Name: Maleimide-NH-PEG4-CH2CH2COOPFP Ester
Brand: BOC Sciences
Rating: 5 (1 reviews)

Synonyms

perfluorophenyl 19-(2,5-dioxo-2H-pyrrol-1(5H)-yl)-17-oxo-4,7,10,13-tetraoxa-16-azanonadecan-1-oate

IUPAC Name

(2,3,4,5,6-pentafluorophenyl) 3-[2-[2-[2-[2-[3-(2,5-dioxopyrrol-1-yl)propanoylamino]ethoxy]ethoxy]ethoxy]ethoxy]propanoate

Canonical SMILES

C1=CC(=O)N(C1=O)CCC(=O)NCCOCCOCCOCCOCCC(=O)OC2=C(C(=C(C(=C2F)F)F)F)F

InChI

InChI=1S/C24H27F5N2O9/c25-19-20(26)22(28)24(23(29)21(19)27)40-18(35)4-7-36-9-11-38-13-14-39-12-10-37-8-5-30-15(32)3-6-31-16(33)1-2-17(31)34/h1-2H,3-14H2,(H,30,32)

InChIKey

SERXRSAEZBDOQG-UHFFFAOYSA-N

Appearance

Soild powder

Shipping

Room temperature, or blue ice upon request.

Storage

Please store the product under the recommended conditions in the Certificate of Analysis.

Maleimide-NH-PEG4-CH2CH2COOPFP Ester is a highly reactive and versatile compound commonly used in bioconjugation for targeted drug delivery and protein labeling. The maleimide group reacts efficiently with thiol groups on biomolecules such as proteins, peptides, or antibodies, allowing for the formation of stable covalent bonds. The PEG4 (polyethylene glycol) spacer provides flexibility and water solubility, enhancing the stability and biocompatibility of the conjugate. The OPFP ester group, which is a reactive electrophilic moiety, facilitates the conjugation of the compound to a wide range of molecules. This reactivity makes Maleimide-NH-PEG4-CH2CH2COOPFP Ester an ideal tool for creating conjugates for drug delivery, diagnostic imaging, and therapeutic applications.

One of the key applications of Maleimide-NH-PEG4-CH2CH2COOPFP Ester is in the development of targeted antibody-drug conjugates (ADCs) for cancer therapy. By attaching cytotoxic drugs to antibodies or peptides through the maleimide linkage, the compound enables the selective delivery of toxic agents to tumor cells. The PEG4 spacer enhances the solubility and circulation half-life of the conjugate, ensuring that the drug reaches the tumor site before being released. The OPFP ester group allows for efficient and controlled conjugation, which can be cleaved or modified as required. This approach helps to minimize off-target toxicity and maximizes the therapeutic effect by delivering the drug directly to the cancer cells. This strategy is particularly useful in treating tumors that overexpress specific cell surface markers.

Another important application of Maleimide-NH-PEG4-CH2CH2COOPFP Ester is in the creation of diagnostic probes for imaging and detection. The maleimide group allows the conjugation of this compound to biomolecules such as peptides or antibodies that target specific tumor-associated antigens. Once conjugated, the compound can be used in imaging techniques such as positron emission tomography (PET) or fluorescence imaging, enabling the precise visualization of tumors in real-time. The PEG4 spacer ensures the conjugate has good solubility and stability in biological environments, which is crucial for in vivo imaging. This application is beneficial for the early detection of cancers, monitoring treatment responses, and assessing tumor localization during surgery.

Maleimide-NH-PEG4-CH2CH2COOPFP Ester is also utilized in the development of peptide-based delivery systems. By attaching therapeutic peptides or nucleic acids to the compound, it is possible to create conjugates with enhanced targeting ability and improved pharmacokinetics. The maleimide group allows for the selective conjugation to cysteine or other thiol-functionalized peptides, while the PEG4 spacer increases the solubility and reduces immunogenicity. This conjugate can be used in gene therapy, protein therapy, or RNA delivery, where targeted delivery to specific tissues or cells is essential for maximizing therapeutic outcomes. The OPFP ester moiety can be used to further modify the conjugates for controlled release or activation, making it a useful tool in drug delivery and gene therapy applications.

