EN PT

Luís Guilherme da Silva Arnaut Moreira

B - Medicinal Chemistry

Luís Arnaut

     Email: lgarnaut@ci.uc.pt

Institutional address: Chemistry Department, University of Coimbra, 3004-535 Coimbra, PORTUGAL
Telephone: (351)239852080
Telefax: (351)239827703
Email: lgarnaut@ci.uc.pt

Biography

Luis Arnaut was born near Coimbra (Portugal), graduated from high school in Coimbra and in 1977/78 received an AFS scholarship to attend the 12th grade in Wisconsin, USA. In 1983 Luis Arnaut completed a BSc in Chemistry at the University of Coimbra (mark 17/20) and then undertook PhD studies with Sebastião Formosinho. In 1988 completed his PhD studies in Coimbra, and received a Visiting Fulbright Scholar grant to do post-doctoral research with Richard Caldwell at the University of Texas at Dallas. In 1989 Luis Arnaut returned to the University of Coimbra to become Assistant Professor, in 1996 was appointed Associate Professor, presented his Habilitation in 2002 and was appointed Professor in 2005.

Research interests

Luis Arnaut was educated as a photochemist and cultivates scientific interests related with the use of light and the study of time. Light triggers new opportunities in molecular, materials, life and earth sciences, and their study over wide timescales may provide answers to human needs and curiosity. In particular, Luis Arnaut used lasers and new bacteriochlorin photosensitizers to propose a new medicine for photodynamic therapy of cancer that is currently in clinical trials. In another project, lasers and novel materials were developed to produce photoacoustic waves that permeabilize biological membranes. A device for cosmetic applications based on this work is in the market and preclinical studies aiming at gene therapy are under way. Curiosity-driven research focuses on chemical reactivity (electron transfer, proton transfer and atom transfer reactions), on photoacoustics and the mechanisms of photodynamic therapy.

Current positions

Professor of Chemistry

Leader of Structure, Energetics & Reactivity research group

Chemistry Department and Coimbra Chemistry Centre

University of Coimbra, Portugal

Member of the Board of Directors

International Photodynamic Association, USA

Chairman of the Advisory Board of Luzitin S.A.

Coimbra · Portugal

Co-founder and Board of Directors

Chairman of LaserLeap SA

Coimbra · Portugal

Co-founder and Chairman of the Board of Directors

Director of Coimbra LaserLab

Member of LaserLab Europe – Consortium of European Laser Research Infrastructures

Research infrastructure of the Portuguese Science Foundation

Research infrastructure of the University of Coimbra

Director of the FCT Medicinal Chemistry PhD Program

Consortium between the University of Coimbra, University of Lisbon, Bial SA, Hovione SA and Bluepharma SA

Director of the Medicinal Chemistry MSc degree

Consortium between the Faculties of Science and Technology, Pharmacy and Medicine

University of Coimbra

Director of the Medicinal Chemistry BSc degree

Faculties of Science and Technology

University of Coimbra

Prizes

  • Gulbenkian Science Prize (1994)

  • BES Innovation Grand Prize (2008)

  • RedEmprendia/Santander AVCRI Prize (2010)

  • INVENTA Grand Prize for the best Portuguese patent registered between 2001-2010 (2011)

  • InnoCentive award ID 9933229 (2014).

  • Assocação de Laserterapia e Tecnologias Afins (ALTEC, 2016)

Selected publications

Since 2013

“Higher Activation Barriers Lift Exothermic Rate Restrictions in Electron Transfers and Enable Faster Reactions”
K. K. Mentel, A. Serra, P. Abreu, L. G. Arnaut, Nature Commun., 9 (2018) 2903. DOI: 10.1038/s41467-018-05267-5

 “Photodynamic therapy with redaporfin targets the endoplasmic reticulum and Golgi apparatus”

L. C. Gomes-da-Silva, L. Zhao, H. Zhou, A. Sauvat, P. Liu, L. Bezu, S. Durand, M. Leduc, G. Pierron, F. Loos, B. Sveinbjørnsson, Ø. Rekdal, G. Boncompain, F. Perez, L.G. Arnaut, O. Kepp, G. Kroemer, EMBO J., 37 (2018) e98354.

