Browse
Submit Data
Databases
API
Help

Dataset Information

22 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Boronic Acid for the Traceless Delivery of Proteins into Cells.

ABSTRACT: The use of exogenous proteins as intracellular probes and therapeutic agents is in its infancy. A major hurdle has been the delivery of native proteins to an intracellular site of action. Herein, we report on a compact delivery vehicle that employs the intrinsic affinity of boronic acids for the carbohydrates that coat the surface of mammalian cells. In the vehicle, benzoxaborole is linked to protein amino groups via a "trimethyl lock." Immolation of this linker is triggered by cellular esterases, releasing native protein. Efficacy is demonstrated by enhanced delivery of green fluorescent protein and a cytotoxic ribonuclease into mammalian cells. This versatile strategy provides new opportunities in chemical biology and pharmacology.

SUBMITTER: Andersen KA

PROVIDER: S-EPMC4900815 | biostudies-literature | 2016 Feb

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Boronic Acid for the Traceless Delivery of Proteins into Cells.

Andersen Kristen A KA Smith Thomas P TP Lomax Jo E JE Raines Ronald T RT

ACS chemical biology 20151215 2

The use of exogenous proteins as intracellular probes and therapeutic agents is in its infancy. A major hurdle has been the delivery of native proteins to an intracellular site of action. Herein, we report on a compact delivery vehicle that employs the intrinsic affinity of boronic acids for the carbohydrates that coat the surface of mammalian cells. In the vehicle, benzoxaborole is linked to protein amino groups via a "trimethyl lock." Immolation of this linker is triggered by cellular esterase ...[more]

PMID: 26629587

Similar Datasets

Inteins as traceless purification tags for unnatural amino acid proteins.

Project description:The expression of proteins containing unnatural amino acids through suppression of a stop codon can be limited by truncation due to competition with release factors. When the site of incorporation is near the C-terminus, it may not be feasible to separate the full-length unnatural amino acid protein from the truncated form. We report a simple, traceless procedure that allows one to isolate the desired protein using a C-terminal intein fusion.

| S-EPMC4473854 | biostudies-literature

Boronic acid liposomes for cellular delivery and content release driven by carbohydrate binding.

Project description:Boronic acid liposomes enable triggered content release and cell delivery driven by carbohydrate binding. Dye release assays using hydrophilic and hydrophobic fluorophores validate dose-dependent release upon carbohydrate treatment. Microscopy results indicate dramatic enhancements in cell delivery, showcasing the prospects of boronic acid lipids for drug delivery.

| S-EPMC5997565 | biostudies-literature

Boronic Acid as Glucose-Sensitive Agent Regulates Drug Delivery for Diabetes Treatment.

Project description:In recent years, glucose-sensitive drug delivery systems have attracted considerable attention in the treatment of diabetes. These systems can regulate payload release by the changes of blood glucose levels continuously and automatically with potential application in self-regulated drug delivery. Boronic acid (BA), especially phenylboronic acid (PBA), as glucose-sensitive agent has been the focus of research in the design of glucose-sensitive platforms. This article reviews the previous attempts at the developments of PBA-based glucose-sensitive drug delivery systems regarding the PBA-functionalized materials and glucose-triggered drug delivery. The obstacles and potential developments of glucose-sensitive drug delivery systems based on PBA for diabetes treatment in the future are also described. The PBA-functionalized platforms that regulate drug delivery induced by glucose are expected to contribute significantly to the design and development of advanced intelligent self-regulated drug delivery systems for treatment of diabetes.

| S-EPMC5459139 | biostudies-other

2,4-Difluoro-phenyl-boronic acid.

Project description:The mol-ecular structure of the title compound, C(6)H(5)BF(2)O(2), is essentially planar (mean deviation = 0.019?Å), indicating electronic delocalization between the dihydroxy-boryl group and the aromatic ring. In the crystal structure, inversion dimers linked by two O-H?O hydrogen bonds arise. An intra-molecular O-H?F hydrogen bond reinforces the conformation and the same H atom is also involved in an inter-molecular O-H?F link, leading to mol-ecular sheets in the crystal.

| S-EPMC2967960 | biostudies-literature

2,4-Dibutoxy-phenyl-boronic acid.

