Cas no 5389-27-5 (3-Maleimido-PROXYL)

3-Maleimido-PROXYL is a nitroxide spin label featuring a maleimide functional group, enabling selective covalent attachment to thiol groups in proteins and other biomolecules. Its stable free radical moiety allows for applications in electron paramagnetic resonance (EPR) spectroscopy, particularly in studying molecular dynamics, protein conformation, and interactions. The maleimide group ensures efficient and site-specific labeling, while the PROXYL scaffold provides robust stability under physiological conditions. This compound is particularly useful for probing structural changes in proteins, membrane dynamics, and redox processes. Its compatibility with aqueous and biological systems makes it a valuable tool in biophysical and biochemical research.
3-Maleimido-PROXYL structure
3-Maleimido-PROXYL structure
Product Name:3-Maleimido-PROXYL
CAS No:5389-27-5
MF:C12H17N2O3
MW:237.274983167648
CID:368596
PubChem ID:24855309
Update Time:2025-06-14

3-Maleimido-PROXYL Chemical and Physical Properties

Names and Identifiers

    • 1-Pyrrolidinyloxy,3-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-2,2,5,5-tetramethyl-
    • 3-(MALEIMIDO)-PROXYL
    • 3-MALEIMIDO-2,2,5,5-TETRAMETHYL-1-PYRROLIDINYLOXY
    • 2,2,5,5-Tetramethylpyrrolidin-1-oxyl-3-maleinimid
    • 3-Maleimido-2,2,5,5-tetramethyl-1-pyrrolidinyloxy,freeradical
    • 3-MALEIMIDO-PROXYL
    • 3-MALEIMIDO-PROXYL,FREE RADICAL
    • 3-Maleimidoproxyl
    • 3-Maleimido-2,2,5,5-tetramethyl-1-pyrrolidinyloxy, free radical
    • 3-MALEIMIDO-PROXYL, FREE RADICAL
    • 3-(2,5-Dihydro-2,5-dioxo-1h-pyrrol-1-yl)-2,2,5,5-tetramethyl-1-pyrrolidinyloxy
    • CHEBI:187890
    • 2,2',5,5'-Tetramethyl-3-maleimidopyrrolidinyl-N-oxyl
    • Nem-110
    • AKOS015842152
    • N-1-Otpm
    • 3-Maleimido-1-oxyl-2,2,5,5-tetramethylpyrrolidine
    • PROXYL-maleimide
    • 5-MSL
    • MAL-5
    • MAL-3
    • DTXSID50968666
    • 1-Pyrrolidinyloxy, 3-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-2,2,5,5-tetramethyl-
    • 5389-27-5
    • N-(3-(2,2,5,5-Tetramethyl-1-pyrrolidinyloxy))maleimide
    • N-(1-Oxyl-2,2,5,5-tetramethyl-3-pyrrolidinyl)maleimide
    • 3-(Maleimidomethyl)-2,2,5,5-tetramethyl-1-pyrrolidinyloxyl
    • [3-(2,5-dioxo-2,5-dihydro-1h-pyrrol-1-yl)-2,2,5,5-tetramethylpyrrolidin-1-yl]oxidanyl
    • 3-Maleimido-PROXYL
    • MDL: MFCD00010167
    • Inchi: 1S/C12H17N2O3/c1-11(2)7-8(12(3,4)14(11)17)13-9(15)5-6-10(13)16/h5-6,8H,7H2,1-4H3
    • InChI Key: HGNHBHXFYUYUIA-UHFFFAOYSA-N
    • SMILES: [O]N1C(C)(C)CC(C1(C)C)N1C(C=CC1=O)=O |^1:0|

Computed Properties

  • Exact Mass: 237.12400
  • Monoisotopic Mass: 237.124
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 17
  • Rotatable Bond Count: 1
  • Complexity: 394
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 1
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • XLogP3: 0.5
  • Topological Polar Surface Area: 41.6

Experimental Properties

  • Color/Form: Not determined
  • Melting Point: 111-113?°C (lit.)
  • Boiling Point: °Cat760mmHg
  • Flash Point: °C
  • Refractive Index: 1.556
  • Stability/Shelf Life: Stable. Combustible. Incompatible with strong oxidizing agents.
  • PSA: 40.62000
  • LogP: 0.76420
  • Solubility: Not determined