DOI: 10.15252/embj.201798354

“Split-face, randomized, placebo-controlled, double-blind study to investigate passive versus active dermal filler administration”

M. J. Freire-dos-Santos, R. Carvalho, L. G. Arnaut, Aesthetic Plastic Surg., (2018) in press.

DOI: 10.1007/s00266-018-1208-9

 “Ultrafast Dynamics of Manganese (III), Manganese (II), and Free-Base Bacteriochlorin: Is There Time for Photochemistry?”

F. A. Schaberle, A. R Abreu, N. P. F. Gonçalves, G. F. F. Sá, M. M. Pereira, L. G Arnaut, Inorg. Chem., 56 (2017) 2677-2689.

DOI: 10.1021/acs.inorgchem.6b02871

 “Phthalocyanine Labels for Near-Infrared Fluorescence Imaging of Solid Tumors”

A. C. S. Lobo, A. D. Silva, V. A. Tomé, S. M. A. Pinto, E. F. F. Silva, M. J. F. Calvete, C. M. F. Gomes, M. M. Pereira, L. G. Arnaut, J. Med. Chem., 59 (2016) 4688-4696.

DOI: 10.1021/acs.jmedchem.6b00054

 “Photodynamic Therapy (PDT) of Cancer: From a Local to a Systemic Treatment”

J. M. Dabrowski, L. G. Arnaut, Photochem. Photobiol. Sc., 14 (2015) 1765-1780.

DOI: 10.1039/C5PP00132C

 “Elimination of primary tumours and control of metastasis with rationally designed bacteriochlorin photodynamic therapy regimens”

L. B. Rocha, L. C. Gomes-da-Silva, J. M. Dabrowski, L. G. Arnaut, Eur. J. Cancer, 51 (2015) 1822-1830.

DOI: 10.1016/j.ejca.2015.06.002

 “Photodynamic Therapy Efficacy Enhanced by Dynamics: The Role of Charge Transfer and Photostability in the Selection of Photosensitizers”

L. G. Arnaut, M. M. Pereira, J. M. Dabrowski, E. F. F. Silva, F. A. Schaberle, A. R. Abreu, L. B. Rocha, M. M. Barsan, K. Urbanska, G. Stochel, C. M. A. Brett, Chem. Eur. J., 20 (2014) 5346-5357

DOI: 10.1002/chem.201304202

 “Stratum corneum permeabilization with photoacoustic waves generated by piezophotonic materials”

G. F. F. Sa, C. Serpa, L. G. Arnaut, J. Control. Release, 167 (2013) 290-300

DOI: 10.1016/j.jconrel.2013.02.005

 “From Elementary Reactions to Chemical Relevance in the Photodynamic Therapy of Cancer”

L. G. Arnaut, S. J. Formosinho, Pure Appl. Chem., 85 (2013) 1389-1403.

DOI: 10.1351/PAC-CON-12-08-16

Classical anthology (1984-2012)

