Porphyrazines: Designer Macrocycles by Peripheral Substituent Change

Matthew J. Fuchter; Chang Zhong; Hong Zong; Brian M. Hoffman; Anthony G. M. Barrett

doi:10.1071/CH07445

RESEARCH FRONT

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Porphyrazines: Designer Macrocycles by Peripheral Substituent Change

Matthew J. Fuchter ^A , Chang Zhong ^B , Hong Zong ^B , Brian M. Hoffman ^B and Anthony G. M. Barrett ^C ^D

+ Author Affiliations

- Author Affiliations

^A Department of Biological and Pharmaceutical Chemistry, School of Pharmacy, University of London, 29–39 Brunswick Square, London WC1N 1AX, UK.

^B Department of Chemistry, Northwestern University, Evanston, IL 60208, USA.

^C Department of Chemistry, Imperial College London, London SW7 2AZ, UK.

^D Corresponding author. Email: agmb@imperial.ac.uk

Matthew Fuchter underwent undergraduate studies at the University of Bristol, where he was awarded the Richard N. Dixon prize. Following this, he completed his Ph.D. under the supervision of Professor A. G. M. Barrett, at Imperial College London. Following a short postdoctoral spell at Imperial College, Dr. Fuchter was appointed as a Research Fellow at the Commonwealth Scientific and Industrial Research Organisation, Australia as well as a visiting fellow at the University of Melbourne, where he worked with Professor A. B. Holmes. Currently he is a RCUK Academic Fellow at The School of Pharmacy, University of London. His research interests include: the development of innovative methods in organic synthesis, and the preparation of novel anti-cancer therapeutics.

Chang Zhong went to the University of Science and Technology of China as an undergraduate, and then received his Ph.D. from Northwestern University under the direction of Dr. Brian Hoffman, and thence to the Los Alamos National Laboratory as a LDRD Postdoctoral Fellow with Dr. Jennifer Martinez and Dr. R. Brian Dyer. His research interests include: preparing fluorescent metallic nanoclusters through dendrimer, polymer, peptide, and protein templates; studying the bio-effect of fullerene derivatives; as well as the preparation/characterization of multimetallic porphyrazines.

Hong Zong is a postdoctoral fellow at Northwestern University. He received his B.Sc. in Chemistry from Fudan University (China) in 1997 and an M.E. in Materials Science from the Chinese Academy of Sciences in 2000. He went on to join the group of Professor Brian M. Hoffman at Northwestern University to study porphyrazines as tumour contrast agents and surface-bound molecules, for which he received his Ph.D. in 2007. His current research focuses on the development of bifunctional PDT and MRI contrast agents.

Brian Hoffman was born in Chicago, as an undergraduate went to the University of Chicago, then wandered to the west coast for a Ph.D. from Caltech under the direction of Dr. Harden McConnell, and thence to the east coast for a postdoctoral year with Dr. Alex Rich at MIT. From there he joined the faculty at Northwestern University, where he is a Professor in the Chemistry and BMBCB departments. His research interests include: electronuclear double resonance (endor) of metallobiomolecules; electron transfer within protein complexes; as well as the preparation/characterization of porphyrazine macrocycles.

Tony Barrett obtained his Ph.D. (1975) with Professor Sir Derek H. R. Barton and was appointed as Lecturer (1975) and Senior Lecturer (1982) at Imperial College. At the age of 31 he was appointed a full Professor of Chemistry at Northwestern University, Evanston, IL (1983) and Colorado State University (1990). In 1993 he returned to his alma mater, Imperial College as Glaxo Professor of Chemistry, Sir Derek Barton Professor of Synthesis, Director of the Wolfson Centre for Organic Chemistry in Medical Science and Head of Synthesis. His research interests include the total synthesis of bioactive natural products, porphyrazine chemistry, the design of methods for organic synthesis including novel catalysis, enantioselective transformations and supported reagents and cancer medicinal chemistry.

Australian Journal of Chemistry 61(4) 235-255 https://doi.org/10.1071/CH07445
Submitted: 24 December 2007 Accepted: 22 February 2008 Published: 24 April 2008

Abstract

It is rare that such a diverse array of applications can be realized from a single basic molecular unit, however, such is the power of the tetrapyrrolic macrocycle motif. Indeed, their potential in areas such as chemical dyes, optical sensors, optoelectronics, and biomedical agents is a function of their rich electronic and optical properties. While the naturally occurring porphyrins and the synthetic phthalocyanines have been extensively studied, the related tetraazaporphyrins or porphyrazines remain comparatively underdeveloped. Since porphyrazines maintain a unique position in this family: analogous derivatives are virtually inaccessible for the porphyrins, and direct fusion of heteroatomic substituents onto the porphyrazine β-positions results in a more pronounced effect compared with the substitution of an equivalent group onto the benzenoid rings of the phthalocyanine; a driving force exists to further explore the synthesis and applications of these novel macrocycles. This review will provide a historical overview of the synthetic strategies towards functionalized porphyrazines and describe new strategies towards the preparation and applications of heteroatom-appended porphyrazines, particularly in the context of their multimetallic complexes, catalysis, surface chemistry, and as biomedical agents.

Acknowledgement

We thank GlaxoSmithKline for the generous endowment (to A.G.M.B.), the Royal Society and the Wolfson Foundation for a Royal Society Wolfson Merit Award (to A.G.M.B.), the Wolfson Centre for establishing the Wolfson Centre for Organic Chemistry in Medical Sciences at Imperial College, the Engineering and Physical Sciences Research Council, the National Science Foundation and CSIRO for grants in support of our studies.

References

Porphyrazines: Designer Macrocycles by Peripheral Substituent Change

Abstract

Acknowledgement

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