11-maleimidoundecanoic acid - CAS 57079-01-3

11-Maleimidoundecanoic acid is a crosslinking reagent for conjugating biochemicals to the polymer chain.

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Molecular Formula
C15H23NO4
Molecular Weight
281.35

11-maleimidoundecanoic acid

    • Specification
      • 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.
        IUPAC Name
        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
    • Properties
      • 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)
        Canonical SMILES
        C1=CC(=O)N(C1=O)CCCCCCCCCCC(=O)O
    • Reference Reading
      • 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.
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