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Volume 3 | Edition 1 | October 2015<br />


EPSA Students' Science Publication<br />

Dear friends,<br />


Another year has passed and it is time for the first edition of the EPSA Students'<br />

Science Publication (ESSP) of this academic year. The ESSP is a project that<br />

allows pharmacy students from around the Europe to publish their scientific<br />

research and outcomes. All of their abstracts are professionally reviewed by the<br />

European Federation for Pharmaceutical Sciences (EUFEPS). The project thus<br />

allows the students insight in the process of writing and publishing abstracts<br />

and, by extension, scientific articles. Every student also has the opportunity to<br />

present themselves and their motivation for conducting the research. Hopefully<br />

reading this edition inspires more students to firstly, try your hand at research<br />

and secondly, write and submit an abstract.<br />

This edition contains four different abstract, covering various topics. You will<br />

learn more about 'Biomedical Potential of Stevia - Stevia rebaudiana (Bert.)<br />

Bertoni', 'Celebrating One Century and Thinking About the Future: Preliminary<br />

Findings for a New MPharm Syllabus at Lisbon Faculty of Pharmacy', 'Synthesis<br />

of a Novel 14-membered Oxo-thia-aza Macrocyclic Compound' and 'The<br />

Influence of Acute Pain on Osmotic Pressure and Cortisol Concentration in<br />

Tears'.<br />

I would like to thank EUFEPS and the EPSA Public Relations Department for<br />

their hard work on this edition and all the students who collaborated on it. This<br />

would not have been possible without all of you.<br />

Looking forward to the future editions!<br />

Eva Shannon Schiffrer, Science Coordinator 2015-2016<br />



Volume 3 | Edition 1 | October 2015<br />

Synthesis of a novel 14-membered oxo-thia-aza macrocyclic compound<br />

Abstract ........................................................................................................... 4<br />

Q&A of the author ............................................................................................ 5<br />

Biomedical potential of Stevia - Stevia rebaudiana (Bert.) Bertoni<br />

Abstract ........................................................................................................... 6<br />

Q&A of the author ............................................................................................ 7<br />

Celebrating one century and thinking about the future: preliminary<br />

findings for a new MPharm syllabus at Lisbon Faculty of Pharmacy<br />

Abstract ........................................................................................................... 8<br />

Q&A of the author ............................................................................................ 9<br />

The influence of acute pain on osmotic pressure and cortisol<br />

concentration in tears<br />

Abstract ......................................................................................................... 10<br />

Q&A of the author .......................................................................................... 11<br />

European Federation for Pharmaceutical Sciences (EUFEPS)<br />

Information .................................................................................................... 12<br />

Upcoming conferences ................................................................................. 13<br />


EPSA Students' Science Publication<br />



João Franco Machado, Judite Costa, Maria F. Cabral<br />

Research Institute for Medicines (iMed.ULisboa), Faculty of Pharmacy, Universidade<br />

de Lisboa, Av. Professor Gama Pinto, 1649-003 Lisbon – Portugal<br />

Background: Macrocyclic compounds have been targets of a widespread<br />

interest in the last decade due to their similarity to the countless analogue<br />

scaffolds found in a variety of biological systems. The unique structural, kinetic<br />

and thermodynamic features of macrocycles, as well as their favourable druglike<br />

properties, have provided a motivation for further study and has had an<br />

enormous impact on the fields of medicine, pharmacy, chemistry and biology.<br />

However, this type of molecule is yet under-exploited as new, effective drugs<br />

and research continues to be fairly limited.<br />

Objective: Following our previous studies, we report the design, synthesis and<br />

structural characterization of a novel oxo-thia-aza macrocyclic compound, the<br />

dioxo-[14]aneN 3<br />

S (1-thia-4,8,12-triazacyclotetradecane-3,13-dione).<br />

Materials and Methods: Dioxo-[14]aneN 3<br />

S was synthesised by reacting<br />

dimethyl thiodiglycolate, previously obtained by Fischer-Speier esterification<br />

