creation of medicinal chemistry learning communities through enhanced technology and...

TEACHERS’ TOPICS

Creation of Medicinal Chemistry Learning Communities Through EnhancedTechnology and Interdisciplinary Collaboration

Brian Henriksen, PhD, and Victoria Roche, PhD

School of Pharmacy and Health Professions, Creighton University, Omaha, NE

Submitted January 30, 2012; accepted April 9, 2012; published October 12, 2012.

Objectives. To build an integrated medicinal chemistry learning community of campus and distancepharmacy students though the use of innovative technology and interdisciplinary teaching.Design. Mechanisms were implemented to bring distance students into campus-based medicinalchemistry classrooms in real time, stimulate interaction between instructors and various student co-horts, and promote group work during class. Also, pharmacy clinician colleagues were recruited tocontribute to the teaching of the 3 medicinal chemistry courses.Assessment. Student perceptions on the value of technology to build community and advance learningwere gleaned from course evaluations, in class feedback, and conversations with class officers andstudent groups. Responses on a survey of second-year students confirmed the benefits of interdisci-plinary content integration on engagement and awareness of the connection between drug chemistryand pharmacy practice. A survey of clinician colleagues who contributed to teaching the 3 medicinalchemistry courses found their views were similar to those of students.Conclusions. The purposeful use of technology united learners, fostered communication, and ad-vanced content comprehension in 3 medicinal chemistry courses taught to campus and distance stu-dents. Teaching collaboration with pharmacy clinicians enhanced learner interest in course content andprovided insight into the integrated nature of the profession of pharmacy.

Keywords: interdisciplinary, technology, medicinal chemistry, learning communities

INTRODUCTIONKnowledge of drug chemistry is foundational to the

practice of pharmacy. At Creighton University, studentsare exposed to medicinal chemistry content in 2 requiredcourses offered in the second year. These courses, entitledthe Chemical Basis of Drug Action I and II, along withselected lessons incorporated within them, have been de-scribed in detail.1-3

In 2010, lessons on acid-base chemistry and receptorchemistry were removed from the Chemical Basis ofDrug Action I course during an extensive revision of theprofessional curriculum. While students are exposed re-peatedly to these topics during their pre-professionalcoursework and in professional biochemistry and phar-maceutics courses, the faculty members recognized thattheir knowledge confidence and optimal understandingcould be improved through additional instruction andpractice. These lessons, along with lessons on physico-chemical principles and properties and stereochemistry,

were bundled into an elective course entitled ScientificFoundations of Drug Action. This elective was offered tointerested first-year pharmacy (P1) students in the springsemester, prior to the first required medicinal chemistrycourse they would take in the fall. This placement wasintended to promote retention of knowledge needed forthe analysis of structure-activity relationships to predictpharmacological actions and therapeutic utility of drugmolecules.

Creighton University offers a campus-based anda distance pathway to earning the PharmD degree. Unlikemany distance pharmacy programs, the distance cohortis widely distributed across the country so students do notgather at a single site to hear course lectures. Rather,students interact with course content via robust courseWeb sites, and with instructors, mentors, and one anothervia conferencing software associated with the AngelLearning Management System (LMS) (Blackboard Col-laborate, Washington, DC, www.blackboard.com). In-structors and mentors are also available to distancestudents via telephone and, in some cases, in-personmeet-ings. All pharmacy students are required to completeChemical Basis of Drug Action I and II in order to earn

Corresponding Author: Brian Henriksen, CreightonUniversity, Hixson-Lied Bldg. 146, 2500 California Plaza,Omaha, NE 68178. Tel: 402-280-2862.E-mail: [email protected]

American Journal of Pharmaceutical Education 2012; 76 (8) Article 158.

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the PharmD degree. Scientific Foundations of Drug Ac-tion is an elective and, in the 2 years of its offering, 63%and 75% of the campus P1 students and 38% and 41%of the distance P1 students have enrolled.

Course evaluation data over the years have con-firmed student appreciation for the interactive lessonhandouts that include periodic quizzing. Likewise, stu-dents have found the use of tablet computers beneficialin medicinal chemistry courses where drawing and reac-tion annotation are routine. The LMS used to delivercourse content is robust and easy for students to navigate,and it allows for the timed distribution of content, includ-ing active-learning exercises and keys to completed ex-aminations and quizzes.

