Bruce Milne

Bruce Milne

Bruce Milne is a post-doctoral researcher whose work focusses mainly on the study the optical properties of organic and organometallic chromophores of biological origin using methods based on time-dependent density functional theory.

Background

Bruce obtained his BSc (Hons) degree in General Chemistry from the University of Aberdeen, Scotland in 1998. His honors project combined organic synthesis with molecular dynamics simulation in an attempt to understand and control features of the synthetic pathway to oligomeric of 1,3-alkylpyridinium salts derived from marine sponges.

Continuing in the marine natural products field he completed his PhD in 2003 under the supervision of Marcel Jaspars at the University of Aberdeen. Central to his studies was understanding the role of amino acid substitutions in determining the conformational properties of a group of post-translationally modified cyclic octapeptides, the patellamides, isolated from collections of the marine ascidian Lissoclinum patella. A combination of molecular dynamics simulation using empirical force fields and density functional theory calculations were used in this work with the DFT calculations being extended to studies of the Cu2+ binding properties of the patellamides.

Following his PhD he worked at the Rowett Research Institute in Aberdeen performing QSAR studies of intestinal absorption of plant polyphenols with cancer preventing properties. Following this he worked for University of Aberdeen spin-off company Tau Therapeutics providing computational medicinal chemistry support in the development of compounds for the treatment of Alzheimer's disease.

As holder of a post-doctoral position at the Faculdade de Farmacía (Universidade de Porto) from 2004 he worked on applying machine learning methods to developing models of the activity of xanthone-based inhibitors of protein kinease C (PKC) and used homology modelling and molecular dynamics to study the structural properties of PKC variants. In addition, he continued his use of molecular simulation and electronic structure calculations to predict and rationalize the properties of compounds of marine origin and extended this to include organometallic compounds (both natural and synthetic). During this time he became interested in the optical properties of the molecules under study and began to work with time-dependent DFT to study optical absorption and circular dichroism in marine compounds.

Moving to the Centro de Fisíca Computacional (Universidade de Coimbra) in 2008 he continued investigations of the optical properties of natural products with studies of color-tuning in firefly bioluminescence. Working in this area led to collaboration with Steen Bronsted Nielsen of the University of Aarhus in Denmark and combined experimental and theoretical investigations of the absorption spectrum of firefly luciferin anion in vacuo. This collaboration continues to this day and has moved into the area of microenvironmental effects on chlorophyll spectral tuning in connection with the Nano-Bio Spectroscopy group of Prof. Angel Rubio at the University of the Basque Country in San Sebastian, Spain.

Through this and other projects he has been involved in collaborative research with experimentalists and other computational scientists in Brazil, France, Germany, Scotland, Sweden, the United Arab Emirates and the USA.

Current research interests

Optical spectroscopy of biological molecules

  • Evaluation of the role of microenvironmental effects in altering biochromophore absorption spectra in protein complexes
  • Real-space TDDFT as a tool for prediction of circular dichroism spectra to aid in structural studies of natural products
  • Extension of real-space TDDFT methods to large systems such as biomacromolecules.

Nonlinear optics

  • Relativistic enhancement of nonlinear optical properties in organic molecules containing heavy p-block elements
  • 'Uninteresting' natural products as a source of novel organic chromophores for optical applications.

 

Publications

2016

Milne, Bruce F; Kjær, Christina; Houmøller, Jørgen; Stockett, Mark H; Toker, Yoni; Rubio, Angel; Nielsen, Steen Brøndsted

On the Exciton Coupling between Two Chlorophyll Pigments in the Absence of a Protein Environment: Intrinsic Effects Revealed by Theory and Experiment Journal Article

Angewandte Chemie, 128 (21), pp. 6356–6359, 2016, ISSN: 1521-3757.

Links | BibTeX | Tags: chlorophyll, photosynthesis

2015

Jornet-Somoza, Joaquim ; Alberdi-Rodriguez, Joseba ; Milne, Bruce F; Andrade, Xavier ; Marques, Miguel A L; Nogueira, Fernando ; Oliveira, Micael J T; Stewart, James J P; Rubio, Angel

Insights into colour-tuning of chlorophyll optical response in green plants Journal Article

Phys. Chem. Chem. Phys., 17 , pp. 26599-26606, 2015.

