damjan makuc

Damjan Makuc

Ph.D.

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damjan.makuc@ki.si

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(01) 47-60-308

Damjan Makuc was born on June 17, 1978, in Ljubljana, Slovenia. He received his B.Sc. degree in biochemistry at University of Ljubljana, Faculty of Chemistry and Chemical Technology in 2003. He has been working at the Slovenian NMR Centre, National Institute of Chemistry (Ljubljana) since 2004. There he acquired skills in studies of structural and conformational properties of small organic molecules by the use of NMR spectroscopy. In 2010, he joined EN-FIST Centre of Excellence (while still partly employed at National Institute of Chemistry). His scientific work at CO EN-FIST included structural studies of complex compounds in solution, intermolecular interactions and dynamic equilibria via NMR spectroscopy. He received his D.Sc. in chemistry at University of Ljubljana in 2011. He got Krka’s prize for his Ph.D. thesis. Scientifically, he has been involved in various aspects of NMR spectroscopy of small organic molecules. During his Ph.D. work and after he has focused on studies of conformational preferences of anion receptors, determination of anion-receptor interactions as well as studies of transport properties of receptors through membranes. He won the Best Poster award at international NMR conference SMASH 2010. Dr. Makuc is a co-author of 25 publications published in scientific journals and was co-organizer of several scientific meetings.

Research Interests:

• Structural elucidation and conformational studies of small organic compounds
• Studies of intermolecular interactions (e.g. hydrogen bonds) and dynamic equilibria (e.g. tautomers) in solution
• Studies of transport properties of anion receptors

SELECTED PUBLICATIONS

1

N. Busschaert, L. E. Karagiannidis, M. Wenzel, C. J. E. Haynes, N. J. Wells, P. G. Young, D. Makuc, J. Plavec, K. A. Joliffe, P. A. Gale
Synthetic transporters for sulfate: a new method for the direct detection of lipid bilayer sulfate transport
Chem. Sci. 2014, 5 (3), 1118-1127.
Web access at RSC Publishing

2

K. N. Farrugia, D. Makuc, A. Podborska, K. Szaciłowski, J. Plavec and D. C. Magri
UV-visible and 1H-15N NMR Spectroscopic Studies of Colorimetric Thiosemicarbazide Anion Sensors
Org. Biomol. Chem. 2015, 13(6), 1662-1672.
Web access at RSC Publishing

3

D. Makuc, J. Fabris, Z. Casar and J. Plavec
Conformational Analysis of Geometric Isomers of Pitavastatin Together With Their Lactonized Analogues
Molecules 2013, 18 (11), 13283-13296.
Web access at MDPI

4

D. Makuc, Triyanti, M. Albrecht, J. Plavec, K. Rissanen, A. Valkonen and C. A. Schalley
The Halide Binding Behavior of 2-Carbamoyl-7-ureido-1H-indoles: Conformational Aspects
Eur. J. Org. Chem. 2009, (28), 4854-4866.

5

D. Makuc, M. Lenarcic, G. W. Bates, P. A. Gale and J. Plavec
Anion-induced conformational changes in 2,7-disubstituted indole-based receptors
Org. Biomol. Chem. 2009, 7 (17), 3505-3511.

LIST OF PUBLICATIONS

2018

32

B. Murovec, D. Makuc, S. Kolbl Repinc, Z. Prevorsek, D. Zavec, R. Sket, K. Pecnik, J. Plavec and B. Stres
1H NMR metabolomics of microbial metabolites in the four MW agricultural biogas plant reactors: A case study of inhibition mirroring the acute rumen acidosis symptoms
J. Environ. Manage. 2018, 222, 428-435.
Web access at Science Direct