technique (η = 89.6 %), with dipropylenetriamine in a large excess of dry<br />

methanol at 40 ºC, under nitrogen atmosphere for 9 days. This procedure<br />

was based on the Tabushi methodology for macrocyclization, which consists<br />

of the condensation of the dimethyl ester of an α,ω-dicarboxylic acid with<br />

a commercially available polyethylenepolyamine. The pure product was<br />

then structurally characterized by infrared and nuclear magnetic resonance<br />

(1H, 13C, COSY, NOESY, HSQC, HMBC) spectroscopies and also by mass<br />

spectrometry.<br />

Results and Conclusion: The improvements in the reaction conditions<br />

introduced to the Tabushi general method (controlled temperature, N 2<br />

atmosphere, increased reaction time, and use of a dry solvent in a large excess)<br />

contributed to achieving - after purification by column chromatography - the<br />

desired macrocycle with a very high yield (η = 76.8 %), compared to the related<br />

compounds synthesised by Tabushi methodology reported in literature (η = 10<br />

~ 20 %). The spectroscopic and spectrometric analyses of dioxo-[14]aneN 3<br />

S<br />

allowed to confirm its chemical structure as well prove its high level of purity.<br />



General information about João Franco Machado<br />

22 years old, Sintra, Portugal, Faculty of Pharmacy,<br />

University of Lisbon, joaomachado@campus.ul.pt<br />

Volume 3 | Edition 1 | October 2015<br />

Why did you select this topic for your research?<br />

I am a trainee volunteer at the Research Institute for<br />

Medicines, where I have been developing a research<br />

work in the field of coordination chemistry of macrocyclic<br />

compounds through three years. During this time, I found<br />

out that macrocyclic ligands have a great potential to be<br />

developed as very promising therapeutic agents due to<br />

their unique physicochemical proprieties and also to their range on medical<br />

applications, which had motivated me to design and study novel and effective<br />

macrocycles.<br />

How do you feel about having coped with the challenges that research brings?<br />

When I started the research project that I am now reporting, I already had a<br />

considerable amount of experience which turned out to facilitate my research<br />

work. However, each project is a completely new challenge, because when<br />

we are designing a novel macrocycle, it is possible to figure out that we can’t<br />

properly synthesise it or that it doesn´t show the proprieties we are expecting.<br />

But at the end, and despite all difficulties we can face, the feeling of getting a<br />

novel and promising pharmaceutical compound is very enthusiastic!<br />

What skills did you develop as a researcher during your research period?<br />

During my research period I have not only improved my knowledge in the<br />

different fields of chemistry, but I also developed a set of valuable skills,<br />

such as patience, perseverance, dedication, hardworking, time management,<br />

adaptability, improvising, and critical thinking.<br />

Would you like to share anything else with the students in Europe? Any<br />

recommendations?<br />

The most important advice I can give is to never give up, even if some of<br />

your objectives seem to be quite unlikely to accomplish. Remember that the<br />

dedication leads to the success and at the end, you will experience the most<br />

rewarding feeling you can’t even imagine!<br />


EPSA Students' Science Publication<br />



Ana Begić and Josip Barilar,<br />

Faculty of Pharmacy and Biochemistry, Zagreb, Croatia<br />

Introduction: Stevia rebaudiana (Bert.) Bertoni (stevia) is a native plant to South<br />

America that is spread worldwide by cultivation due to its use as a natural<br />

sweetener, which is linked to the content of steviol glycoside. In this study,<br />

for the first time in Croatia, pharmacobotanical, phytochemical and biological<br />

studies of stevia were conducted, in order to evaluate its potential biomedical<br />

application possibilities in prevention and treatment.<br />

Aim: The aim of this study was to evaluate micromorphological and anatomical<br />

characteristics of the leaves and young stems, phytochemical composition,<br />

antioxidant effect, reducing power and total antioxidant capacity, ability to<br />

inhibit acetylcholinesterase and inhibitory effect on Src tyrosine kinase.<br />

Materials and Methods: The plant material - Stevia rebaudiana (Bert.) Bertoni<br />

was cultivated in Croatia and collected in August 2012, just before flowering,<br />

and air-dried at room temperature. Identification of plant material was<br />

carried out at the Department of Pharmacognosy, Faculty of Pharmacy and<br />

Biochemistry. The presence of flavonoids, phenolic acids, tannins, saponins,<br />

triterpenoids, sterols and essential oils were detected in methanolic leaf extract<br />

by thin layer chromatography. Contents of total polyphenols, tannins, flavonoids<br />

and phenolic acids in stevia leaves were determined spectrophotometrically.<br />

