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Supramolecular control of photoeliminations

Principal investigator

Category
Projekti Hrvatske zaklade za znanost
Project code
HRZZ-6312
Finance value
922.000,00
HRK
Start date
Jul 1st 2015
End date
Aug 31st 2019
Status
Done
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Supramolecular control of photoeliminations

Dynamics of supramolecular systems facilitates control of the photochemical reactivity and opens opportunities for reactions which cannot be conducted by conventional synthetic methods, in the thermal reactions in isotropic solution. The main strategy of the proposed project is to apply different supramolecular systems to control photochemical reactivity. The proposed research should increase the fundamental knowledge in supramolecular chemistry, photophysics and photochemistry of the polycyclic molecules in isotropic media and the supramolecular complexes. The research will be focused on three photoelimination reactions. The aspects which we will address include the effects of molecular geometry on reactivity and stability constants of the inclusion complexes, as well as influence of the complexation on the photophysical properties of different chromophores, efficiency of the photochemical reactions and product distribution. In connection with the proposed investigations it will be necessary to synthesize a large number of well defined and in some cases extremely complex molecules which will certainly ask for substantial innovations in the synthetic methodology and development of the existing techniques. The scientific goals of the project will go beyond the state of the art and search for bio-medical applications. A series of compounds will be screened for antiproliferative activity, providing lead molecules for further research and potential development of cancer treatment with minimal side effects.

The photoelimination reactions are studied on three systems:

a) extrusion of nitrogen giving carbene intermediates;

b) photodecarboxylation of different compounds activated by phthalimide chromophore;

c) photodehydration and photodeamination giving quinone methides (QMs)

 

PublicationsMandić, Leo; Benčić, Patricia; Mlinarić-Majerski, Kata; Liekens, Sandra; Snoeck, Robert; Andrei, Graciela; Kralj, Marijeta; Basarić, Nikola; Substituted Adamantylphthalimides: Synthesis, Antiviral and Antiproliferative ActivityArchiv der pharmazie. (2020) (in press)

Zlatić, Katarina; Antol, Ivana; Uzelac, Lidija; Mikecin Dražić, Ana-Matea; Kralj, Marijeta; Bohne, Cornelia; Basarić, Nikola.
Labeling of Proteins by BODIPY-Quinone Methides utilizing Anti-Kasha PhotochemistryACS Applied Materials & Interfaces. 12 (2020) , 1; 347-351 (članak, znanstveni).

Zlatić, Katarina; Ayouchia, Hicham Ben El; Anane, Hafid; Mihaljević, Branka; Basarić, Nikola; Rohand, Taoufik.
Spectroscopic and photophysical properties of mono- and dithiosubstituted BODIPY dyes. Journal of photochemistry and photobiology. A, Chemistry. 388 (2020) , 112206; 1-8 (članak, znanstveni)

T. Šumanovac, M. Alešković, M. Šekutor, M. Matković, T. Baron, K. Mlinarić-Majerski; C. Bohne, N. Basarić: "Photoelimination of Nitrogen from Adamantane and Pentacycloundecane (PCU) Diazirines: Spectroscopic Study and Supramolecular Control"  Photochemical & photobiological sciences. 18 (2019) ; 1806-1822 DOI:10.1039/c9pp00124g

Erben, Antonija; Matić, Josipa; Basarić, Nikola; Piantanida, Ivo; The phenanthridine - modified tyrosine dipeptide: synthesis and non-covalent binding to DNA and RNA. Croatica chemica acta. 92 (2019) , 2; 249-258 (članak, znanstveni).

P. Benčić, L. Mandić, I. Džeba, I. Tartaro Bujak, L. Biczók, B. Mihaljević, K. Mlinarić-Majerski, I. Weber, M. Kralj, N. Basarić: "Application of 4-amino-N-adamantylphthalimide solvatochromic dye for fluorescence microscopy in selective visualization of lipid droplets and mitochondria"  Sensors and actuators. B, Chemical. 286 (2019) , x; 52-61 DOI:10.1016/j.snb.2019.01.102

J. Ma, M. Šekutor, Đ. Škalamera, N. Basarić, D.L. Phillips:"Formation of Quinone Methides by Ultrafast Photodeamination: A Spectroscopic and Computational Study"  Journal of organic chemistry. 84 (2019) ; 8630-8637 DOI:10.1021/acs.joc.9b01085