Interprofessional education is a goal of all pharmacyprograms, in part because it is expected by accreditationstandards.4 With the implementation of the revised cur-riculum, which emphasizes vertical and horizontal con-tent integration, themedicinal chemistry facultymembersrecognized the need to bemore proactive in linking chem-istry content to the practice of the profession. Clinicalrelevance has always been stressed in the Chemical Basisof Drug Action courses, but it was made more explicit bythe inclusion of clinical practitioners in the presentationof selected lessons.5 When designing Scientific Founda-tions of Drug Action the authors proactively engagedclinicians in lectures and active-learning sessions. Thefaculty also recognized the value of bringing the 2 learningcohorts (campus and distance) together to engage in class-room activities in real-time. Techniques which allowed forthe broadening of the in-class learning community will bedescribed, and the robust use of technology to both unitelearners and advance deep learning will be addressed. Ourcourse objective was the creation of a learning communitythat integrated campus students, distance students, coursefaculty and clinical faculty through the purposeful use oftechnology.

DESIGNOverview of Course Management and Instruction

Both authors were highly involved in the instructionof the 3 medicinal chemistry courses over the 2-year pe-riod described here and brought a similar pedagogy toeach. Lesson content was delivered via conversationalhandouts constructed in Word or SoftChalk, which stu-dents were responsible for reading before class. Pre-classreading comprehension quizzes, sometimes referred toas team readiness assurance tests, or tRATs, could becompleted collaboratively but had to be submitted in-dividually.6 Completion of the open-book quizzes pre-pared students for in-depth discussion, problem solving,and active-learning exercises during the lecture periods.

In-class problem solvingwas facilitated by ResponseWare(TurningPoint Technologies, Youngstown, OH ) personalresponse system technology that permits polling of classresponses to content application questions. Examinationsin all 3 courses were administered online, and focusedsignificantly on clinical application and problem-solving,as opposed to information recall.

Active learning was purposefully incorporated intothe 3 medicinal chemistry courses, albeit in differentways. Lecture-embedded active-learning strategies suchas think-pair-share exercises and structure challengeswere used in Chemical Basis of Drug Action I and II,and voluntary recitation periods were used for more in-depth active-learning activities such as computerizedmedicinal chemistry case studies5 and Patched-Up DrugExercises (described below). Defined active-learning ses-sions were an integral component of Scientific Founda-tions of Drug Action, and always comprised the secondhour of the 2-hour weekly class session. Examples ofactive-learning exercises used in Scientific Foundationsof Drug Action include a double-entry journal activityon a published article on acid-base chemistry, case stud-ies related to acid-base chemistry, an acid-base strengthJigsaw Challenge, an Induction-Deduction Challenge(acid-base strength) and a functional group treasurehunt. Copies of all active-learning exercises are avail-able from the authors.7,8

Interdisciplinary CollaborationTo advance content integration of the 3 courses,

interdisciplinary collaboration was pursued. Clinicalcolleagues from within the university were invited toparticipate in selected sessions of The Chemical Basisof Drug Action and the Scientific Foundations of DrugAction courses. For example, the medicinal chemistry ofantihyperlipidemic statins is addressed in Chemical Basisof DrugAction I, and the pharmacy practice facultymem-ber who practices at a regional VAMC contributed to theclass session where the SAR of statin products was ap-plied to therapeutic decision-making. The entire classsession was comprised of a series of therapeutic applica-tion problems/questions posed to the class. After the stu-dents applied their knowledge of drug chemistry to makeappropriate therapeutic recommendations for specific pa-tients described in the problems, the pharmacy practicefaculty member reinforced the validity of their analysesby sharing related patient care experiences and emphasiz-ing the importance of chemical understanding to compre-hensive patient care.

In Scientific Foundations of Drug Action, clinicalfaculty colleagues shared class sessions on acid basechemistry and physicochemical properties. With regard


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to the former topic, the pharmacy practice colleagueshared experiences that reinforced why pharmacists re-quire an in-depth understanding of acid base chemistry tokeep patients safe in a hospital setting. With regard to thelatter topic, the pharmacy practice faculty member whoworks with bariatric patients shared the podium with themedicinal chemist in a fully integrated class sessionaddressing the clinical relevance of molecular lipophi-licity (Log P) and its significant impact on therapeuticdecision-making.

TechnologyBy using specific, cross-platform technologies, stu-

dent and faculty cohorts were able to actively dialog aboutcourse content in the Chemical Basis of Drug Action Iand II course and the elective course. Through the Learn-ing Management System (LMS), distance students en-tered the classroom online, permitting them to hear andview what the campus-based students were experiencing.The instructor’s desktopwas shared and distance studentscould make comments or ask questions by texting if theywere online or by voice if they were in the classroom.Through a voice over Internet protocol, distance studentsalso could be given audio ability so that everyone, in-cluding campus-based learners, could hear them, or theirrights could be restricted to typing out their question ina textbox. When questions were typed, the faculty mem-ber monitoring the chat repeated the question aloud foreveryone to hear before it was addressed. Lecture capturerecorded the entire class session for students to review ifdesired.