Antioxidant activities of ethanolic leaf extract were examined by different<br />

spectrophotometric methods in comparison with polyphenolic components and<br />

trolox as a reference. Effect of stevia and its individual bioactive components<br />

on Src tyrosine kinase was investigated by appropriate in vitro assay and<br />

compared with staurosporine.<br />

Results and Conclusion: Our results showed strong antioxidant potential<br />

of stevia, mostly attributed to the phenolic compounds contained.<br />

Acetylcholinesterase (AChE) inhibitory activity of ethanolic leaf extract was<br />

evaluated in comparison with chlorogenic acid and galantamine as a reference.<br />

Stevia showed ability to inhibit AChE exceeding a 50% effect at 1000 μg/mL. It<br />

was also found that chlorogenic acid contributes significantly to its anti-AChE<br />

activity. This research showed that stevia leaves contain a significant amount of<br />

various bioactive components which demonstrated strong antioxidant activity<br />

and ability to inhibit acetylcholinesterase and Src tyrosine kinase. Obtained<br />

results suggested a great potential of stevia in prevention and treatment of<br />

various diseases and that is not just a plant that serves as means of sweetening<br />

food and pharmaceutical products.<br />



General information about Ana Begić and Josip<br />

Barilar<br />

Both 25 years, Zagreb, Croatia, ana.<br />

begich@gmail.com, josip.barilar@gmail.com,<br />

University of Zagreb, Faculty of Pharmacy and<br />

Biochemistry<br />

Volume 3 | Edition 1 | October 2015<br />

Why did you select this topic for your research?<br />

The stevia plant caught our attention when we<br />

realized that it has other beneficial biomedical<br />

properties besides being only a natural<br />

sweetener. As the population was using it more in the food industry, we wanted<br />

to prove that stevia also has a potential of prevention and treatment of various<br />

diseases.<br />

How do you feel about having coped with the challenges that research brings?<br />

During a student research, confrontation with different challenges and problems<br />

are fairly common.<br />

One should always try to approach difficulties rationally and try to use different<br />

methods and procedures to minimize the risk of getting bad results. Critical<br />

thinking in the process of research is crucial.<br />

What skills did you develop as a researcher during your research period?<br />

During our research period we've learned to be more tolerant and more<br />

respective of people who dedicate their lives to science. We've also learned<br />

that a round bottom flask should not be placed on a flat surface, because you<br />

will lose the material you've been working on for weeks.<br />

Would you like to share anything else with the students in Europe? Any<br />

recommendations?<br />

We'd like to advise them not to stick their heads in books and blindly believe<br />

what is written. In order to become a successful scientist it is of great importance<br />

to develop creativity because creativity is, along with knowledge, a core to<br />

scientific endeavour.<br />


EPSA Students' Science Publication<br />




Madalena Plácido, Joana Catarino, Diogo Raimundo and Diana Ferreira<br />

Faculty of Pharmacy of the University of Lisbon, Lisbon, Portugal<br />

Supervisors: Afonso Cavaco, Maria Henriques and Andreia Bruno<br />

Others that contributed to the abstract: Diogo Simões and Francisca Lopes<br />

Introduction: The current curriculum of the Master degree in Pharmacy<br />

(MPharm) of the University of Lisbon is under an accreditation process during<br />