  • “Combined Effects between Singlet Oxygen and Hydroxyl Radical in Photodynamic Therapy with Photostable Bacteriochlorins: Evidence from Intracellular Fluorescence and Increased Photodynamic Efficacy In Vitro” J. M. Dabrowski, L. G. Arnaut, M. M. Pereira, K. Urbanska, S. Simões, G. Stochel, L. Cortes, Free Radic Biol. Med., 52 (2012) 1188-1200.
  • “Design of Porphyrin-Based Photosensitizers for Photodynamic Therapy” L. G. Arnaut, Adv. Inorg. Chem., 63 (2011) 187-234.
  • “Mechanisms of singlet-oxygen and superoxide-ion generation by porphyrins and bacteriochlorins and their implications in photodynamic therapy” E. F. F. Silva, C. Serpa, J. M. Dabrowski, C. J. P. Monteiro, S. J. Formosinho, G. Stochel, K. Urbaska, S. Simões, M. M. Pereira, L. G. Arnaut, Chem. Eur. J. 16 (2010) 9273-9286.
  • “Photoacid for extremely long-lived and reversible pH-jumps” R. M. D. Nunes, M. Pineiro, L. G. Arnaut, J. Am. Chem. Soc., 131 (2009) 9456-9462.
  • “Understanding Chemical Reactivity. The Case for Atom, Proton and Methyl Transfers” L. G. Arnaut, S. J. Formosinho, Chem. Eur. J., 14 (2008) 6578-6587.
  • “Photoacoustic Measurement of Electron Injection Efficiencies and Energies from Excited Sensitizer Dyes into Nanocrystalline TiO2 Films” C. Serpa, J. Schabauer, A. P. Piedade, C. J. P. Monteiro, M. M. Pereira, P. Douglas, H. D. Burrows, L. G. Arnaut, J. Am. Chem. Soc., 130 (2008) 8876-8877.
  • “Electron Transfers in Supercritical CO2. Ultra-Exothermic Charge Recombinations at the End of the ‘Inverted Region’” C. Serpa, P. J. S. Gomes, L. G. Arnaut, S. J. Formosinho, J. Seixas de Melo, J. Pina. Chem. Eur. J., 12 (2006) 5014-5023.
  • “Excited-State Proton Transfer in Gas-Expanded Liquids: The Roles of Pressure and Composition in Supercritical CO2/Methanol Mixtures” R. M. D. Nunes, L. G. Arnaut, K. M. Solntsev, L. M. Tolbert, S. J. Formosinho. J. Am. Chem. Soc., 127 (2005) 11890-11891.
  • “Absolute Rate Calculations for Atom Abstractions by Radicals. Energetic, Structural and Electronic Factors” L. G. Arnaut, A. A. C. C. Pais, S. J. Formosinho, M. Barroso, J. Am. Chem. Soc., 125 (2003) 5236-5246.
  • “Heavy-atom effects on metalloporphyrins and polyhalogenated porphyrins” M. E. Azenha, A. C. Serra, M. Pineiro, M. M. Pereira, J. Seixas de Melo, L. G. Arnaut, S. J. Formosinho, A. M. d’A. Rocha Gonsalves., Chem. Phys., 280 (2002) 177-190.
  • “Photoacoustic Measurements of Porphyrin Triplet State Quantum Yields and Singlet Oxygen Efficiencies” M. Pineiro, A. L. Carvalho, M. M. Pereira, A. M.d’A. Rocha Gonsalves, L. G. Arnaut, S. J. Formosinho, Chem. Eur. J., 4 (1998) 2299-2307.
  • “A Critical Assessment of Classical and Semi-Classical Models for Electron Transfer Reactions in Solution” S. J. Formosinho, L. G. Arnaut, R. Fausto, Prog. Reaction Kinetics, 23 (1998) 1-90.
  • "Excited-State Proton Transfer Reactions. II. Intramolecular Reactions" S. J. Formosinho, L. G. Arnaut, J. Photochem. Photobiol. A: Chem., 75 (1993) 21-48.
  • "Excited-State Proton Transfer Reactions. I. Fundamentals and Intermolecular Reactions" L. G. Arnaut, S. J. Formosinho, J. Photochem. Photobiol. A: Chem., 75 (1993) 1-20.
  • “Recent Advances in Photoacoustic Calorimetry: Theoretical Basis and Improvements in Experimental Design" L. G. Arnaut, R. A. Caldwell, J. E. Elbert, L. A. Melton, Rev. Sci. Instruments, 63 (1992) 5381-89.

Licensed Patent Families

5. Low molecular weight derivatives of carboxamide halogenated porphyrins, namely chlorins and bacteriochlorins, and their applications in photodynamic therapy

G. P. N. Costa, N. P. F. Gonçalves, C. J. P. Monteiro, A. C. R. Abreu, H. T. Soares, L. B. Rocha, F. A. Schaberle, M. M. Pereira, L. G. Arnaut Moreira

Luzitin SA and University of Coimbra. PT patent application no. 20151000038067. 7/5/2015. PCT/IB2016/052606. WO2016178191.

Granted and in force: Europe.

Pending: elsewhere.

