Professor Ray Bonnett

Profile

Previous positions

1957-8 Salters’ Fellow, Cambridge. 

1958-9 Research Fellow, Harvard 

1959-61 Assistant Professor, Chemistry, UBC, Canada 

1961-94 Lecturer, Reader, Professor of Organic Chemistry, Department of Chemistry, Queen Mary College, later QMW, University of London 

1982-87 Head of Chemistry Department, Queen Mary College 

1994-2000 Scotia Research Professor 

1994- present position 

Professional memberships

• Fellow of the Royal Society of Chemistry. 
• Member of the Biochemical Memberships: Society, the American Chemical Society, the Tetrapyrrole Discussion Group (Chairman 1996-2000), the Royal Institution.

Research

Research Interests:

Field of interest: Chemistry and biochemistry of porphyrins , metalloporphyrins and related compounds. About 250 publications to date. 

Keywords: Porphyrin, chlorin, bilin, corrin, phthalocyanine. Haem, chlorophyll, bile pigments and vitamin B12. Heterocyclic chemistry; metal complexes. Synthesis, structure, reactivity, spectroscopy, photochemistry, geochemistry in this series. Photosensitisation, especially in relation to medical applications ( eg tumour phototherapy, and other phototherapies) and photomicrobicidal activity, especially in relation to smart packaging and water photodisinfection. 

Collaborative work::especially on biological, clinical, photophysical and molecular electronic aspects in UK and in Europe. In the past, the major international collaborations have been with Belarus, Bulgaria, Germany, Italy, Lithuania, Poland, Portugal, Russia and Spain. 

Research highlights 

Vitamin B12 - Structure – chemistry (publications 1, 3- PhD work with AR Todd and Alan Johnson); early review (14); cobyric acid preparation (51 - Godfrey, Redman); neovitamin B12 structure (61- Godfrey, Math, Evans). 

Chlorophyll a Synthesis – postdoc work with RB Woodward (8). At the request of Harvard, the full paper was written up by me (with the assistance of Aslam Galia, Diana Garside, and Asun Vallés) at the Chemistry Department, Queen Mary, 30 years later with the support of the Maxwell Foundation. (8a).

Porphyrin Reactivity – electrophilic meso-substitution (26, 48, 158 - Stephenson, Gale, Dimsdale, Andrews, Appelman); radical substitution (88 - McDonagh, Cornell); reactions of metal complexes (72 –Dimsdale); protiodevinylation (93 – Campion-Smith); discovery of porphyrin N-oxides (127 – Ridge, Appelman, Andrews); synthesis of opp-dibenzoporphyrins (220 – McManus); 2,3-dioxo-2,3-secochlorin system (222 – Adams, Burke, Salgado, Vallés). 

Haem Catabolism – oxidative cleavage of haem system - the four isomeric biliverdins (75 McDonagh). 

Bile Pigment Chemistry – acid-catalysed scrambling of bilirubin isomers (56, McDonagh, Hamzehtash, Buckley); photo-oxidation of bilirubin to give propentdyopent adducts (81, 89 - Stewart); first X-ray crystal structure analysis of bilirubin IXα (101 – Hursthouse, Neidle, Davies, Sheldrick); substitution and addition reactions of bilindiones (125– Bonfiglio, Hamzehtash, Trotter); propentdyopent adduct structure & chemistry (148, 161 – Dimsdale, Ioannou, Stephenson, Vallés). 

Organic Geochemistry – metalloporphyrins in coals and lignites (116, reviewed in 221 – Czechowski, Burke, Dewey, Latos-Grazynski, Ioannou, Shukina). 

