Name: m-C-tri(CH2-PEG1-NHS ester)
Brand: BOC Sciences
Price: 439 USD
Availability: MadeToOrder

Synonyms

bis(2,5-dioxopyrrolidin-1-yl) 3,3'-(2-((3-(2,5-dioxopyrrolidin-1-yloxy)-3-oxopropoxy)methyl)-2-methylpropane-1,3-diyl)bis(oxy)dipropanoate; 3,3',3''-[Ethylidynetris(methyleneoxy)]tris(propionic acid succinimidyl) ester

IUPAC Name

(2,5-dioxopyrrolidin-1-yl) 3-[3-[3-(2,5-dioxopyrrolidin-1-yl)oxy-3-oxopropoxy]-2-[[3-(2,5-dioxopyrrolidin-1-yl)oxy-3-oxopropoxy]methyl]-2-methylpropoxy]propanoate

Canonical SMILES

CC(COCCC(=O)ON1C(=O)CCC1=O)(COCCC(=O)ON2C(=O)CCC2=O)COCCC(=O)ON3C(=O)CCC3=O

InChI

InChI=1S/C26H33N3O15/c1-26(14-39-11-8-23(36)42-27-17(30)2-3-18(27)31,15-40-12-9-24(37)43-28-19(32)4-5-20(28)33)16-41-13-10-25(38)44-29-21(34)6-7-22(29)35/h2-16H2,1H3

InChIKey

IMRQCGBFYSSHHS-UHFFFAOYSA-N

Appearance

Soild powder

Shipping

Room temperature

Storage

-20°C

m-C-tri(CH2-PEG1-NHS ester) is a versatile chemical reagent used primarily for bioconjugation and surface modification applications. Here are some key applications of m-C-tri(CH2-PEG1-NHS ester):

Bioconjugation: m-C-tri(CH2-PEG1-NHS ester) is widely used for the conjugation of biomolecules such as proteins, antibodies, and peptides. The NHS ester group readily reacts with primary amine groups on these biomolecules, forming stable amide bonds. This facilitates the creation of functionalized biomolecule conjugates that can be used in diagnostic assays and therapeutic applications.

Surface Modification: This compound is used in modifying surfaces to improve biocompatibility and prevent nonspecific binding in biomedical devices. By attaching m-C-tri(CH2-PEG1-NHS ester) to surfaces, a hydrophilic PEG layer is formed, which reduces protein adsorption and cell adhesion. This application is vital in the fabrication of biosensors and implantable devices where surface performance is crucial.

Drug Delivery Systems: m-C-tri(CH2-PEG1-NHS ester) is employed in the development of drug delivery systems that require polyethylene glycol (PEG) modification. By conjugating PEG to drug molecules or carriers, the solubility and stability of drugs can be enhanced while also prolonging their circulation time in the bloodstream. This PEGylation process helps in achieving better therapeutic outcomes and reducing immunogenicity.

Nanoparticle Functionalization: In nanotechnology, m-C-tri(CH2-PEG1-NHS ester) is used to functionalize nanoparticles, improving their dispersion and stability in biological systems. The compound enables the attachment of targeting ligands to nanoparticle surfaces, facilitating targeted delivery of therapeutics to specific tissues or cells. This application is important for advancing precision medicine and the efficacy of nanoparticle-based therapies.

1. Lactose esters: synthesis and biotechnological applications

Maciej Guzik, Ewelina Cichoń, Janusz M Dąbrowski, Jakub Staroń Crit Rev Biotechnol . 2018 Mar;38(2):245-258. doi: 10.1080/07388551.2017.1332571.

Biodegradable nonionic sugar esters-based surfactants have been gaining more and more attention in recent years due to their chemical plasticity that enables the various applications of these molecules. In this review, various synthesis methods and biotechnological implications of lactose esters (LEs) uses are considered. Several chemical and enzymatic approaches are described for the synthesis of LEs, together with their applications, i.e. function in detergents formulation and as additives that not only stabilize food products but also protect food from undesired microbial contamination. Further, this article discusses medical applications of LEs in cancer treatment, especially their uses as biosensors, halogenated anticancer drugs, and photosensitizing agents for photodynamic therapy of cancer and photodynamic inactivation of microorganisms.