4. Atropisomers of halogenated tetraphenylbacteriochlorins and chlorins and their use in photodynamic therapy

N. P. F. Gonçalves, T. P. C. M. Santos, G. P. N. Costa, C. J. P. Monteiro, F. A. Schaberle, S. C. Alfar, A. C. R. Abreu, M. M. Pereira, L. G. Arnaut Moreira

Luzitin SA and University of Coimbra. PT patent application no. 20151000023583, 20/3/2015.

PCT/IB2016/051552. WO2016151458.

Pending.

3. Device for the efficient delivery of compounds to or through the skin or biological barriers, using light-absorbing thin films

Gonçalo F. F. Sá, Carlos A. L. Serpa Soares, Luis. G. S. Arnaut Moreira

Universidade de Coimbra. PT Patent Application no. 105635, 19/04/2011.

PCT/PT2012/000013, 19/04/2012. WO/2012/144916

Granted and in force: Europe, Australia, Canada, China, Colômbia, Israel, Japan, Mexico, Russia, South Coreia, South Africa, United States.

Pending: Brazil, India.

2. Process for Preparing Chlorins and their Pharmaceutical Uses

L. G. Arnaut Moreira, M. M. Pereira, S. J. Formosinho, S. Simões, G. Stochel, K. Urbanska

Universidade de Coimbra. UK Patent Application no. 0819594.3, 24/10/2008.

PCT/PT2009/000057, 22/10/2009. WO/2010/047611.

Granted and in force: Australia, Canada, China, Europe, India, Japan, Russia, South Africa, United States.

Pending: Brazil.

1. Nouveaux dérivés de porphirine, notamment chlorines et/ou bactériochlorine, et leurs applications en thérapie photodynamique

M. M. Pereira, L. G. Arnaut, S. J. Formosinho, C. J. P. Monteiro

Universidade de Coimbra. Patente francesa nº 0412149, 16/11/2004.

PCT/EP/012212, 10/11/2005. WO2006/053707.

Granted and in force: Austria, Belgium, Denmark, France, Germany, Great Britain, Greece, Ireland, Italy, Luxemburg, Norway, Monaco, Netherlands, Poland, Portugal, Spain, Switzerland, Australia, Canada, China, India, Japan, Russia, South Africa, United States.

Pending: Brazil.

Leadership in recent projects

The Integrated Initiative of European Laser Research Infrastructures

H2020-INFRAIA-2014-2015, 654148 — LASERLAB-EUROPE

Funding (2015-2018): 10.000.000 € (under management in Coimbra: 110.190 €)

Coimbra PI: Luis Arnaut

Photoacoustic Permeabilization of Biological Barriers – A Window for Drug Delivery and Gene Transfection

FCT/PTDC/QEQ-MED/3521/2014

Funding (2016-2019): 232.800 € (under management of PI: 166.800 €)

PI: Luis Arnaut

LaserLab Portugal

FCT/ROTEIRO/0152/2013

Funding (2017-2020): 2.510.290 € (under management in Coimbra: 1.864.190 €,

Coimbra PI: Luis Arnaut

PhD Programme on Medicinal Chemistry

FCT/PD/00147/2013

Funding (2014-2022): 100.000 € and 24 PhD scholarships (under management in Coimbra: 100.000 € and 12 PhD scholarships)

PI: Luis Arnaut

Optical Biopsy Dyes

FCT/POCTI/QUI-QUI/120182/2010

Funding (2012-14): 127.590€,

PI: Luis Arnaut

Stable Bacteriochlorins — Opportunities in Infrared Chemistry

European Research Area CHEM/0002/2008

Funding (2010-2012): 350.000€ (under management in Coimbra: 199.392€)

PI: Luis Arnaut

Present and past PhD Students

11. Maria Inês Mendes. University of Coimbra. Ongoing.

Portuguese Science Foundation. FCT Medicinal Chemistry Program

10. Helder Tão Soares, University of Coimbra. Ongoing.

Portuguese Science Foundation SFRH/BD/111290/2015

9. Ana Catarina Lobo, University of Coimbra. Ongoing.

Portuguese Science Foundation. FCT Medicinal Chemistry Program

8. “New Free-energy Relationships in Electron Transfer Reactions”

Kamila K. Mentel, University of Coimbra. September 2017.

