C20-diacid-Trx-γGlu-Glu-PEG3-ethylmaleimide X [HO-Ste-CYH-Glu(OH)-Glu(OH)-AEEA-Mal]

C20-diacid-Trx-γGlu-Glu-PEG3-ethylmaleimide X, simplified as HO-Ste-CYH-Glu(OH)-Glu(OH)-AEEA-Mal, is a complex amphiphilic molecule designed for targeted drug delivery and bioconjugation. It combines a 20-carbon dicarboxylic acid (or stearic acid) for membrane interaction, a thioredoxin-derived tripeptide (CYH) that may aid cellular uptake or redox activity, two glutamic acid residues for water solubility and linker attachment, a triethylene glycol (PEG3) spacer for flexibility, and an ethylmaleimide group for selective thiol conjugation. This modular design creates a versatile, biocompatible building block for advanced therapeutic and diagnostic delivery systems.

Appearance

• White to off-white solid or powder

• Lyophilized or amorphous form

• Odorless

• Hygroscopic; absorbs moisture readily, especially due to PEG component

Source

• Synthesized by multi-step methods involving SPPS, organic synthesis, and polymer chemistry

• Components prepared separately:

  • C20-diacid/Stearic acid commercially sourced then functionalized

  • Trx/CYH peptide synthesized via Fmoc-SPPS

  • γGlu-Glu derived from protected glutamic acid derivatives

  • PEG3-ethylmaleimide commercially sourced and coupled

• Custom synthesis typical due to molecule complexity

Molecular Weight and Structure

• Molecular formula: Complex, varies with precise Trx sequence and linker chemistry

• Molecular weight: Estimated 1500–3000 Da depending on sequence and PEGylation

• IUPAC name: Too complex for simple representation

• Structure components:

  • C20-diacid: HOOC-(CH₂)₁₈-COOH or CH₃(CH₂)₁₆COOH

  • Trx (CYH): Cys-Tyr-His tripeptide

  • γGlu-Glu: γ-linked glutamic acid dimer

  • PEG3: triethylene glycol spacer

  • Ethylmaleimide (Mal): thiol-reactive group

• Simplified SMILES: CCCCCCCCCCCCCCCCCCC(=O)OC@HC(=O)NC@@HC(=O)NCC(=O)CC@@HC(=O)OCCC(=O)NC1C=CC(=O)NC1

Biological Activity

• Scaffold without inherent bioactivity alone

• Thiol-specific conjugation via maleimide group for targeted attachment of drugs, proteins

• Membrane interaction facilitated by C20-diacid/stearic acid tail

• Potential enhanced cellular uptake via thioredoxin-derived sequence

• Versatile platform for targeted drug delivery and bioconjugation

Purity and Microbial Contamination

• Purity: >95% by HPLC or LC-MS

• Peptide content: Verified by amino acid analysis

• Water content: <5% by Karl Fischer titration

• Microbial contamination: <100 CFU/g or per mg

• Endotoxin: <10 EU/mg

Identity and Quality Control

Shelf Life and Storage

• Store at –20 °C or –80 °C

• Protect from light and moisture

• Shelf life: 1-2 years

• Avoid freeze-thaw cycles

• Prefer storage under inert atmosphere (argon or nitrogen)

Application

• Targeted drug delivery vehicles

• Liposome or nanoparticle surface functionalization

• Protein or peptide bioconjugation

• Development of amphiphilic biomaterials

• Biosensor surface modification

Key Characteristics

• Amphiphilic structure with hydrophobic C20 tail and hydrophilic PEG spacer

• Maleimide group for selective thiol conjugation

• Potential for improved cellular uptake due to Trx/CYH sequence

• Biocompatible and modular design

• Tunable properties via modification of peptide sequence and linkers

Citation

• https://pubchem.ncbi.nlm.nih.gov/compound/10078

• https://pubchem.ncbi.nlm.nih.gov/compound/7228

• https://pubchem.ncbi.nlm.nih.gov/compound/443407

• https://pubchem.ncbi.nlm.nih.gov/compound/7914

• https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3491443/

• https://doi.org/10.1016/j.jconrel.2010.10.004

• https://doi.org/10.1021/acs.bioconjchem.5b00554

• https://doi.org/10.1021/cr500579j

• https://doi.org/10.1039/C3CS60278K

• https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4617138/