2. [Evaluation of the Oral Absorption of Ester-type Prodrugs]

Kayoko Ohura Yakugaku Zasshi . 2020;140(3):369-376. doi: 10.1248/yakushi.19-00225.

The first-pass hydrolysis of oral ester-type prodrugs in the liver and intestine is mediated mainly by hCE1 and hCE2 of the respective predominant carboxylesterase (CES) isozymes. In order to provide high blood concentrations of the parent drugs, it is preferable that prodrugs are absorbed as an intact ester in the intestine, then rapidly converted to active parent drugs by hCE1 in the liver. In the present study, we designed a prodrug of fexofenadine (FXD) as a model parent drug that is resistant to hCE2 but hydrolyzed by hCE1, utilizing the differences in catalytic characteristics of hCE1 and hCE2. In order to precisely predict the intestinal absorption of an FXD prodrug candidate, we developed a novel high-throughput system by modifying Caco-2 cells. Further, we evaluated species differences and aging effects in the intestinal and hepatic hydrolysis of prodrugs to improve the estimation of in vivo first-pass hydrolysis of ester-type prodrugs. Consequently, it was possible to design a hepatotropic prodrug utilizing the differences in tissue distribution and substrate specificity of CESs. In addition, we successfully established three useful in vitro systems for predicting the intestinal absorption of hCE1 substrate using Caco-2 cells. However, some factors involved in estimating the bioavailability of prodrugs in human, such as changes in recognition of drug transporters by esterification, and species differences of the first-pass hydrolysis, should be comprehensively considered in prodrug development.

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.

What is m-C-tri(CH2-PEG1-NHS ester) and its primary application in ADC synthesis?

m-C-tri(CH2-PEG1-NHS ester) is a multi-arm polyethylene glycol-based NHS ester designed for site-specific conjugation in antibody-drug conjugates. It facilitates efficient attachment of cytotoxic payloads to antibodies while maintaining solubility and stability of the ADC.

17/5/2022

Dear team, how does m-C-tri(CH2-PEG1-NHS ester) enhance linker stability in ADCs?

The structure of m-C-tri(CH2-PEG1-NHS ester) provides steric shielding and hydrophilic character, reducing aggregation and proteolytic degradation, thus improving overall stability of the ADC during storage and circulation.

12/9/2018

Dear team, what types of payloads can be conjugated using m-C-tri(CH2-PEG1-NHS ester)?

m-C-tri(CH2-PEG1-NHS ester) can react with amine-containing cytotoxins and fluorescent probes, making it compatible with a range of payloads, including auristatins, maytansinoids, and other small molecule drugs.

6/11/2018

Good afternoon! What are the recommended conditions for conjugation using m-C-tri(CH2-PEG1-NHS ester)?

Optimal conjugation with m-C-tri(CH2-PEG1-NHS ester) is achieved in slightly basic aqueous or mixed organic solvents (pH 7.5–8.5) at controlled temperature to ensure high efficiency while minimizing hydrolysis of the NHS ester.

14/5/2019

Good afternoon! What storage conditions and handling precautions are recommended for m-C-tri(CH2-PEG1-NHS ester)?

m-C-tri(CH2-PEG1-NHS ester) should be stored at low temperatures, preferably -20°C, in a dry environment protected from moisture and light. Handling should minimize exposure to humidity and air to prevent hydrolysis of the NHS ester. For long-term stability, aliquoting under inert gas is recommended. Relevant supporting documents including SDS and handling protocols are available upon request.

29/12/2022

— Dr. Kevin Hughes, Biochemist (UK)

m-C-tri(CH2-PEG1-NHS ester) allowed highly efficient ADC linker coupling with excellent stability.

6/11/2018

— Ms. Julia Fischer, Research Scientist (Germany)

Batch consistency and purity of m-C-tri(CH2-PEG1-NHS ester) were excellent, supporting our research deadlines.

29/12/2022

— Dr. Lukas Bauer, Protein Chemist (Germany)

m-C-tri(CH2-PEG1-NHS ester) enabled efficient multi-arm PEGylation of proteins. The batch-to-batch consistency and purity were outstanding.

14/5/2019

— Dr. Lukas Bauer, Protein Chemist (Germany)

BOC Sciences’ m-C-tri(CH2-PEG1-NHS ester) enabled efficient multi-arm PEGylation of proteins. Purity and reactivity met all our project requirements.