Name: DBCO-NHS ester
Brand: BOC Sciences
Price: 1344 USD
Availability: MadeToOrder

Size

Price

Stock

Quantity

1 g

$1344

In stock

Synonyms

DBCO-NHS;N-Succinimidyl 4-[(5-Aza-3,4:7,8-dibenzocyclooct-1-yne)-5-yl]-4-oxobutyrate

IUPAC Name

Canonical SMILES

C1CC(=O)N(C1=O)OC(=O)CCC(=O)N2CC3=CC=CC=C3C#CC4=CC=CC=C42

InChI

InChI=1S/C23H18N2O5/c26-20(13-14-23(29)30-25-21(27)11-12-22(25)28)24-15-18-7-2-1-5-16(18)9-10-17-6-3-4-8-19(17)24/h1-8H,11-15H2

InChIKey

XCEBOJWFQSQZKR-UHFFFAOYSA-N

Solubility

DMSO: 100 mg/ml (24851 mm, need ultrasonic)

PSA

83.99000

Appearance

White powder

Shipping

-20°C (International: -20°C)

Storage

Keep in freezer under -20 °C upon receipt of the product.

DBCO-NHS ester, a highly reactive compound utilized for bioconjugation in biosciences, offers a multitude of applications. Here are four key applications:

Bioconjugation: Widely embraced for its proficiency in conjugating proteins, peptides, and other biomolecules, DBCO-NHS ester forms amide bonds with primary amines on the target molecule, facilitating the attachment of diverse tags, dyes, or functional groups. This process plays a pivotal role in advancing diagnostic assays, drug delivery systems, and therapeutic proteins, serving as a cornerstone for cutting-edge biomedical innovations.

Surface Functionalization: Embracing the versatility of DBCO-NHS ester, researchers can modify the surfaces of nanoparticles, hydrogels, and various materials for a spectrum of biomedical applications. By attaching specific ligands or biomolecules, they elevate the targeting precision, biocompatibility, and functionality of these materials, catalyzing the creation of precise drug delivery systems and biosensors tailored for intricate medical scenarios.

Click Chemistry: At the heart of dynamic biological exploration lies DBCO-NHS ester, a vital component in strain-promoted alkyne-azide cycloaddition (SPAAC), an intricate bioorthogonal “click” reaction. This precise mechanism enables the specific and efficient labeling of biomolecules without disrupting native biological processes, granting scientists unparalleled insight into the dynamic inner workings of live cells and organisms through sophisticated imaging, tracking, and study methodologies.

Immunoassays: In the realm of immunoassays, DBCO-NHS ester takes center stage, facilitating the covalent linkage of antibodies to various labeled probes, like fluorescent dyes or enzymes. This robust conjugation technique enables the detection and quantification of specific antigens within complex samples, heightening assay sensitivity and accuracy.

1. Catalytic antibodies

R A Lerner, K D Janda, A Tramontano Science . 1986 Dec 19;234(4783):1566-70. doi: 10.1126/science.3787261.

Monoclonal antibodies elicited to haptens that are analogs of the transition state for hydrolysis of carboxylic esters behaved as enzymic catalysts with the appropriate substrates. These substrates are distinguished by the structural congruence of both hydrolysis products with haptenic fragments. The haptens were potent inhibitors of this esterolytic activity, in agreement with their classification as transition state analogs. Mechanisms are proposed to account for the different chemical behavior of these antibodies with two types of ester substrates. The generation of an artificial enzyme through transition state stabilization by antibodies was thus demonstrated. These studies indicate a potentially general approach to catalyst design.

2. α-Imino Esters in Organic Synthesis: Recent Advances

Maryam Zirak, Bagher Eftekhari-Sis Chem Rev . 2017 Jun 28;117(12):8326-8419. doi: 10.1021/acs.chemrev.7b00064.

α-Imino esters are useful precursors for the synthesis of a variety of types of natural and unnatural α-amino acid derivatives, with a wide range of biological activities. Due to the adjacent ester group, α-imino esters are more reactive relative to other types of imines and undergo different kinds of reactions, including organometallics addition, metal catalyzed vinylation and alkynylation, aza-Henry, aza-Morita-Baylis-Hillman, imino-ene, Mannich-type, and cycloaddition reactions, as well as hydrogenation and reduction. This review discusses the mechanism, scope, and applications of the reactions of α-imino esters and related compounds in organic synthesis, covering the literature from the last 12 years.

3. A Ketone Ester Drink Lowers Human Ghrelin and Appetite

Kieran Clarke, Malgorzata Cyranka, Brianna J Stubbs, Pete J Cox, Rhys D Evans, Heidi de Wet Obesity (Silver Spring) . 2018 Feb;26(2):269-273. doi: 10.1002/oby.22051.

Objective:The ketones d-β-hydroxybutyrate (BHB) and acetoacetate are elevated during prolonged fasting or during a "ketogenic" diet. Although weight loss on a ketogenic diet may be associated with decreased appetite and altered gut hormone levels, it is unknown whether such changes are caused by elevated blood ketones. This study investigated the effects of an exogenous ketone ester (KE) on appetite.Methods:Following an overnight fast, subjects with normal weight (n = 15) consumed 1.9 kcal/kg of KE, or isocaloric dextrose (DEXT), in drinks matched for volume, taste, tonicity, and color. Blood samples were analyzed for BHB, glucose, insulin, ghrelin, glucagon-like peptide 1 (GLP-1), and peptide tyrosine tyrosine (PYY), and a three-measure visual analogue scale was used to measure hunger, fullness, and desire to eat.Results:KE consumption increased blood BHB levels from 0.2 to 3.3 mM after 60 minutes. DEXT consumption increased plasma glucose levels between 30 and 60 minutes. Postprandial plasma insulin, ghrelin, GLP-1, and PYY levels were significantly lower 2 to 4 hours after KE consumption, compared with DEXT consumption. Temporally related to the observed suppression of ghrelin, reported hunger and desire to eat were also significantly suppressed 1.5 hours after consumption of KE, compared with consumption of DEXT.Conclusions:Increased blood ketone levels may directly suppress appetite, as KE drinks lowered plasma ghrelin levels, perceived hunger, and desire to eat.