Chemiluminescence and Bioluminescence

Past, Present and Future

By Aldo Roda

The Royal Society of Chemistry

Copyright © 2011 Royal Society of Chemistry
All rights reserved.
ISBN: 978-1-84755-812-1

Contents

Part 1: Basics of Chemiluminescence and Bioluminescence,
Chapter 1 A History of Bioluminescence and Chemiluminescence from Ancient Times to the Present Aldo Roda, 3,
Chapter 2 The Nature of Chemiluminescent Reactions Gijsbert Zomer, 51,
Chapter 3 Progress and Perspectives on Bioluminescence: from Luminous Organisms to Molecular Mechanisms J. Woodland Hastings, 91,
Chapter 4 Instrumentation for Chemiluminescence and Bioluminescence Fritz Berthold, Manfred Hennecke and Jürgen Wulf, 113,
Part 2: Analytical Applications of Chemiluminescence and Bioluminescence,
Chapter 5 “Classical” Applications of Chemiluminescence and Bioluminescence Massimo Guardigli, Arne Lundin and Aldo Roda, 143,
Chapter 6 Flow-assisted Analysis Aldo Roda, Mara Mirasoli, Barbara Roda and Pierluigi Reschiglian, 191,
Chapter 7 Analytical Applications of Chemiluminescence in Chromatography and Capillary Electrophoresis Ana M. García-Campaña, Laura Gámiz-Gracia, José F. Huertas-Pérez and Francisco J. Lara, 227,
Chapter 8 Chemiluminescence to Immunoassays Michael Seidel and Reinhard Niessner, 289,
Chapter 9 Gene Assays Based on Bio(Chemi)luminescence Eleftheria Laios, Penelope C. Ioannou and Theodore K. Christopoulos, 334,
Chapter 10 Biomolecular Interactions Elisa Michelini, Luca Cevenini, Laura Mezzanotte, Andrea Coppa and Aldo Roda, 378,
Chapter 11 Ultrasensitive Bioanalytical Imaging Mara Mirasoli, Simona Venturoli, Massimo Guardigli, Luisa Stella Dolci, Patrizia Simoni, Monica Musiani and Aldo Roda, 398,
Chapter 12 “In vivo” Molecular Imaging Eric L. Kaijzel, Thomas J. A. Snoeks, Ivo Que, Martin Baiker, Peter Kok, Boudewijn P. Lelieveldt and Clemens W. G. M. Löwik, 425,
Chapter 13 Biotechnological Improvements of Bioluminescent Systems Krystal Teasley Hamorsky, Emre Dikici, C. Mark Ensor, Sylvia Daunert, Audrey L. Davis and Bruce R. Branchini, 443,
Chapter 14 Chemiluminescent and Bioluminescent Biosensors Christophe A. Marquette and Loïc J. Blum, 488,
Chapter 15 Cell-based Bioluminescent Biosensors Kendrick Turner, Nilesh Raut, Patrizia Pasini, Sylvia Daunert, Elisa Michelini, Luca Cevenini, Laura Mezzanotte and Aldo Roda, 511,
Chapter 16 Miniaturized Analytical Devices Based on Chemiluminescence, Bioluminescence and Electrochemiluminescence Larry J. Kricka and Jason Y. Park, 543,
Chapter 17 Recent Analytical Application Areas of Chemiluminescence and Bioluminescence Massimo Guardigli, Mara Mirasoli, Elisa Michelini, Luisa Stella Dolci and Aldo Roda, 557,
Subject Index, 574,

CHAPTER 1

A History of Bioluminescence and Chemiluminescence from Ancient Times to the Present

ALDO RODA

Laboratory of Analytical and Bioanalytical Chemistry, Department of Pharmaceutical Sciences, Alma Mater Studiorum-University of Bologna, Via Belmeloro 6, 40126 Bologna, Italy

1.1 Introduction

My interest in the historical aspects of bioluminescence (BL) and chemiluminescence (CL) began in 1988. That year Mario Pazzagli of Florence and I organized the 5th International Symposium of the International Society for Bioluminescence and Chemiluminescence (ISBC), held in Florence and Bologna. During this meeting a day in Bologna was set aside to honor the distinguished scientist William McElroy for his work on firefly luciferase machinery. A Degree ad honorem in Pharmaceutical Chemistry was conferred on him by the Faculty of Pharmacy of the University of Bologna. I had became acquainted with McElroy when, as a visiting scholar in San Diego in 1982, I worked under the direction of his wife Marlene DeLuca.