The Angel LMS system permitted the establish-ment of several breakout online “rooms” in which dis-tance Scientific Foundations of Drug Action studentscould “gather” to work on in-class active-learning ex-ercises. The course mentor (a senior medicinal chemis-try faculty member at another institution), who waspresent during each Scientific Foundations of Drug Ac-tion class session, moved from virtual room to room toaddress questions while the campus-based instructorswere working with campus-based students. The courseinstructors also checked in with the distance studentsduring active-learning sessions to ensure that all ques-tions were being addressed.

A suite of question types were made available inSoftchalk through an electronic Quiz Me feature. ThroughQuizMe pop-up windows, answers to embedded questionswere invisible to the students until the questionwas attemp-ted. True-false, multiple-choice, andmultiple-answer ques-tionswere available, asweremore complex challenges suchas crossword puzzles and structure drawings with “hotspots” that corresponded to the questions asked. In addition

to Quiz Me questions, SoftChalk pop-up windows couldbe embedded with images, chemical structures, or addi-tional text. The pop-ups could display full motion videosor movies embedded in the document or hyperlinked to anoutside source. Embedded videos with proper citation werepreferred in case unanticipated changes were made to theoriginal Web site URL.

The tablet computer is a highly useful tool for in-teractive problem solving.When used in class, instructorscould spontaneously draw on slides or graphics to illus-trate concepts in response to student questions. Likewise,students could “ink” (write) on their lesson notes or on thePowerPoint slides used to deliver a lesson in class, andforward captured images of thosemodified pages or slidesto faculty members when asking questions or requestingclarification of a concept. The capabilities of the tabletcomputer allowed faculty members to understand andcorrect areas of confusion, ask students to demonstratetheir understanding of topics under discussion, and rein-force accurate thinking. Tablet PCs are uniformly config-ured and issued to all Creighton pharmacy students andfaculty members.

The VOIP has built-in presentation functions thatallowed faculty members to hold virtual office hours whenstudents and faculty members could speak to one another.Students in both cohorts could join an online help sessionduring which questions could be asked verbally or in writ-ing. The presenter’s desktop or files could be shared andconfusing concepts could be addressed explicitly.

PRSs such as TurningPoint Technologies’ Response-Ware allowed students to respond immediately and anon-ymously to questions posed in class. Responses weredisplayed as a percentage of respondents selecting eachpossible answer, allowing faculty member to recognizewhen students’ understanding was suboptimal and givingthem the option to reinforce principles before proceedingwith the lesson/presentation. PRSs were also used as anindicator of individual students’ grasp of content so thatfocused remediation could be offered. Unlike the use oftraditional “clickers,”which demand the user be physicallypresent in the classroom to participate, ResponseWareallowed both campus and distance students to engage inin-class polling.

The PatchedUpDrugExercise (CreightonUniversity)allowed students to practice constructing and modifyingpharmacophores to build drug molecules (real or envi-sioned) that accomplish specific therapeutic goals. The pro-gram facilitated understanding of how key drug functionalgroups honor known structure activity relationships andpermit a compound to elicit desired therapeutic actions.When using the Patched Up Drug Exercise, the facultymember uploaded functional group images appropriate


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for a given class of therapeutic agents as transparent *.pngfiles or smiles strings.9 The students logged into the ap-plication and selected a chemically-based therapeuticcase designed by the faculty member. As preloaded ques-tions appeared at the top of the screen, students dragged,dropped, and rotated selected functional groups on a phar-macophoric skeleton to create a compound that accept-ably addressed the case question. Students had the optionto view a structure uploaded by the faculty member as anideal solution to the case question, and/or they could useembedded e-mail to send their molecule to the facultymember for feedback. When responding, the instructorwas able to annotate the student’s image to highlight func-tional groups of importance, as well as provide narrativecomments and corrections.

Several new cases were added to the ComputerizedMedicinal Chemistry case studies (reported on previ-ously10,11), the most complex of which was based on StarWars characters and addresses adrenoceptor agonist andcorticosteroid drugs used in the treatment of asthma.12

Synchronous use of this computer-assisted learningtool by distance students in the Scientific Foundations ofDrugAction coursewas required and these students had torearrange their work and or study schedules to accommo-date the 2-hour weekly class session and at least a third ofthe distance class did so over the 2 years of the coursedescribed here. TheVOIP technology permitted seamlessintegration of the distance cohort into the class setting.Students could be heard easily by the campus students andthey were proactive participants in class discussions.

