Name: Mal-PEG6-NHS ester
Brand: BOC Sciences
Rating: 5 (1 reviews)

Synonyms

Mal-PEG6-NHS; 2,5-dioxopyrrolidin-1-yl 1-(2,5-dioxo-2H-pyrrol-1(5H)-yl)-3,6,9,12,15,18-hexaoxahenicosan-21-oate; 4,7,10,13,16,19-Hexaoxaheneicosanoic acid, 21-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-, 2,5-dioxo-1-pyrrolidinyl ester; 1-{21-[(2,5-Dioxo-1-pyrrolidinyl)oxy]-21-oxo-3,6,9,12,15,18-hexaoxahenicos-1-yl}-1H-pyrrole-2,5-dione; 1H-Pyrrole-2,5-dione, 1-[21-[(2,5-dioxo-1-pyrrolidinyl)oxy]-21-oxo-3,6,9,12,15,18-hexaoxaheneicos-1-yl]-

IUPAC Name

(2,5-dioxopyrrolidin-1-yl) 3-[2-[2-[2-[2-[2-[2-(2,5-dioxopyrrol-1-yl)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]propanoate

Canonical SMILES

C1CC(=O)N(C1=O)OC(=O)CCOCCOCCOCCOCCOCCOCCN2C(=O)C=CC2=O

InChI

InChI=1S/C23H34N2O12/c26-19-1-2-20(27)24(19)6-8-32-10-12-34-14-16-36-18-17-35-15-13-33-11-9-31-7-5-23(30)37-25-21(28)3-4-22(25)29/h1-2H,3-18H2

InChIKey

UUNUCVXNAHYFJP-UHFFFAOYSA-N

Density

1.32±0.1 g/cm3 (Predicted)

Solubility

Soluble in DCM, DMSO

Appearance

Pale Yellow Oily Matter

Shipping

Room temperature

Storage

Store at 2-8°C

Boiling Point

635.8±65.0°C (Predicted)

Mal-PEG6-NHS ester is a multifunctional reagent widely used in the fields of drug delivery, diagnostics, and biomolecule labeling. The compound features a maleimide (Mal) group, which enables selective conjugation with thiol-containing molecules, such as peptides, proteins, and antibodies. The PEG6 spacer improves the solubility and stability of the conjugate in aqueous solutions, which is crucial for enhancing the pharmacokinetics of drug conjugates. The NHS ester group allows efficient coupling to amine-containing molecules, making Mal-PEG6-NHS ester a valuable tool in the development of antibody-drug conjugates (ADCs), peptide-based therapies, and molecular diagnostics.

One of the most prominent applications of Mal-PEG6-NHS ester is in the creation of antibody-drug conjugates (ADCs) for targeted cancer therapy. By attaching cytotoxic drugs or small molecule payloads to monoclonal antibodies through the NHS ester, Mal-PEG6-NHS ester enables the targeted delivery of potent therapeutic agents directly to tumor cells. The maleimide group reacts with thiol-containing antibodies or proteins, while the PEG6 spacer ensures increased solubility, reducing immunogenicity and improving circulation time in the bloodstream. This targeted approach minimizes off-target toxicity and enhances the therapeutic efficacy of chemotherapy drugs.

Mal-PEG6-NHS ester is also highly effective in the development of peptide-drug conjugates (PDCs), which are used for the delivery of small molecules or bioactive agents to specific targets. The PEG6 spacer provides excellent solubility and stability, ensuring that the conjugates remain biologically active over extended periods. The NHS ester facilitates the coupling of drugs to peptides via amine groups, which allows for precise control over the release and delivery of the therapeutic agents. This application is particularly beneficial in precision medicine, where customized drug delivery systems are needed for effective treatment with minimal side effects.

In addition to its role in drug delivery, Mal-PEG6-NHS ester is widely utilized in molecular imaging and diagnostic applications. By conjugating antibodies or peptides to imaging agents, this compound enables the precise targeting of disease biomarkers for enhanced imaging accuracy. The PEG6 spacer helps improve the pharmacokinetic properties of the conjugates, ensuring better tissue penetration and prolonged circulation. The NHS ester reacts efficiently with amine groups, allowing for the creation of stable conjugates that are ideal for applications such as positron emission tomography (PET), magnetic resonance imaging (MRI), or fluorescence-based detection. This makes Mal-PEG6-NHS ester an essential tool for both in vivo imaging and diagnostic studies.

1. Lactose esters: synthesis and biotechnological applications

Maciej Guzik, Jakub Staroń, Janusz M Dąbrowski, Ewelina Cichoń 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. Catalytic antibodies

A Tramontano, R A Lerner, K D Janda 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.

3. [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.

Catalog	Product Name	CAS
BADC-00442	Mal-PEG6-NHS	1137109-21-7
BADC-00448	Mal-PEG-NHS	1260092-50-9
BADC-00443	Mal-PEG5-NHS	1315355-92-0
BADC-00450	Mal-PEG4-NHS	1325208-25-0
BADC-01679	Mal-PEG2-Val-Cit-PABA-PNP	1345681-52-8
BADC-00936	Mal-PEG2-acid	1374666-32-6
BADC-00449	Mal-PEG4-PFP	1415800-42-8
BADC-00453	Mal-PEG2-NHS ester	1433997-01-3
BADC-00603	Mal-PEG3-NHS ester	1537892-36-6
BADC-00966	Mal-PEG4-VC-PAB-DMEA	1569261-93-3