Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

4,4-Difluoro-1,3,5,7-tetra-methyl-8-penta-fluoro-phenyl-4-bora-3a,4a-diaza-s-indacene.

ABSTRACT: In the title dye compound, C(19)H(14)BF(7)N(2), the boron-dipyrromethene core lies on a crystallographic mirror plane which bis-ects the BF(2) and penta-fluoro-phenyl groups. The dihedral angle between the penta-fluoro-phenyl ring and the tricyclic system is thus 90° by symmetry. The sp(3)-hybridized B atom has a slightly distorted tetra-hedral coordination.

SUBMITTER: Zhou X

PROVIDER: S-EPMC2983759 | biostudies-literature | 2010 Mar

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

4,4-Difluoro-1,3,5,7-tetra-methyl-8-penta-fluoro-phenyl-4-bora-3a,4a-diaza-s-indacene.

Zhou Xiaofeng X

Acta crystallographica. Section E, Structure reports online 20100306 Pt 4

In the title dye compound, C(19)H(14)BF(7)N(2), the boron-dipyrromethene core lies on a crystallographic mirror plane which bis-ects the BF(2) and penta-fluoro-phenyl groups. The dihedral angle between the penta-fluoro-phenyl ring and the tricyclic system is thus 90° by symmetry. The sp(3)-hybridized B atom has a slightly distorted tetra-hedral coordination. ...[more]

PMID: 21580602

Similar Datasets

4,4-Difluoro-1,3,5,7-tetra-methyl-4-bora-3a,4a-diaza-s-indacene.

Project description:In the title compound, C(13)H(15)BF(2)N(2), the two pyrrole rings are almost coplanar, with a dihedral angle of 3.08 (10)°. The BF(2) plane is almost perpendicular to the boron-dipyrromethene ring plane, with a dihedral angle of 89.99 (7)°.

| S-EPMC2960520 | biostudies-literature

Functionalization of the 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) core.

Project description:The new BODIPY systems 1 and 2 were prepared and then used as substrates to explore S(N)Ar and F-B displacement reactions. Chloride was easily displaced from 1 by a piperidine/ester, methylmagnesium bromide selectively displaced fluoride, and cyanide could attack both sites. System 2 readily added soft nucleophiles to the electrophilic carbon atoms, providing a new method for bioconjugation of BODIPYs to proteins while also introducing a (19)F probe.

| S-EPMC2430868 | biostudies-literature

Synthesis and characterization of high-affinity 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene-labeled fluorescent ligands for human ?-adrenoceptors.

Project description:The growing practice of exploiting noninvasive fluorescence-based techniques to study G protein-coupled receptor pharmacology at the single cell and single molecule level demands the availability of high-quality fluorescent ligands. To this end, this study evaluated a new series of red-emitting ligands for the human ?-adrenoceptor family. Upon the basis of the orthosteric ligands propranolol, alprenolol, and pindolol, the synthesized linker-modified congeners were coupled to the commercially available fluorophore BODIPY 630/650-X. This yielded high-affinity ?-adrenoceptor fluorescent ligands for both the propranolol and alprenolol derivatives; however, the pindolol-based products displayed lower affinity. A fluorescent diethylene glycol linked propranolol derivative (18a) had the highest affinity (log K(D) of -9.53 and -8.46 as an antagonist of functional ?2- and ?1-mediated responses, respectively). Imaging studies with this compound further confirmed that it can be employed to selectively label the human ?2-adrenoceptor in single living cells, with receptor-associated binding prevented by preincubation with the nonfluorescent ?2-selective antagonist 3-(isopropylamino)-1-[(7-methyl-4-indanyl)oxy]butan-2-ol (ICI 118551) ( J. Cardiovasc. Pharmacol.1983, 5, 430-437. ).

| S-EPMC3188295 | biostudies-literature

Further investigation on the nitration of BODIPY with cupric nitrate: crystal structures of 4,4-di-fluoro-1,3,5,7,8-penta-methyl-2-nitro-4-bora-3a,4a-di-aza-s-indacene, 4,4-di-fluoro-3-nitro-8-phenyl-4-bora-3a,4a-di-aza-s-indacene, and 3-chloro-6-ethyl-5,7,8-trimethyl-2-nitro-4,4-diphenyl-4-bora-3a,4a-di-aza-s-indacene.

