Name: Fmoc-PEG4-NHS ester
Brand: BOC Sciences
Price: -- USD
Availability: MadeToOrder

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Synonyms

Fmoc-NH-PEG4-NHS ester; Fmoc-PEG4-C2-NHS ester; Fmoc-NH-PEG4-NHS; FmocNH-PEG4-CH2CH2COONHS; Fmoc-PEG4-CH2CH2-NHS ester; Fmoc-N-amido-PEG4-NHS ester; α-(fmoc-amino)-omega-(succinimidyl propionate) tetra(ethylene glycol); 2,5-Dioxopyrrolidin-1-yl 1-(9H-fluoren-9-yl)-3-oxo-2,7,10,13,16-pentaoxa-4-azanonadecan-19-oate; 9H-Fluoren-9-ylmethyl {15-[(2,5-dioxo-1-pyrrolidinyl)oxy]-15-oxo-3,6,9,12-tetraoxapentadec-1-yl}carbamate; Carbamic acid, N-[15-[(2,5-dioxo-1-pyrrolidinyl)oxy]-15-oxo-3,6,9,12-tetraoxapentadec-1-yl]-, 9H-fluoren-9-ylmethyl ester

IUPAC Name

(2,5-dioxopyrrolidin-1-yl) 3-[2-[2-[2-[2-(9H-fluoren-9-ylmethoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoate

Canonical SMILES

C1CC(=O)N(C1=O)OC(=O)CCOCCOCCOCCOCCNC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24

InChI

InChI=1S/C30H36N2O10/c33-27-9-10-28(34)32(27)42-29(35)11-13-37-15-17-39-19-20-40-18-16-38-14-12-31-30(36)41-21-26-24-7-3-1-5-22(24)23-6-2-4-8-25(23)26/h1-8,26H,9-21H2,(H,31,36)

InChIKey

NMCTTZZPHFQEQB-UHFFFAOYSA-N

Density

1.3±0.1 g/cm3

Solubility

Soluble in DCM, DMF, DMSO

Appearance

Pale Yellow or Colorless Oily Liquid

Shipping

Room temperature, or blue ice upon request.

Storage

Store at 2-8°C

Fmoc-PEG4-NHS ester, a versatile reagent in the realm of bioconjugation and peptide synthesis, offers enhanced solubility and stability. Here are four key applications of Fmoc-PEG4-NHS ester:

Peptide Synthesis: Serving as a linchpin in solid-phase peptide synthesis, Fmoc-PEG4-NHS ester emerges as a critical linker facilitating the introduction of polyethylene glycol (PEG) spacers. These PEG spacers not only amplify the solubility of peptides but also streamline their handling and purification processes. The true brilliance of this reagent shines through when synthesizing lengthy or hydrophobic peptides, which present challenges in aqueous environments owing to their inherent properties.

Protein Labeling: In protein science, Fmoc-PEG4-NHS ester empowers the efficient labeling of proteins with PEG chains, thereby enhancing their solubility and stability. Such modifications play a foundational role in the realm of protein-based therapeutics, as PEGylation can effectively dampen immunogenic responses and prolong the half-life of proteins in vivo. These enhancements catalyze the efficacy and longevity of protein drugs in clinical settings.

Bioconjugation: In bioconjugation chemistry, Fmoc-PEG4-NHS ester emerges as a versatile linker for attaching small molecules, fluorophores, or drugs to biomolecules such as antibodies or enzymes. The PEG component deftly minimizes steric hindrance and enhances solubility, ensuring optimal performance of bioconjugates. This methodology plays a pivotal role in sculpting precision-targeted therapies, diagnostics, and cutting-edge biosensors.

Surface Modification: Spearheading advancements in biomaterial engineering, Fmoc-PEG4-NHS ester plays a pivotal role in customizing the surfaces of biomaterials and medical devices to imbue hydrophilicity and curb nonspecific protein adsorption. By conjugating PEG chains to surfaces, the biocompatibility and functionality of implants, drug delivery systems, and diagnostic tools undergo a profound enhancement.