2015. Induced by this evaluation, the Committee for the Centennial Celebrations<br />

of the Students’ Association (CENTAEFFUL) aimed to collect input from<br />

several parties involved in pharmacy education that could contribute to the<br />

improvement of the syllabus towards pharmacy labour opportunities.<br />

Methodology: The research project was divided into three phases. Phase<br />

one consisted of two focus groups, with six pharmaceutical professionals in<br />

each. The second phase was an online survey answered by a national sample<br />

of pharmacy students and pharmacists. The answers were collected through<br />

open and closed questions, including Likert scales to measure the agreement<br />

with sentences stated by professionals from the focus groups. The third<br />

phase was comprised of the presentation and discussion of the survey results<br />

at an Educational Forum (EF). The EF consisted of a two day debate using<br />

an amplification of survey results fed by live presentations of five experts in<br />

educational matters. The actual EF conclusions were accomplished through<br />

small group discussions between pharmacists, students and professors,<br />

complemented by a plenary session opened to the public.<br />

Results: The need to include internships within the first four years of the degree<br />

was mentioned in the focus groups. It was mentioned that having practitioners<br />

outside the university teaching some classes would be beneficial for students.<br />

Concerning the online survey, there were 473 answers. The majority of the<br />

respondents (51.8%) either ‘agreed’ or ‘strongly agreed’ that the current<br />

MPharm curriculum is not completely adapted to practice. Moreover, 77.8%<br />

strongly ‘agreed’ that students would benefit from internships within the first<br />

four years of the degree. EF conclusions supported the opinions previously<br />

mentioned and reinforced the need to introduce new mandatory subjects, such<br />

as non-prescription medicines pharmacotherapy, clinical trials and seminars<br />

about soft-skills. Introducing one more optional subject and increasing the use<br />

of real case studies during classes was also suggested.<br />

Conclusions: Most participants agreed with the need to adapt MPharm to<br />

the competencies required in the pharmaceutical labour market. Throughout<br />

the project several suggestions were able to be collected, which then were<br />

submitted to the Scientific Council, in order to support the changes that needed<br />

to be reflected for the proposal to be submitted for accreditation.<br />

Acknowledges: We would like to acknowledge the Pedagogical Council,<br />

the local and national Students’ Association (AEFFUL and APEF) and all<br />

professionals and students that contributed to this project. We are also grateful<br />

for the support of Merck Sharp & Dohme Portugal.

General information about Madalena<br />

Plácido<br />

During 2014 a Committee for the<br />

Centennial Celebrations of the<br />

Students’ Association (CENTAEFFUL)<br />

was formed. This Committee aimed<br />

to analyse all Students’ Association<br />

journey: its past, present and future<br />

challenges. Focused on a more<br />

educational and scientific aspect, a<br />

Bureau for Education was born.<br />


Volume 3 | Edition 1 | October 2015<br />

Why did you select this topic for your research?<br />

The current curriculum of the Master degree in Pharmacy (MPharm) of<br />

the University of Lisbon is under an accreditation process during 2015. As<br />

members of Bureau for Education we wanted to take this opportunity to analyze<br />

the adequacy of the MPharm syllabus to the labor market through pharmacy<br />

students and professionals’ eyes.<br />

How do you feel about having coped with the challenges that research brings?<br />

The main challenge was to define the right modus operandi for our research.<br />

Luckily we benefited from the help of professionals and faculty professors, to<br />

whom we are deeply grateful. Another challenge was the gap between academy<br />

and practice, which we tried to shorten through this investigation work.<br />

What skills did you develop as a researcher during your research period?<br />

This kind of research allowed us to develop our critical thinking and data<br />

analysis abilities. We also improved our communication and organizational<br />

skills. Moreover, our awareness about the current MPharm syllabus and the<br />

labor market needs also increased.<br />

Would you like to share anything else with the students in Europe? Any<br />

recommendations?<br />

Research is not only discovering new drugs or a cure for a disease. If you<br />

believe that you can make a difference in your own university, go ahead!<br />

Understand the opinion of professionals from different areas, professors and<br />

your colleagues. Certainly you will learn something new and contribute to<br />

improve your university.<br />


EPSA Students' Science Publication<br />



Maja Lukić and Matea Ćurčić,<br />

Faculty of Pharmacy and Medical Biochemistry, University of Zagreb, Croatia<br />

Introduction: Tears are far more than just a fluid on the surface of our eyes.<br />

