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

Synonyms

(2,5-dioxopyrrolidin-1-yl) 3-[2-[3-(2,5-dioxopyrrol-1-yl)propanoylamino]ethoxy]propanoate;2,5-dioxopyrrolidin-1-yl 3-(2-(3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanamido)ethoxy)propanoate

IUPAC Name

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

Canonical SMILES

C1CC(=O)N(C1=O)OC(=O)CCOCCNC(=O)CCN2C(=O)C=CC2=O

InChI

InChI=1S/C16H19N3O8/c20-11(5-8-18-12(21)1-2-13(18)22)17-7-10-26-9-6-16(25)27-19-14(23)3-4-15(19)24/h1-2H,3-10H2,(H,17,20)

InChIKey

QXGYXAOYQWRQRZ-UHFFFAOYSA-N

Appearance

Soild powder

Shipping

Room temperature, or blue ice upon request.

Storage

- 20 °C for long term storage

Mal-PEG-NHS is a versatile reagent used extensively in bioconjugation applications, particularly for the attachment of various biomolecules to surfaces or other molecules. The compound features a maleimide (Mal) group, which enables selective conjugation to thiol-containing molecules such as proteins, antibodies, or peptides. The polyethylene glycol (PEG) spacer improves solubility, stability, and biocompatibility, while the NHS (N-hydroxysuccinimide) ester group facilitates efficient coupling with amine-containing biomolecules, making this reagent ideal for applications in drug delivery, diagnostics, and molecular labeling.

A key application of Mal-PEG-NHS is in the development of antibody-drug conjugates (ADCs) for targeted cancer therapy. In this context, the NHS ester reacts with amine groups on monoclonal antibodies, allowing for the attachment of cytotoxic drugs or therapeutic molecules. The maleimide group facilitates conjugation to thiol-containing molecules, such as antibodies or peptides, while the PEG spacer ensures increased solubility and improved pharmacokinetics. This results in the enhanced stability of the conjugate in circulation and the targeted delivery of potent therapeutic agents to tumor cells, minimizing off-target effects and improving efficacy.

Mal-PEG-NHS is also widely used in diagnostic applications, particularly in the development of imaging agents and biosensors. By coupling imaging molecules to antibodies or peptides via the NHS ester group, Mal-PEG-NHS enables the precise targeting of disease biomarkers. The PEG spacer ensures solubility and reduces nonspecific binding, improving the sensitivity and accuracy of diagnostic assays. This is particularly valuable in molecular imaging techniques such as PET (positron emission tomography) or fluorescence-based imaging, where targeted and stable conjugates are essential for reliable detection of diseases such as cancer.

In addition to drug delivery and diagnostics, Mal-PEG-NHS is used in the functionalization of surfaces for biosensor applications. By attaching biomolecules, such as proteins or nucleic acids, to solid surfaces or nanoparticles via the maleimide group, Mal-PEG-NHS enables the development of highly sensitive biosensors. The PEG spacer reduces steric hindrance, allowing for efficient binding of the target biomolecule, while improving the stability and reproducibility of the sensor’s performance. This application is critical for the development of advanced diagnostic tools, including point-of-care devices and personalized medicine technologies.

1. Substance P-modified human serum albumin nanoparticles loaded with paclitaxel for targeted therapy of glioma

Qin Guo, Yifei Lu, Chunhui Ruan, Xinli Chen, Xi He, Lisha Liu, Yujie Zhang, Tao Sun, Yu Zhang, Qinjun Chen, Chen Jiang Acta Pharm Sin B . 2018 Jan;8(1):85-96. doi: 10.1016/j.apsb.2017.09.008.

The blood-brain barrier (BBB) and the poor ability of many drugs to cross that barrier greatly limits the efficacy of chemotherapies for glioblastoma multiforme (GBM). The present study exploits albumin as drug delivery vehicle to promote the chemotherapeutic efficacy of paclitaxel (PTX) by improving the stability and targeting efficiency of PTX/albumin nanoparticles (NPs). Here we characterize PTX-loaded human serum albumin (HSA) NPs stabilized with intramolecular disulfide bonds and modified with substance P (SP) peptide as the targeting ligand. The fabricated SP-HSA-PTX NPs exhibited satisfactory drug-loading content (7.89%) and entrapment efficiency (85.7%) with a spherical structure (about 150 nm) and zeta potential of -12.0 mV. Thein vitrodrug release from SP-HSA-PTX NPs occurred in a redox-responsive manner. Due to the targeting effect of the SP peptide, cellular uptake of SP-HSA-PTX NPs into brain capillary endothelial cells (BCECs) and U87 cells was greatly improved. The low IC50, prolonged survival period and the obvious pro-apoptotic effect shown by TUNEL analysis all demonstrated that the fabricated SP-HSA-PTX NPs showed a satisfactory anti-tumor effect and could serve as a novel strategy for GBM treatment.