Portuguese Science Foundation SFRH/BD/91209/2012

7. “Development of a novel photosensitizer for photodynamic therapy of cancer”

Luis B. Rocha, University of Coimbra. May 2016

Bluepharma SA

6. “Transparent Photochemistry: Infrared Sensitizers and Singlet Oxygen Microscopy”

Elsa Fernanda Freitas da Silva, University of Coimbra. November 2013

Portuguese Science Foundation SFRH/BD/46658/2008

5. “Photoacoustic waves for transdermal delivery”

Gonçalo Fernando Ferreira de Sá, University of Coimbra. December 2012.

Portuguese Science Foundation SFRH/BD/45555/2008

4. “Corantes para células solares”

Carlos Jorge Pereira Monteiro, University of Coimbra. April 2012.

Portuguese Science Foundation SFRH/BD/37652/2007

3. “Concepção Síntese e Caracterização de Fotoácidos Peristentes e Reversíveis”

Rui Miguel Duarte Rodrigues Nunes, University of Coimbra. February 2010.

Portuguese Science Foundation SFRH/BD/24005/2005

2. “Cálculo de Constantes de Velocidade Absolutas — Reacções de Transferência de Átomo e de Protão”

Mónica Barroso, University of Coimbra. December 2005.

Portuguese Science Foundation

1. “Reacções Fotoinduzidas de Transferência de Electrão em Fluidos Supercríticos”

Carlos Serpa, University of Coimbra. May 2004.

Portuguese Science Foundation

List of scientific publications in indexed peer-reveiwer journals

Updated lists of publications can be found in:

ORCID: 0000-0002-3223-4819

Google Scholar: “Luis Arnaut”

Books and Book Chapters

14. “Photoacoustic Waves as a Skin Permeation Method"

G. F. F. Sá, C. Serpa, L. G. Arnaut, in “Percutaneous Permeation Enhancers”, N. Dragicevic-Curic, H. I. Maibach (Eds.), Springer, 2017. ISBN 978-3-662-53271-3.

13. “Terapia fotodinâmica para tratamento do cancro”

L. B. Rocha, L. G. Arnaut, M. M. Pereira, L. Almeida, S. Simões, in “Biomateriais aplicados ao desenvolvimento de sistemas terapêuticos avançados / Biomateriales aplicados al diseño de sistemas terapéuticos avanzados”, H. C. de Sousa, M. Braga, A. Sosnik (Eds.), Imprensa da Universidade de Coimbra, 2015, 636-674.

12. “Solar Energy Conversion"

L. G. Arnaut, M. Barroso, C. Serpa, in “Applied Photochemistry”, H. D. Burows, P. Douglas, R. C. Evans (Eds.), Springer, 2013, 267-304.

11. “Proton-Coupled Electron Transfers in Natural and Artificial Photosynthesis”

M. Barroso, L. G. Arnaut, S. J. Formosinho, in Proton-Coupled Electron Transfers: A Carrefour of Chemical Reactivity Traditions, Ed. S. J. Formosinho, M. Barroso, RSC Catalysis Book Series, 2012, 126-151.

10. “A Transition-State Perspective of Proton-Coupled Electron Transfers”

L. G. Arnaut, in Proton-Coupled Electron Transfers: A Carrefour of Chemical Reactivity Traditions, Ed. S. J. Formosinho, M. Barroso, RSC Catalysis Book Series, 2012, 32-56.

9. “Kinetics of Homogeneous Catalytic Processes"

L. G. Arnaut, in Catalysis from Theory to Application”, J. L. Figueiredo, M. M. Pereira, J. Faria (Eds.), Imprensa da Universidade de Coimbra, 2008, 299-318.