Consisting of three distinct layers, they are essential for eye protection,<br />

lubrication and nourishment as well as maintaining health of the eyes and<br />

optical function of their surface and for providing clear vision. Furthermore, tears<br />

prevent eye infections by continually removing foreign matter thus, keeping the<br />

surface of the eyes smooth and clear. Tear production is controlled both by the<br />

central and autonomic nervous system. While basal tears’ production is under<br />

control of the accessory lacrimal glands, reflex lacrimation is mediated by the<br />

neural reflex arc that stimulates the secretion of the main lacrimal glands. Pain<br />

causes stress to the organism and therefore, production of stress mediators<br />

is stimulated. Cortisol is, along with DHEA, adrenalin and noradrenalin, one of<br />

the four main stress mediators. Although the origin of cortisol in tears is not<br />

known yet, it is assumed it might derive from the lacrimal gland. The final result<br />

of the dynamic changes of the lacrimal fluid is determined by measuring the<br />

osmolarity of the lacrimal fluid.<br />

Aim: In this study, the applicability of tears in the diagnostics of acute stress<br />

was evaluated. The main objectives of the study were to evaluate cortisol values<br />

and osmotic concentration in tears before and after stimulus and whether a<br />

consistent answer to stress could be diagnosed in tears.<br />

Materials and Methods: The study included 18 volunteers (10 women and 8<br />

men) whose tears were collected and analysed at the Clinical Hospital Center<br />

'Sestre Milosrdnice'. The tear samples were collected before and after nasal<br />

hair trimming. The concentration of cortisol was measured using ELISA whilst<br />

osmometry was used as a method to determine the osmolar concentration.<br />

Results and Conclusion: Basal cortisol values in men showed good correlation<br />

with osmolarity in tears. After acute stress, this correlation was lost, which<br />

can be due to the higher sensitivity to pain in males. After stimulus, cortisol<br />

and osmolar concentration decreased due to the dilution caused by tear<br />

production. Osmolarity and cortisol showed a moderate correlation before the<br />

painful stimulus, which is completely lost after the stimulus. Pain stimulus at<br />

the root hairs activates the sympathetic nervous system and its possible effect<br />

on the secretion of glands.<br />



General information about Maja Lukić<br />

27 years old, Osijek, Republic of Croatia<br />

E-mail: maja__lukic@hotmail.com<br />

The faculty of Pharmacy and Medical Biochemistry<br />

(Graduated 2015), University of Zagreb<br />

Why did you select this topic for your research?<br />

The idea of the topic came spontaneously but from the<br />

very beginning Matea and I knew we wanted to conduct<br />

an investigation on tears, as they as a sample are rarely<br />

used in clinical practice.<br />

Volume 3 | Edition 1 | October 2015<br />

How do you feel about having coped with the challenges that research brings?<br />

From the very beginning, there were a lot of challenging aspects of our<br />

investigation. Firstly, tears collection and limited sample volume, as well as<br />

analyte measurement in a low concentration range. Moreover, there was no<br />

available literature on studies of human tears. Despite all, we did not give up<br />

and succedeed in obtaining our results.<br />

What skills did you develop as a researcher during your research period?<br />

Above all, patience, organizational skills, accuracy and punctuality.<br />

Would you like to share anything else with the students in Europe? Any<br />

recommendations?<br />

I strongly recommend conducting an investigation during their studies. In<br />

this way, you can gain great experience in the field of your study and through<br />

cooperation with your colleagues, gain new friends.<br />


EPSA Students' Science Publication<br />



The European Federation for Pharmaceutical Sciences is a voluntary federation<br />

of national associations and societies of pharmaceutical scientists, established<br />

in 1991 to advance research in the pharmaceutical sciences in Europe.<br />

This can be achieved by promoting cooperation between national, regional<br />

and European societies or associations which aim at the advancement of<br />

pharmaceutical sciences, and by promoting cooperation between and with<br />

other pharmaceutical organisations and between individual pharmaceutical<br />

scientists.<br />

The Mission<br />

EUFEPS exists to help to meet the challenges and seize the opportunities<br />

created by the consolidations occurring both within Europe and globally,<br />

driven on by a combination of rapid advances in science and technology,<br />

economic pressures, and by political will. Within this frame, EUFEPS’s mission<br />

