BCN-OH CAS 1263166-90-0
Identification
CAS Number
1263166-90-0
Name
BCN-OH
Synonyms
(1R,8S,9s)-Bicyclo[6.1.0]non-4-in-9-ylmethanol
[German]
[IUPAC name – generated by ACD/Name]
(1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-ylmethanol
[IUPAC name – generated by ACD/Name]
(1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-ylméthanol
[French]
[IUPAC name – generated by ACD/Name]
(1α,8α,9β)-Bicyclo[6.1.0]non-4-yne-9-methanol
1263166-90-0
[RN]
9-Hydroxymethylbicyclo[6.1.0]nonyne
BCN-OH
Bicyclo[6.1.0]non-4-yne-9-methanol, (1R,8S)-
[IUPAC index name – generated by ACD/Name]
endo-9-Hydroxymethylbicyclo[6.1.0]non-4-yne
MFCD26142970
[MDL number]
SMILES
OC[C@H]1[C@H]2CCC#CCC[C@@H]12
StdInChI
InChI=1S/C10H14O/c11-7-10-8-5-3-1-2-4-6-9(8)10/h8-11H,3-7H2/t8-,9+,10-
StdInChIKey
NSVXZMGWYBICRW-ILWJIGKKSA-N
Molecular Formula
C10H14O
Molecular Weight
150.221
Beilstein Registry Number
21037713
MDL Number
MFCD26142970
Properties
Appearance
White to off-white powder
Safety Data
Symbol
Signal Word
Warning
MSDS Download
Specifications and Other Information of Our BCN-OH CAS 1263166-90-0
Identification Methods
HNMR, GC
Purity
98% min
Shelf Life
1 year
Storage
Store at 2~8℃ for long time
Known Application
BCN-OH, a strained alkyne building block, is a mitochondrial probe based on the lyophilic bidentate bicyclic ligand BCN. The TPP group is a reactive sulfenic acid probe that targets mitochondria. It is primarily used in copper-free click chemistry and is commonly used for protein and antibody labeling and the preparation of bioprobes.
1. Biomolecule Modification and Labeling
Protein/Antibody Labeling: BCN-OH derivatives are conjugated to azide-modified proteins or antibodies for imaging, diagnostics, or drug-drug conjugates (ADCs).
Nucleic Acid and Carbohydrate Labeling: Conjugation to azide-modified oligonucleotides or polysaccharides for tracking or functionalization.
2. Drug Delivery and Nanomaterials
Drug conjugates: They can serve as carriers for linking small molecule drugs to targeting vectors (e.g., antibodies or peptides) via click reactions.
Nanoparticle Surface Modification: BCN-OH can be used to modify the surfaces of polymers, liposomes, or quantum dots, and then conjugated with azides for precise targeted delivery.
3. Materials Science
Polymer Chemistry: Used as a monomer or cross-linker to construct functionalized polymers or hydrogels.
Surface Modification: BCN groups are introduced onto glass, metal, and polymer surfaces, followed by click reactions with azides to achieve surface functionalization (e.g., biosensors and chips).
4. Diagnostics and Imaging
Fluorescent Probes: Highly sensitive probes are obtained through click coupling with azide-containing fluorophores.
Radioactive Probes: In molecular imaging, they are coupled with azide-containing radiolabels for PET/SPECT imaging.
5. Research Tools
Metabolic Labeling: Azide-modified compounds (e.g., azidosugars) are introduced into cellular metabolism and then coupled with BCN to track cellular metabolic pathways.
Protein Interaction Studies: Used as a cross-linking reagent to help immobilize or pull down target complexes.
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Links
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