Nitrosation – of tryptophan derivatives (113 – Holleyhead, Ooi, Venitt); of porphyrins and haems (103, 112 – Charalambides, Nicolaidou, Martin, Trotter, Sales); 

Isoindoles – by pyrrole self-condensation (44 – JD White, Bender); metallo tetrabenzporphyrins from isoindole precursors (58, 66 – Bender, RG Smith); first synthesis of parent isoindole (65, 78 -RFC Brown, RG Smith); chemistry & review (118, 128 – North, Newton); 

Photoreactions – photobilirubin II (120 - Stoll, Gray); photomicrobicidal materials (192, 247 – Galia, Saville, Krysteva); photobleaching of porphyrins & chlorins (233, 238 , review 237 - Martinez). 

Chemical Aspects of Photodynamic Therapy – chemistry of Haematoporphyrin Derivative HpD (119 – Berenbaum, Ridge, Scourides); bioactivity of HpD components, and proposal that dimers/oligomers were active component (124 – Berenbaum, Scourides); discovery of efficient tumour photosensitisation by m-THPC [FOSCAN®] (163, 202, 236 – Berenbaum, RD White, Winfield, Djelal, Hawkes, Truscott, Nguyen; reviews/book 164, 213, 244/ 235); amphiphilicity (184). RSC George and Christine Sosnovsky Award 2012. 

Miscellaneous – synthesis of chlorobactene (19) and structure of fucoxanthin (46- Weedon principal investigator). Ultraviolet absorption and CD of unconjugated azomethines (22). Porphyrins of oral bacteria (106 – Shah, Mateen, Williams) and medusae (108 – Head, Herring).

Publications

1. R.Bonnett, J.R. Cannon, A. W. Johnson, I. Sutherland and A. R. Todd, ‘The Structure of Vitamin B12 and its Hexacarboxylic Acid Degradation Product’, Nature (London), 1955, 176, 328-330. 

3. R. Bonnett, J. R. Cannon, A. W. Johnson, L. F. J. Parker, E. Lester Smith and Sir Alexander Todd, ‘Part V. The Structure of the Chromophoric Grouping’, J. Chem. Soc., 1957, 1148-1158. 

8. R. B. Woodward, W. A. Ayer, J. M. Beaton, F. Bickelhaupt, R. Bonnett, P. Buchschacher, G. L. Closs, H. Dutler, J. Hannah, S. Ito, A. Langemann, E. Le Goff, W. Leimgruber, W. Lwowski, J. Sauer, Z. Valenta, and H. Volz, ‘The Total Synthesis of Chlorophyll a’, J. Am. Chem. Soc., 1960, 82, 3800-3801. 8a Tetrahedron, 1990, 46, 7599-7660.

14. R. Bonnett, The Chemistry of the Vitamin B12 Group’, Chem. Rev.,1963, 573-605.

19. R. Bonnett, A. A. Spark and B. C. L. Weedon, ‘Synthese of Chlorobactene, ‘HO-Chlorobactene’ and Rhodopin’, Acta Chem. Scand., 1964, 18, 1739-1744. 

22. R. Bonnett, ‘Studies in the Pyrroline Series IV. The Ultraviolet Absorption of the Unconjugated Azomethine Group’, J. Chem. Soc., 1965, 2313-2318. 

26. R. Bonnett and G. F. Stephenson, ‘The meso-Reactivity of Porphyrins and Related Compounds. 1 Nitration’, J. Org. Chem., 1965, 30, 2791-2798. 

46. R. Bonnett, A. K. Mallams, A. A. Spark, B. C. L. Weedon and A. McCormick, ‘Structure and Reactions of Fucoxanthin’, J. Chem. Soc. (C ), 1969, 429-454. 

48. R. Bonnett, M. J. Dimsdale and G. F. Stephenson, ‘The meso-Reactivity of Porphyrins and Related Compounds. Part IV. The Introduction of Oxygen Functions’, J. Chem. Soc.(C), 1969, 564-570. 

51. R. Bonnett, J. M. Godfrey and D. G. Redman, ‘Cobyric acid and Related Compounds from Vitamin B12’, J. Chem. Soc. (C), 1969, 1163-1166. 

