Bromoacetamido-PEG4-NHS ester - CAS 1260139-70-5

Bromoacetamido-PEG4-NHS ester - CAS 1260139-70-5 Catalog number: BADC-00572

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Bromoacetamido-PEG4-NHS ester is a PEG derivative containing a bromide group and an NHS ester. The bromide (Br) is a very good leaving group for nucleophilic substitution reactions. The NHS ester can be used to label the primary amines (-NH2) of proteins, amine-modified oligonucleotides, and other amine-containing molecules. Bromoacetamido-PEG4-NHS ester is a PEGn linker for antibody-drug-conjugation (ADC).

Category
ADCs Linker
Product Name
Bromoacetamido-PEG4-NHS ester
CAS
1260139-70-5
Catalog Number
BADC-00572
Molecular Formula
C17H27BrN2O9
Molecular Weight
483.31
Bromoacetamido-PEG4-NHS ester

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Description
Bromoacetamido-PEG4-NHS ester is a PEG derivative containing a bromide group and an NHS ester. The bromide (Br) is a very good leaving group for nucleophilic substitution reactions. The NHS ester can be used to label the primary amines (-NH2) of proteins, amine-modified oligonucleotides, and other amine-containing molecules. Bromoacetamido-PEG4-NHS ester is a PEGn linker for antibody-drug-conjugation (ADC).
Synonyms
Bromoacetamido-PEG4-C2-NHS ester; BrCH2CONH-PEG4-NHS ester; 2,5-dioxopyrrolidin-1-yl 1-bromo-2-oxo-6,9,12,15-tetraoxa-3-azaoctadecan-18-oate; 2,5-dioxopyrrolidin-1-yl 1-(2-bromoacetamido)-3,6,9,12-tetraoxapentadecan-15-oate; 3-[2-(2-{2-[2-(2-bromo-acetylamino)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester; 4,7,10,13-Tetraoxa-16-azaoctadecanoic acid, 18-bromo-17-oxo-, 2,5-dioxo-1-pyrrolidinyl ester; Acetamide, 2-bromo-N-[15-[(2,5-dioxo-1-pyrrolidinyl)oxy]-15-oxo-3,6,9,12-tetraoxapentadec-1-yl]-; 2-Bromo-N-{15-[(2,5-dioxo-1-pyrrolidinyl)oxy]-15-oxo-3,6,9,12-tetraoxapentadec-1-yl}acetamide
IUPAC Name
(2,5-dioxopyrrolidin-1-yl) 3-[2-[2-[2-[2-[(2-bromoacetyl)amino]ethoxy]ethoxy]ethoxy]ethoxy]propanoate
Canonical SMILES
C1CC(=O)N(C1=O)OC(=O)CCOCCOCCOCCOCCNC(=O)CBr
InChI
InChI=1S/C17H27BrN2O9/c18-13-14(21)19-4-6-26-8-10-28-12-11-27-9-7-25-5-3-17(24)29-20-15(22)1-2-16(20)23/h1-13H2,(H,19,21)
InChIKey
BONNYNBXMCRXBJ-UHFFFAOYSA-N
Density
1.4±0.1 g/cm3
Solubility
Soluble in DMSO
Appearance
Solid powder
Purity
>95%
Shipping
Room temperature, or blue ice upon request.
Storage
Store at 2-8°C for short term (days to weeks) or -20°C for long term (months to years)
1.Antiviral Lipopeptide-Cell Membrane Interaction Is Influenced by PEG Linker Length
Augusto MT, Hollmann A, Porotto M, Moscona A, Santos NC.
A set of lipopeptides was recently reported for their broad-spectrum antiviral activity against viruses belonging to the Paramyxoviridae family, including human parainfluenza virus type 3 and Nipah virus. Among them, the peptide with a 24-unit PEG linker connecting it to a cholesterol moiety (VG-PEG24-Chol) was found to be the best membrane fusion inhibitory peptide. Here, we evaluated the interaction of the same set of peptides with biomembrane model systems and isolated human peripheral blood mononuclear cells (PBMC). VG-PEG24-Chol showed the highest insertion rate and it was among the peptides that induced a larger change on the surface pressure of cholesterol rich membranes. This peptide also displayed a high affinity towards PBMC membranes. These data provide new information about the dynamics of peptide-membrane interactions of a specific group of antiviral peptides, known for their potential as multipotent paramyxovirus antivirals.
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.Short PEG-linkers improve the performance of targeted, activatable monoclonal antibody-indocyanine green optical imaging probes
Sano K, Nakajima T, Miyazaki K, Ohuchi Y, Ikegami T, Choyke PL, Kobayashi H.
The ability to switch optical imaging probes from the quenched (off) to the active state (on) has greatly improved target to background ratios. The optimal activation efficiency of an optical probe depends on complete quenching before activation and complete dequenching after activation. For instance, monoclonal antibody-indocyanine green (mAb-ICG) conjugates, which are promising agents for clinical translation, are normally quenched, but can be activated when bound to a cell surface receptor and internalized. However, the small fraction of commonly used ICG derivative (ICG-Sulfo-OSu) can bind noncovalently to its mAb and is, thus, gradually released from the mAb leading to relatively high background signal especially in the liver and the abdomen. In this study, we re-engineered a mAb-ICG conjugate, (Panitumumab-ICG) using bifunctional ICG derivatives (ICG-PEG4-Sulfo-OSu and ICG-PEG8-Sulfo-OSu) with short polyethylene glycol (PEG) linkers. Higher covalent binding (70-86%) was observed using the bifunctional ICG with short PEG linkers resulting in less in vivo noncovalent dissociation. Panitumumab-ICG conjugates with short PEG linkers were able to detect human epidermal growth factor receptor 1 (EGFR)-positive tumors with high tumor-to-background ratios (15.8 and 6.9 for EGFR positive tumor-to-negative tumor and tumor-to-liver ratios, respectively, at 3 d postinjection).
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

Historical Records: Bromoacetamido-PEG4-NHS ester
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