Abstract | Links | BibTeX | Tags: chlorophyll, light harvesting complex, photosynthesis

Stockett, Mark H; Musbat, Lihi ; Kjær, Christina ; Houmøller, Jørgen ; Toker, Yoni ; Rubio, Angel ; Milne, Bruce F; Brøndsted Nielsen, Steen

The Soret absorption band of isolated chlorophyll a and b tagged with quaternary ammonium ions Journal Article

Phys. Chem. Chem. Phys., 17 , pp. 25793-25798, 2015.

Abstract | Links | BibTeX | Tags: action spectroscopy, chlorophyll, photosynthesis

Milne, Bruce F; Toker, Yoni ; Rubio, Angel ; Brøndsted Nielsen, Steen

Unraveling the Intrinsic Color of Chlorophyll Journal Article

Angewandte Chemie International Edition, 54 (7), pp. 2170–2173, 2015.

Abstract | Links | BibTeX | Tags: action spectroscopy, chlorophyll, photosynthesis

Milne, Bruce F; Norman, Patrick

Resonant-Convergent PCM Response Theory for the Calculation of Second Harmonic Generation in Makaluvamines A–V: Pyrroloiminoquinone Marine Natural Products from Poriferans of Genus Zyzzya Journal Article

The Journal of Physical Chemistry A, 119 (21), pp. 5368-5376, 2015.

Abstract | Links | BibTeX | Tags: marine natural products, nonlinear optics

Martín-Ramos, Pablo ; Silva, Pedro Pereira S; Chamorro-Posada, Pedro ; Ramos Silva, Manuela ; Milne, Bruce F; Nogueira, Fernando ; Martín-Gil, Jesús

Synthesis, structure, theoretical studies and luminescent properties of a ternary erbium(III) complex with acetylacetone and bathophenanthroline ligands Journal Article

Journal of Luminescence, (0), pp. -, 2015, ISSN: 0022-2313.

Abstract | Links | BibTeX | Tags: Erbium, heavy metals, β-diketonate

Stockett, Mark H; Houmøller, Jørgen ; Kjær, Christina ; Milne, Bruce F; Musbat, Lihi ; Rubio, Angel ; Toker, Yoni ; Brøndsted Nielsen, Steen

Action spectroscopy of chlorophyll and other coordination complexes. Journal Article

Journal of Physics: Conference Series, 635 (11), pp. 112015, 2015.

Abstract | Links | BibTeX | Tags: action spectroscopy, chlorophyll, photosynthesis

2014

Jensen, Marianne W; Støchkel, Kristian ; Kjær, Christina ; Knudsen, Jeppe L; Maltsev, Oleg V; Hintermann, Lukas ; Naumov, Panče ; Milne, Bruce F; Brøndsted Nielsen, Steen

Photoinduced dissociation mass spectroscopy of firefly oxyluciferin anions Journal Article

International Journal of Mass Spectrometry, 365–366 (0), pp. 3 - 9, 2014, ISSN: 1387-3806, (Special issue: Tilmann mark).

Abstract | Links | BibTeX | Tags: action spectroscopy, bioluminescence, Oxyluciferin

de Lima Ferreira, Marcelle ; Milne, Bruce F; de Souza, Marcus V N; Tiekink, Edward R T; Wardell, James L; Wardell, Solange M S V

Structures of Two Rotamers of the HCl Salt of 4-Methyl-2-[(1E)-[2-(quinolin-4-yl)hydrazin-1-ylidene]methyl]phenol: Different Supramolecular Arrays Journal Article

Journal of Chemical Crystallography, 44 (1), pp. 36-41, 2014, ISSN: 1074-1542.

Abstract | Links | BibTeX | Tags: hydrogen bonding, rotamers

Milne, Bruce F

Enhancement of nonlinear optical properties in late group 15 tetrasubstituted cubanes Journal Article

Dalton Trans., 43 , pp. 6333-6338, 2014.

Abstract | Links | BibTeX | Tags: Antimony, Arsenic, Bismuth, group 15, heavy atom effect, heavy metals, Nitrogen, Phosphorus

Milne, Bruce F

Red-shifting the optical response of firefly oxyluciferin with group 15/16 substitutions Journal Article

Phys. Chem. Chem. Phys., 16 , pp. 24971-24977, 2014.

