital environment 389Frundzhyan VG, Ugarova NN, Gabriyelyan NI, Arepeva LI andPreobrazhenskay TB
Control of microorganisms by singlet oxygen 393Fujimura A, Toshitoku Y, Mese Y, Suzuki N, Nagai T, Mizumoto I,Sato H, Kanazawa R, Go A, Nakaguchi K and Yoda B
Quantitative analysis of chemiluminescence intensity and toxicity in silico 397Hanai T and Tachikawa T
Rapid detection of microorganisms in aseptic products using an ATPbioluminescent system 401
Igarashi T
Chemiluminescence detection of 3-nitrobenzanthrone and2-nitrotriphenylene in airborne particles with on-line reductionHPLC system 405
Inazu K, Saito T, Vu ND, Aika K and Hisamatsu Y
Contents x x v
Determination of particle-associated nitro-PAH usingHPLC/chemiluminescence detection system 409
Kameda T, Inazu K, Hisamatsu Y, TakenakaN and Bandow H
Biosensors based on bacterial bioluminescence forenvironmental monitoring 413
Kratasyuk VA, Esimbekova EN and Vetrova EV
Hospital testing of a rapid bioluminescent assay for MRS A 417Leslie RL, Murphy MJ, Squirrell DJ, Cotterill SL, Matthews SCWand Skyrme M
Microchip electrophoresis with chemiluminescent detection and itspossible applications 421
Lin J-M and Su R
Overview of new analytical tools for bioluminescent biomass estimation 425Lundin A and Elvdng A
The use of ATP bioluminescence for monitoring biocide or disinfectanttreatment of water 429
Ramsay CM, Wayman D, Davenport K and Michie I
Bioluminescent bioreporter integrated circuit sensing of the chemical andbiological spacecraft environment 433
Ripp SA, Garland JL, Blalock BJ, Islam SK and Sayler GS
Rapid and onsite BOD sensing system by luminouscells-immobilised-chip 437
Sakaguchi T, Morioka Y and Tamiya E
Simultaneous determination of twenty-one mutagenic nitropolycyclicaromatic hydrocarbons by high-performance liquid chromatography withchemiluminescence detection 441
Tang N, Taga R, Hattori T, Toriba A, Kizu R andHayakawa K
Bioenergetic confirmation of viable pathogens in foods byATP-bioluminescence
Tu S, Gehring A and Irwin P
Applications of bioluminescence-based assay in monitoringmicrobial burden
Venkateswaren K, Matsuyama A and Kern R
x x v j Contents
Application of imaging detection using XYZ emission system forfood analysis 453
Yoshiki Y and Okubo K
PART 11. LUMINESCENT IMMUNOASSAYS
Tandem bioluminescent enzyme immunoassay for BDNF and NT-4/5 459Akahane S, Ito K, Arakawa H and Maeda M
Calcium-regulated photoprotein obelin as a label in immunoassay:an outlook for applications 463
Frank LA, Borisova Wand VysotskiES
Highly sensitive CLEIA for C-peptide in serum with chemiluminescentsubstrate using a new CLEIA system 467
Hayama S, Moriyama K and Kitajima S
Development of tandem bioluminescent enzyme immunoassay forAngiotensinI and Endothelin-1 471
Ito K, Ohwaki K, Arakawa H and Maeda M
New methods for development of FRET-based biosensors with expandeddynamic range 475
Nagai T and Miyawaki A
Chagas assay using recombinant antigens on a fully automatedchemiluminescence immunoassay analyzer 479
Shah D, Chang CD, Cheng K, Jiang L, Salbilla V, Holier A andSchochetman G
Development of the enzyme immunoassay using newchemiluminescence substrate 483
Yamada M, Matsumoto M and Watanabe N
Development of a new chemiluminescence substrate for theenzyme immunoassay 487
Yamada M, Kitaoka K, Matsumoto M and Watanabe N
Chemiluminescent immunometric detection of SARS-CoV in sera as anearly marker for the diagnosis of SARS 491
Yang X and Sun X
Contents xxvii
Development and validation of an avidin-biotin chemiluminescenceELISA for the quantitative detection of albumin in urine 495
Zhao LX, Lin J-M, Wei YL, Li ZJ and Ma SJ
PART 12. LUMINESCENT ASSAYS FOR ENZYMES, SUBSTRATES,INHIBITORS & CO-FACTORS
Use of the peroxyoxalate chemiluminescent reaction in acetone in thepresence of Nile Red for the analysis of glucose 501
Castro-Hartmann P, Guerrero S and Daban J-R
Chemiluminescence assay for lipase activity in human serum by using aproenhancer substrate 505
Ichibangase T, Hamabe C, Ohba Y, Kishikawa N, Nakashima K andKuroda N
Rapid and simultaneous bioluminescent assay of aequorin andfirefly luciferase 509
Nishimura W, Ito K, Arakawa H, Maeda M, Inouye S and Tatsumi H
Repetitive assay for enhanced detection of immobilized horseradishperoxidase by imidazole chemiluminescence coupled to the technique ofon-line regeneration of inactivated peroxidase 513
Nozaki O, Munesue M and Kawamoto H
PART 13. LUMINESCENT DNA PROBE, GENE EXPRESSION &REPORTER GENE ASSAYS
A new assay for determining pyrophosphate using pyruvate phosphatedikinase and its application to DNA analysis 519
Arakawa H, Karasawa K, Suzuki S and Maeda M
BART-NAAT — a novel bioluminescent assay for real-time nucleicacid amplification 523
Gandelman OA, Church VL, Murray JAH and Tisi LC
A single-step bioluminescent endpoint assay for nucleic acidamplification technologies 527
Gandelman O, Murray JAH and Tisi LC
Bioluminescent detection of RNA hydrolysis probes in DNA testing 531Gandelman 0, Tisi L, White PJ, Murray JAH and Squirrell DJ
xxviii Contents
Flashing a protein-protein interaction in living cells via split Renillaluciferase complementation 535
Kaihara A and Umezawa Y
DNA analysis method by luciferase-based bioluminescence detection anda miniaturized luminometer for bioluminescence assay 539
Kamahori M, Harada K and Kambara H
Optimisation of conditions for the use of a novel bioluminescent reportersystem in Mycobacterium spp. 543
Wiles S, Ferguson K, Robertson B and Young D
Monitoring of colonization and clearance of light-emitting bacteria fromtumors, cutaneous wounds, and inflammatory sites in live animals 547
Yu YA, Shabahang S and Szalay AA
Index 551