773888-45-2

Usage

Uses

Used in Bioconjugation Applications:
1H-Thieno[3,4-d]iMidazole-4-pentanaMide, hexahydro-2-oxo-N-2-propynyl-, (3aS,4S,6aR)is used as a biotinylation reagent for the conjugation of biomolecules such as antibodies and proteins. The alkyne group of 1H-Thieno[3,4-d]iMidazole-4-pentanaMide, hexahydro-2-oxo-N-2-propynyl-, (3aS,4S,6aR)- enables the formation of a stable triazole linkage with azide-containing biomolecules through a Cu(I)-catalyzed Click Chemistry reaction, facilitating the attachment of biotin to the target molecules.
Used in Research and Diagnostics:
In the field of research and diagnostics, 1H-Thieno[3,4-d]iMidazole-4-pentanaMide, hexahydro-2-oxo-N-2-propynyl-, (3aS,4S,6aR)is utilized for the development of assays and detection systems. The biotinylation of target molecules allows for their specific recognition and interaction with streptavidin-coated surfaces or other streptavidin-based reagents, enhancing the sensitivity and specificity of assays.
Used in Drug Delivery Systems:
1H-Thieno[3,4-d]iMidazole-4-pentanaMide, hexahydro-2-oxo-N-2-propynyl-, (3aS,4S,6aR)can also be employed in the development of drug delivery systems. By biotinylating drug molecules or drug carriers, 1H-Thieno[3,4-d]iMidazole-4-pentanaMide, hexahydro-2-oxo-N-2-propynyl-, (3aS,4S,6aR)- can facilitate the specific targeting and delivery of therapeutic agents to desired sites within the body, potentially improving the efficacy and reducing the side effects of treatments.
Used in Biomaterials and Tissue Engineering:
In the field of biomaterials and tissue engineering, 1H-Thieno[3,4-d]iMidazole-4-pentanaMide, hexahydro-2-oxo-N-2-propynyl-, (3aS,4S,6aR)can be used for the functionalization of biomaterials. The biotinylation of materials can enable the immobilization of biomolecules, such as growth factors or extracellular matrix components, on the material surface, promoting cell adhesion, proliferation, and tissue regeneration.

Upstream product

• 35013-72-0 biotin N-Hydroxysuccinimide ester 
• 2450-71-7 Propargylamine 
• 58-85-5 biotin 

Downstream Products

• 1223357-71-8 C₂₂H₃₀N₈O₇S 
• 1255088-56-2 N-({1-[6-(1H-pyrrol-1-yl)hexyl]-1H-1,2,3-triazol-4-yl}methyl)biotinamide 
• 1233927-60-0 C₄₆H₆₅F₃N₁₀O₁₀S 
• 1191052-99-9 C₄₉H₅₃BrN₈O₈S 
• 1014613-81-0 C₂₃H₃₂N₇O₇PS 

Relevant academic research and scientific papers

Synthesis and Evaluation of 1,2,3-Triazole-Containing Vinyl and Allyl Sulfones as Anti-Trypanosomal Agents

An approach is described to access 1,2,3-triazole-derived peptidyl vinyl sulfones as Trypanosoma brucei brucei inhibitors by using click chemistry, starting from a common azide intermediate. Among the triazole analogues, biotinylated inhibitors 11 and 12 offer possibilities as probes for the elucidation of target proteases for this compound class. The development of two syntheses of a 1,2,3-triazole-based vinyl sulfone 5 are also presented. This compound was accessed through a click reaction of a lysine-derived azide (itself accessed by diazo transfer), and a phenylalanine-derived alkyne synthesised by both Ohira–Bestmann and Corey–Fuchs-based alkynylation protocols. Several members of this family of compounds showed promising anti-trypanosomal activity. Unexpectedly, one of the most active compounds was allyl sulfone 24, which stems from the isomerisation of vinyl sulfone 5, and is presumably a reversible inhibitor. A docking study of the analogues in the active site of the parasitic cysteine protease rhodesain was carried out in order to gain an insight into their likely interactions with these enzymes.

Oligonucleotide-Addressed Covalent 3′-Terminal Derivatization of Small RNA Strands for Enrichment and Visualization

The HEN1 RNA 2′-O-methyltransferase plays important roles in the biogenesis of small non-coding RNAs in plants and proved a valuable tool for selective transfer of functional groups from cofactor analogues onto miRNA and siRNA duplexes in vitro. Herein, we demonstrate the versatile HEN1-mediated methylation and alkylation of small RNA strands in heteroduplexes with a range of complementary synthetic DNA oligonucleotides carrying user-defined moieties such as internal or 3′-terminal extensions or chemical reporter groups. The observed DNA-guided covalent functionalization of RNA broadens our understanding of the substrate specificity of HEN1 and paves the way for the development of novel chemo-enzymatic tools with potential applications in miRNomics, synthetic biology, and nanomedicine.