Abstract | Links | BibTeX | Tags: bioluminescence, group 15, group 16, heavy atom effect, Oxyluciferin

2013

Milne, Bruce F; Nogueira, Fernando ; Cardoso, Claudia

Theoretical study of heavy-atom tuning of nonlinear optical properties in group 15 derivatives of N,N,N-trimethylglycine (betaine) Journal Article

Dalton Trans., 42 , pp. 3695-3703, 2013.

Abstract | Links | BibTeX | Tags: Antimony, Arsenic, Bismuth, group 15, heavy atom effect, Nitrogen, nonlinear optics, Phosphorus

Milne, Bruce F; Norman, Patrick ; Nogueira, Fernando ; Cardoso, Claudia

Marine natural products from the deep Pacific as potential non-linear optical chromophores Journal Article

Phys. Chem. Chem. Phys., 15 , pp. 14814-14822, 2013.

Abstract | Links | BibTeX | Tags: marine natural products, nonlinear optics

Støchkel, Kristian ; Hansen, Christian Nygaard ; Houmøller, Jørgen ; Nielsen, Lisbeth Munksgaard ; Anggara, Kelvin ; Linares, Mathieu ; Norman, Patrick ; Nogueira, Fernando ; Maltsev, Oleg V; Hintermann, Lukas ; Brøndsted Nielsen, Steen ; Naumov, Panče ; Milne, Bruce F

On the Influence of Water on the Electronic Structure of Firefly Oxyluciferin Anions from Absorption Spectroscopy of Bare and Monohydrated Ions in Vacuo Journal Article

J. Am. Chem. Soc., 135 (17), pp. 6485-6493, 2013.

Links | BibTeX | Tags: action spectroscopy, bioluminescence, hydrogen bonding, Oxyluciferin

2011

Støchkel, Kristian ; Milne, Bruce F; Brøndsted Nielsen, Steen

Absorption Spectrum of the Firefly Luciferin Anion Isolated in Vacuo Journal Article

J. Phys. Chem. A, 115 (11), pp. 2155–2159, 2011.

Abstract | Links | BibTeX | Tags: action spectroscopy, bioluminescence, luciferin

2010

Abdel-Mageed, Wael M; Milne, Bruce F; Wagner, Marcell ; Schumacher, Marc ; Sandor, Peter ; Pathom-aree, Wasu ; Goodfellow, Michael ; Bull, Alan T; Horikoshi, Koki ; Ebel, Rainer ; Diederich, Marc ; Fiedler, Hans-Peter ; Jaspars, Marcel

Dermacozines, a new phenazine family from deep-sea dermacocci isolated from a Mariana Trench sediment Journal Article

Org. Biomol. Chem., 8 (10), pp. 2352, 2010, ISSN: 1477-0520.

Links | BibTeX | Tags: marine natural products

Cai, Duanjun ; Marques, Miguel A L; Milne, Bruce F; Nogueira, Fernando

Bioheterojunction Effect on Fluorescence Origin and Efficiency Improvement of Firefly Chromophores Journal Article

Journal of Physical Chemistry Letters, 1 (19), pp. 2781–2787, 2010.

Abstract | Links | BibTeX | Tags: bioluminescence, Oxyluciferin

Cardoso, Claúdia ; Abreu, Paulo E; Milne, Bruce F; Nogueira, Fernando

Computational Study of Molecules with High Intrinsic Hyperpolarizabilities Journal Article

J. Phys. Chem. A, 114 (39), pp. 10676–10683, 2010.

Abstract | Links | BibTeX | Tags: nonlinear optics

Milne, Bruce F; Marques, Miguel A L; Nogueira, Fernando

Fragment molecular orbital investigation of the role of AMP protonation in firefly luciferase pH-sensitivity Journal Article

Phys. Chem. Chem. Phys., 12 (42), pp. 14285, 2010, ISSN: 1463-9076.