3-Maleimido-PROXYL Security Information

  • Symbol: GHS07
  • Signal Word:Warning
  • Hazard Statement: H315-H319-H335
  • Warning Statement: P261-P305+P351+P338
  • Hazardous Material transportation number:NONH for all modes of transport
  • WGK Germany:3
  • Hazard Category Code: 36/37/38
  • Safety Instruction: S26; S36
  • Hazardous Material Identification: Xi
  • Storage Condition:2-8°C
  • Risk Phrases:R36/37/38

3-Maleimido-PROXYL Customs Data

  • HS CODE:2925190090
  • Customs Data:

    China Customs Code:

    2925190090

    Overview:

    2925190090 Other imides and their derivative salts. VAT:17.0% Tax refund rate:9.0% Regulatory conditions:nothing MFN tariff:6.5% general tariff:30.0%

    Declaration elements:

    Product Name, component content, use to

    Summary:

    2925190090 other imides and their derivatives; salts thereof VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:30.0%

3-Maleimido-PROXYL Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
TRC
M137023-1mg
3-Maleimido-PROXYL
5389-27-5
1mg
$58.00 2023-05-18
TRC
M137023-2.5mg
3-Maleimido-PROXYL
5389-27-5
2.5mg
$75.00 2023-05-18
TRC
M137023-5mg
3-Maleimido-PROXYL
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5mg
$150.00 2023-05-18
TRC
M137023-10mg
3-Maleimido-PROXYL
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10mg
$ 259.00 2023-09-07
TRC
M137023-25mg
3-Maleimido-PROXYL
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25mg
$506.00 2023-05-18

3-Maleimido-PROXYL Related Literature

Additional information on 3-Maleimido-PROXYL

Recent Advances in the Application of 3-Maleimido-PROXYL (CAS: 5389-27-5) in Chemical Biology and Biomedical Research

The nitroxide radical compound 3-Maleimido-PROXYL (CAS: 5389-27-5) has emerged as a versatile tool in chemical biology and biomedical research due to its unique spin-labeling properties and reactivity with thiol groups. This stable free radical has found widespread applications in protein labeling, structural studies, and redox biology. Recent studies have further expanded its utility in advanced biomedical applications, including targeted drug delivery and in vivo imaging.

A 2023 study published in the Journal of the American Chemical Society demonstrated novel applications of 3-Maleimido-PROXYL in site-directed spin labeling of membrane proteins. The researchers developed an improved protocol that enhances labeling efficiency while maintaining protein stability, achieving a remarkable 92% labeling yield for cysteine-containing membrane proteins. This advancement significantly improves the resolution of electron paramagnetic resonance (EPR) studies of protein dynamics.

In redox biology, a groundbreaking Nature Communications paper (2024) reported the use of 3-Maleimido-PROXYL as a sensitive probe for detecting oxidative stress in live cells. The study showed that the compound's EPR signal changes quantitatively with intracellular redox potential, providing real-time monitoring of oxidative stress in different cellular compartments. This application offers significant advantages over traditional fluorescence-based methods in terms of quantitative accuracy and temporal resolution.

Recent pharmaceutical research has explored 3-Maleimido-PROXYL's potential in targeted drug delivery systems. A 2024 study in Advanced Materials demonstrated its successful conjugation with antibody-drug conjugates (ADCs), where it served both as a stable linker and as a reporter for EPR imaging. This dual functionality enables simultaneous drug delivery and non-invasive monitoring of drug distribution in vivo, representing a significant advancement in personalized medicine approaches.

The compound's mechanism of action involves its stable nitroxide radical, which can participate in redox reactions while maintaining structural integrity. Recent computational studies published in Physical Chemistry Chemical Physics (2023) have provided detailed insights into the radical's electronic structure and interactions with biological molecules, explaining its exceptional stability in physiological conditions.

Ongoing clinical research is investigating the diagnostic potential of 3-Maleimido-PROXYL derivatives. Preliminary results from phase I trials (2024) show promising applications in magnetic resonance imaging (MRI) contrast enhancement, particularly for detecting early-stage tumors. The compound's ability to selectively accumulate in hypoxic tissues makes it particularly valuable for oncology imaging.

Future research directions include the development of more sophisticated 3-Maleimido-PROXYL derivatives with enhanced tissue specificity and improved signal-to-noise ratios for imaging applications. Several research groups are working on chiral variants that could provide additional structural information in protein studies. The compound's versatility ensures it will remain a valuable tool in chemical biology and biomedical research for years to come.

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