M. Sambol, K. Ester, S. Landgraf, B. Mihaljević, M. Cindrić, M. Kralj, N. Basarić: "Competing photochemical reactions of bis-naphthols and their photoinduced antiproliferative activity" Photochemical & photobiological sciences. 1 (2019) ; 1-16 DOI:10.1039/C8PP00532J

M. Sambol, K. Ester, A. Husak, Đ. Škalamera, I. Piantanida, M. Kralj, N. Basarić: "Bifunctional Phenol Quinone Methide Precursors: Synthesis and Biological Activity", Croatica chemica acta. 92 (2019) , 1; 1-12  DOI:10.5562/cca3455

M. Sohora, M. Vazdar, I. Sović, K. Mlinarić-Majerski, N. Basarić: "Photocyclization of tetra- and pentapeptides containing adamantylphthalimide and phenylalanines: reaction efficiency and diastereoselectivity", J. Org. Chem. 83 (2018) ; 14905-14922 DOI: 10.1021/acs.joc.8b01785

Đ. Škalamera, M. Matković, L. Uzelac, M. Kralj, K. Mlinarić-Majerski, C. Bohne, N. Basarić:
Đ. Škalamera, I. Antol, K. Mlinarić-Majerski, H. Vančik, D.Lee Phillips, J. Ma, N. Basarić:
"Ultrafast Adiabatic Photodehydration of o-hydroxymethylphenol and Formation of Quinone Methide", Chem. a Eur. J. 2018, 24, 9426-9435. doi:10.1002/chem.201801543

J. Ma, X. Zhang, N. Basarić, D.L. Phillips: "Direct Observation of Photoinduced Ultrafast Generation of Singlet and Triplet Quinone Methides in Aqueous Solutions and Insight into the Roles of Acidic and Basic Sites in Quinone Methide Formation", J. Am. Chem. Soc. 2017, 139, 18349-18357 doi:10.1021/jacs.7b10387

Novak, Jurica; Prlj, Antonio; Basarić, Nikola; Corminboeuf, Clémence; Došlić, Nađa; Photochemistry of 1- and 2-Naphthols and Their Water Clusters : The Role of 1 ππ*(La ) Mediated Hydrogen Transfer to Carbon Atoms. Chemistry : a European journal. 23 (2017) , 34; 8244-8251 (članak, znanstveni)

Đ. Škalamera, V. Blažek Bregović, I. Antol, C. Bohne, N. Basaric: "Hydroxymethylaniline photocages for carboxylic acids and alcohols", J. Org. Chem.  2017, 82, 23, 12554-12568, doi: 10.1021/acs.joc.7b02314

V. Blažek Bregović, N. Basarić: "Competing processes in the photochemistry of picolines and their N-methyl salts: photoinduced charge transfer, phototransposition and photohydration", Res. Chem. Intermed. 2017, 43, 2; 859-871, doi:10.1007/s11164-016-2669-6

S. Chaiwongwattana, Đ. Škalamera, N. Doslic, C. Bohne, N. Basarić: "Substitution Pattern on Anthrol Carbaldehydes: Excited State Intramolecular Proton Transfer (ESIPT) with a Lack of Phototautomer Fluorescence", Phys. Chem. Chem. Phys. 2017, 19, 28439-28449, doi: 10.1039/c7cp05472f

Đ. Škalamera, J. Veljković, L. Ptiček, M. Sambol, K. Mlinarić-Majerski, N. Basarić:
"Synthesis of asymmetrically disubstituted anthracenes", Tetrahedron. 2017, 73, 40; 5892-5899 doi.org/10.1016/j.tet.2017.08.038

L. Uzelac, Đ. Škalamera, K. Mlinarić-Majerski, N. Basarić, M. Kralj:"Selective photocytotoxicity of anthrols on cancer stem-like cells: the effect of quinone methides or reactive oxygen species",Eur. J. Med. Chem. 2017, 137; 558-574, doi:10.1016/j.ejmech.2017.05.063