It was Marlene’s premature death in 1987 that inspired the ISBC board to have a day of our symposium dedicated to McElroy, during which almost all of his pupils, including J. W. Hastings, H. H. Selinger, T. O. Baldwin, F. McCapra and K. V. Wood, presented a lecture in honor of Marlene DeLuca. Several of the speakers made references to a book by McElroy’s mentor, Edmond Newton Harvey, that piqued my curiosity. I subsequently learned that Harvey’s text A History of Luminescence from the Earliest Times until 1900, published by the American Philosophical Society, Philadelphia, in 1957 is by far the most complete and definitive work on the subject. Since becoming acquainted with Harvey’s book I have had a growing fascination with the history of the study of luminescent phenomena, particularly after learning that the first description of a formal study of luminescence was performed in my home town of Bologna. In 1603, one Casciarolo, a shoemaker by trade and alchemist by passion, accidentally discovered a phosphor that glowed after exposure to light. This substance eventually became known as the Bolognian Stone or the Bolognian Phosphor.

Ten year later, for the 10th International Symposium of the ISBC held in Bologna, I decided to give a presentation on the Bolognian Stone. The story of its discovery is quite interesting, and I enjoyed the opportunity to present some local history as well. Hunting for more detailed information I went to our historical University library to look for the ancient book quoted by Harvey on this subject. To my surprise, the research done by Harvey was so detailed there was little left for me to discover. My recounting of the story of the Bolognian Stone can be found in the Proceedings of the Symposium, as well as on the ISBC web site. While preparing for the present chapter I naturally referred again to Harvey’s book, and found myself freshly amazed at how much information it contains – essentially all existing knowledge of the history of the study of luminescence from ancient times until 1900. The scope of this work is all the more impressive when one considers that when it was written in the 1950s our means of communication were much less sophisticated, and collection of all this information must have been a very arduous task. I should add that, since then, very little has been published in the way of an update. I feel very fortunate indeed to have found a copy of Harvey’s book through Amazon, used but still in good condition, because, as for many others in our field, it has become a sort of bible for me. Because Harvey did such a thorough job of telling the history of the study of luminescence from ancient times until 1900, I will give only an overview of that period, emphasizing instead the period subsequent to 1900, up to and including the present. In more recent years BL and CL have become fundamental tools in molecular biology and related sciences, with analytical chemistry in particular benefitting from implementation of highly sensitive, rapid, miniaturized methods based on BL and CL. Attesting to the importance of these tools, in 2008 the Nobel Prize for Chemistry was awarded jointly to Osamu Shimomura, Martin Chalfie and Roger Y. Tsien for the discovery and development of green fluorescent protein (GFP).

1.2 Ancient Era

Highlights from this period include texts from China in the East as well as from Greece and Rome in the West.

The oldest known written observations on bioluminescent phenomena in nature were made in China, dating roughly from 1500 to 1000 BCE, regarding fireflies and glow-worms; in these writings, however, there is no mention of any effort being directed at understanding or applying the knowledge of such phenomena.