31

R. Sket, T. Debevec, S. Kublik, M. Schloter, A. Schoeller, B. Murovec, K.F. Mikus, D. Makuc, K. Pecnik, J. Plavec, I.B. Mekjavic, O. Eiken, Z. Prevorsek and B. Stres
Intestinal metagenomes and metabolomes in healthy young males: Inactivity and hypoxia generated negative physiological symptoms precede microbial dysbiosis
Front. Physiol. 2018, 9, article number: 198.
Web access at Frontiers media

30

I. S. Ozdemir, C. Dag, D. Makuc, E. Ertas, J. Plavec and S. Bekiroglu
Characterisation of the Turkish and Slovenian extra virgin olive oils by chemometric analysis of the presaturation 1H NMR spectra
LWT-Food Sci. Technol. 2018, 92, 10-15.
Web access at Science Direct

29

A. Bistrovic, P. Grbcic, A. Harej, M. Sedic, S. Kraljevic Pavelic, S. Kostrun, J. Plavec, D. Makuc and S. Raic-Malic
Small molecule purine and pseudopurine derivatives: synthesis, cytostatic evaluations and investigation of growth inhibitory effect in non-small cell lung cancer A549
J. Enzyme Inhib. Med. Chem. 2018, 33 (1), 271-285.
Web access at Taylor and Francis Online

2017

28

M. A. Cardona, D. Makuc, K. Szaciłowski, J. Plavec and D. C. Magri
Water-Soluble Colorimetric Amino[bis(ethanesulfonate)] Azobenzene pH Indicators: A UV–Vis Absorption, DFT, and 1H-15N NMR Spectroscopy Study
ACS Omega 2017, 2 (9), 6159–6166.
Web access at ACS Publication

2016

27

R. Schwarzlin, N. Pusenjak, D. Makuc, M. Krizman, I. Vovk, J. Plavec and U. Svajger
Synergistic complex from plants Solanaceae exhibits cytotoxicity for the human hepatocellular carcinoma cell line HepG2
BMC Complementary and Alternative Medicine 2016, 16:395.
Web access at Biomed Central

26

K. N. Farrugia, D. Makuc, A. Podborska, K. Szacilowski, J. Plavec and D. C. Magri
Colorimetric Naphthalene-based Thiosemicarbazide Anion Chemosensors with an Internal Charge Transfer Mechanism
Eur. J. Org. Chem. 2016, (25), 4415-4422.
Web access at Wiley Online Library

25

I. Crnolatac, I. Rogan, B. Majic, S. Tomic, T. Deligeorgiev, G. Horvat, D. Makuc, J. Plavec, G. Pescitelli and I. Piantanida
Small molecule probes finely differentiate between various ds- and ss-DNA and RNA by fluorescence, CD and NMR response
Anal. Chim. Acta 2016, 940, 128-135.
Web access at Science Direct

24

D. Makuc, T. Merckx, W. Dehaen and J. Plavec
Conformational NMR Study of Bistriazolyl Anion Receptors
Acta Chim. Slov. 2016, 63(3), 484-488.
Web access at Acta Chimica Slovenica

23

E. Kranjc, A. Albreht, I. Vovk, D. Makuc and J. Plavec
Non-targeted chromatographic analyses of cuticular wax flavonoids from Physalis alkekengi L.
J. Chromatogr. A 2016, 1437, 95-106.
Web access at ScienceDirect.

2015

22

M. Stipković Babić, D. Makuc, J. Plavec, T. Martinović, S. Kraljević Pavelić, K. Pavelić, R. Snoeck, G. Andrei, D. Schols, K. Wittine and M. Mintas
Novel halogenated 3-deazapurine, 7-deazapurine and alkylated 9-deazapurine derivatives of L-ascorbic or imino-L-ascorbic acid: Synthesis, antitumour and antiviral activity evaluations
Eur. J. Med. Chem. 2015, 102, 288-302.
Web access at ScienceDirect

21

S. Kristafor, A. Bistrovic, J. Plavec, D. Makuc, T, Martinovic, S. Kraljevic Pavelic and S. Raic-Malic
One-pot click synthesis of 1,2,3-triazole-embedded unsaturated uracil derivatives and hybrids of 1,5- and 2,5-disubstituted tetrazoles and pyrimidines
Tetrahedron Lett. 2015, 56 (10), 1222-1228.
Web access at ScienceDirect.

