Lanthanide Complexes as Fluorescent Indicators for Neutral Sugars and Cancer Biomarkers

Simple water-soluble lanthanum and europium complexes are effective at detecting neutral sugars as well as glycolipids and phospholipids. In solutions at physiologically relevant pH the fluorescent lanthanum complex binds neutral sugars with apparent binding constants comparable to those of arylboro...

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Published inProceedings of the National Academy of Sciences - PNAS Vol. 103; no. 26; pp. 9756 - 9760
Main Authors Alptürk, Onur, Rusin, Oleksandr, Fakayode, Sayo O., Wang, Weihua, Escobedo, Jorge O., Warner, Isiah M., Crowe, William E., Král, Vladimir, Pruet, Jeff M., Strongin, Robert M.
Format Journal Article
LanguageEnglish
Published United States National Academy of Sciences 27.06.2006
National Acad Sciences
Subjects
Biochemistry
Biological Sciences
Biomarkers, Tumor - analysis
Cancer
Carbohydrate Sequence
Europium - chemistry
Female
Fluorescence
Fluorescent Dyes - chemistry
Gangliosides
Gangliosides - analysis
Genetic markers
Humans
Hydrogen-Ion Concentration
Lanthanum - chemistry
Lectins
Ligands
Lysophospholipids
Lysophospholipids - analysis
Methanol - chemistry
Molecular Sequence Data
Neoplasms - diagnosis
Oligosaccharides
Ovarian cancer
Ovarian Neoplasms - diagnosis
Phospholipids
Physical Sciences
Salicylates - chemistry
Sugar
Sugars
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Summary:Simple water-soluble lanthanum and europium complexes are effective at detecting neutral sugars as well as glycolipids and phospholipids. In solutions at physiologically relevant pH the fluorescent lanthanum complex binds neutral sugars with apparent binding constants comparable to those of arylboronic acids. Interference from commonly occurring anions is minimal. The europium complex detects sialic acid-containing gangliosides at pH 7.0 over an asialoganglioside. This selectivity is attributed, in large part, to the cooperative complexation of the oligosaccharide and sialic acid residues to the metal center, based on analogous prior studies. In MeOH, lysophosphatidic acid (LPA), a biomarker for several pathological conditions including ovarian cancer, is selectively detected by the europium complex. LPA is also detected via a fluorescence increase in human plasma samples. The 2-sn-OH moiety of LPA plays a key role in promoting binding to the metal center. Other molecules found in common brain ganglioside and phospholipid extracts do not interfere in the ganglioside or LPA fluorescence assays.
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Author contributions: O.A., O.R., J.O.E., V.K., and R.M.S. designed research; O.A., O.R., S.O.F., W.W., and J.M.P. performed research; W.W. contributed new reagents/analytic tools; O.A., O.R., J.O.E., I.M.W., W.E.C., and R.M.S. analyzed data; and O.A., J.O.E., and R.M.S. wrote the paper.
Communicated by Josef Michl, University of Colorado, Boulder, CO, May 10, 2006
ISSN:0027-8424
1091-6490
DOI:10.1073/pnas.0603758103