According to legend, in 1000 BCE, a Chinese emperor possessed a magical painting on which the image of an ox appeared at sunset. This was the first known case of a man-made substance that is capable of storing and emitting light. Unfortunately, the chemical composition of the paint was unknown. In later Chinese literature the BL of sea water is described as a glow that could have been due to Protozoa and minute Metazoa. In the Hai Neishih Chou Chi, an account of marvelous sea islands attributed to Tung Fang Shuo (second century BCE), the author states that “if one travels on the sea, one may see fiery sparks when the water is stirred,” which was likely due to the presence of dinoflagellates. Mention of the BL of fireflies and glowworms is frequently found in texts from this period. For example, in the Shin Chung, a book of odes written in the first century CE, these creatures are referred to as night travelers. In some later writings from this period a more methodical approach was taken, with descriptions of the anatomy of bioluminescent animals and their behaviors.

Many folklore-based, artistic works, including poems and paintings, document awareness of bioluminescent phenomena among the peoples of ancient Japan, India, Africa as well as Central and South America. For example, one of the most common insects depicted in Mayan art, especially on ceramic bowls, is the firefly. There are several interesting references to fireflies in Conquest-period documents, most importantly, in the “Popol Vuh,” a sacred text that gives the firefly a role in religion and mythology. The reference in the “Popol Vuh” is particularly interesting as it associates fireflies with the practice of cigar smoking (Figure 1.1). Firefly and glowworm are mentioned in the ancient Indian text, the Vedas and in the poem Mahabharata (200 BCE). In the Buddhist scripture, the Dhammapada, the Pali word khajjopakana is used for firefly.

What is probably the first written record of BL in marine fauna has been attributed to Anaximenes of Miletus (585–528 BCE), a Greek philosopher. It was the great Aristotle (384–322 BCE) who wrote the first detailed observations on light from marine species, in addition to insects, describing up to 180 animals. He was also the first to identify cold light, i.e., he recognized that the self-luminosity of BL organisms was not accompanied by heat, unlike the light from a candle flame. Aristotle wrote about the luminosity of dead fish, now known to be due to infection by luminescent bacteria, and also about the above-mentioned light that occurs when sea water containing dinoflagellates is agitated by stirring with a rod.

In 215 BCE Titus Livius reported that in Sardinia “the shores were also luminous with frequent fires.”

A few centuries later, a more complete record of BL organisms was made by Pliny the Elder (23–79 CE) in his Naturalis Historia (Figure 1.2), in which he gives detailed descriptions of many luminescent animals, from glow-worms and fireflies to a luminous mollusk (Pholas dactylus – a Roman delicacy). The specific name was the one given by the Romans, who liked to eat them, as is attested by Pliny in Naturalis Historia (IX, 87):

“Concharum e genere sunt dactyli ab humanorum unguium similitudine appellati. His natura in tenebris remoto lumine, alio fulgere claro, et quanto magis humorem habeant, lucere in ore mandentium, lucere in manibus, atque etiam in solo ac veste, decidentibus guttis: ut procul dubio pateat, succi illam naturam esse, quam miraremur etiam in corpora.”

[The group of shells are dactyls, so named for their similarity to human fingernails. By their nature they are in the dark without light, shine forth clearly, and have as much humor, they shine in the mouth of someone who eats them, gleamed in his hand, and even for land and among his clothes, releasing drops: from which it is obvious that the nature of the juice is that which we admire in the body.]

Pliny also describes the purple luminescent jellyfish Pelagia nocticula that are common in the bay of Naples, where Pliny died during the eruption of Vesuvius (79 CE). They were called Pulmo marinus by the Romans owing to a slime secreted from the outer surface of the bell that was considered to be a remedy for fevers.

1.3 Middle Ages to the Sixteenth Century

The period extending from the fall of the Roman Empire (around 500 CE) to the Renaissance in Europe is known as the Middle Ages, a time dominated by superstition and belief in magic. All learning and study were controlled by the church, and many studies of natural phenomena such as luminescence were of an “applied” nature, that is, used to maintain belief in spirit or for producing magical potions. During this time, in other parts of the world, such as Japan, Arabia, India, China, South and Central America, civilizations with rich cultures were flourishing, but we have little information about any studies of BL or CL that may have been performed in those areas.

