Boron-Based Compounds

Noted experts review the current status of boron-containing drugs and materials for molecular medical diagnostics

Boron-Based Compounds offers a summary of the present status and promotes the further development of new boron-containing drugs and advanced materials, mostly boron clusters, for molecular medical diagnostics. The knowledge accumulated during the past decades on the chemistry and biology of bioorganic and organometallic boron compounds laid the foundation for the emergence of a new area of study and application of boron compounds as lipophilic pharmacophores and modulators of biologically active molecules.This important text brings together in one comprehensive volume contributions from renowned experts in the field of medicinal chemistry of boron compounds.

The authors cover a range of the most relevant topics including boron compounds as modulators of the bioactivity of biomolecules, boron clusters as pharmacophores or for drug delivery, boron compounds for boron neutron capture therapy (BNCT) and for diagnostics, as well as in silico molecular modeling of boron- and carborane-containing compounds in drug design. Authoritative and accessible, Boron-Based Compounds:

• Contains contributions from a panel of internationally renowned experts in the field
• Offers a concise summary of the current status of boron-containing drugs and materials used for molecular diagnostics
• Highlights the range and capacity of boron-based compounds in medical applications
• Includes information on boron neutron capture therapy and diagnostics

Designed for academic and industrial scientists, this important resource offers the cutting-edge information needed to understand the current state of boron-containing drugs and materials for molecular medical diagnostics.

List of Contributors vii

Preface xi

Part 1 Design of New Boron‐based Drugs 1

1.1 Carboranes as Hydrophobic Pharmacophores: Applications for Design of Nuclear Receptor Ligands 3
Yasuyuki Endo

1.2 Boron Cluster Modifications with Antiviral, Anticancer, and Modulation of Purinergic Receptors’ Activities Based on Nucleoside Structures 20
Anna Adamska‐Bartłomiejczyk, Katarzyna Bednarska, Magdalena Białek‐Pietras, Zofia M. Kiliańska, Adam Mieczkowski, Agnieszka B. Olejniczak, Edyta Paradowska, Mirosława Studzińska, Zofia Sułowska, Jolanta D. Żołnierczyk, and Zbigniew J. Lesnikowski

1.3 Design of Carborane‐Based Hypoxia‐Inducible Factor Inhibitors 35
Guangzhe Li, Hyun Seung Ban, and Hiroyuki Nakamura

1.4 Half‐ and Mixed‐Sandwich Transition Metal Dicarbollides and nido‐Carboranes(–1) for Medicinal Applications 60
Benedikt Schwarze, Marta Gozzi, and Evamarie Hey‐Hawkins

1.5 Ionic Boron Clusters as Superchaotropic Anions: Implications for Drug Design 109
Khaleel I. Assaf, Joanna Wilinska, and Detlef Gabel

1.6 Quantum Mechanical and Molecular Mechanical Calculations on Substituted Boron Clusters and Their Interactions with Proteins 126
Jindřich Fanfrlík, Adam Pecina, Jan Řezáč, Pavel Hobza, and Martin Lepšík

Part 2 Boron Compounds in Drug Delivery and Imaging 139

2.1 Closomers: An Icosahedral Platform for Drug Delivery 141
Satish S. Jalisatgi

2.2 Cobaltabisdicarbollide‐based Synthetic Vesicles: From Biological Interaction to in vivo Imaging 159
Clara Viñas, Francesc Teixidor, and Adrian J. Harwood

2.3 Boronic Acid–Based Sensor for Determination of Sugars 174
Igor B. Sivaev and Vladimir I. Bregadze

2.4 Boron Compounds in Molecular Imaging 205
Bhaskar C. Das, Devi Prasan Ojha, Sasmita Das, and Todd Evans

2.5 Radiolabeling Strategies for Boron Clusters: Toward Fast Development and Efficient Assessment of BNCT Drug Candidates 232
Kiran B. Gona, Vanessa Gómez‐Vallejo, Irina Manea, Jonas Malmquist, Jacek Koziorowski, and Jordi Llop

Part 3 Boron Compounds for Boron Neutron Capture Therapy 269

3.1 Twenty Years of Research on 3‐Carboranyl Thymidine Analogs (3CTAs): A Critical Perspective 271
Werner Tjarks

3.2 Recent Advances in Boron Delivery Agents for Boron Neutron Capture Therapy (BNCT) 298
Sunting Xuan and Maria da Graça H. Vicente

3.3 Carborane Derivatives of Porphyrins and Chlorins for Photodynamic and Boron Neutron Capture Therapies: Synthetic Strategies 343
Valentina A. Ol’shevskaya, Andrei V. Zaitsev, and Alexander A. Shtil

3.4 Nanostructured Boron Compounds for Boron Neutron Capture Therapy (BNCT) in Cancer Treatment 371
Shanmin Gao, Yinghuai Zhu, and Narayan Hosmane

3.5 New Boronated Compounds for an Imaging-Guided Personalized Neutron Capture Therapy 389
Nicoletta Protti, Annamaria Deagostino, Paolo Boggio, Diego Alberti, and Simonetta Geninatti Crich

3.6 Optimizing the Therapeutic Efficacy of Boron Neutron Capture Therapy (BNCT) for Different Pathologies: Research in Animal Models Employing Different Boron Compounds and Administration Strategies 416
Amanda E. Schwint, Andrea Monti Hughes, Marcela A. Garabalino, Emiliano C.C. Pozzi, Elisa M. Heber, and Veronica A. Trivillin

Index

Prof. Dr. Evamarie Hey-Hawkins has been a Full Professor of Inorganic Chemistry at Leipzig University since 1993. Her research interests include the synthesis of novel reagents for BNCT and use of boron clusters as pharmacophores or modulators for biomolecules.

Prof. Dr. Clara Viñas Teixidor is a Research Professor at the Institut de Ciència de Materials de Barcelona, Spanish Council for Scientific Research, Spain. Her fields of research involve synthesis and derivatisation of boron clusters to be applied in medicine and biosensing, among others. Previously, she worked in industry and at public institutions involved in food science analysis as well as environmental control.

Noted experts review the current status of boron-containing drugs and materials for molecular medical diagnostics

Boron-Based Compounds offers a summary of the present status and promotes the further development of new boron-containing drugs and advanced materials, mostly boron clusters, for molecular medical diagnostics. The knowledge accumulated during the past decades on the chemistry and biology of bioorganic and organometallic boron compounds laid the foundation for the emergence of a new area of study and application of boron compounds as lipophilic pharmacophores and modulators of biologically active molecules. This important text brings together in one comprehensive volume contributions from renowned experts in the field of medicinal chemistry of boron compounds.

The authors cover a range of the most relevant topics including boron compounds as modulators of the bioactivity of biomolecules, boron clusters as pharmacophores or for drug delivery, boron compounds for boron neutron capture therapy (BNCT) and for diagnostics, as well as in silico molecular modeling of boron- and carborane-containing compounds in drug design. Authoritative and accessible, Boron-Based Compounds:

• Contains contributions from a panel of internationally renowned experts in the field
• Offers a concise summary of the current status of boron-containing drugs and materials used for molecular diagnosticse
• Highlights the range and capacity of boron-based compounds in medical applications
• Includes information on boron neutron capture therapy and diagnostics

Designed for academic and industrial scientists, this important resource offers the cutting-edge information needed to understand the current state of boron-containing drugs and materials for molecular medical diagnostics.