1.An immunostimulatory dual-functional nanocarrier that improves cancer immunochemotherapy

Chen Y, Xia R, Huang Y, Zhao W, Li J, Zhang X, Wang P, Venkataramanan R, Fan J, Xie W, Ma X, Lu B

Immunochemotherapy combines a chemotherapeutic agent with an immune-modulating agent and represents an attractive approach to improve cancer therapy. However, the success of immunochemotherapy is hampered by the lack of a strategy to effectively co-deliver the two therapeutics to the tumours. Here we report the development of a dual-functional, immunostimulatory nanomicellar carrier that is based on a prodrug conjugate of PEG with NLG919, an indoleamine 2,3-dioxygenase (IDO) inhibitor currently used for reversing tumour immune suppression. An Fmoc group, an effective drug-interactive motif, is also introduced into the carrier to improve the drug loading capacity and formulation stability. We show that PEG2k-Fmoc-NLG alone is effective in enhancing T-cell immune responses and exhibits significant antitumour activity in vivo. More importantly, systemic delivery of paclitaxel (PTX) using the PEG2k-Fmoc-NLG nanocarrier leads to a significantly improved antitumour response in both breast cancer and melanoma mouse models.

2.Effective co-delivery of doxorubicin and dasatinib using a PEG-Fmoc nanocarrier for combination cancer chemotherapy

Zhang P, Li J, Ghazwani M, Zhao W, Huang Y, Zhang X, Venkataramanan R, Li S.

A simple PEGylated peptidic nanocarrier, PEG5000-lysyl-(α-Fmoc-ε-Cbz-lysine)2 (PLFCL), was developed for effective co-delivery of doxorubicin (DOX) and dasatinib (DAS) for combination chemotherapy. Significant synergy of DOX and DAS in inhibition of cancer cell proliferation was demonstrated in various types of cancer cells, including breast, prostate, and colon cancers. Co-encapsulation of the two agents was facilitated by incorporation of 9-Fluorenylmethoxycarbonyl (Fmoc) and carboxybenzyl (Cbz) groups into a nanocarrier for effective carrier-drug interactions. Spherical nanomicelles with a small size of ∼30 nm were self-assembled by PLFCL. Strong carrier/drug intermolecular π-π stacking was demonstrated in fluorescence quenching and UV absorption. Fluorescence study showed more effective accumulation of DOX in nuclei of cancer cells following treatment with DOX&DAS/PLFCL in comparison with cells treated with DOX/PLFCL. DOX&DAS/PLFCL micelles were also more effective than other treatments in inhibiting the proliferation and migration of cultured cancer cells. Finally, a superior anti-tumor activity was demonstrated with DOX&DAS/PLFCL. A tumor growth inhibition rate of 95% was achieved at a respective dose of 5 mg/kg for DOX and DAS in a murine breast cancer model. Our nanocarrier may represent a simple and effective system that could facilitate clinical translation of this promising multi-agent regimen in combination chemotherapy.

3.PEG-Fmoc-Ibuprofen Conjugate as a Dual Functional Nanomicellar Carrier for Paclitaxel

Zhao M, Huang Y, Chen Y, Xu J, Li S, Guo X.

Ibuprofen is a kind of nonsteroidal anti-inflammatory drug (NSAIDs), and it is considered to possess some antitumor effect. In this study, a novel nanomicellar carrier based on PEG-derivatized ibuprofen, PEG2K-Fmoc-Ibuprofen (PEG2K-FIbu), was developed for delivery of anticancer agents such as paclitaxel (PTX). This conjugate readily forms stable mixed micelles with PTX with a relatively high PTX loading capacity of 67%. The release of PTX from PTX-loaded PEG2K-FIbu micelles was significantly slower than that from Taxol formulation. PTX-loaded PEG2K-FIbu micelles and Taxol showed a comparable in vitro cytotoxicity. Importantly, PTX-loaded PEG2K-FIbu micelles demonstrated a much more pronounced in vivo therapeutic efficacy compared with Taxol with respect to both inhibition of tumor growth and animal survival. Our system may represent an attractive dual-functional delivery system to achieve synergistic activity with PTX while minimizing the carrier-associated toxicity.