8. “Chemical Kinetics”

L. G. Arnaut, S. J. Formosinho, H. D. Burrows, Elsevier, Amsterdão (Holanda), 2007, 549 páginas.

7. "O Tempo da Química-Física"

L. G. Arnaut, "Tempo e Ciência", R. Fausto, R. Marnoto (Eds.), Gradiva, Lisboa (Portugal), 2006, 69-79.

6. “Cinética Química”

S. J. Formosinho, L. G. Arnaut, Imprensa da Universidade de Coimbra, 2003, 640 páginas.

5. "Homogeneous Proton Transfer Photocatalysis"

L. G. Arnaut, S. J. Formosinho, "Homogeneous Photocatalysis", M. Chanon (Ed.), J. Wiley & Sons, Sussex, 1997, 55-96.

4. J. Photochem. Photobiol. A: Chem., número especial "Photoinduced Electron Transfer Reactions"

L. G. Arnaut (Guest Editor); Elsevier: Lausanne (Switzerland), 1994, 250 pp.

3. "Theoretical Study of Electron Transfer Reactions in Porphyrins and Cytochromes"

L. G. Arnaut, "Molecular Electrochemistry of Inorganic, Bioinorganic and Organomettallic Compounds", A. J. L. Pombeiro, J. A. McCleverty (Eds.), NATO ASI Series, Kluwer, Dordrecht (The Netherlands),, 1993, 207-214.

2. "A Kinetic Model for Proton Transfers in Solution"

L. G. Arnaut, "Proton Transfer in Hydrogen-Bonded Systems", T. Bountis (Ed.), NATO ASI Series, Plenum, New York, 1992, 281-295.

1. "Theoretical and Computational Models for Organic Chemistry"

S. J. Formosinho, I. G. Csizmadia, L. G. Arnaut (Eds.); Kluwer: Dordrecht (The Netherlands), 1991, 434 pp.

Past projects

15. Desenvolvimento de novos fotossensilizadores para Terapia Fotodinâmica da acne

QREN 30218, 2013-2014 –1,223,615.73 €

14. Desenvolvimento de dispositivo médico baseado em tecnologia laser não invasiva para a administração transdérmica de fármacos

QREN 22959, LaserLeap – 110.042,03 €, 2012-2014.

13. Desenvolvimento de Novos Medicamentos para Aplicação na Terapia Fotodinâmica do Cancro

QREN 5356, PDT – 1.122.337,67€, 2010-2011.

12. Aplicações Farmacêuticas baseadas em Terapia Fotodinâmica para Tratamento Oncológico

ICentro – 364.580 €, 2008-2009.

11. A Terapia Fotodinâmica no Tratamento do Cancro

PO Centro – 478.779 €, 2006-2007.

10. Bombas Fotónicas de Protões

Portuguese Science Foundation POCTI/QUI/55505/2004 – 71.000 €, 2005-08

9. Ultrafast Structural Dynamics in Physics, Chemistry, Biology and Material Science (DYNA)

European Science Foundation, 2005-09.

8. Estrutura e Dinâmica de Processos Térmicos e Fotoinduzidos

Portuguese Science Foundation REEQ/1245/QUI/2005 – 592.437,79 €, 2006-09

7. Síntese de Novos Sensibilizadores para a Terapia Fotodinâmica Modelados por Factores de Franck-Condon

Portuguese Science Foundation POCTI/QUI/42536/2001– 85.700 €, 2002-04

6. Modelling of Organic Materials for Light-emitting Diodes

Indo-Portuguese Research Cooperation (GRICES) – 6.600 €, 2002-04

5. Femtochemistry and Femtobiology (ULTRA)

European Science Foundation, 2000-04.

4. Reacções Fotoinduzidas em Fluídos Supercríticos

Portuguese Science Foundation PCEX/C/QUI/108/96 – 197.075 €, 1998-2001.

3. Estudo Fotofísico de Fotossensibilizadores Utilizados em Fotomedicina

Portuguese Science Foundation Program Stride – 670.000 PESC, 1990-93.

2. Rede Nacional de Fotoquímica e Fotofísica

Portuguese Science Foundation Program Ciência – 12.300.000 PESC, 1990-93.

1. Desenvolvimento e Aplicação da Calorimetria Fotoacústica

Portuguese Science Foundation Program C&T/C/CEN/385/90 – 6.700.000 PESC, 1990-93.