One of the few such references we have is to the two most common firefly species in Japan, the genji-botaru and the heike-botaru, whose names have an interesting history: it is said that the souls of countless soldiers who were killed in the Battle of Dannoura (1185) turned into fireflies. The larger and more profuse genji-botaru fireflies were no doubt named after the winning Genji, and the smaller heike-botaru after the defeated Heike (Figure 1.3).

In China, Li Shin-Chen (1518–1593) traveled widely in major Chinese provinces (Honan, Kiangsu, Anhwei), collecting specimens and studying the natural occurrences of minerals, plants and animals. After completion of the final draft in 1587 he visited Nanking to arrange for publication of his findings. The first printed edition (the so-called Chin-ling xylograph) did not appear until 1596, after Li’s death. In the book he distinguished three main kinds of luminous insects: the common firefly (Luciola spp.) and many other genera, the glowworm and the luminescent flies living in or near water (probably midges, or mayflies infected with luminous bacteria).

In the text “Tractatus de Simplicibus” Arab writers and the Persian botanist Ibn-al-Baithar (1197–1248) describe the Hobaheb, a beetle with wings that light up during the night. In 1372 Al-Damiri (1344–1405), a great Arab zoologist of Cairo, in his zoological dictionary Hayat-alHayawan (The life of animals) describes an insect with wings that emits light, as if it were on fire.

In Europe, Isidore, the Archbishop of Seville (560–636) who was later canonized, wrote the “Etymologiae”, in which he described luminous stones as well as the cincidela (firefly) a genus of beetles that shines while either walking or flying.

In the thirteenth century Albert Magnus (1206–1280), who came to be regarded as the first naturalist, described and catalogued many luminous species, but not many more than Pliny did several centuries earlier. His work was published only after the invention of the printing press in 1478, in the form of a book that was given the title De Animalibus. He made an extract of fireflies, Liquor lucidus, that had permanent luminescence.

Dante was one of the few Italians fearless enough to mention BL in his prose. In the Canto XXVI of “Inferno” of The Divine Comedy, one of the last poems he penned before his death in 1321, he wrote of peering down into the Eighth Chasm of Hell and seeing “fireflies innumerous spangling o’er the vale.”

The Renaissance was a time of tremendous growth in the Arts, and it was also a time of exploration of parts of the world that had been largely unknown to Europeans. Among other novelties, explorers brought back reports of burning seas, now known as milky seas, a phenomenon that remains little understood. Christopher Columbus in 1492 observed a mysterious light in the sea near San Salvador that was likely due to the presence of a marine worm, Odontosyllis, that is known to inhabit those Caribbean waters.

The Spaniard Gonzalo Fernandez Oviedo (1478–1557) who was the official chronicler of Indian affairs during his stay in different parts of the new world, published extensive data on natural history; among other creatures he identified the elaterid beetle (Pyrophorus), bioluminescent caterpillar and what eventually came to be known as the railroad worm (Phenogoides).

Conrad Gesner (1516–1565), Professor of Natural History and Medicine in Zurich, is credited with writing the first book devoted to luminescence, De Lunaris, in which he writes about luminescent animals and plants, as well as luminous stones (Figure 1.4). This book, together with the Historia Animalium (also written by Conrad Gesner), probably contains the first mention of luminous sea pens, although the Romans knew BL sea pens (Pennatulaceans), referring to them as Penna marina.

In 1551 in the Russian Church code called the Stoglav there is the curious and poetic pronouncement that on the Summer Solstice, the Feast of Kupala, a fern (in Russian paparotnik) blooms on this Mid-Summer Night, and that whoever finds this flower and takes it home will have good fortune ensured for the rest of his life. We know that this fern does not exist, but we also know that there is a mushroom (Mycena sp.) that is a bioluminescent mycelium that was used to mark the paths in the forest at night, and perhaps the legend was born here.

(Continues…)Excerpted from Chemiluminescence and Bioluminescence by Aldo Roda. Copyright © 2011 Royal Society of Chemistry. Excerpted by permission of The Royal Society of Chemistry.
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