2. CXCL12/CXCR4 Axis-Targeted Dual-Functional Nano-Drug Delivery System Against Ovarian Cancer

Dingding Gao, Fenghua Chen, Ruixiang Li, Jiyang Xue, Hongjuan Xie Int J Nanomedicine . 2020 Aug 7;15:5701-5718. doi: 10.2147/IJN.S257527.

Introduction:Traditional chemotherapy for ovarian cancer is limited due to drug resistance and systemic side effects. Although various targeted drug delivery strategies have been designed to enhance drug accumulation at the tumor site, simply improvement of targeting capability has not consistently led to satisfactory outcomes. Herein, AMD3100 was selected as the targeting ligand because of its high affinity to chemokine receptor 4 (CXCR4), which was highly expressed on ovarian cancer cells. Moreover, the AMD3100 has been proved having blockage capability of stromal cell-derived factor 1 (SDF-1 or CXCL12)/CXCR4 axis and to be a sensitizer of chemotherapeutic therapy. We designed a dual-functional targeting delivery system by modifying paclitaxel (PTX)-loaded PEGylation bovine serum albumin (BSA) nanoparticles (NPs) with AMD3100 (AMD-NP-PTX), which can not only achieve specific tumor-targeting efficiency but also enhance the therapeutic outcomes.Methods:AMD3100 was chemically modified to Mal-PEG-NHS followed by reacting with BSA, then AMD-NP-PTX was synthesized and characterized. The targeting efficiency of AMD-NP was evaluated both in vitro and in vivo. The anticancer effect of AMD-NP-PTX was determined on Caov3 cells and ovarian cancer-bearing nude mice. Finally, the potential therapeutic mechanism was studied.Results:AMD-NP-PTX was synthesized successfully and well characterized. Cellular uptake assay and in vivo imaging experiments demonstrated that NPs could be internalized by Caov3 cells more efficiently after modification of AMD3100. Furthermore, the AMD-NP-PTX exhibited significantly enhanced inhibition effect on tumor growth and metastasis compared with PTX, NP-PTX and free AMD3100 plus NP-PTX both in vitro and in vivo, and demonstrated improved safety profile. We also confirmed that AMD-NP-PTX worked through targeting CXCL12/CXCR4 axis, thereby disturbing its downstream signaling pathways including epithelial-mesenchymal transition (EMT) processes and nuclear factor κB (NF-κB) pathway.Conclusion:The AMD-NP-PTX we designed would open a new avenue for dual-functional NPs in ovarian cancer therapy.

3. Trastuzumab Targeted Neratinib Loaded Poly-Amidoamine Dendrimer Nanocapsules for Breast Cancer Therapy

Manar Alghamdi, Hosam Gharib Abdelhady, Fadilah Sfouq Aleanizy, Bushra Alquadeib, Hamad Alkahtani, Nora Al Khalil, Sara Seto, Qamraa Hamad Alqahtani, Fulwah Yahya Alqahtani, Amal Aldarwesh, Ibrahim Alsarra, Lama Aleshaiwi Int J Nanomedicine . 2020 Jul 30;15:5433-5443. doi: 10.2147/IJN.S256898.

Background:Human epidermal growth factor receptor2 (Her2) positive breast cancer represents 25% of breast cancer cases. Targeted therapy with Her2 monoclonal antibody, trastuzumab (TZ), represents the first-line treatment for this type of breast cancer. In addition, neratinib, an irreversible inhibitor of the HER-2 receptor tyrosine kinase, has recently been approved as adjuvant therapy to TZ. This study aims to formulate (TZ)-grafted dendrimers loaded with neratinib, allowing a dual treatment alongside reducing the associated resistance as well as targeted therapy.Methods:TZ was conjugated on the surface of dendrimer using hetero-cross linker, MAL-PEG-NHS, and the zeta potential, and in vitro release of neratinib from dendrimers was characterized. Formulated dendrimers were also fluorescently conjugated with fluorescein isothiocyanate to visualize and quantify their SKBR-3 cellular uptake.Results:The G4 PAMAM dendrimer showed successful encapsulation of neratinib and a sustained release profile. Comparative in vitro studies revealed that these TZ-targeted dendrimers loaded with neratinib were more selective and have higher antiproliferation activity against SKBR-3 cells compared to neratinib alone and neratinib loaded dendrimer.Conclusion:In the current study, neratinib loaded in plain and trastuzumab-grafted dendrimer were successfully prepared. Enhanced cellular uptake of trastuzumab conjugated dendrimers was shown, together with a higher cytotoxic effect than plain neratinib dendrimers. These findings suggest the potential of TZ-conjugated dendrimers as targeting carrier for cytotoxic drugs, including neratinib.

Catalog	Product Name	CAS
BADC-00442	Mal-PEG6-NHS	1137109-21-7
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
BADC-00499	Mal-PEG6-NHS ester	1599472-25-9