PubMed Health⌕ Search
Home/Archive/PubMed

PubMed · 17140224

Tricarboranyl pentaerythritol-based building block.

Alexis Mollard·Ilya Zharov
View original source ↗Export metadata ↓

Abstract

A new tricarborane building block based on pentaerythritol was prepared for applications in boron neutron capture therapy (BNCT). Its X-ray single-crystal structure revealed a high degree of steric congestion. To enable the attachment of the building block to other moieties, a succinimidyl linker has been introduced at the focal point, and a generation-2 hexacarborane-containing dendron carrying 60 boron atoms has been prepared using a 2,2-bis(hydroxymethyl)propionic acid core.

Explore related subjects

Boron CompoundsBoron Neutron Capture TherapyCrystallography, X-RayModels, ChemicalPropionatesPropylene GlycolsStereoisomerismSuccinimidesJournal ArticleResearch Support, Non-U.S. Gov't

Keep this discovery

Explore connections, maps & timelines

BibTeXRIS

Alexis Mollard, Ilya Zharov. 2006-12-11. Tricarboranyl pentaerythritol-based building block.. https://doi.org/10.1021/ic061297q

Cite the original work for its findings. Save a collection to share your selection of sources.

KEEP EXPLORING

Related citations

PubMed2007

Tetrahedral boron chemistry for the preparation of highly efficient "cascatelle" devices.

The replacement of the two fluorine atoms on the boron center of the well-known Bodipy fluorophore by functionalized acetylenic groups opens the way to a new family of highly luminescent, redox active, and stable fluorophores termed "E-Bodipy" species. The substitution is effective for ethynyl-lithium reagents incorporating tolyl, naphthyl, pyrenyl, fluorenyl, and terpyridinyl units. The protocol also tolerates the presence of various functional groups in the dipyrromethene meso position such as pyrene, phenylethynylpyrene, 4'-terpyridine, and iodophenyl. The last of these is particularly useful for a further coupling reaction enabling introduction of a flexible arm bearing a succinimidyl unit reactive toward primary amines. X-ray structure determinations of two E-Bodipy compounds confirm the introduction of the ethynyl units and show the boron atoms to have a distorted tetrahedral environment, with B-C(ethynyl) approximately 1.59 A and both boron atoms lying essentially in the mean planes of the dipyrromethene units. All the new compounds show intense electronic absorption bands (epsilon 60,000-70,000 M-1 cm-1), high quantum yields (>80%), and slow rates of nonradiative decay. Absorption by the aromatic substituents results in a "cascatelle" process leading to emission exclusively through the boradiazaindacene entity and thus large virtual Stokes' shift (>10,000 cm-1). The new compounds are also redox active, with the formation of both Bodipy+* and Bodipy-* occurring more readily than for F-Bodipy species. The molecules in their excited states are strong reducing agents.

Boron Compounds↗
PubMed2007

Characterization of a BODIPY-labeled fluorescent fatty acid analogue. Binding to fatty acid-binding proteins, intracellular localization, and metabolism.

The BODIPY-labeled fatty acid analogues are a useful addition to the tools employed to study the cellular uptake and metabolism of lipids. In this study, we show that BODIPY FL C(16) binds to purified liver and intestinal fatty acid-binding proteins with high affinity at a site similar to that for the physiological fatty acid oleic acid. Further, in human intestinal Caco-2 cells BODIPY FL C(16) co-localizes extensively with mitochondria, endoplasmic reticulum/Golgi, and L-FABP. Virtually no esterification of BODIPY FL C(16) was observed under the experimental conditions employed. We conclude that BODIPY FL C(16) may be a useful tool for studying the distribution and function of FABPs in a cellular environment.

Boron Compounds↗