Project description:In the crystal of the title compound, C(14)H(23)BO(4), centrosymmetric dimers linked by pairs of O-H?O hydrogen bonds occur. The dimers are linked via C-H?O contacts, generating a two-dimensional array parallel to (12). These are inter-connected by weak O-H?O hydrogen bonds, as well as C-H?? inter-actions.

| S-EPMC2969364 | biostudies-literature

(4-Carbamoylphen-yl)boronic acid.

Project description:In the title compound, C(7)H(8)BNO(3), the mol-ecule lies on an inversion center leading to a statistical disorder of the B(OH)(2) and CONH(2) groups. In the crystal structure, mol-ecules are linked by N-H?O and O-H?O hydrogen bonds, forming sheets parallel to the bc plane. The B(OH)(2) and CONH(2) groups are twisted out of the mean plane of the benzene ring by 23.9?(5) and 24.6?(6)°, respectively.

| S-EPMC2979401 | biostudies-literature

(2,4-Dipropoxyphen-yl)boronic acid.

Project description:In the crystal, the title compound, C(12)H(19)BO(4), exists as a centrosymmetric O-H⋯O hydrogen-bonded dimer. Dimers are linked via C-H⋯O hydrogen bonds, generating an infinite zigzag chain oriented parallel to [1[Formula: see text]1]. The chains are assembled, giving sheets aligned parallel to (21[Formula: see text]) and inter-connected by weak C-H⋯π inter-actions, producing a three-dimensional network.

| S-EPMC3239085 | biostudies-literature

Traceless and site-specific ubiquitination of recombinant proteins.

Project description:Protein ubiquitination is a post-translational modification that regulates almost all aspects of eukaryotic biology. Here we discover the first routes for the efficient site-specific incorporation of ?-thiol-L-lysine (7) and ?-hydroxy-L-lysine (8) into recombinant proteins, via evolution of a pyrrolysyl-tRNA synthetase/tRNA(CUA) pair. We combine the genetically directed incorporation of 7 with native chemical ligation and desulfurization to yield an entirely native isopeptide bond between substrate proteins and ubiquitin. We exemplify this approach by demonstrating the synthesis of a ubiquitin dimer and the first synthesis of ubiquitinated SUMO.

| S-EPMC3135006 | biostudies-literature

VSV-G-Enveloped Vesicles for Traceless Delivery of CRISPR-Cas9.

Project description:The method of delivery of CRISPR-Cas9 into target cells is a strong determinant of efficacy and specificity in genome editing. Even though high efficiency of Cas9 delivery is necessary for optimal editing, its long-term and high levels of expression correlate with increased off-target activity. We developed vesicles (VEsiCas) carrying CRISPR-SpCas9 ribonucleoprotein complexes (RNPs) that are efficiently delivered into target cells through the fusogenic glycoprotein of the vesicular stomatitis virus (VSV-G). A crucial step for VEsiCas production is the synthesis of the single guide RNA (sgRNA) mediated by the T7 RNA polymerase in the cytoplasm of producing cells as opposed to canonical U6-driven Pol III nuclear transcription. In VEsiCas, the absence of DNA encoding SpCas9 and sgRNA allows rapid clearance of the nuclease components in target cells, which correlates with reduced genome-wide off-target cleavages. Compared with SpCas9 RNPs electroporation, which is currently the method of choice to obtain transient SpCas9 activity, VEsiCas deliver the nuclease with higher efficiency and lower toxicity. We show that a wide variety of cells can be edited through VEsiCas, including a variety of transformed cells, induced pluripotent stem cells (iPSCs), and cardiomyocytes, in vivo. VEsiCas is a traceless CRISPR-Cas9 delivery tool for efficient and safe genome editing that represents a further advancement toward the therapeutic use of the CRISPR-Cas9 technology.

| S-EPMC6041463 | biostudies-literature

(2-Butoxy-phen-yl)boronic acid.

Project description:The title compound, 2-(CH(3)CH(2)CH(2)CH(2)O)C(6)H(4)B(OH)(2), exists as a centrosymmetric hydrogen-bonded dimer. Dimers are linked via C-H⋯π and π-π [with closest C⋯C contact of 3.540 (3) Å] inter-actions to produce a two-dimensional array.

| S-EPMC2960415 | 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