BDP FL maleimide

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BDP FL maleimide

BDP FL maleimide | 773859-49-7

Catalog Number F01-0013
Category BODIPY
Molecular Formula C20H21BF2N4O3
Molecular Weight 414.21
Catalog Number Size Price Quantity
F01-0013 -- $--

Product Introduction

Thiol reactive BDP FL maleimide is a reactive dye for protein labeling, which has identical structure with BODIPY® FL maleimide.BDP FL is a borondipyrromethene dye which has absorption and fluorescence spectra similar to fluorescein (FAM). However, this dye exhibits very high photostability. It is non-charged, and has low molecular weight. Its brightness is similar to fluorescein, R110 and xanthene dye derivatives like Alexa Fluor® 488. This fluorophore is ideal for fluorescent microscopy and many other applications. The fluorophore can substitute fluorescein for almost any application, and it is compatible with any FAM-capable fluorescent instrumentation.

Chemical Information

Synonyms BDPFLmaleimide; 3-(2,2-difluoro-10,12-dimethyl-1-aza-3-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-3,5,7,9,11-pentaen-4-yl)-N-[2-(2,5-dioxopyrrol-1-yl)ethyl]propanamide
Purity NMR 1H, HPLC-MS (95%)
IUPAC Name 3-(2,2-difluoro-10,12-dimethyl-1-aza-3-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-3,5,7,9,11-pentaen-4-yl)-N-[2-(2,5-dioxopyrrol-1-yl)ethyl]propanamide
Canonical SMILES [B-]1(N2C(=CC(=C2C=C3[N+]1=C(C=C3)CCC(=O)NCCN4C(=O)C=CC4=O)C)C)(F)F
InChI InChI=1S/C20H21BF2N4O3/c1-13-11-14(2)26-17(13)12-16-4-3-15(27(16)21(26,22)23)5-6-18(28)24-9-10-25-19(29)7-8-20(25)30/h3-4,7-8,11-12H,5-6,9-10H2,1-2H3,(H,24,28)
InChI Key OEMKXDGSMCHMJQ-UHFFFAOYSA-N
Solubility Good in organic solvents (DMF, DMSO), limited in water
Appearance orange solid
  • Product Specification
  • Application
ε, L⋅mol-1⋅cm-1 92000
Fluorescence Quantum Yield 0.97
Excitation 503
Emission 509
Storage 24 months after receival at -20°C in the dark. Transportation: at room temperature for up to 3 weeks. Avoid prolonged exposure to light. Desiccate.

BDP FL maleimide is widely utilized in bioconjugation techniques due to its high specificity and reactivity towards thiol groups. This property makes it an ideal tool for site-specific labeling of cysteine residues in proteins, peptides, and other biomolecules. Researchers often use BDP FL maleimide to create fluorescently labeled proteins for tracking and imaging studies, as it enables the precise attachment of fluorescent tags without disturbing the biological function of the target molecule. The stable conjugation and bright fluorescence of BDP FL maleimide allow for sensitive detection and analysis in various bioanalytical applications.

Another critical application of BDP FL maleimide is in the development of fluorescence-based assays and biosensors. Its strong fluorescence emission and high photostability make it an excellent reporter molecule in real-time monitoring of biological processes. BDP FL maleimide can be conjugated to specific biomolecules, enabling the detection of target analytes through fluorescence resonance energy transfer (FRET) or other fluorescence-based mechanisms. This capability is particularly valuable in the study of protein-protein interactions, enzyme kinetics, and the detection of low-abundance biomolecules in complex biological samples.

BDP FL maleimide is also instrumental in the field of drug discovery and development, where it is used to label and track small molecules, peptides, and drug candidates. By attaching the BDP FL fluorophore to these molecules, researchers can visualize and study their cellular uptake, distribution, and target engagement in live cells or animal models. This application is crucial for evaluating the pharmacokinetics and pharmacodynamics of new therapeutic agents, as well as for optimizing their design and delivery. The use of BDP FL maleimide in drug research helps accelerate the identification of promising candidates and enhances the understanding of their biological behavior.

In materials science, BDP FL maleimide is employed for the functionalization of polymers and nanomaterials with fluorescent properties. By incorporating BDP FL maleimide into these materials, researchers can create novel fluorescent probes and sensors with tailored properties for specific applications, such as environmental monitoring, bioimaging, and diagnostics. The ability of BDP FL maleimide to form stable covalent bonds with thiol-containing compounds allows for the precise modification of material surfaces, enabling the development of advanced materials with enhanced performance and functionality.

Computed Properties

Hydrogen Bond Donor Count 1
Hydrogen Bond Acceptor Count 6
Rotatable Bond Count 6
Exact Mass 414.1674770 g/mol
Monoisotopic Mass 414.1674770 g/mol
Topological Polar Surface Area 74.4Ų
Heavy Atom Count 30
Formal Charge 0
Complexity 909
Isotope Atom Count 0
Defined Atom Stereocenter Count 0
Undefined Atom Stereocenter Count 0
Defined Bond Stereocenter Count 0
Undefined Bond Stereocenter Count 0
Covalently-Bonded Unit Count 1
Compound Is Canonicalized Yes
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