56. R. Bonnett and A. F. McDonagh, ‘The Isomeric Heterogeneity of Biliverdin Dimethyl Esters Derived from Bilirubin’, Chem. Commun., 1970, 238. 

57. C. O. Bender, R. Bonnett and R. G. Smith, ‘The Chemistry of 1,3,4,7-Tetramethylisoindole and a route to the Tetrabenzporphyrin System, ‘ J. Chem. Soc. (C), 1970, 1251-1257. 

61. R. Bonnett, J. M. Godfrey, V. B. Math, E. Edmond, H. Evans and O. J. R. Hodder, ‘ Neovitamin B12 Identified’, Nature (London), 1971, 227, 473-476. 

66. C. O. Bender, R. Bonnett and R. G. Smith, ‘The Formation of Metal Octamethyltetrabenzporphyrins from Isoindole Precursors,’ J. Chem. Soc., Perkin Trans 1,1972, 771-776. 

72. R. Bonnett and M. J. Dimsdale, ‘The meso-Reactivity of Porphyrins and Related Compounds. Part V. The meso-Oxidation of Metalloporphyrins’, J. Chem. Soc., Perkin Trans. I, 1972, 2540-2548. 

75. R. Bonnett and A. F. McDonagh, ‘The meso-Reactivity of Porphyrins and Related Compounds. Part VI. Oxidative Cleavage of the Haem System. The Four Isomeric Biliverdins of the IX Series’, J. Chem. Soc., Perkin Trans. 1, 1973, 881-888. 

78. R. Bonnett, R. F. C. Brown and R. G. Smith, ‘Isoindole’, J. Chem. Soc., Perkin Trans. 1,1973, 1432-1436. 

81. R. Bonnett and J. C.M. Stewart, ‘Photo-oxidation of Bilirubin in Hydroxylic Solvents’, J. Chem. Soc., Perkin Trans. 1, 1975, 224-231. 

88. R. Bonnett, P. Cornell and A. F. McDonagh, ‘ The meso-Reactivity of Porphyrins and Related Compounds. Part VII. Benzoyloxylation of Phenylpyrroles and of Octaethylporphyrin’, J. Chem. Soc., Perkin Trans I, 1976, 794-800. 

89. R. Bonnett, ‘ Mechanisms of the Photodegradation of Bilirubin’, Biochem. Soc. Trans.,1976, 4, 222-226. 

93. R. Bonnett, I. H. Campion-Smith and A. J. Page, ‘Protodevinylation: the Schumm Reaction of Vinylporphyrins,’ J. Chem. Soc., Perkin Trans. I, 1977, 68-71. 

101. R. Bonnett, J. E. Davies, M. B. Hursthouse and G. M. Sheldrick, ‘The Structure of Bilirubin’, Proc. R. Soc. London, Ser. B, 1978, 202, 249-268. 

103. R. Bonnett, A. A. Charalambides and R. A. Martin, ‘Nitrosation and Nitrosylation of Haemoproteins and Related Compounds. Part 1. Porphyrins and Metalloporphyrins,’ J. Chem. Soc., Perkin Trans. 1, 1978, 974- 980. 

106. H. N. Shah, R. Bonnett, B. Mateen and R. A. D. Williams, ‘The Porphyrin Pigmentation of Subspecies of Bacteroides melaninogenicus’, Biochem. J., 1979, 108, 45-50. 

108. R. Bonnett, E. J. Head and P. J. Herring, ‘Porphyrin Pigments of some Deep-sea Medusae’, J. Mar. Biol. Assn. U.K., 1979, 59, 565-573. 

112. R. Bonnett, S. Chandra, A. A. Charalambides, K. D. Sales and P. A. Scourides, ‘ Nitrosation and Nitrosylation of Haemoproteins and Related Compounds. Part 4. Pentacoordinate Nitrosylprotohaem as the Pigment of Cooked Cured Meat. Direct Evidence from ESR Spectroscopy,’ J. Chem. Soc., Perkin Trans. 1, 1980, 1706- 1710. 