20

K. N. Farrugia, D. Makuc, A. Podborska, K. Szaciłowski, J. Plavec and D. C. Magri
UV-visible and 1H-15N NMR Spectroscopic Studies of Colorimetric Thiosemicarbazide Anion Sensors
Org. Biomol. Chem. 2015, 13(6), 1662-1672.
Web access at RSC Publishing

2014

19

N. Busschaert, L. E. Karagiannidis, M. Wenzel, C. J. E. Haynes, N. J. Wells, P. G. Young, D. Makuc, J. Plavec, K. A. Joliffe, P. A. Gale
Synthetic transporters for sulfate: a new method for the direct detection of lipid bilayer sulfate transport
Chem. Sci. 2014, 5 (3), 1118-1127.
Web access at RSC Publishing

2013

18

K. Wittine, K. Poljak, M. Kovac, D. Makuc, J. Plavec, J. Balzarini, T. Martinovic, S. Kraljević Pavelic, K. Pavelic and M. Mintas
The Novel [4,5-e][1,3]Diazepine-4,8-dione and Acyclic Carbamoyl Imino-Ureido Derivatives of Imidazole: Synthesis, Anti-Viral and Anti-Tumor Activity Evaluations
Molecules 2013, 18 (11), 13385-13397.
Web access at MDPI

17

D. Makuc, J. Fabris, Z. Casar and J. Plavec
Conformational Analysis of Geometric Isomers of Pitavastatin Together With Their Lactonized Analogues
Molecules 2013, 18 (11), 13283-13296.
Web access at MDPI

16

J. Fabris, D. Makuc, Z. Časar and J. Plavec
Conformational Analysis of E/Z-isomeric Pairs of Rosuvastatin and Its Lactonized Analogues
Tetrahedron 2013, 69 (30), 6262-6268.
Web access at ScienceDirect

15

A. Mescic, D. Glavac, A. Osmanovic, D. Zavrsnik, M. Cetina, D. Makuc, J. Plavec, S. M. Ametamey and S. Raic-Malic
N-alkylated and O-alkylated Regioisomers of 5-(Hydroxyalkyl)pyrimidines: Synthesis, Structural and Conformational Study
J. Mol. Struct. 2013, 1039, 160-166.
Web access at ScienceDirect

2012

14

K. Wittine, M. Stipković Babić, D. Makuc, J. Plavec, S. Kraljević Pavelić, M. Sedić, Krešimir Pavelić, P. Leyssen, J. Neyts and Mladen Mintas
Novel 1,2,4-Triazole and Imidazole Derivatives of L-Ascorbic and Imino-Ascorbic Acid: Synthesis, Anti-HCV and Antitumor Activity Evaluations
Bioorg. Med. Chem. 2012, 20 (11), 3675-3685.
Web access at ScienceDirect

2011

13

D. Makuc, J. R. Hiscock, M. E. Light, P. A. Gale and J. Plavec
NMR studies of anion-induced conformational changes in diindolylureas and diindolylthioureas
Beilstein J. Org. Chem. 2011, 7, 1205–1214.
Web access at Beilstein Journals

12

D. Završnik, S. Muratovic, D. Makuc, J. Plavec, M. Cetina, A. Nagl, E. De Clercq, J. Balzarini and M. Mintas
Benzylidene-bis-(4-Hydroxycoumarine) and Benzopyranocoumarine Derivatives: Synthesis, 1H/13C NMR Conformational and X-ray Crystal Structure Studies and in vitro Antiviral Activity Evaluations
Molecules 2011, 16 (7), 6023-6040.
Open access at MDPI

