Rational Design of Fluorophores for In Vivo Applications - Progress in Molecular Biology and Translational Science - page 59

CHAPTER THREE

Rational Design of Fluorophores
for In Vivo Applications

Marcin Ptaszek
Department of Chemistry and Biochemistry, University of Maryland Baltimore County, Baltimore,
Maryland, USA

Contents
1. Introduction 60

2. Cyanine and Related Fluorophores 62

2.1 General characterization 62

2.2 Bioconjugation 63

2.3 Improvement of water solubility and chemical stability 67

3. Squaraines 71

4. Boron Dipyrromethene and Related Fluorophores 74

4.1 General characterization 74

4.2 Energy-transfer dyads for increasing the Stokes shift of BDPs 77

4.3 Related fluorophores 78

5. Porphyrins, Phthalocyanines, and Related Macrocycles 79

5.1 General characterization 79

5.2 Benzoporphyrins 80

5.3 Strongly conjugated porphyrin arrays 81

5.4 Chlorins and bacteriochlorins 81

5.5 Hydroporphyrin arrays for increased Stokes shift and multicolor in vivo imaging 85

5.6 Water solubility and aggregation 85

5.7 Photocytotoxicity of tetrapyrrolic macrocycle 87

5.8 Phthalocyanines 88

6. Special Types of Fluorophores 90

6.1 Fluorophores for multicolor imaging 90

6.2 Self-illuminating fluorophores 92

7. Conclusion 94

Acknowledgment 94

References 95

Abstract
Several classes of small organic molecules exhibit properties that make them suitable for
fluorescence in vivo imaging. The most promising candidates are cyanines, squaraines,
boron dipyrromethenes, porphyrin derivatives, hydroporphyrins, and phthalocyanines.