Quenched-phosphorescence detection of molecular oxygen: applications in life sciences

385 Pages·2018·23.584 MB·English

by  Papkovsky, Dmitri B

Quenched-phosphorescence Detection of Molecular Oxygen
Applications in Life Sciences
Detection Science Series
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8: Biological Fluid–Surface Interactions in Detection and Medical Devices
9: Advanced Environmental Analysis: Applications of Nanomaterials, Volume 1
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11: Quenched-phosphorescence Detection of Molecular Oxygen: Applications
in Life Sciences
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Quenched-phosphorescence
Detection of Molecular Oxygen
Applications in Life Sciences
Edited by
Dmitri B. Papkovsky
University College Cork, Ireland
Email: [email protected]
and
Ruslan I. Dmitriev
University College Cork, Ireland
Email: [email protected]
Detection Science Series No. 11
Print ISBN: 978-1-78801-175-4
PDF ISBN: 978-1-78801-345-1
EPUB ISBN: 978-1-78801-455-7
ISSN: 2052-3068
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Preface
Quenched-phosphorescence oxygen sensing has now emerged as one of the
most versatile, flexible and successful sensor technologies. This is largely
because of the paramount significance of O in life and biomedical sciences
2
and the capabilities of this detection method to quantify oxygen concentration
and other related parameters - directly, reversibly, non-invasively, accurately
and in various gaseous, liquid and biological samples.
Since the pioneering proofs of concept studies of Dietrich Lubbers and
David Wilson and their colleagues back in the late 70s and early 80s, this
sensor technology has undergone major development and diversification.
This work has produced a comprehensive panel of high-performance indi-
cator dyes, sensing materials on their basis, advanced detection schemes,
analytical methodologies and measurement instrumentation. Based on this
technology and materials, a diverse range of applications has been developed
and demonstrated in various settings. Over the three decade-long history of
optical O sensing, life science and biomedical applications have remained
2
as its central pillar, while many other industrial and research applications
have advanced as well.
On the other hand, only in the last 5–10 years, has O sensing technology
2
come to a stage, when it became widely accessible and affordable for ordinary
users (researchers, clinicians, industry), and transferrable from high tech-
nology research and development labs into real-life environment, practical
research and industrial applications. A number of commercial instruments
and systems designed for routine laboratory use and also suitable for large-
scale and large-volume applications such as biological screening, packaging,
environmental and process control, quality assurance, have been introduced.
In many research labs, solid-state O sensors have already become routine
2
analytical tools used on a daily basis, like pH meters or UV-Vis spectroscopy.

Detection Science Series No. 11
Quenched-phosphorescence Detection of Molecular Oxygen: Applications in Life Sciences
Edited by Dmitri B. Papkovsky and Ruslan I. Dmitriev
© The Royal Society of Chemistry 2018
Published by the Royal Society of Chemistry, www.rsc.org
v
vi Preface
Further development of bioanalytical systems, which rely on quenched-
phosphorescence oxygen sensing continues with great pace. At the same
time, the level of awareness of both the research community and industry
about such systems, their analytical and research capabilities and potential
benefits of their adoption and use still remain low. These factors limit wider
uptake and practical use of these technologies. More demonstrational and
educational work needs to be conducted to break these barriers.
In this book we aimed to assemble a comprehensive collection of papers
covering all core aspects of quenched-phosphorescence oxygen sensing
technology and its applications. The first group of chapters describe the
fundamentals and core aspects of O sensing technique, the range of most
2
common sensor dyes (Pt(ii)-porphyrins, Ru(ii)- and Ir(iii)-cyclometallated
complexes), materials (solid-state sensors, soluble probes and nanoparticle
formulations), fabrication technologies and dedicated instrumentation.
The second group of chapters describes specific life science applications
and customized experimental setups and sensor systems (e.g. marine
research and aquatic organisms, live cell analysis, oxygen imaging and oxygen
transport in tissue, in vivo oxygen sensing and imaging) and application areas
(cancer and stem cell research, photodynamic therapy, vascular biology and
clinical applications, bio-imaging, microfluidic biochips, food packaging
and safety). Some of these applications have already been commercialized or
are close to this stage and therefore available for ordinary users.
The leading experts in respective areas, who have extensive hands-on expe-
rience with corresponding sensor systems and biological applications and
know their merits and limitations, provided the chapters for the book. Alto-
gether, this gives a comprehensive picture of the current status in this area,
performance and capabilities of the different sensor systems and applica-
tions, and future avenues of research and development in this field.
The book is targeted at potential new users and young researchers who
are not very familiar with these technologies and applications, but who can
benefit from them. It is also of significant interest for established experts
and researchers in O sensing and current users of adjacent life science appli-
2
cations. Presenting them with the recent achievements in the broader area
and related applications can further stimulate their work. We are hoping to
attract many new researchers, young scientists and end-users to this very
exciting technology.
Dmitri B. Papkovsky
Ruslan I. Dmitriev
Contents
Chapter 1 Fundamentals of Quenched Phosphorescence
O Sensing and Rational Design of
2
Sensor Materials 1
Sergey M. Borisov
1.1 Introduction 1
1.2 Mechanism of Oxygen Quenching 2
1.3 Requirements for Phosphorescent
Indicators 4
1.4 Brief Overview of the Most Common
Indicators 6
1.5 Rational Design of Optical Sensing Materials 9
1.6 Sensitivity and Dynamic Range of
Oxygen Sensors 11
1.7 Referenced Oxygen Sensing and Imaging 13
1.8 Artefacts in Oxygen Sensing 14
1.9 Conclusions and Outlook 16
References 16
Chapter 2 New Polymer-based Sensor Materials and
Fabrication Technologies for Large-scale
Applications 19
Efe Armagan, Dmitri B. Papkovsky and Claudio Toncelli
2.1 Introduction 19
2.2 Physical Entrapment of Phosphors Within
Inorganic and Organic Matrices 21