11

T. Gazivoda Kraljevic, M. Petrovic, S. Kristafor, D. Makuc, J. Plavec, T. L. Ross, S. M. Ametamey and S. Raic-Malic
Methoxymethyl (MOM) group nitrogen protection of pyrimidines bearing C-6 acyclic side-chains
Molecules 2011, 16 (6), 5113-5129.
Open access at MDPI

10

M. Sala, D. Makuc, J. Kolar, J. Plavec and B. Pihlar
Potentiometric and 31P NMR studies on inositol phosphates and their interaction with iron(III) ions
Carbohydr. Res. 2011, 346 (4), 488-494.
Web access at ScienceDirect

2010

9

D. Makuc, M. Albrecht and J. Plavec
Conformational changes of functionalised indole receptors upon their interaction with anions
Supramol. Chem., 2010, 22 (10), 603-611.
Web access at informaworld

2009

8

S. Kristafor, T. Gazivoda Kraljevic, D. Makuc, J. Plavec, L. Suman, M. Kralj and S. Raic-Malic
Synthesis, Structural Studies and Antitumoral Evaluation of C-6 Alkyl and Alkenyl Side Chain Pyrimidine Derivatives
Molecules 2009, 14 (12), 4866-4879.

7

D. Makuc, Triyanti, M. Albrecht, J. Plavec, K. Rissanen, A. Valkonen and C. A. Schalley
The Halide Binding Behavior of 2-Carbamoyl-7-ureido-1H-indoles: Conformational Aspects
Eur. J. Org. Chem. 2009, (28), 4854-4866.

6

D. Makuc, M. Lenarcic, G. W. Bates, P. A. Gale and J. Plavec
Anion-induced conformational changes in 2,7-disubstituted indole-based receptors
Org. Biomol. Chem. 2009, 7 (17), 3505-3511.

5

S. Kristafor, T. Gazivoda, M. Cetina, D. Makuc, J. Plavec and S. Raic-Malic
Synthesis and structural characterization of the C-6 fluoroalkylated pyrimidine derivatives
J. Mol. Struct. 2009, 923 (1-3), 19-23.

2008

4

T. Gazivoda, S. Raic-Malic, V. Kristafor, D. Makuc, J. Plavec, S. Bratulic, S. Kraljevic-Pavelic, K. Pavelic, L. Naesens, G. Andrei, R. Snoeck, J. Balzarini and M. Mintas
Synthesis, cytostatic and anti-HIV evaluations of the new unsaturated acyclic C-5 pyrimidine nucleoside analogues
Bioorg. & Med. Chem. 2008, 16, 5624-5634.

2007

3

S. Prekupec, D. Makuc, J. Plavec , L. Suman, M. Kralj, K. Pavelic, J. Balzarini, E. de Clercq, M. Mintas and S. Raic-Malic
Novel C-6 Fluorinated Acyclic Side Chain Pyrimidine Derivatives: Synthesis, 1H and 13C NMR Conformational Studies, Antiviral and Cytostatic Evaluations
J. Med. Chem. 2007, 50 (13), 3037-3045.

2006

2

T. Gazivoda, K. Wittine, I. Lovric, D. Makuc, J. Plavec, M. Cetina, D. Mrvos-Sermek, L. Suman, M. Kralj, K. Pavelic, M. Mintas and S. Raic-Malic
Synthesis, structural studies, and cytostatic evaluation of 5,6-di-O-modified L-ascorbic acid derivatives
Carbohydr. Res. 2006, 341 (4), 433-442.

2005

1

S. Prekupec, D. Makuc, J. Plavec, S. Kraljevic, M. Kralj, K. Pavelic, G. Andrei, R. Snoeck, J. Balzarini, E. De Clercq, S. Raic-Malic and M. Mintas
Antiviral and cytostatic evaluation of the novel 6-acyclic chain substituted thymine derivatives
Antiviral Chemistry and Chemotherapy 2005, 16, 327-338.