Project description:The treatment of non-fully substituted 4,4-di-fluoro-4-bora-3a,4a-di-aza-s-indacene (BODIPY) with cupric nitrate leads to the introduction of a nitro group at different positions of the BODIPY core, depending on the substitution pattern. This methodology complements the treatment of fully substituted BODIPY with cupric nitrate that was previously reported. The crystal structures of 4,4-di-fluoro-1,3,5,7,8-penta-methyl-2-nitro-4-bora-3a,4a-di-aza-s-indacene, C14H16BF2N3O2 (5a) 4,4-di-fluoro-3-nitro-8-phenyl-4-bora-3a,4a-di-aza-s-indacene, C15H10BF2N3O2(5b) and 3-chloro-6-ethyl-5,7,8-trimethyl-2-nitro-4,4-diphenyl-4-bora-3a,4a-di-aza-s-indacene, C26H25BClN3O2 (5d) are presented. In all three structures, the fused ring system is in a very flattened 'V-shape', with dihedral angles between the two outer five membered rings of 8.12 (14), 6.67 (9) and 12.30 (18) Å for 5a, 5b and 5d, respectively. In each case, the central six-membered ring is in a flattened sofa conformation. In the crystal of 5a, mol-ecules are linked by weak C-H⋯O and C-H⋯F hydrogen bonds forming sheets parallel to (10-1). In the crystal of 5b mol-ecules are linked by weak C-H⋯O and C-H⋯F hydrogen bonds and π-π inter-actions forming sheets parallel to (001). In the crystal of 5d, weak C-H⋯O hydrogen bonds link mol-ecules into chains along [001]. In compound 5d, the atoms of the nitro group were refined as disordered over two sets of sites with occupancies 0.618 (12) and 0.382 (12).

| S-EPMC5956316 | biostudies-literature

Designing a green-emitting viscosity-sensitive 4,4-difluoro-4-bora-3a,4a-diaza-<i>s</i>-indacene (BODIPY) probe for plasma membrane viscosity imaging.

Project description:Viscosity is a key characteristic of lipid membranes - it governs the passive diffusion of solutes and affects the lipid raft formation and membrane fluidity. Precise determination of viscosity values in biological systems is of great interest and viscosity-sensitive fluorescent probes offer a convenient solution for this task. In this work we present a novel membrane-targeting and water-soluble viscosity probe BODIPY-PM, which is based on one of the most frequently used probes BODIPY-C10. Despite its regular use, BODIPY-C10 suffers from poor integration into liquid-ordered lipid phases and lack of water solubility. Here, we investigate the photophysical characteristics of BODIPY-PM and demonstrate that solvent polarity only slightly affects the viscosity-sensing qualities of BODIPY-PM. In addition, with fluorescence lifetime imaging microscopy (FLIM), we imaged microviscosity in complex biological systems - large unilamellar vesicles (LUVs), tethered bilayer membranes (tBLMs) and live lung cancer cells. Our study showcases that BODIPY-PM preferentially stains the plasma membranes of live cells, equally well partitions into both liquid-ordered and liquid-disordered phases and reliably distinguishes lipid phase separation in tBLMs and LUVs.

| S-EPMC10291278 | biostudies-literature

4,4-Di-fluoro-2,3;5,6-bis-(tetra-methylene)-4-bora-3a,4a-di-aza-s-indacene (LD540).