is to advance sciences for better medicines and health and serving the<br />

pharmaceutical sciences and innovative drug research in Europe. Spearheading<br />

a number of initiatives, EUFEPS works with its membership, throughout many<br />

nations in Europe.<br />

European Dimension<br />

EUFEPS is unique being the only pan-European organisation that represents,<br />

under one umbrella, all the pharmaceutical sciences and pharmaceutical<br />

scientists engaged in drug research and development, drug regulation and drug<br />

policy making. The existence of such an umbrella platform facilitates the highly<br />

innovative, integrative and interdisciplinary approaches that are essential if we,<br />

in Europe, are to deliver to our citizens safe, effective, economic and timely<br />

medicines. The ultimate benefits are an improving health, quality of life, and<br />

wealth of our continent.<br />

EUFEPS is recognised by the European Commission, as representing the<br />

integrative pharmaceutical sciences within Europe. EUEFPS is also recognised<br />

by the EMEA as a neutral scientific resource for independent opinions on draft<br />

regulatory guidelines, while EUFEPS works with other European organisations,<br />

such as EFPIA, to help identify and promote training to meet industrial<br />

needs. EUFEPS has the ambition to provide a forum for policy development<br />

in the pharmaceutical sciences, particularly in relations to the discovery and<br />

development of new drugs and their introduction into the market, but also as<br />

to medicines usage. This includes policies on and leadership development as<br />

to: research, education & training, profiling and regulatory affairs.<br />


Volume 3 | Edition 1 | October 2015<br />

In addition, EUFEPS plays an active and influential role also in the global arena.<br />

It is recognised by the USA FDA and it works actively with its sister organisation<br />

AAPS to develop co-sponsored meetings and workshops that run alternatively<br />

in Europe and the USA, and is developing links with Asian scientists. Through<br />

involvement with its Board of Pharmaceutical Sciences, EUFEPS is also<br />

working with FIP to advance the pharmaceutical sciences globally.<br />



8 th International Symposium on Microdialysis<br />

Preclinical, Clinical, Analytical<br />

25-27 May 2016, Uppsala, Sweden<br />

EUFEPS Annual Meeting 2016<br />

Clinical Outcome and Regulation of Advanced Drug Delivery Products<br />

13-15 June 2016, Istanbul, Turkey<br />

8 th Pan-European Science Conference on QbD and PAT Sciences<br />

Inventing Tomorrow’s Development and Manufacturing<br />

3-4 October 2016, Cork, Ireland<br />

2 nd Conference on the Global Bioequivalence Harmonisation Initiative<br />

Autumn 2016, Washington DC, United States of America<br />

For more information see conferences at: www.eufeps.org<br />


EPSA Students' Science Publication

Volume 3 | Edition 1 | October 2015<br />


Next to the EPSA Students' Science Publication (ESSP) that you are reading<br />

now, EPSA also offers two other projects in the field of Science: the Science<br />

Day and the Science Excursion.<br />

Science Day<br />

The Science Day is an annual<br />

educational event that takes place<br />

during the EPSA Annual Congress<br />

and is dedicated to students’<br />

scientific work. Participants are<br />

given the opportunity to present<br />

the scientific research they have<br />

conducted orally and through a<br />

poster exhibition. This year fourteen students in total participated in one or two<br />

parts of the event. A jury, consisting of the European Federation for Pharmaceutical<br />

Sciences, EUFEPS representative, a Pierre Fabre Lab. Representative<br />

and the EPSA Science Coordinator Successor, assessed the presentations.<br />

Since the competition this year was extremely tough, the jury agreed on two<br />

winners for the oral presentation.<br />

Science Excursion<br />

The idea of the Science<br />

Excursion is to bring students<br />

closer to science and to broaden<br />

the Congress experience to an<br />

interactive and local surrounding.<br />

It is a project that is planned to<br />

be held at all major EPSA events.<br />

The upcoming excursion will<br />

be held during the Autumn<br />

Assembly in the restored oldest pharmacy in the Santo Spirito Hospital in<br />

Malta. Participants will visit the pharmacy museum and witness a compounding<br />

demonstration.<br />


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