113. S. Venitt, C. Crofton-Sleigh, S. L. Ooi and R. Bonnett, ‘Mutagenicity of Nitrosated α-Amino Acid Derivatives N-acetyl-N’-nitrosotryptophan and its Methyl ester in Bacteria’, Carcinogenesis, 1980, 1, 523-532. 

116. R. Bonnett and F. Czechowski, ‘Metals and Metal Complexes in Coal’, Philos. Trans. R. Soc. London, Ser. A, 1981, 300, 51-63. 

118. R. Bonnett and S. A. North, ‘The Chemistry of the Isoindoles’, Advances in Heterocyclic Chemistry,1981, 29, 341-399. 119. R. Bonnett, R. J. Ridge, P. A. Scourides and M. C. Berenbaum, ‘On the Nature of Haematoporphyrin Derivative’, J. Chem. Soc., Perkin Trans. 1, 1981, 3135-3140. 

120. M. S. Stoll, N. Vicker, C. H. Gray and R. Bonnett, ‘Concerning the Structure of Photobilirubin II’, Biochem. J., 1982, 201, 179-188. 

124. M. C. Berenbaum, R. Bonnett and P. A. Scourides, ‘In vivo Biological Activity of the Components of Haematoporphyrin Derivative’, Br. J. Cancer, 1982, 45, 571-581. 

125. J. V.Bonfiglio, R. Bonnett, D. G. Buckley, D. Hamzehtash, M. B. Hursthouse, K. M. A. Malik, S. C. Naithani and J. Trotter, ‘ The meso-Reactivity of Porphyrins and Related Compounds. Part VIII. Substitution and Addition Reactions of Octaethyl-21H,24H-bilin-1,19-dione , a Model Verdin System. X-ray Analysis of Octaethyl-5-nitro-21H,24H-bilin-1,19-dione, J. Chem. Soc., Perkin. Trans. 1, 1982, 1291-1302. 

127. L. E. Andrews, R. Bonnett, R. J. Ridge and E. H. Appelman, ‘The Preparation and Reactions of Porphyrin N-Oxides’, J. Chem. Soc., Perkin Trans I, 1983, 103-107. 

128. R. Bonnett, S. A. North, R. F. Newton and D. I. C. Scopes, ‘ Substitution and Addition Reactions of Isoindoles’, Tetrahedron, 1983, 39, 1401-1405. 

148. R. Bonnett, M. J. Dimsdale and G. F. Stephenson, ‘Propentdyopents and Related Compounds, 1. On the Structure of the Propentdyopent-alkanol Adducts’, J. Chem. Soc., Perkin Trans. 1, 1987, 439-443. 

158. L. E. Andrews, R. Bonnett, A. N. Kosyrev and E. A. Appelman, ‘ The meso-Reactivity of Porphyrins and Related Compounds. Part X. Direct Fluorination with Caesium Fluoroxysulphate’, J. Chem. Soc., Perkin Trans. I, 1988, 1735-1738. 

161. R. Bonnett, S. Ioannou and F. J. Swanson, ‘Propentdyopents and Related Compounds. Part 4. Propentdyopent- Alkanol Adducts by the Photo-oxygenation of Pyrromethenones’, J. Chem. Soc., Perkin Trans. 1, 1989, 711- 714. 

163. R. Bonnett, R. D. White, U-J. Winfield and M.C. Berenbaum, ‘Hydroporphyrins of the meso- Tetra(hydroxyphenyl)porphyrin Series as Tumour Photosensitisers’, Biochem. J., 1989, 261, 277-280. 