1. [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.

2. Safety Assessment of Saccharide Esters as Used in Cosmetics

Ronald A Hill, Ronald C Shank, Paul W Snyder, Thomas J Slaga, Curtis D Klaassen, Donald V Belsito, Bart Heldreth, James G Marks Jr, Daniel C Liebler, Laura N Scott, Wilma F Bergfeld, Lillian J Gill Int J Toxicol . 2021 Oct;40(2_suppl):52S-116S. doi: 10.1177/10915818211016378.

This is a safety assessment of 40 saccharide ester ingredients as used in cosmetics. The saccharide esters are reported to function in cosmetics as emollients, skin-conditioning agents, fragrance ingredients, and emulsion stabilizers. The Expert Panel for Cosmetic Ingredient Safety (Panel) reviewed the relevant data for these ingredients. The Panel concluded that the saccharide esters are safe in cosmetics in the present practices of use and concentrations described in this safety assessment.

3. [Esters and stereoisomers]

V Nigrovic, C Diefenbach, H Mellinghoff Anaesthesist . 1997 Apr;46(4):282-6. doi: 10.1007/s001010050402.

This review discusses concepts of isomers, stereoisomers, chirality, and enantiomers as applied to drugs used in anaesthesia. The inhalational anaesthetics enflurane and isoflurane are examples of stereoisomers. A chiral centre is formed when a carbon or quaternary nitrogen atom is connected to four different atoms. A molecule with one chiral centre is then present in one of two possible configurations termed enantiomers. A racemate is a mixture of both enantiomers in equal proportions. Many of the drugs used in anaesthesia are racemic mixtures (the inhalation anaesthetics, local anaesthetics, ketamine, and others). The shape of the atracurium molecule is comparable to that of a dumb-bell:the two isoquinoline groups representing the two bulky ends connected by an aliphatic chain. In each isoquinoline group there are two chiral centres, one formed by a carbon and the other by a quaternary nitrogen atom. From a geometric point of view, the connections from the carbon atom to a substituted benzene ring and from the quaternary nitrogen to the aliphatic chain may point in the same direction (cis configuration) or in opposite directions (trans configuration). The two isoquinoline groups in atracurium are paired in three geometric configurations: cis-cis, trans-trans, or cis-trans. However, the two chiral centres allow each isoquinoline group to exist in one of four stereoisometric configurations. In the symmetrical atracurium molecule, the number of possible stereoisomers is limited to ten. Among these, 1 R-cis, 1'R-cis atracurium was isolated and its pharmacologic properties studied. This isomer, named cis-atracurium, offers clinical advantages over the atracurium mixture, principally due to the lack of histamine-releasing propensity and the higher neuromuscular blocking potency. The ester groups appear in one of two steric configurations true and reverse esters. In the true esters, oxygen is positioned between the nitrogen atom and the carbonyl group, while in the reverse esters in its positioned on the other side of the carbonyl group. True esters, suxamethonium and mivacurium, are hydrolysed by the enzyme plasma cholinesterase (butyrylcholinesterase), albeit at different rates. The more rapid degradation of suxamethonium is responsible for its fast onset and short duration of action in comparison with mivacurium. The reverse esters, atracurium, cisatracurium, and remifentanil, are hydrolysed by nonspecific esterases in plasma (carboxyesterases). Remifentanil is hydrolysed rapidly; the degradation leads to its inactivation and short duration of action. Cis-atracurium is preferentially degraded and inactivated by a process known as Hofmann elimination. In a second step, one of the degradation products, the monoester acrylate, is hydrolysed by a nonspecific esterase.

Catalog	Product Name	CAS
BADC-00874	Maleimide-DOTA	1006711-90-5
BADC-00440	Maleimide-NH-PEG10-CH2CH2COONHS Ester	1137109-22-8
BADC-00445	Maleimide-NH-PEG3-CH2CH2COOPFP Ester	2101206-13-5
BADC-01270	Maleimide-PEG2-hydrazide TFA