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Raman spectroscopic measurements and theoretical calculation revealed that the Raman bands corresponding to the B-H stretching vibrations of two types of simple icosahedral boron clusters, ortho -carborane 3 and closo -dodecaborate 4 appeared at approximately 2450-2700 cm -1 , and did not overlap with those of cellular components. Although ortho -carborane 3 possesses a possible property as a Raman probe, it was difficult to measure Raman imaging in the cell due to its poor water solubility. In fact, ortho -carborane derivative 6, which internally has an alkyne moiety, exhibited very weak Raman signals of the C[triple bond, length as m-dash]C stretching and the B-H stretching vibrations were barely detected at a 400 ppm boron concentration in HeLa cells. In contrast, closo -dodecaborate derivatives such as BSH (5) were found to be a potential Raman imaging probe cluster for target molecules in the cell. BSH-conjugated cholesterol 7 (BSH-Chol) was synthesized and used in Raman imaging in cells. Raman imaging and spectral analysis revealed that BSH-based Raman tags provide a versatile platform for quantitative Raman imaging.

Raman cell imaging with boron cluster molecules conjugated with biomolecules