Temporal Labeling of Nascent RNA Using Photoclick Chemistry in Live Cells

We report the first cellular application of a photoclick SPAAC reagent to label azide-functionalized RNA. 350 nm irradiation of a cyclopropenone caged oxo-dibenzocyclooctyne (photo-ODIBO) biotin yields formation of the SPAAC reactive species, which rapidly forms adducts with RNA containing 2′-azidoadenosine (2′N3-A). Photo-ODIBO was found to be highly stable in the presence of thiols, conferring greater stability relative to ODIBO. Light activated photo-ODIBO enabled tagging of cellular RNA, in addition to fluorescent imaging as well as enrichment of RNA in cell subpopulations via selective irradiation.

"Clickable" polymersomes

Polymersomes, composed of amphiphilic polystyrene-block-poly(acrylic acid) (PS-b-PAA), with the periphery being covered with azide groups, were used for further functionalization using "click" chemistry. The Royal Society of Chemistry.

Identification of Pyruvate Carboxylase as the Cellular Target of Natural Bibenzyls with Potent Anticancer Activity against Hepatocellular Carcinoma via Metabolic Reprogramming

Cancer cell proliferation in some organs often depends on conversion of pyruvate to oxaloacetate via pyruvate carboxylase (PC) for replenishing the tricarboxylic acid cycle to support biomass production. In this study, PC was identified as the cellular target of erianin using the photoaffinity labeling-click chemistry-based probe strategy. Erianin potently inhibited the enzymatic activity of PC, which mediated the anticancer effect of erianin in human hepatocellular carcinoma (HCC). Erianin modulated cancer-related gene expression and induced changes in metabolic intermediates. Moreover, erianin promotes mitochondrial oxidative stress and inhibits glycolysis, leading to insufficient energy required for cell proliferation. Analysis of 14 natural analogs of erianin showed that some compounds exhibited potent inhibitory effects on PC. These results suggest that PC is a cellular target of erianin and reveal the unrecognized function of PC in HCC tumorigenesis; erianin along with its analogs warrants further development as a novel therapeutic strategy for the treatment of HCC.

BIOPROBES FOR LYSYL OXIDASES AND USES THEREOF

The present invention relates to novel bioprobes which are capable of binding to certain amine oxidase enzymes. These bioprobes are useful in methods of detecting and determining the concentration of certain amine oxidase enzymes in a sample as well as in methods for the quantitative assessment of inhibition of certain amine oxidases.

Synthesis of functionalized copillar[4+1]arenes and rotaxane as heteromultivalent scaffolds

In this study, novel copillar[4+1]arenes were used as central heteromultivalent scaffolds via orthogonal couplings with a series of biologically relevant molecules such as carbohydrates, α-amino acids, biotin and phenylboronic acid. Further modifications by introducing maleimides or cyclooctyne groups provided molecular probes adapted to copper-free click chemistry. An octa-azidated fluorescent rotaxane bearing two distinct ligands was also generated in a fully controlled manner.

Novel Labelled Cannabinergic Ligands and Related Analogs

Novel cannabinoid ligands represented by the general formulas I, II, and III and methods for preparation and use within which one or more of a fluorescent ligand, nitroxide spin label, metal chelate, biotin moiety, or group with enhanced polarity may be incorporated. The compounds can bind to and modulate the cannabinoid CB1 and CB2 receptors and thereby considered specific ligands for these receptors. Some of the disclosed compounds that bind to cannabinoid CB1 and CB2 receptors can exhibit tight or irreversible binding characteristics for these receptors. Due to the presence of the imaging/diagnostic and/or therapeutic functional groups including fluorescent groups, nitroxide spin labels, metal chelates, biotin moieties, and groups with enhanced polarity, the disclosed compounds may be useful as imaging/diagnostic tools and/or therapeutic agents.

COMPOUNDS COMPRISING CLEAVABLE LINKER AND USES THEREOF

Provided are a compound including a cleavable linker, a use thereof, and an intermediate compound for preparing the same, and more particularly, the compound including a cleavable linker of the present invention may include an active agent (for example, a drug, a toxin, a ligand, a probe for detection, etc.) having a specific function or activity, a -S(=0)(=N-)- functional group which is capable of selectively releasing the active agent, and a functional group which triggers a chemical reaction, a physicochemical reaction and/or a biological reaction by external stimulation, and may further include a ligand (for example, oligopeptide, polypeptide, antibody, etc.) having binding specificity for a desired target receptor.

Citrulline probe compound and application thereof

The invention discloses a compound which is shown as a formula 2-GBA, 2-GBA-1, 2-GBA-N3, 2-GBA-N3-1, 2-GBA-Biotin or 2-GBA-Biotin-1. The compound shown as 2-GBA can react with citrulline under a neutral condition, namely, the compound can remove protein o