Links | BibTeX | Tags: bioluminescence, luciferase, Oxyluciferin

Tadesse, Margey ; Strøm, Morten B; Svenson, Johan ; Jaspars, Marcel ; Milne, Bruce F; Tørfoss, Veronika ; Andersen, Jeanette H; Hansen, Espen ; Stensvåg, Klara ; Haug, Tor

Synoxazolidinones A and B: Novel Bioactive Alkaloids from the Ascidian Synoicum pulmonaria Journal Article

Org. Lett., 12 (21), pp. 4752–4755, 2010.

Abstract | Links | BibTeX | Tags: circular dichroism, marine natural products

2009

de Lima, Geraldo M; Milne, Bruce F; Pereira, Robson P; Rocco, Ana Maria ; Skakle, Janet M S; Travis, Anthony J; Wardell, James L; Wardell, Solange M S V

Experimental and ab initio structural study of estertin compounds, X3SnCH2CH2CO2Me: Crystal structures of Cl3SnCH2CH2CO2Me at 120 K and Br3SnCH2CH2CO2Me at 120 and 291 K Journal Article

J. Mol. Struct., 921 (1-3), pp. 244–250, 2009.

Abstract | Links | BibTeX | Tags: Tin

2008

Krupp, Eva ; Milne, Bruce F; Mestrot, Adrien ; Meharg, Andrew ; Feldmann, Jørg

Investigation into mercury bound to biothiols: structural identification using ESI-ion-trap MS and introduction of a method for their HPLC separation with simultaneous detection by ICP-MS and ESI-MS Journal Article

Anal. Bioanal. Chem., 390 (7), pp. 1753–1764, 2008.

Abstract | Links | BibTeX | Tags: heavy metals, Mercury

Latifi, Reza ; Bagherzadeh, Mojtaba ; Milne, Bruce F; Jaspars, Marcel ; de Visser, Sam P

Density functional theory studies of oxygen and carbonate binding to a dicopper patellamide complex Journal Article

J. Inorg. Biochem., 102 (12), pp. 2171–2178, 2008.

Abstract | Links | BibTeX | Tags: Carbonate, Copper, Oxygen, Tyrosinase

Wright, Stephen H; Raab, Andrea ; Tabudravu, Jioji N; Feldmann, Jørg ; Long, Paul F; Battershill, Christopher N; Dunlap, Walter C; Milne, Bruce F; Jaspars, Marcel

Marine Metabolites and Metal Ion Chelation: Intact Recovery and Identification of an Iron(II) Complex in the Extract of the Ascidian Eudistoma gilboviride Journal Article

Angew. Chem. Int. Ed., 47 (42), pp. 8090–8092, 2008.

Abstract | Links | BibTeX | Tags: circular dichroism, marine natural products

2007

Regmi, Rajendra ; Milne, Bruce F; Feldmann, Jørg

Hydride generation activity of arsenosugars and thioarsenicals Journal Article

Anal. Bioanal. Chem., 388 (4), pp. 775–782, 2007.

Abstract | Links | BibTeX | Tags: Arsenic, marine natural products

2006

Milne, Bruce F; Long, Paul F; Starcevic, Antonio ; Hranueli, Daslav ; Jaspars, Marcel

Spontaneity in the patellamide biosynthetic pathway Journal Article

Org. Biomolec. Chem., 4 , pp. 631 – 638, 2006.

Abstract | Links | BibTeX | Tags: marine natural products, patellamides

2005

Milne, Bruce F; Pereira, Robson P; Rocco, Ana Maria ; Skakle, Janet M S; Travis, Anthony J; Wardell, James L; Wardell, Solange M S V

Experimental and ab initio structural study of the ketotin compounds, X3SnCR2CH2COMe: crystal structures of X3SnCMe2CH2COMe (X = Cl and I) Journal Article

Appl. Organomet. Chem., 19 (3), pp. 363–371, 2005, ISSN: 1099-0739.

Abstract | Links | BibTeX | Tags: Tin

Tabudravu, Jioji N; Morris, Linda A; Milne, Bruce F; Jaspars, Marcel

Conformational studies of free and Li+ complexed jasplakinolide, a cyclic depsipeptide from the Fijian marine sponge Jaspis splendens. Journal Article

Org. Biomolec. Chem., 3 (5), pp. 745–9, 2005.