164. R. Bonnett and M. C. Berenbaum, ‘Porphyrins as Photosensitisers’, Ciba Foundation Symp., 1989, 146, 40-59. 

184. K. R. Adams, M. C. Berenbaum, R. Bonnett, A. N.Nizhnik, A. Salgado and M. A. Vallés, ‘Second generation Tumour Photosensitisers: The Synthesis and Biological Activity of Octaalkyl Chlorins and Bacteriochlorins with Graded Amphiphilic Character’, J. Chem. Soc., Perkin Trans. I, 1992, 1465-1470. 

192. R. Bonnett, D. G. Buckley, T. Burrow, A. B. B. Galia, B. Saville and S. P. Songca, ‘Photobactericidal Materials Based on Porphyrins and Phthalocyanines,’ J. Mater. Chem., 1993, 3, 323-324. 

202. M. C. Berenbaum, R. Bonnett, E. B. Chevretton, S. L. Akande-Adebakin and M. Ruston, ‘Selectivity of meso- Tetra(hydroxyphenyl)porphyrins and chlorins and of Photofrin II in Causing Photodamage in Tumour, Skin, Muscle and Bladder. The Concept of Cost-Benefit in Analysing the Results’, Lasers Med. Sci., 1993, 8, 235- 243. 

213. R. Bonnett, ‘Photosensitisers of the Porphyrin and Phthalocyanine Series for Photodynamic Therapy’, Chem. Soc, Rev., 1995, 24, 19-33. 

220. R. Bonnett and K. A. McManus, ‘Approaches to the Stepwise Synthesis of Benzoporphyrins and Phthalocyanines. Part 1. Synthesis of opp-Dibenzoporphyrins (dibenzo[g,q]porphyrins), J. Chem.Soc., Perkin Trans . 1,1996, 2461-2466. 

221. R. Bonnett, ‘Porphyrins in Coal’, Intern. J. Coal Geol.,1996, 32, 137-149. 222. K. R. Adams, R. Bonnett, P. J. Burke, A. Salgado and M. A. Vallés, ‘Cleavage of (octaethyl-2,3- dihydroxychlorinato) nickel(II) to give the novel 2,3-dioxo-2,3-secochlorin system’, J. Chem. Soc., Perkin Trans 1, 1997, 1769-1772. 

233. R. Bonnett, B. D. Djelal, P. A. Hamilton, G. Martinez and F. Wierrani, ‘Photobleaching of 5,10,15,20- Tetrakis(m-hydroxyphenyl)porphyrin and the corresponding Chlorin (m-THPC) and Bacteriochlorin (m-THPBC). A Comparative Study’, J. Photochem. Photobiol., 1999, 53, 136-143. 

235. R. Bonnett, ‘Chemical Aspects of Photodynamic Therapy’, Gordon and Breach Publishers, Amsterdam, 2000, pp. 1-305. 

236. R. Bonnett, B. D. Djelal and A. Nguyen, ‘Physical and Chemical Studies Related to the Development of m-THPC (FOSCAN®) for the Phototherapy of Tumours’, J. Porphyrins Phthalocyanines, 2001, 5, 652-661. 237. R. Bonnett and G. Martinez, ‘Photobleaching of Sensitisers used in Photodynamic Therapy’, Tetrahedron, 2001, 54, 9513-9547. 

238. R. Bonnett and G. Martinez, ‘Photobleaching of Compounds of the 5,10,15,20-Tetrakis(m- hydroxyphenyl)porphyrin Series (m-THPP, m-THPC, m-THPBC)’, Org. Lett., 2002, 4, 2013-2016. 

244. R. Bonnett, ‘Metal Complexes in Photodynamic Therapy’. In ‘Comprehensive Coordination Chemistry II’, Elsevier Pergamon, Oxford 2004. Volume 9, pp. 945-1003. 

247. R. Bonnett, M. A. Krysteva, I. G. Lalov and S. V. Artarsky, ‘Water Disinfection using Photosensitisers Immobilised on Chitosan’, Water Research, 2006, 40, 1269-1275.

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