David A. Lightner
R. C. Fuson Professor
Organic and Bioorganic Chemistry
A.B. (1960), University of California at Berkeley; Ph.D. (1963), Stanford University (Carl Djerassi); NSF Postdoctoral Fellow (1963-64), Stanford University (Carl Djerassi) and (1964-65), University of Minnesota (Albert Moscowitz).
E-mail: lightner![[at]](../images/at.png)
unr.nevada.edu
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Office: CB 325
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David A. Lightner
Research Interests
Current research is directed toward synthesis, stereochemistry, molecular recognition and photochemistry, with an emphasis on (i) dipyrrole and tetrapyrrole synthetic analogs of bilirubin, the yellow pigment of jaundice; (ii) organic conformational analysis from circular dichroism and NMR spectroscopy; (iii) photobiology, molecular mechanisms of phototherapy for neonatal jaundice, bilirubin metabolism, pyrrole chemistry and photochemistry, photooxidation and singlet oxygen; (iv) chiral molecular recognition; (v) chiroptical properties and electronic interaction of non-adjacent chromophores, long-range interactions; (vi) exciton interactions in organic and biological systems as detected by circular dichroism; and (vii) stereochemistry of cyclic ketones and the Octant Rule.
Selected Publications
“Amphiphilic dipyrrinones,” Dey, S.K.; Lightner, D.A. Monatsh. Chem. 2007, 138, 687-697.
“Converting 9-methyldipyrrinones to 9-H and 9-CHO dipyrrinones,” Boiadjiev, S.E.; Lightner, D.A. Tetrahedron 2007, 63, 8962-8976.
“Influence of conformation on intramolecular hydrogen bonding on the acyl glucuronidation and biliary excretion of acetylenic bis-dipyrrinones related to bilirubin,” McDonagh, A.F.; Lightner, D.A. J. Med. Chem. 2007, 50, 480-488.
“Synthesis and hepatic metabolism of xanthobilirubinic acid regioisomers,” Boiadjiev, S.E.; Conley, B.A.; Brower, J.O.; McDonagh, A.F.; Lightner, D.A. Monatsh. Chem. 2006, 137, 1463-1476.
“Carboxylic acid to amide hydrogen bonding. Oxo-semirubins,” Salzameda, N.T.; Huggins, M.T.; Lightner, D.A. Tetrahedron 2006, 62, 8610-8619.
“Synthesis, properties, and hepatic metabolism of strongly fluorescent fluorodipyrrinones,” Boiadjiev, S.E.; Woydziak, Z.R.; McDonagh, A.F.; Lightner, D.A. Tetrahedron 2006, 62, 7043-7055.
“Exciton chirality: (A) Origins of and (B) Applications from strongly-fluorescent dipyrrinone chromophores,” Boiadjiev, S.E.; Lightner, D.A. Monatsh. Chem. 2005, 136, 489-508.
“Synthesis and hepatic transport of strongly fluorescent cholephilic dipyrrinones,” Woydziak, Z.R.; Boiadjiev, S.E.; Norona, W.S.; McDonagh, A.F.; Lightner, D.A. J. Org. Chem. 2005, 70, 8417-8423.
“pKa and aggregation of bilirubin: Titrimetric and ultracentrifugation studies on water-soluble pegylated conjugates of bilirubin and fatty acids,” Boiadjiev, S.E.; Watters, K.; Lai, B.; Wolf, S.; Welch, W.; McDonagh, A.F.; Lightner, D.A. Biochemistry 2004, 43, 15617-15632.
“NICHD Conference on Kernicterus: Research on prevention of bilirubin-induced brain injury and kernicterus: Bench-to-bedside - Diagnostic methods and prevention and treatment strategies,” Stevenson, D.K.; Wong, R.J.; Vreman, H.J.; McDonagh, A.F.; Maisels, M.J.; Lightner, D.A. J. Perinatol. 2004, 24, 1-5.
“The gem-dimethyl effect: Amphiphilic bilirubins,” Tu, B.; Ghosh, B.; Lightner, D.A. Tetrahedron 2004, 60, 9017-9029.