Project description:The title compound, C18H21BF2N2, is a lipophilic dye based on a BODIPY fluoro-phore backbone, which was developed for microscopic imaging of lipid droplets; the mol-ecule has a planar BODIPY core [dihedral angle between the pyrrole rings = 2.3?(3)°] and two tetra-methyl-ene substituents at the 2,3- and 5,6-positions in a half-chair conformation. One of the tetra-methyl-ene substituents is disordered over two two sets of sites with site occupancies of 0.5. In the crystal, pairs of C-H?F inter-actions link the mol-ecules into inversion dimers. Neighbouring dimers are linked by further C-H?F inter-actions, forming an infinite array. C-H?? and ?-? [centroid-centroid distance = 4.360?(3)?Å] inter-actions are observed between the BODIPY core and the tetra-methyl-ene substituents of neighbouring dimer pairs.

| S-EPMC3914101 | biostudies-literature

4,4-Difluoro-8-(4-iodo-phen-yl)-1,3,5,7-tetra-methyl-3a-aza-4a-azonia-4-borata-s-indacene.

Project description:In the title compound, C(19)H(18)BF(2)IN(2), which is a boron-dipyrromethene (BODIPY) derivative, the BODIPY mean plane forms dihedral angles of 88.95?(4) and 78.21?(3)° with the F/B/F and 4-iodo-phenyl planes, respectively.

| S-EPMC3344447 | biostudies-literature

(S)-(-)-1-Phenyl-ethanaminium 4-(4,4-di-fluoro-1,3,5,7-tetra-methyl-3a,4a-diaza-4-borata-s-indacen-8-yl)benzoate.

Project description:The title compound, C(8)H(12)N(+)·C(20)H(18)BF(2)N(2)O(2) (-), crystallizes with a significant amount of void space [4.0 (5)%] in the unit cell. The structure displays N-H⋯O hydrogen bonding between the components. The plane formed by the benzoic acid moiety of the BODIPY-CO(2) (-) is twisted by 80.71 (6)° relative to the plane formed by the ring C and N atoms of the tetramethyldipyrrin portion of the molecule.

| S-EPMC3200683 | biostudies-literature

4-(4,4-Difluoro-1,3,5,7-tetra-methyl-3a-aza-4a-azonia-4-borata-s-indacen-8-yl)benzonitrile.

Project description:The title compound, C(20)H(18)BF(2)N(3), contains one C(9)BN(2) (Bodipy) framework and one cyano-benzyl group. The Bodipy framework is essentially planar with a maximum deviation of 0.041?(2)?Å. The introduction of two methyl groups at positions 1 and 7 of s-indacene in the Bodipy unit results in almost orthogonal configuration between the mean plane of the Bodipy unit and the cyano-benzyl group [dihedral angle = 89.78?(4)°].

| S-EPMC3100033 | biostudies-literature

Crystal structure and solvent-dependent behaviours of 3-amino-1,6-diethyl-2,5,7-trimethyl-4,4-di-phenyl-3a,4a-di-aza-4-bora-<i>s</i>-indacene.

Project description:In the title compound (3-amino-4,4-diphenyl-BODIPY), C28H32BN3, the central six-membered ring has a flattened sofa conformation, with one of the N atoms deviating by 0.142 (4) Å from the mean plane of the other five atoms, which have an r.m.s. deviation of 0.015 Å. The dihedral angle between the two essentially planar outer five-membered rings is 8.0 (2)°. In the crystal, mol-ecules are linked via weak N-H⋯π inter-actions, forming chains along [010]. The com-pound displays solvent-dependent behaviours in both NMR and fluorescence spectroscopy. In the 1H NMR spectra, the aliphatic resonance signals virtually coalesce in solvents such as chloro-form, di-chloro-methane and di-bromo-ethane; however, they are fully resolved in solvents such as dimethyl sulfoxide (DMSO), methanol and toluene. The excitation and fluorescence intensities in chloro-form decreased significantly over time, while in DMSO the decrease is not so profound. In toluene, the excitation and fluorescent intensities are not time-dependent. This behaviour is presumably attributed to the assembly of 3-amino-4,4-diphenyl-BODIPY in solution that leads to the formation of noncovalent structures, while in polar or aromatic solvents, the formation of these assemblies is disrupted, leading to resolution of signals in the NMR spectra.

| S-EPMC5347059 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data