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