Links | BibTeX | Tags: marine natural products, metal-binding peptides

2004

Hansen, Helle R; Raab, Andrea ; Jaspars, Marcel ; Milne, Bruce F; Feldmann, Jørg

Sulfur-containing arsenical mistaken for dimethylarsinous acid [DMA(III)] and identified as a natural metabolite in urine: major implications for studies on arsenic metabolism and toxicity. Journal Article

Chem. Res. Toxicol., 17 (8), pp. 1086–91, 2004.

Abstract | BibTeX | Tags: Arsenic

Rocco, Ana Maria ; Pereira, Robson Pacheco ; Bonapace, José A P; Comerlato, Nadia M; Wardell, James L; Milne, Bruce F; Wardell, Solange M S V

A theoretical study of tetrabutylammonium [bis(1,3-dithiole-2-thione-4,5-dithiolato)bismuthate], [NBu4][Bi(dmit)2]: infrared spectrum in the solid state and solvation effects on the molecular geometry Journal Article

Inorg. Chim. Acta, 357 (4), pp. 1047–1053, 2004.

BibTeX | Tags: Bismuth

2002

Low, J N; Milne, Bruce F; Ross, J N; Wardell, James L

Derivatives of N,N '-bis[2-hydroxy-1,1- bis(hydroxymethyl)ethyl]ethanediamide Journal Article

J. Braz. Chem. Soc., 13 (2), pp. 207–217, 2002.

Abstract | BibTeX | Tags:

Milne, Bruce F

Theoretical studies of cyclic octapeptides from the marine ascidian Lissoclinum patella PhD Thesis

University of Aberdeen, Chemistry department, 2002, (PhD. Thesis).

BibTeX | Tags: Copper, marine natural products, metal-binding peptides, patellamide

Milne, Bruce F; Morris, Linda A; Jaspars, Marcel ; Thompson, Gary S

Conformational change in the thiazole and oxazoline containing cyclic octapeptides, the patellamides. Part 2. Solvent dependent conformational change Journal Article

J. Chem. Soc.-Perkin Trans. 2, (6), pp. 1076–1080, 2002.

Abstract | BibTeX | Tags: marine natural products, metal-binding peptides

Morris, Linda A; Milne, Bruce F; Thompson, Gary S; Jaspars, Marcel

Conformational change in the thiazole and oxazoline containing cyclic octapeptides, the patellamides. Part 1. Cu2+ and Zn2+ induced conformational change Journal Article

J. Chem. Soc.-Perkin Trans. 2, (6), pp. 1072–1075, 2002.

Abstract | BibTeX | Tags: Copper, marine natural products, metal-binding peptides

2001

Morris, Linda A; Milne, Bruce F; Jaspars, Marcel ; Kettenes-van den Bosch, Jantina J; Versluis, Kees ; Heck, Albert J R; Kelly, Sharon M; Price, Nick C

Metal binding of Lissoclinum patella metabolites. Part 2: Lissoclinamides 9 and 10 Journal Article

Tetrahedron, 57 (15), pp. 3199–3207, 2001.

Abstract | Links | BibTeX | Tags: marine natural products

2000

Chohan, Z H; Harrison, William T A; Howie, Alan R; Milne, Bruce F; Wardell, James L

Crystallographic and molecular mechanics investigation of an order-disorder transition and dimorphism in 5H,10H- dithiolo[2,3-b]-2,5-benzodithiocine-2-thione Journal Article

Acta Crystallogr. Sect. B-Struct. Sci., 56 , pp. 1011–1017, 2000.

Abstract | BibTeX | Tags:

Scott, Roderick H; Whyment, A D; Foster, A; Gordon, Kirsten H; Milne, Bruce F; Jaspars, Marcel

Analysis of the structure and electrophysiological actions of halitoxins: 1,3 alkyl-pyridinium salts from Callyspongia ridleyi Journal Article

J. Membr. Biol., 176 (2), pp. 119–131, 2000.

Abstract | BibTeX | Tags: ion channels, marine natural products

1998

Milne, Bruce F

Development of a Synthetic Route to Oligomeric 1,3-Alkylpyridinium Salts. Miscellaneous

1998, (Honours thesis; BSc; (Hons.)).

BibTeX | Tags: marine natural products, synthesis