11-maleimidoundecanoic acid

 CAS No.: 57079-01-3  Cat No.: BP-501708  Purity: 99% (HPLC) 4.5  

11-Maleimidoundecanoic acid is a bifunctional linker featuring a terminal maleimide group for chemoselective thiol conjugation and a terminal carboxylic acid for subsequent coupling or handle installation. The linker provides an approximately eleven-carbon hydrophobic spacer that helps position the reactive maleimide away from the conjugation site, often improving accessibility to cysteine-containing ligands or engineered proteins. In PROTAC and targeted protein degradation workflows, this type of maleimide–carboxylate linker is commonly used to connect a thiol-bearing binding moiety (e.g., a cysteine-functionalized ligand) to another component through stable thioether formation, while the carboxylate enables orthogonal attachment strategies such as amide coupling to a second functional group. Its value lies in enabling modular, stepwise assembly of degraders with controlled geometry and reproducible conjugation chemistry, facilitating systematic structure–activity studies and optimization of ternary-complex formation.

11-maleimidoundecanoic acid

Structure of 57079-01-3

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Category
PROTAC Linker
Molecular Formula
C15H23NO4
Molecular Weight
281.35
Appearance
White to Light Yellow Solid

* For research and manufacturing use only. Not for human or clinical use.

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Popular Publications Citing BOC Sciences Products
Purity
99% (HPLC)
Solubility
Soluble in Methanol, Chloroform; Slightly soluble in Acetonitrile (Sonicated), Chloroform, Dichloromethane
Appearance
White to Light Yellow Solid
Storage
-20 °C
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
11-(2,5-dioxopyrrol-1-yl)undecanoic acid
Synonyms
N-(10-Carboxydecyl)maleimide; 2,5-Dihydro-2,5-dioxo-1H-pyrrole-1-undecanoic Acid; KMUA; UNII-LG78EY7HVB; maleimidoundecanoic acid; AM-10; MUDA; 1H-Pyrrole-1-undecanoic acid, 2,5-dihydro-2,5-dioxo-; LG78EY7HVB; Maleimide-(CH2)10-COOH; N-(10-Carboxydecyl)maleimide
Boiling Point
452.8±18.0 °C (Predicted)
Melting Point
89-90 °C
Density
1.139±0.06 g/cm3 (Predicted)
InChI Key
UVZTZBRGZXIBLZ-UHFFFAOYSA-N
InChI
InChI=1S/C15H23NO4/c17-13-10-11-14(18)16(13)12-8-6-4-2-1-3-5-7-9-15(19)20/h10-11H,1-9,12H2,(H,19,20)
SMILES
C1=CC(=O)N(C1=O)CCCCCCCCCCC(=O)O
1. Thermal Traits of MNPs under High-Frequency Magnetic Fields: Disentangling the Effect of Size and Coating
David Aurélio, Jiří Mikšátko, Miroslav Veverka, Magdalena Michlová, Martin Kalbáč, Jana Vejpravová Nanomaterials (Basel). 2021 Mar 19;11(3):797. doi: 10.3390/nano11030797.
We investigated the heating abilities of magnetic nanoparticles (MNPs) in a high-frequency magnetic field (MF) as a function of surface coating and size. The cobalt ferrite MNPs were obtained by a hydrothermal method in a water-oleic acid-ethanol system, yielding MNPs with mean diameter of about 5 nm, functionalized with the oleic acid. By applying another cycle of hydrothermal synthesis, we obtained MNPs with about one nm larger diameter. In the next step, the oleic acid was exchanged for 11-maleimidoundecanoic acid or 11-(furfurylureido)undecanoic acid. For the heating experiments, all samples were dispersed in the same solvent (dichloroethane) in the same concentration and the heating performance was studied in a broad interval of MF frequencies (346-782 kHz). The obtained results enabled us to disentangle the impact of the hydrodynamic, structural, and magnetic parameters on the overall heating capabilities. We also demonstrated that the specific power absorption does not show a monotonous trend within the series in the investigated interval of temperatures, pointing to temperature-dependent competition of the Brownian and Néel contributions in heat release.
2. Development of a Negative-Biased Zwitterionic Polypeptide-Based Nanodrug Vehicle for pH-Triggered Cellular Uptake and Accelerated Drug Release
Ashish Trital, Weili Xue, Shengfu Chen Langmuir. 2020 Jul 7;36(26):7181-7189. doi: 10.1021/acs.langmuir.0c00166. Epub 2020 Jun 18.
Albumin mimics could be an attractive platform for nanodrug carriers through systematic administration because of high safety and plentiful properties to be adjusted for a high drug efficacy, such as pH-triggered targeting cellular uptake and drug release. In this work, negative-biased zwitterionic nanodrug carriers based on zwitterionic polypeptide chains that mimic albumin were prepared, which have an outermost layer of zwitterionic glutamic acid (E) and lysine (K) pairs with a small amount of aspartic acid (D) to adjust the overall ζ potential. On the other hand, doxorubicin (Dox) was encapsulated in a hydrophobic core by 11-maleimidoundecanoic acid covalently linked with additional cysteine (C) residues on the polypeptide. The results show that the negative-biased zwitterionic nanodrug carriers can sensitively enhance the cellular uptake in responding to a pH change from 7.4 to 6.7 without reversing the ζ potential to a positive charge, leading to accelerating the Dox release rate in a slightly acidic environment through the polypeptide secondary structure change. Moreover, the anionic nanodrug carrier can also be easily enzymatically digested by trypsin for quick drug release. In short, this negative-biased zwitterionic nanodrug delivery vector could be an ideal candidate for a safer tumor inhibition with a high efficacy than conventional synthetic polymer-based ones.

11-maleimidoundecanoic acid is a long-chain bifunctional linker widely used in targeted protein degradation workflows where stable conjugation chemistry is required. Its maleimide functionality enables selective coupling to thiol-bearing ligands or protein surrogates, supporting the modular assembly of PROTACs with controlled linker length and flexibility. The subsequent points provide detailed descriptions of its structural features and practical reactivity considerations for experimental preparation.

Structure: The linker contains a terminal maleimide ring conjugated to an aliphatic undecanoic acid chain. It features an electrophilic alkene within the maleimide moiety and a carboxylic acid group for further derivatization. Overall, it is an amphiphilic, flexible hydrophobic scaffold with stable covalent conjugation potential.

Reactivity: Maleimides react with nucleophilic thiols via Michael-type addition, forming a stable thioether linkage under mildly basic to neutral aqueous conditions. For PROTAC assembly, thiol presentation on the ligand or intermediate is typically achieved using reducing agents compatible with maleimide stability, followed by thiol–maleimide coupling. Solvents are commonly buffered aqueous systems or mixed organic/aqueous media to maintain solubility, while avoiding strong nucleophiles and conditions that promote maleimide hydrolysis.

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It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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