Detection Science Series No. 11
Quenched-phosphorescence Detection of Molecular Oxygen: Applications in Life Sciences
Edited by Dmitri B. Papkovsky and Ruslan I. Dmitriev
© The Royal Society of Chemistry 2018
Published by the Royal Society of Chemistry, www.rsc.org
vii
viii Contents
2.2.1 Casting of Polymer ‘Cocktails’ 25
2.2.2 Physical Mixing of Phosphors
with Ormosils 29
2.2.3 Phosphor Integration in Silicone
Rubbers 30
2.2.4 Impregnation of Microporous
Membranes and Microparticles
with Phosphor Molecules 32
2.2.5 Solvent Crazing 33
2.2.6 Electrospinning 34
2.2.7 Electrophoretic Deposition 35
2.2.8 Layer-by-layer Deposition (LbL) 35
2.3 Covalent and Coordinative Binding
of Phosphors to Substrates 36
2.4 Conclusions and Outlook 38
Abbreviations 39
Acknowledgement 39
References 40
Chapter 3 Evolution of Cell-penetrating Phosphorescent
O Probes 50
2
Dmitri B. Papkovsky and Ruslan I. Dmitriev
3.1 Evolution of Cell-penetrating
Phosphorescent O probes 50
2
3.1.1 Introduction 50
3.1.2 Why and How to Measure
Intracellular O ? 52
2
3.1.3 Different Classes of Cell-penetrating
O Probes and Their Evolution 55
2
3.2 Conclusions and Future Outlook 63
Acknowledgement 64
References 64
Chapter 4 Hydrophilic Ir(iii) Complexes for In vitro and
In vivo Oxygen Imaging 71
Toshitada Yoshihara, Yosuke Hirakawa, Masaomi Nangaku
and Seiji Tobita
4.1 Introduction 71
4.2 Experimental 73
4.2.1 Synthesis of BTP-PEG (n = 12, 24, 48)
n
and PPY-PEG 73
24
4.2.2 Photophysical Properties in Aqueous
Solutions 76
Contents ix
4.2.3 Octanol/Water Partition Coefficients
(log P ) 76
O/W
4.2.4 Fluorescence and Phosphorescence
Lifetime Imaging Microscopy 77
4.2.5 Cell Culture and Imaging 77
4.2.6 In vivo Imaging 77
4.3 Results and Discussion 78
4.3.1 Electronic Structures of the
Ir(iii) Complexes 78
4.3.2 Hydrophilicity and Photophysical
Properties in Water 79
4.3.3 Phosphorescence Quenching by
Molecular Oxygen in Solution 81
4.3.4 Temperature Effects on
Phosphorescence Quenching by O 83
2
4.3.5 Cellular Uptake and Oxygen Response 84
4.3.6 In vivo O Imaging by PLIM
2
Measurements 86
4.4 Conclusion 89
Acknowledgement 89
References 89
Chapter 5 Protection of Triplet Excited State Materials
from Oxygen Quenching and Photooxidation
in Optical Sensing Applications 91
Mikhail A. Filatov
5.1 Introduction 91
5.2 Phosphorescent Probes with Appended
Protective Groups 93
5.2.1 Phosphorescent Dendrimers 93
5.2.2 “Self-healing” Phosphorescent
Complexes 97
5.3 Host-guest Complexes and Aggregates 99
5.3.1 Tryptophan Phosphorescence
in Proteins 99
5.3.2 Phosphorescence of Cyclodextrin
Complexes in the Presence
of Oxygen 100
5.3.3 Steroids as Protective Matrixes 103
5.3.4 Gel Matrixes 104
5.4 Application of Oxygen Scavengers 105
5.4.1 Inorganic Oxygen Scavengers 105
5.4.2 Application of Natural
Antioxidants 106