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Section of Medicinal Chemistry, Amsterdam Institute for Molecules, Medicines and Systems, VU University Amsterdam,
Amsterdam, The Netherlands
Department of Research and Theory in Education, VU University Amsterdam, Amsterdam, The Netherlands
S Supporting Information
*
ABSTRACT: Interactive teaching with larger groups of students can be a challenge, but the
use of mobile electronic devices by students (smartphones, tablets, laptops) can be used to
improve classroom interaction. We have examined several types of tasks that can be
electronically enacted in classes and practical courses using these devices: multiple choice
(MC) questions; open-ended questions; and 3D visualization of (bio)molecules and
complexes. We have introduced these tasks dynamically in several educational contexts in
our teaching programs. Specically, attention is paid to applying devices in introductory quizzes
at the start of a course, throughout lectures, and in practical courses. Each application has been
found by us to oer signicant merits in terms of connecting theory and practice, full formative
assessment (including an improvement in interactions of introverted students), monitoring
progress, engaging students early on in research, stimulating 3D molecular feeling, and
maintaining student attention. From the student perspective, evaluations revealed overall
positive feedback on several key aspects of our approaches. In all, we believe that this mutually
benecial way of teaching can be of broader application, also in nonchemistry-related curricula.
KEYWORDS: First-Year Undergraduate/General, High School/Introductory Chemistry, Second-Year Undergraduate,
Upper-Division Undergraduate, Internet/Web-Based Learning, Testing/Assessment, Medicinal Chemistry, Drugs/Pharmaceuticals,
Molecular Modeling
INTRODUCTION
Article
GLMol
Operating
system
Purpose
All (browserbased)
All (browserbased)
Android/iOS
MC/open-ended
questions
MC/open-ended
questions
3D visualization
Android
Android
Android
3D visualization
3D visualization
3D visualization
iOS
iOSc
iOSc
Windows/
Macintosh
Windows/
Macintosh
3D
3D
3D
3D
visualization
visualization
visualization
visualization
3D visualization
Database Source
PDB/Drugbank/
PubChemd
PDB/PubChem
PDB/PubChem
PDB/PubChem or
NCI/NIH resolver
PDB/PubChem
PDB/PubChem
PDB
PDB/PubChem or
NCI/NIH resolver
PDB/PubChem
the highest and disclose a basic tutorial for this app. For
laptops, Jmol10 has proven to be an ecient tool because it too
can handle small molecules and PDB structures. We refer to the
Supporting Information for more details on these key apps/
programs.
Article
3D Visualization
Article
Lectures
Article
guest complexation between ferrocene and cucurbit[7]uril.28 Figure S11 (Supporting Information) shows the
format of this question.
4. What is your hypothesis? concerning the mode of
action of cisplatin and referring to research in which a
crystal structure of a cisplatin-bound double-stranded
DNA decamer was reported (vide infra).29
Regularly, 3D visualization tasks were applied during lectures,
all accompanied by a task/question and tailored to the subject
at hand that day. In a sense, this is formative assessment
concerning 3D thinking. Here, we list a few exemplary tasks:
1. Are these two structures superimposable? For historical
reasons, the enantiomers of thalidomide are used for this
purpose ((R)- and (S)-2-(2,6-dioxopiperidin-3-yl)-1Hisoindole-1,3(2H)-dione). Students were asked to work
in pairs so as to be able to compare the involved
structures on two screens by rotating etc.
2. Is the orientation of the two phenyl rings in a biphenyl
unit parallel? The structures of the drugs losartan and
urbiprufen are used.
3. Find the hydrogen bonds concerning a small peptide
with alpha-helices. PDB structure 1IYT is used.30 The
format of this question is shown in Figure S12
(Supporting Information).
4. Find the hydrogen bonds concerning a pleated sheet.
PDB structure 1SA8 is used.31
5. Pinpoint the seven transmembrane helices in a G
protein-coupled receptor. PDB structure 3P0G is
used.32
6. Pinpoint the proposed halogen bond in a complex of a
protein and an iodine-containing ligand. PDB structure
2YJ8 is used.33
Open-ended questions were occasionally used in lectures. An
interesting protocol is one in which 3D visualization and openended questions are combined. Illustrative is a research-based
question concerning the drug cisplatin (vide supra). Students
were asked to work in pairs and compare, in 3D on their
devices, the crystal structures of two double-stranded DNA
decamers, one without bound cisplatin (PDB 309D)34 and one
with bound cisplatin (PDB 1A2E).29 Figures 3A3C show
screen captures of the latter on devices common among
students. An accompanying research-oriented question on the
mode of action of cisplatin (What is your hypothesis?) was
answered in class as an open-ended question on their devices.
Plenary feedback was then given, and the spreadsheet gave a
broad overview of thoughts afterward. Figure S13 (Supporting
Information) shows the format of this question.
Practical Courses
Practical courses play a vital role in any chemistry- and/or drugoriented curriculum, because they aim to have students
combine various learning goals such as technical skills, theory
and concepts, planning, and reporting techniques. This
combination of focus points sometimes diminishes the time
students allow themselves to spend on correlating practice with
theory. In an eort to stimulate this correlation, we have set up
a daily quiz during a month-long full-time second-year practical
course in organic chemistry. Every day starts with a plenary
gathering during which a quiz is administered. This quiz is
dierent every day and consists of 3 to 5 MC questions with
associated text and pictures being shown on devices and not on
the plenary screen (see Figure S14A,B in the Supporting
E
Article
EVALUATION
Teachers
CONCLUSION
IT (information technology) is nding its way into
contemporary education. We have demonstrated that this is
for the better as it can provide a means to rapidly and
simultaneously activate groups of students. Using appropriate
apps/software and tasks, one can turn electronic devices
(smartphones, tablets, laptops) into a powerful tool that can be
used for formative assessment in the classroom. Larger groups
of students, bold and shy ones alike, can be triggered to
participate in small tasks such as answering MC and openended questions on class material. Moreover, the use of 3D
visualization oers an in-class way to have students acquaint
themselves with 3D structures of organic molecules, biomolecules, and drugtarget complexes. These tasks should be
thought of as being on one axis of a matrix, with the other axis
being the application in any educational context (introquizzes,
lectures, practical courses, etc.). Besides the positive experiences among teachers, we have found that students also
appreciate and value these collective activating approaches.
Taken together, we demonstrate that the use of mobile devices
is a mutually benecial way of teaching and therefore should
deserve attention in other curricula, not only chemistry-based
ones. Thus, while we have tailored all our electronic
questioning to chemistry- and drug-related topics, it is evident
that our protocols can be extended to nonchemistry classrooms
too.
Students
ASSOCIATED CONTENT
S Supporting Information
*
AUTHOR INFORMATION
Corresponding Author
*E-mail: m.wijtmans@vu.nl.
Notes
ACKNOWLEDGMENTS
From the VU University Amsterdam, we wish to express thanks
to Rob Leurs, Iwan de Esch, Chris de Graaf, Martine Smit,
Henry Vischer, Marco Siderius, Chris Vos, Nico Vermeulen,
F
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