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

N-Hydroxysuccinimide (NHS) activates carboxylic acid groups (on biotin) to facilitate coupling reactions. Biotin-NHS is a compound used to attach biotin to primary amines under alkaline conditions (pH~8-9). For example, lysines on the surface of proteins, including antibodies, are ideal targets for biotinylation with this compound.

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 35013-72-0 differently. You can refer to the following data:
1. amine reactive biotinylation reagent
2. Biotin-NHS is used in the biotinylation of proteins and peptides. Couples with primary amine in the pH range 6.5-8.5.
3. Amino reactive biotin reagent for preparing biotinylated surfaces or polypeptides.

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

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

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 
• 184296-68-2 (2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-carboxylic acid {2-[5-((3aR,6S,6aS)-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-ethyl}-amide 
• 188584-23-8 5-((3aR,6S,6aS)-2-Oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoic acid undec-10-ynylamide 
• 188257-55-8 N-biotinyl-(4,4'-dimethoxytrityloxymethyl)-5-(hydroxymethyl)benzylamine 
• 402725-75-1 12-benzylthiododecanoic-(8-biotinoylamido-3,6-dioxaoctyl)amide 
• 440359-01-3 N-[3-(N-cholesteryl-2-nitrobenzenesulfonamido)propyl]biotinamide 
• 183896-00-6 N-(13-amino-4,7,10-trioxatridecanyl)-D-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 
• 773888-45-2 N-(prop-2-ynyl)biotinamide 
• 6929-40-4 4-[5-(2-oxohexahydrothieno[3,4-d]imidazol-6-yl)pentanoylamino]benzoic acid 
• 576-19-2 biocytin 

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.