Đ. Škalamera, K. Mlinarić-Majerski, I. Martin Kleiner, M. Kralj, J. Oake, P. Wan, C. Bohne, N. Basaric: "Photochemical formation of anthracene quinone methide derivatives", J. Org. Chem. 2017, 82,12; 6006-6021; doi:10.1021/acs.joc.6b02735

M. Sohora, N. Vidović, K. Mlinarić-Majerski, N. Basarić: "Synthesis and photochemical reactivity of phthalimidoadamantane-tyrosine conjugates", Res. Chem. Intermed. 2017, doi:10.1007%2Fs11164-017-2927-2

A. Husak, B.P. Noichl, T. Šumanovac Ramljak, M. Sohora, Đ. Škalamera, N. Budiša, N. Basarić: "Photochemical formation of quinone methides from peptides containing modified tyrosine", Org. & biomol. chem. 2016, 14, 10894-10905, doi:10.1039/C6OB02191C

L. Mandić, K. Mlinarić-Majerski, A. G. Griesbeck, N. Basarić: "Photodecarboxylation of Adamantane Amino Acids Activated by Phthalimide", Eur. J. Org. Chem. 2016, 4404-4414, doi: 10.1002/ejoc.201600491

V. Blažek Bregović, N. Basarić: "Competing processes in the photochemistry of picolines and theirN-methyl salts: photoinduced charge transfer, phototransposition and photohydration", Res. Chem. Intermed. 2017, 43, 2; 859-871, doi: 10.1007/s11164-016-2669-6

T. Govender, U. Govinden, C. Mocktar, H. G. Kruger, J. Veljković, N. Cindro, D. Bobinac, I. Žabčić, K. Mlinarić-Majerski, N. Basarić: "In vitro Investigation of Antimicrobial Activity of a Series of Lipophilic Phenols and Naphthols", S. Afr. J. Chem. 2016,69, 44-50, doi:10.17159/0379-4350/2016/v69a6

N. Cindro, I. Antol, K. Mlinarić-Majerski, I. Halasz, P. Wan, N. Basarić: "Reactivity of Cations and Zwitterions Formed in Photochemical and Acid-Catalyzed Reactions from m-Hydroxycycloalkyl-Substituted Phenol Derivatives",J. Org. Chem.2015,80, 12420-12430, doi:10.1021/acs.joc.5b02297

Đ. Škalamera, C. Bohne, S. Landgraf, N. Basarić: "Photodeamination Reaction Mechanism in Aminomethyl p-CresolDerivatives: Different Reactivity of Amines and Ammonium Salts", J. Org. Chem.2015,80, 10817-10828, doi:10.1021/acs.joc.5b01991

Patentna prijava:

N. Basarić, M. Kralj, AM. Mikecin, M.Cindrić: "Quinone methide precursors with bodipy chromophore, method of preparation, biological activity and application in fluorescent labeling", EP16169771.9, 16. 05. 2016. ; PCT/HR2017/000005, 18446744073709551615, HR15.05.2016.

Patent application:

N. Basarić, M. Kralj, AM. Mikecin, M.Cindrić: "Quinone methide precursors with bodipy chromophore, method of preparation, biological activity and application in fluorescent labeling", EP16169771.9, 16. 05. 2016. ; PCT/HR2017/000005, 18446744073709551615, HR15.05.2016.

 

Public presentations and participation at the conferences

K. Zlatić, L. Uzelac, M. Kralj, N. Basarić: Synthesis, photochemical reactivity and biological activity of a quinone methide precursors containing BODIPY chromophore - potential photoactive anticancer drugs // VIII EFMC International Symposium on Advances in Synthetic and Medicinal Chemistry / Atena, Grčka.
K. Zlatić, I. Antol, N. Basarić: Photophysical properties and photochemical reactivity of a quinone methide precursor containing BODIPY chromophore // 26th Croatian Meeting of Chemists and Chemical Engineers, Šibenik, 2019.
M. Alešković, T. Šumanovac, M. Matković, K. Mlinarić-Majerski, M. Šekutor, N. Basarić: From polycyclic diazirines to carbenes: supramolecular control of photoreactivity // 691. WE-Heraeus-seminar / Physical organic chemistry: Recent development in istrumentation, structure, theory and mechanisms / Bad Honnef, Njemačka.
N. Basarić: Photochemical dehydration and deamination of phenols to quinone methides  // First International Conference on Excited State Aromaticity and Antiaromaticity – ICESAA.
2019. IL-10-IL-10 / Sigtuna, Švedska 2019, (pozvano predavanje)

