35013-72-0

Basic information

• Product Name: BIOTIN-NHS
• Synonyms: SUCCINIMIDO-(+)-BIOTIN;SUCCINIMIDYL D-BIOTIN;N-HYDROXYSUCCINIMIDOBIOTIN;NHS-BIOTIN;NHS-D-BIOTIN;N-SUCCINIMIDYL D-BIOTINATE;N-SUCCINIMIDO-(+)-BIOTIN;5-(2-OXO-HEXAHYDRO-THIENO[3,4-D]IMIDAZOL-6-YL)-PENTANOIC ACID 2,5-DIOXO-PYRROLIDIN-1-YL ESTER
• CAS NO: 35013-72-0
• Molecular Formula: C₁₄H₁₉N₃O₅S
• Molecular Weight: 341.38
• EINECS: 1592732-453-0
• Product Categories: Biotin Derivatives;Cross Linking Reagents;BiotinylationReagents;Biotinylation Reagents;biotinyl
• Mol File: 35013-72-0.mol
• Article Data: 19

Chemical Properties

• Melting Point: 212-214 °C
• Appearance: White to off-white/powder
• Density: 1.45 g/cm³
• Refractive Index: 1.616
• Storage Temp.: −20°C
• Solubility: DMF: ≤50 mg/mL Stable for at least one month in dry D
• PKA: 13.89±0.40(Predicted)
• Stability: Stable. Incompatible with strong oxidizing agents.
• BRN: 4720781
• CAS DataBase Reference: BIOTIN-NHS(CAS DataBase Reference)
• NIST Chemistry Reference: BIOTIN-NHS(35013-72-0)
• EPA Substance Registry System: BIOTIN-NHS(35013-72-0)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 10-23
• Hazardous Substances Data: 35013-72-0(Hazardous Substances Data)

Usage

Description

BIOTIN-NHS, also known as N-Hydroxysuccinimide activated biotin, is a compound used to attach biotin to primary amines under alkaline conditions. It is a white solid that activates carboxylic acid groups on biotin, facilitating coupling reactions. BIOTIN-NHS is particularly useful for biotinylating proteins, peptides, and preparing biotinylated surfaces or polypeptides.

Uses

Used in Biochemical Research:
BIOTIN-NHS is used as an amine reactive biotinylation reagent for the biotinylation of proteins and peptides. It couples with primary amines in the pH range of 6.5-8.5, making it an essential tool in various biochemical research applications.
Used in Diagnostics and Detection:
In the diagnostics industry, BIOTIN-NHS is used as a biotinylation agent to create biotinylated probes, which can be used for the detection and identification of specific target molecules in various diagnostic assays.
Used in Drug Delivery Systems:
BIOTIN-NHS can be employed in the development of targeted drug delivery systems, where biotinylated molecules can be used to specifically bind to receptors or other molecular targets on the surface of cells, enhancing the selectivity and efficacy of drug delivery.
Used in Surface Functionalization:
In the materials science and engineering industry, BIOTIN-NHS is used as an amino reactive biotin reagent for preparing biotinylated surfaces. These surfaces can be utilized in various applications, such as biosensors, cell culture substrates, and immobilization of biomolecules for analytical purposes.
Used in Immunoassays:
In the biotechnology industry, BIOTIN-NHS is used as a key component in the development of immunoassays, where biotinylated antibodies or other binding molecules can be employed for the detection and quantification of specific analytes.

Purification Methods

Recrystallise the ester from refluxing isoPrOH and dry it in a vacuum over P2O5 + KOH. [Jasiewicz et al. Exp Cell Biol 100 213 1976.]

InChI:InChI=1/C14H19N3O5S/c18-10-5-6-11(19)17(10)22-12(20)4-2-1-3-9-13-8(7-23-9)15-14(21)16-13/h8-9,13H,1-7H2,(H2,15,16,21)/t8-,9-,13-/m0/s1

Upstream product

• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 101187-31-9 (3aS,4S,6aR)-4-[5-(1H-imidazol-1-yl)-5-oxopentyl]tetrahydro-1H-thieno-[3,4-d]imidazol-2(3H)-one 
• 105832-38-0 O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 
• 58-85-5 biotin 
• 74124-79-1 di(succinimido) carbonate 

