Green-Light-Sensitive BODIPY Photoprotecting Groups for Amines
نویسندگان
چکیده
We describe a series of easily accessible, visible-light-sensitive (λ > 500 nm) BODIPY (boron-dipyrromethene)-based photoprotecting groups (PPGs) for primary and secondary amines, based on a carbamate linker. The caged compounds are stable under aqueous conditions for 24 h and can be efficiently uncaged in vitro with visible light (λ = 530 nm). These properties allow efficient photodeprotection of amines, rendering these novel PPGs potentially suitable for various applications, including the delivery of caged drugs and their remote activation.
منابع مشابه
meso-Methylhydroxy BODIPY: a scaffold for photo-labile protecting groups.
Here, we show that by installing a meso-methylhydroxy moiety, the boron dipyrromethene (BODIPY) scaffold can be converted into an efficient caging group, removable by green light. We describe caging and uncaging of important chemical functionalities and demonstrate green light mediated control over biological processes in cultured cell lines and neurons.
متن کاملLight-driven Au(III)-promoted cleavage of triazole-bearing amine derivatives and its application in the detection of ionic gold.
Light-driven Au(III)-promoted oxidative cleavage of triazole-bearing amine derivatives is utilized for the detection of ionic gold in aqueous media. A bistriazole-bearing boron dipyrromethane (1(BODIPY)) exhibited selective and sensitive fluorescence enhancement by the addition of Au(3+) and subsequent UV irradiation.
متن کاملBODIPY-derived photoremovable protecting groups unmasked with green light.
Photoremovable protecting groups derived from meso-substituted BODIPY dyes release acetic acid with green wavelengths >500 nm. Photorelease is demonstrated in cultured S2 cells. The photocaging structures were identified by our previously proposed strategy of computationally searching for carbocations with low-energy diradical states as a possible indicator of a nearby productive conical inters...
متن کاملMaterial for ‘Two-Photon Time-Lapse Microscopy of BODIPY- Cholesterol Reveals Anomalous Sterol Diffusion in Chinese Hamster Ovary Cells’
Figure S 1: Chemical structure of BODIPY-cholesterol (BChol) and dehydroergosterol (DHE). A, structure of BODIPY-cholesterol with the fluorophore (green, with light green underlay to highlight the fluorescent group) at carbon 24 of the sterol side chain. B, structure of DHE. Differences to cholesterol are indicated in green and red; i.e., an extra methyl group and double bond in the alkyl side ...
متن کاملWavelength-selective cleavage of photoprotecting groups: strategies and applications in dynamic systems.
Photocleavable protecting groups (PPGs) are extensively used in chemical and biological sciences. In their application, advantage is taken of using light as an external, non-invasive stimulus, which can be delivered with very high spatiotemporal precision. More recently, orthogonally addressing multiple PPGs, in a single system and with different wavelengths of light, has been explored. This ap...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
دوره 83 شماره
صفحات -
تاریخ انتشار 2018