The option to participate in the Chemical Basis ofDrugAction I and II class sessions routinely drew up to 15distance students (20.5% of the class) each period. Thecohort participating in real time was consistent over thecourse of the semester. Approximately half of the partici-pants gained familiarity and comfort with the VOIP tech-nology through previous enrollment in the ScientificFoundations of Drug Action course, indicating that thetechnology is sufficiently intuitive to use without exten-sive past experience.

ASSESSMENTAn assessment of the impact of clinician involve-

ment in the chemistry classroom the previous fall in theChemical Basis of Drug Action I course was conductedby surveying students enrolled in the Chemical Basis ofDrug Action II in January 2012 using a self-reported,aggregate, de-identified survey instrument with Likertscale responses. Of the 180 students enrolled in thecourse, 56 (30.9% of the class) completed the voluntarysurvey instrument. The survey was sent to students at theend of the semester and was voluntary, and both factors

may have contributed to the low overall response rate.Responses were clustered at the 80%-82% agree/stronglyagree end of the scale and confirmed the positive impactof the integrated class session on content interest andawareness of the importance of chemistry to the prac-tice of pharmacy. Between 3.5% and 7% of respondentsdisagreed/strongly disagreed with the statements on inter-est in the content and relevance of the course. Slightly over27% of the respondents either agreed or disagreed that theintegrated session stimulated additional student questionsduring class, while 45.5% were not sure of the session’simpact on their in-class questioning.

Approximately 55% (31 students) of the respondentshad also taken the Scientific Foundations of Drug Actionelective course the previous spring. Between 75%-80%ofPHA 391 participants found value in the involvement ofclinicians in those class sessions. Specifically, they feltclinician involvement reinforced the clinical relevance ofmedicinal chemistry and increased their interest in theclass session. Only 1 respondent disagreed with thesestatements.

The 3 clinical colleagues who participated in theScientific Foundations of Drug Action and/or ChemicalBasis of Drug Action I classes were given a post-lessonsurvey. Responses indicated that they felt prepared tocontribute to the session and that their session effectivelypromoted interdisciplinary content integration. One re-spondent was not sure if their session appropriately rein-forced the clinical relevance of medicinal chemistry,while the other 2 strongly agreed with the statement. Allindicated theywerewilling to participate in future classes.

DISCUSSIONThe strategies used in the medicinal chemistry-

related courses at Creighton (all of which are facilitatedby technology) were intended to advance higher-levellearning, engage learners across pathways, and/or pro-mote interdisciplinary content integration.

The interactive nature of SoftChalk questions com-plements the collaborative and open-book nature of thepre-class reading comprehension quizzes, or tRATs. Stu-dents can treat the Quiz Me questions like a game, whichencourages intellectual debate between students aboutright answers and focused discussion on course content.QuizMequestions can be inserted in sections of the lessonhandout that cover material found in the tRAT to prompt/guide student thinking and promote success on the quizand in the course. As the instructors improve the coursesin their quest for purposeful integration of clinical exper-tise in the classroom, more structurally based therapeuticapplication questions can be embedded to stimulate student-clinician dialog.


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Likewise, properly executed-videos that illustrateabstract concepts are aboon to studentswhoself-identify asvisual learners. For example, envisioning the 3-dimensionalorientation in space of a drugwith 1 ormore chiral centersdocked in a receptor active site can be overwhelming fora student whose primary resource for understanding isthe written lesson handout. However, the Softchalk les-son with embedded 3D video allow students to play theanimation of the drug-docking process and stop it at keypoints to discuss what is happening, and to take screencaptures to send to faculty members with questions.

The use of tablet computers greatly enhanced theefficiency of faculty-student interaction around confus-ing concepts. Instead of trying to articulate a chemicalconfusion only in words, students can also illustrate theirthoughts by drawing on a faculty-generated document orslide, which usually highlights the pivotal issue muchmore quickly. The ability for both students and facultymembers to spontaneously draw on computer-based doc-uments without the need for a drawing program has beenparticularly invaluable in online office sessions or exami-nation review sessions.

Faculty members often embrace personal responsesystem (PRS) tools as a way to titrate the learning ongoingin a given class session, but the capabilities for learningadvancement are significantly more robust. Using theResponseWare software, each class session’s PRS datacan be collated into 1 report, and students performing ata selected level (eg, , 70% correct responses) can behighlighted. Faculty members can then reach out to stu-dents who do not appear to understand content at an ac-ceptable level or who may be at risk for examination orcourse failure. Focused content remediation can be con-structed in areas where PRS responses indicate a lackof understanding, although the responsibility for fol-lowing through remains with the learner. Targeted in-person and online review sessions can be offered toaddress problem areas, and the tutors supported by phar-macy organizations and the school administration can beprompted to work on these identified issues with theirproteges.

