New BODIPY derivatives with one 4-hydroxy-1-butynyl group at the 2 position and two 4-hydroxy-1-butynyl groups at the 2, 6, or 4, 4' positions were conveniently synthesized using TBDMS protected alcohols. Deprotection of TBDMS of 4, 4' substituted BODIPY was achieved using TBAF while deprotection of 2 and 2, 6 substituted BODIPY was achieved with acetyl chloride to obtain corresponding alcohols in excellent yields. All BODIPY derivatives with TBDMS protected alcohols fluoresce in higher quantum yields when compared to those with free hydroxyl groups. Cell uptake experiments showed that these compounds are accumulated in human osteosarcoma (Saos-2) cells. The main site of localization for 4, 4' substituted compound was found to be the endoplasmic reticulum (ER). Some of these compounds form excimers inside cells as well as in CH2Cl2 solution.

Synthesis and   properties of BODIPY derivatives with terminal hydroxyl groups

245th National Meeting (2013)

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