N. Basarić, I. Antol, J. Ma, M. Šekutor, Đ. Škalamera, H. Vančik, K. Mlinarić-Majerski, D.L. Phillips: "ULTRAFAST FORMATION OF QUINONE METHIDES: SPECTROSCOPIC AND COMPUTATIONAL STUDY", // 27th PhotoIUPAC / International Symposium on Photochemistry / Dublin, 2018. str. 2D3-2D3 (predavanje)

M. Šekutor, J. Ma, Đ. Škalamera, D.L. Phillips, N. Basarić: "THEORETICAL INSIGHTS INTO QUINONE METHIDES FORMED FROM p-CRESOLS" //27th PhotoIUPAC / International Symposium on Photochemistry, Dublin, 2018. str. P165-P165 (poster)

N. Basarić, T. Šumanovac Ramljak, M. Alešković, M. Šekutor, M. Matković, C. Bohne, K. Mlinarić-Majerski: "Photoelimination of Nitrogen from Polycyclic Diazirines: Spectroscopic Study and Supramolecular Control of Photoreactivity" // CECP 2018 - Central European Conference on Photochemistry, Bad Hofgastein, Austrija, 2018. O12-O12 (predavanje)

A. Husak, N. Basarić: "Photophysical properties and photochemical reactivity of tripeptides containing quinone methide precursors" // CECP 2018 - Central European Coference on Photochemistry, Bad Hofgastein, Austrija, 2018. P30-P30 (poster)

N. Basarić, S. Chaiwongwattana, N. Došlić, Đ. Škalamera, C. Bohne, Cornelia: "Excited State Intramolecular Proton Transfer (ESIPT) in Anthrol Carbaldehydes" // 28th International Conference on Photochemistry / ICP 2017 / Strasbourg, Francuska. 2017. 54-54 (poster)

L. Uzelac, Đ. Škalamera, K. Mlinarić-Majerski, N. Basarić, M. Kralj: "ANTITUMOR ACTIVITY OF ANTHROLS THAT PHOTOCHEMICALLY GENERATE QUINONE METHIDES OR REACTIVE OXYGEN SPECIES AND THEIR SELECTIVITY TOWARDS CANCER STEM CELLS" //10th Joint Meeting of Medicinal Chemistry / Dubrovnik, Hrvatska. 2017. 144-144 (poster)

M. Cindrić, K. Mlinarić-Majerski, N. Basarić, I. Martin Kleiner, L. Uzelac, M. Kralj: "ANTIPROLIFERATIVE ACTIVITY OF QUINONE METHIDES WITH BODIPY CHROMOPHORE" // 10th Joint Meeting of Medicinal Chemistry; Dubrovnik, Hrvatska. 25-28.6.2017. 97-97 (poster)

A. Husak, J. Matić, I. Piantanida, N. Basarić: "SYNTHESIS OF DIPEPTIDES CONTAINING PHOTOCHEMICALLY REACTIVE MODIFIYED TYROSINE AND EVALUATION OF THEIR DNA BINDING" // 10th Joint Meeting of Medicinal Chemistry; Dubrovnik, Hrvatska. 25-28.6.2017. 121-121 (poster)

M. Sambol, K. Ester, M. Kralj, K. Mlinarić-Majerski, N. Basarić:"Antiproliferative activity of photogrenerated naphthalene and antracene bis(quinone methides) derivatives" // 4th EFMC Young Medicinal Chemist Symposium; Beč, Austrija. 2017. 121-121 (poster)

M. Sohora, I. Sović, K. Mlinarić-Majerski, N. Basarić: "Stereoselectivity in Phthalimide Initiated Photocyclization of Peptides" // 25. Hrvatski skup kemičara i kemijskih inženjera s međunarodnim sudjelovanjem 3. simpozij "Vladimir Prelog", Poreč, Hrvatska. 2017. 65-65 (predavanje)

T. Šumanovac Ramljak, M. Alešković, M. Matković, N. Basarić, K. Mlinarić-Majerski: "Photoelimination of nitrogen from polycyclic diazirines in inclusion complexes" // 20th European Symposium on Organic Chemistry, Cologne, University of Cologne, 2017. 102-102 (poster)

Đ. Škalamera, V. Blažek Bregović, N. Basarić: "New aniline photocage for carboxylic acids" // 25. Hrvatski skup kemičara i kemijskih inženjera s međunarodnim sudjelovanjem 3. simpozij "Vladimir Prelog", Poreč, Hrvatska.
// Simpozij studenata doktorskih studija PMF-a, Prirodoslovno-matematički fakultet Sveučilišta u Zagrebu, veljača 2016 (poster).