Use of PRSs challenge questions engaged studentsin the lesson.13-16 Three polling questions per 50-minuteclass session spaced every 15 minutes appeared optimal.Student interest in performing well was also enhanced ifpoints were awarded for correct responses.17 A key ad-vantage of ResponseWare is cross-platform access topolling questions. As long as students have an Internet-capable device (eg, laptop computer, smart phone, tabletcomputer, etc) and are appropriately logged in to theResponseWare session, they can participate. This cross-platform access is attractive when there is not a uniform

technology infrastructure, such as a mandatory laptopprogram, or if a student’s laptop is in for repairs.

A benefit of distance students’ real-time participa-tion in the campus-based classroomwas enhanced studentengagement. Despite faculty encouragement to ask ques-tions and contribute comments during class, campus stu-dents often did not want to raise their hand for fear ofdisrupting the flow of the lecture. However, distance stu-dent questions, which were initially written in a chat logassociatedwith theVOIP, were not viewed by the campuscohort as disruptive because the faculty members wereable to address the question at a natural break in theirdelivery. Campus students could also interact with thedistance students through the VOIP associated chat logif they chose to do so. The faculty member could stop thelecture at planned times to ask all students for questions.

One caution to the use of technology to bring dis-tance learners into the campus classroom is the level ofpreparation and practice required by the facultymembers.In addition, all classroom technologiesmust be fully com-patible to avoid malfunctions that disrupt learning andfrustrate all concerned. Faculty members should workproactively with their technology support staff membersto troubleshoot potential compatibility issues. Studentsmust be patient as new technologies are implementedbecause, despite everyone’s best intentions, challengeswill inevitably occur. The goal is to keep them at an ab-soluteminimumand to address any issues related to learn-ing in a manner equitable to all cohorts.

As a result of the steps taken to increase interdisci-plinary collaboration, student engagement and proactivequestioning in the Chemical Basis of Drug Action I ses-sion on antihyperlipidemic statins was higher than hadbeen noted in past lessons. Because the clinical facultymember was able to share how her knowledge of drugchemistry helped her make important therapy decisionsfor at-risk patients, students could better relate what theywere learning in the classroom to their future practice.Based on the positive results of clinician involvement inthe antihyperlipidemic statins lesson, additional phar-macy practice faculty members have agreed to contributeto similar Chemical Basis of Drug Action I and II classsessions on drug metabolism, antineoplastic agents, andopioid analgetics.

Likewise, in the Scientific Foundations ofDrugActioncourse, havinga respectedclinical facultymember reinforcehow his knowledge of science allows him to solve acid basechemistry problems encountered at the bedside and keeppatients safewas a powerful lesson on the clinical relevanceof drug chemistry.18 It also allowed both faculty members(clinician and chemist) to demonstrate how their differentapproaches to solving Henderson-Hasselbalch-related


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problems result in identical answers, reinforcing the uni-versal truth of this pivotal mathematical/chemical concept.

In an active-learning session inwhich thePatchedUpDrug Exercise beta software was used, the students statedthat the drag-and-drop nature of the exercise was intui-tive. Within moments of the students logging into theprogram they were able to begin working on assemblingstructures that met the SAR criteria for answering a case-based question. Highlighting the functional groups androtating them to fit the desired orientationwas also simpleand intuitive for the students. Student buy-in on the utilityof the software was strong, as they could clearly makeassociations between a drug’s functional groups and therole of each functional group in meeting the criteria foreliciting a therapeutic outcome.

The fully integrated chemistry/clinical lesson ondrug lipophilicity took the concept of interdisciplinarycollaboration even further. The chemist first set the stageby presenting foundational material. The clinician thenillustrated how she applies these realities when address-ing the specific needs of extremely obese patients, someof whom may be facing or recovering from bariatric sur-gery (eg, bypass, banding).19

CONCLUSIONSMedicinal chemistry learning communities that span

3 courses were successfully created through interdisci-plinary collaboration in teaching and use of enhancedtechnology. The participation of clinical colleagues inscience-focused coursesmay serve as the first step towardachieving a fully integrated and interprofessional curric-ulum, a goal of all pharmacy programs. An additionalbenefit of interprofessional teaching is the establishmentof relationships that can lead to interprofessional scholar-ship and publication. ‘Also, the technologies described inthismanuscript united campus and distance learning com-munities, fostered communication with faculty members,provided opportunities for active learning and commandof content, and advanced meaningful learning.

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