Downstream Products

• 175885-18-4 tert-butyl-N-(2-(2-(2-(5-(2-oxo-1,3,3a,4,6,6a-hexahydrothieno(3,4-d)imidazol-6-yl)pentanoylamino)ethoxy)ethoxy)ethyl)carbamate 
• 576-19-2 biocytin 
• 1001060-43-0 (3S,6S,10aS)-6-((S)-2-(methylamino)propanamido)-5-oxo-N-((S)-(4-(3-(6-(5-((3aS,rS,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido)hexanamido)propyl)phenyl)(phenyl)methyl)decahydropyrrolo[1,2-a]azocine-3-carboxamide 
• 1175002-26-2 biotin-LPRT-OMe 
• 1112265-71-0 biotinyl-2-aminoethyl methacrylate 
• 6929-40-4 4-[5-(2-oxohexahydrothieno[3,4-d]imidazol-6-yl)pentanoylamino]benzoic acid 
• 908007-17-0 N-(3-azidopropyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide 
• 773888-45-2 N-(prop-2-ynyl)biotinamide 
• 918300-29-5 diethyl 2,2’-((5-((2-(5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido)ethyl)carbamoyl)-1,3-phenylene)bis(oxy))diacetate 
• 183896-00-6 N-(13-amino-4,7,10-trioxatridecanyl)-D-biotinamide 
• 440359-01-3 N-[3-(N-cholesteryl-2-nitrobenzenesulfonamido)propyl]biotinamide 
• 402725-75-1 12-benzylthiododecanoic-(8-biotinoylamido-3,6-dioxaoctyl)amide 

Relevant articles and documents

Synthesis and properties of a biotin-tagged NHC-gold complex

The first synthesis of a biotin-tagged NHC-gold complex is described. The key step is the coupling of alkyne-substituted biotin derivative 4b with azido-imidazolium salt 8a by copper-catalyzed azide alkyne cycloaddition (CuAAC). Gold complex 2 catalyzes the cycloisomerization of α-hydroxyallenes to 2,5-dihydrofurans.

Synthesis and Avidin Binding of Ruthenium Complexes Functionalized with a Light-Cleavable Free Biotin Moiety

In this work the synthesis, photochemistry, and streptavidin interaction of new [Ru(tpy)(bpy)(SRR′)](PF6)2 complexes where the R′ group contains a free biotin ligand, are described. Two different ligands SRR′ were investigated: An asymmetric ligand 1 where the Ru-bound thioether is a N-acetylmethionine moiety linked to the free biotin fragment via a triethylene glycol spacer and a symmetrical ligand 2 containing two identical biotin moieties. The coordination of these two ligands to the precursor [Ru(tpy)(bpy)Cl]Cl was studied in water at 80 °C. In such conditions the coordination of the asymmetric ligand 1 occurred under thermodynamic control. After the reaction, a mononuclear and a binuclear complex were isolated. In the mononuclear complex, the ratio of methionine- {[6](PF6)2} vs. biotin-bound {[7](PF6)2} regioisomer was 5.3 and the free biotin fragment of [6](PF6)2 allowed to purify it from its isomer [7](PF6)2 at small scales using avidin affinity chromatography. Coordination of the symmetrical ligand 2 afforded [Ru(tpy)(bpy)(2)](PF6)2 {[8](PF6)2} in synthetically useful scales (100 mg), good yield (82 %), and without traces of the binuclear impurity. In this complex, one of the biotin remains free whereas the second one is coordinated to ruthenium. Photochemical release of ligand 2 from [8](PF6)2 occurred upon blue light irradiation (465 nm) with a photosubstitution quantum yield of 0.011 that was independent of the binding of streptavidin to the free biotin ligand.

Carbohydrate dependent targeting of cancer cells by bleomycin-microbubble conjugates

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Synthesis of Na2S2O4 mediated cleavable affinity tag for labeling of O-GlcNAc modified proteins via azide-alkyne cycloaddition

A facile and convergent procedure for the synthesis of azobenzene-based probe was reported, which could selectively release interested proteins conducted with sodium dithionite. Besides, the cleavage efficiency is closely associated with the structural features, in which an ortho-hydroxyl substituent is necessary for reactivity. In addition, the azobenzene tag applied in the Ac4GlcNAz-labled proteins demonstrated high efficiency and selectivity in comparison with Biotin-PEG4-Alkyne, which provides a useful platform for enrichment of any desired bioorthogonal proteomics.

THERAPY

The invention generally relates to sonodynamic therapy using microbubble-sonosensitiser complexes and, more specifically, to such therapy for the treatment of deeply-sited tumours and associated metastatic disease. In particular, the invention relates to a combination therapy in which sonodynamic treatment of deeply-sited tumours with microbubble-sonosensitiser complexes is combined with treatment using immune checkpoint inhibitors. It further relates to methods of sonodynamic therapy in which a sonodynamic-induced abscopal response modulates a systemic regression of metastatic disease. In such methods the abscopal response may be further enhanced by co-administration of an immune checkpoint inhibitor. The invention is particularly suitable for the treatment of pancreatic cancer (e.g. pancreatic ductal adenocarcinoma) and associated metastasis.