L. Mandić, K. Mlinarić-Majerski, N. Basarić: "Synthesis and photochemistry of activated adamantyl amino acids" // Simpozij studenata doktorskih studija PMF-a, Prirodoslovno-matematički fakultet Sveučilišta u Zagrebu, veljača 2016 (predavanje).

L. Mandić, K. Mlinarić-Majerski, N. Basarić: "Influence of distance in adamantane rigid spacer between electron donor and acceptor to photoinduced electron transfer and photodecarboxylation efficiency" // CECP 2016 - Central European Conference on Photochemistry,  Bad Hofgastein, Austrija, veljača, 2016 (poster).

Đ Škalamera, C. Bohne, S. Landgraf, N. Basarić: "Photogeneration of quinone methides in supramolecular complexes: Potential for new drug delivery" // CECP 2016 - Central European Conference on Photochemistry, Bad Hofgastein, Austrija, veljača, 2016 (poster).

N. Basarić, Đ. Škalamera, K. Mlinarić-Majerski, H. Vančik, P. Wan: "Mechanistic investigation of dehydration and deamination in photochemical formation of quinone methides" // 2015 International Chemical Congres of Pacific Basin Societis, Honolulu, prosinac 2015 (poster).

V. Blažek Bregović, N. Basarić: "The NMR Study of Products Obtained by Photorearrangement of Pyridinium Salts"  // met4pharm - Pharma NMR Conference, Rovinj - Crveni Otok, Hrvatska, studeni 2015 (poster).

N. Basarić: "Biological activity of photochemically generated quinone methides" // IXth Joint Meeting in Medicinal Chemistry, Atena, lipanj 2015 (predavanje).

 

Diploma thesis:

Z. Spahić: "Synthesis and photochemistry of alanine and 3-(N-phtalidimo)adamantane carboxylic acide dipeptide", BsC thesis, Faculty of Science, University of Zagreb, 10. 09. 2015.

L. Uzelac: "Učinak novosintetiziranih policikličkih i makrocikličkih spojeva na tumorske i tumorske matične stanice čovjeka", PhD thesis, Faculty of Science, University of Zagreb, 30.01. 2017.

K. Becker: "SINTEZA I FOTOKEMIJA ADAMANTIL-FENIL-DIAZOMETANA", BsC thesis, Faculty of Science, University of Zagreb, 21.01. 2019

L. Mandić:"FOTOKEMIJSKA DEKARBOKSILACIJA FTALIMIDNIH DERIVATA", PhD thesis, Faculty of Science, University of Zagreb, 21.12. 2018.

M. Sambol: "PRIPRAVA KINON-METIDA I ISPITIVANJE NJIHOVOG BIOLOŠKOG UČINKA" PhD thesis, Faculty of Science, University of Zagreb, 19.12. 2018.

Mandić, Leo.
 FOTOKEMIJSKA DEKARBOKSILACIJA FTALIMIDNIH DERIVATA / PhD thesis, Faculty of Science, University of Zagreb, 21.12. 2018.

Other associates

PhD Kata Majerski

PhD Marija Alešković

PhD Tatjana Šumanovac Ramljak

PhD Margareta Sohora

PhD Marina Šekutor (2015-2018)

PhD Vesna Blažek Bregović (2015-2017)

PhD Đani Škalamera

Mag. appl. chem. Leo Mandić

Mag. pharm. Matej Cindrić (2016-2017)

Mag. appl. chem. Antonija Husak

PhD Ivana Antol

PhD Lidija Uzelac

PhD Iva Džeba

Mag.Chem. Matija Sambol

Mag. chem. Katarina Zlatić (2018- )

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