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Mal-amido-PEG8-acid

  CAS No.: 1334177-86-4   Cat No.: BADC-00584   Purity: >97% 4.5  

Mal-amido-PEG8-acid is a PEG derivative containing a maleimide group and a terminal carboxylic acid. The hydrophilic PEG spacer increases solubility in aqueous media. The terminal carboxylic acid can be reacted with primary amine groups in the presence of activators (e.g. EDC, or DCC) to form a stable amide bond. The maleimide group will react with a thiol group to form a covalent bond, enabling the connection of biomolecule with a thiol.

Mal-amido-PEG8-acid

Structure of 1334177-86-4

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ADC Linker
Molecular Formula
C26H44N2O13
Molecular Weight
592.63
Shipping
-20°C (International: -20°C)
Shipping
Store at -18°C

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Popular Publications Citing BOC Sciences Products
Synonyms
Mal-amido-PEG8-C2-acid; 3-[2-[2-[2-[2-[2-[2-[2-[2-[3-(2,5-dioxopyrrol-1-yl)propanoylamino]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid
IUPAC Name
3-[2-[2-[2-[2-[2-[2-[2-[2-[3-(2,5-dioxopyrrol-1-yl)propanoylamino]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid
Canonical SMILES
C1=CC(=O)N(C1=O)CCC(=O)NCCOCCOCCOCCOCCOCCOCCOCCOCCC(=O)O
InChI
InChI=1S/C26H44N2O13/c29-23(3-6-28-24(30)1-2-25(28)31)27-5-8-35-10-12-37-14-16-39-18-20-41-22-21-40-19-17-38-15-13-36-11-9-34-7-4-26(32)33/h1-2H,3-22H2,(H,27,29)(H,32,33)
InChIKey
ARKUDJPBDMAVBL-UHFFFAOYSA-N
PSA
177.62000
Appearance
Solid powder
Shipping
-20°C (International: -20°C)
Storage
Store at -18°C

Mal-amido-PEG8-acid is a versatile compound used extensively in biochemical and pharmaceutical research due to its unique properties. Here are some key applications of Mal-amido-PEG8-acid:

Bioconjugation: Mal-amido-PEG8-acid is often used in bioconjugation to link biomolecules, such as proteins and peptides, with various labels or carriers. Its maleimide group specifically reacts with thiol groups to form stable thioether bonds, making it ideal for creating targeted drug delivery systems. This application is crucial for developing novel therapeutics where precise molecular alignment is essential.

Drug Delivery Systems: In pharmaceutical sciences, Mal-amido-PEG8-acid plays a role in the formation of drug delivery systems. By attaching drugs to PEGylated compounds, it enhances solubility, stability, and bioavailability, leading to improved pharmacokinetic profiles. This approach is especially beneficial for delivering cancer therapeutics, offering targeted action with reduced side effects.

Surface Modification: Mal-amido-PEG8-acid is used to modify surfaces of nanoparticles or medical devices to enhance biocompatibility. Its PEGylation properties help reduce protein adsorption and cellular uptake, minimizing immune recognition and clearance. This application is crucial in developing implants and biosensors with prolonged in vivo stability.

Diagnostics: Mal-amido-PEG8-acid is employed in the design of diagnostic tools, where it facilitates attachment of dyes or markers to molecules. By enabling precise conjugation to antibodies or nucleic acids, it improves the sensitivity and specificity of assays.

