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The American Chemical Society has awarded a grant to William Miles, associate professor of chemistry, to continue his work with students to develop synthetic forms of Vitamin D that can help treat diseases such as cancer, osteoporosis, and psoriasis.
Research conducted with biochemistry major Katelyn Connell ’04(Modena, N.Y.) laid the foundation for the grant proposal, says Miles, who presented their work at last summer’s American Chemical Society national conference and coauthored an article with her that has been published in the journal Tetrahedron Letters.
“I am still amazed at what transpired in one of the most productive summers of my professional career,” he says. “We were able to synthesize an important compound…She did an excellent job of developing and optimizing several steps in the synthesis, which required handling water- and air-sensitive reagents, working up reactions, and purifying the products This level of achievement is a testimony to Katelyn’s intelligence and lab skills.”
The pair collaborated through Lafayette’s EXCEL Scholars program, in which students conduct research with faculty while earning a stipend. The program has helped make Lafayette a national leader in undergraduate research. Many of the 180 students who participate in EXCEL each year go on to share their research through academic journal articles or conference presentations.
Vitamin D is widely known as an essential nutrient that regulates calcium in the blood, bones, and cells. What is less known, says Miles, is that many types of human cells are Vitamin D receptors.
“It does a lot more than regulate calcium,” he says. “Because of that, a number of analogues of Vitamin D have become important pharmaceuticals, including some exciting leads in treating cancer.”
After Vitamin D is ingested, the body turns it into calcitriol, an active, potent compound that elevates calcium levels in the blood, which can lead to hypercalcemia, a potentially fatal condition. The medicinal field has enormous interest in the development of Vitamin D analogues with the benefits, but not risks, of calcitriol, says Miles.
He and Connell developed a synthetic approach and proved that it could produce a necessary component of a Vitamin D analogue.
“It was great to see how the concepts I learned in class are used in the ‘real world,'” Connell says. “It was exciting to see things fall into place and ultimately work out for us.”
Miles used this methodology for the synthesis of part of calcitriol, which he accomplished last summer with EXCEL Scholar and mechanical engineering major Varun Mehta ’06 (New Delhi, India). He also worked last summer with Gozde Ulas ’05 (Mersin, Turkey), who is pursuing B.S. biochemistry and A.B. French degrees, to synthesize a pre-active form of calcitriol. The two will continue their collaboration this summer.
“This project balances two goals that I have always strived to achieve in my research lab: producing exciting and innovative research that is published in prestigious journals, and introducing students to the basics of the research endeavor,” says Miles. “I have mentored 29 research students during my 13 years at Lafayette College, and continue to enjoy introducing undergraduate students to the intellectual challenges and inevitable frustrations of research.”
Miles’ collaborators have included Daniel Swarr ’03 (Clifton Park, N.Y.) and Daniel Ruddy ’03 (Dunmore, Pa.), both summa cum laude graduates, members of the Sigma Xi (scientific and engineering research) and Pi Mu Epsilon (math) honor societies, and recipients of the Goldwater Scholarship, the premier undergraduate award of its type in the fields of mathematics, science, and engineering. Swarr graduated with a B.S in physics and a B.A. with a major in mathematics and was invited to join Phi Beta Kappa. He is enrolled in the M.D. program at University of Pennsylvania in Philadelphia. Ruddy graduated with honors in chemistry and as a member of the Phi Lambda Upsilon honor society for all branches of pure and applied chemistry. He is studying inorganic chemistry, with a particular interest in polymers/materials, at the University of California at Berkeley.
Students mentored by Miles have continued their education in other leading graduate schools at institutions such as Stanford, Brown, and Virginia; pursued graduate studies in the biochemical field; enrolled in medical or dental school; and become industrial chemists.
“In doing research at Lafayette, I benefit from a highly talented pool of undergraduate students, healthy institutional support from the College, and newly renovated facilities,” says Miles. “When my students are working I am always in my lab, exploring new reactions or finishing old research, or in my nearby office, so I am continuously interacting with them.”
As a national leader in undergraduate research, Lafayette sends one of the largest contingents to the National Conference on Undergraduate Research each year. Over the past five years, more than 130 Lafayette students have presented results from research conducted with faculty mentors, or under their guidance, at the conference.
Miles has published his research through 29 academic journal articles, given 21 presentations at scientific meetings, and participated in a dozen research seminars. He previously received two grants from the American Chemical Society and one from the National Science Foundation — for which he served as co-principal investigator with other Lafayette professors — that provided equipment for undergraduate laboratories. The Organic Division of the American Chemical Society honored him with a travel award, and Miles received the 2001 Marquis Distinguished Teaching Award from Lafayette.
He has served as a reviewer for Journal of the American Chemical Society, Organometallics and several other journals since 1986. He has been a member of the Sigma Xi honor society for scientific and engineering research since 1994, serving as treasurer for Lafayette’s chapter of the society since then. He also belongs to the American Chemical Society and the Council on Undergraduate Research. He was a member of the Program Committee and chairman of the Organic Division for the 24th Middle Atlantic Regional ACS Meeting at Fairleigh Dickinson University, Madison, N.J.
Miles has served as acting head and assistant head of chemistry at Lafayette and has been faculty adviser to its student chapter of the American Chemical Society since 1996.
He earned a Ph.D. in organic chemistry from the University of Wisconsin-Madison in 1984 and a B. S. with Distinction in chemistry from the University of Delaware in 1979.