1.Feasibility of poly(ethylene glycol) derivatives as diagnostic drug carriers for tumor imaging. J Control Release
Kanazaki K, Sano K, Makino A, Yamauchi F, Takahashi A, Homma T, Ono M, Saji H.
Poly(ethylene glycol) (PEG) is an artificial but biocompatible hydrophilic polymer that has been widely used in clinical products. To evaluate the feasibility of using PEG derivative itself as a tumor imaging carrier via an enhanced permeability and retention (EPR) effect, we prepared indium-111-labeled PEG ((111)In-DTPA-PEG) and indocyanine green (ICG)-labeled PEG (ICG-PEG) with PEG molecular weights of 5-40kDa and investigated their in vivo biodistribution in colon26 tumor-bearing mice. Thereafter, single-photon emission computed tomography (SPECT) and photoacoustic (PA) imaging studies were performed. The in vivo biodistribution studies demonstrated increased tumor uptake and a prolongation of circulation half-life as the molecular weight of PEG increased. Although the observed differences in in vivo biodistribution were dependent on the labeling method ((111)In or ICG), the tumor-to-normal tissue ratios were comparable. Because PEG-based probes with a molecular weight of 20kDa (PEG20) showed a preferable biodistribution (highest accumulation among tissues excised and relatively high tumor-to-blood ratios), an imaging study using (111)In-DTPA-PEG20 and ICG-PEG20 was performed. Colon26 tumors inoculated in the right shoulder were clearly visualized by SPECT 24h after administration. Furthermore, PA imaging using ICG-PEG20 also detected tumor regions, and the detected PA signals increased in proportion with the injected dose. These results suggest that PEG derivatives (20kDa) serve as robust diagnostic drug carriers for tumor imaging.
2.Gold nanoparticle surface functionalization: mixed monolayer versus hetero bifunctional peg linker
Harrison E, Coulter JA, Dixon D.
To create a clinically relevant gold nanoparticle (AuNP) treatment, the surface must be functionalized with multiple ligands such as drugs, antifouling agents and targeting moieties. However, attaching several ligands of differing chemistries and lengths, while ensuring they all retain their biological functionality remains a challenge. This review compares the two most widely employed methods of surface cofunctionalization, namely mixed monolayers and hetero-bifunctional linkers. While there are numerous in vitro studies successfully utilizing both surface arrangements, there is little consensus regarding their relative merits. Animal and preclinical studies have demonstrated the effectiveness of mixed monolayer functionalization and while some promising in vitro results have been reported for PEG linker capped AuNPs, any potential benefits of the approach are not yet fully understood.
3.Solution conformation of the extracellular domain of the human tumor necrosis factor receptor probed by Raman and UV-resonance Raman spectroscopy: structural effects of an engineered PEG linker. Biochemistry
Tuma R, Russell M, Rosendahl M, Thomas GJ Jr.
The solution structure of the Escherichia coli-expressed extracellular domain, residues 12-172, of the human 55 kDa type I tumor necrosis factor receptor (TNFR) has been probed by Raman (514.5 nm) and ultraviolet-resonance Raman (244 nm) excitations. The Raman spectra have been collected from both the free TNFR domain and an engineered "dumbbell-like" derivative, consisting of two mutant receptor moieties linked by a 20 kDa polyethylene glycol (PEG) tether. The results demonstrate a TNFR secondary structure which is rich in beta-sheet and deficient in alpha-helix, consistent with the reported X-ray crystal structure of baculovirus expressed receptor complexed with factor beta [Banner, D. W., D'Arcy, A., Janes, W., Gentz, R., Schoenfeld, H.-J., Broger, C., Loetscher, H., & Lesslauer, W. (1993) Cell 73, 431-445]. Conversely, the solution structure of TNFR differs from the crystal structure in its distribution of disulfide rotamers and in the orientation of its unique indole side chain (tryptophan-107). These differences are attributed, respectively, to N-terminal truncation and factor binding in the TNFR crystal structure. The tryptophan configuration, which is easily monitored in both Raman and UVRR spectra, is proposed as a potential signal of receptor/factor recognition and binding. Application of the Raman probes to the engineered TNFR dumbbell, which is of interest as a potential therapeutic, shows that TNFR moieties of the dumbbell exhibit secondary structures and side chain environments which are indistinguishable from those of the native, wild-type moiety. The results suggest that the PEGylated dumbbell may function as an effective TNFR drug delivery system without the consequence of a deleterious antigenic response.

The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

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