173341-32-7

Basic information

• Product Name: biotin 2,3,5,6-tetrafluorophenyl ester
• Synonyms: biotin 2,3,5,6-tetrafluorophenyl ester
• CAS NO: 173341-32-7
• Molecular Weight: 392.374
• Mol File: 173341-32-7.mol

Chemical Properties

• CAS DataBase Reference: biotin 2,3,5,6-tetrafluorophenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: biotin 2,3,5,6-tetrafluorophenyl ester(173341-32-7)
• EPA Substance Registry System: biotin 2,3,5,6-tetrafluorophenyl ester(173341-32-7)

Safety Data

• Hazardous Substances Data: 173341-32-7(Hazardous Substances Data)

Upstream product

• 142685-25-4 2,3,5,6-tetrafluorophenyl 2,2,2-trifluoroacetate 
• 58-85-5 biotin 
• 769-39-1 2,3,5,6-tetraflourophenol 

Downstream Products

• 175885-18-4 tert-butyl-N-(2-(2-(2-(5-(2-oxo-1,3,3a,4,6,6a-hexahydrothieno(3,4-d)imidazol-6-yl)pentanoylamino)ethoxy)ethoxy)ethyl)carbamate 
• 295322-45-1 C₂₄H₂₉F₄N₃O₆S 
• 1313369-15-1 (C₅H₇N₂OS)(CH₂)4C(O)NHC₆H₄CH₂N(CH₂C₅H₃NCO₂Me)2 
• 99938-68-8 N-(2-mercaptoethyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide 
• 183896-00-6 N-(13-amino-4,7,10-trioxatridecanyl)-D-biotinamide 
• 157446-76-9 N-((4-pyridyl)methyl)biotinamide 

Relevant articles and documents

Synthesis, characterization, and biological evaluation of new biotinylated 99mTc/Re-tricarbonyl complexes

The synthesis and biological evaluation of three new biotinylated fac-[99mTc/Re(CO)3]+ complexes with the tridentate ligands L1, L2, and L3 are reported. L1-L3 contain the chelators 2-((5-aminopentyl)(pyridin-2-ylmethyl)am

Bio-functionalized gold nanoparticles for surface-plasmon-absorption-based protein detection

Bio-functionalized gold nanoparticles (AuNPs), which bio-specifically interact with biotin-(strept)avidin, were investigated in this study. AuNPs were functionalized with a synthetically-provided biotin-linked thiol (BLT), which was synthesized by amidati

Design and synthesis of bis-biotin-containing reagents for applications utilizing monoclonal antibody-based pretargeting systems with streptavidin mutants

Previous studies have shown that pretargeting protocols, using cancer-targeting fusion proteins, composed of 4 anti-CD20 single chain Fv (scFv) fragments and streptavidin (scFv4-SAv), followed by a biotinylated dendrimeric N-acetyl-galactosamine blood clearing agent (CA), 1, then a radiolabeled DOTA-biotin derivative (a monobiotin), 3a, can provide effective therapy for lymphoma xenografts in mouse models. A shortcoming in this pretargeting system is that endogenous biotin may affect its efficacy in patients. To circumvent this potential problem, we investigated a pretargeting system that employs anti-CD20 scFv4-SAv mutant fusion proteins with radioiodinated bis-biotin derivatives. With that combination of reagents, good localization of the radiolabel to lymphoma tumor xenografts was obtained in the presence of endogenous biotin. However, the blood clearance reagents employed in the studies were ineffective, resulting in abnormally high levels of radioactivity in other tissues. Thus, in the present investigation a bis-biotin-trigalactose blood clearance reagent, 2, was designed, synthesized, and evaluated in vivo. Additionally, another DOTA-biotin derivative (a bis-biotin), 4a, was designed and synthesized, such that radiometals (e.g., 111In, 90Y, 177Lu) could be used in the pretargeting protocols employing scFv4-SAv mutant fusion proteins. Studies in mice demonstrated that the CA 2 was more effective than CA 1 at removing [125I]scFv4-SAv-S45A mutant fusion proteins from blood. Another in vivo study compared tumor targeting and normal tissue concentrations of the new reagents (2 and [111In]4b) with standard reagents (1 and [111In]3b) used in pretargeting protocols. The study showed that lymphoma xenografts could be targeted in the presence of endogenous biotin when anti-CD20 fusion proteins containing SAv mutants (scFv 4-SAv-S45A or scFv4-SAv-Y43A) were employed in combination with CA 2 and [111In]4b. Importantly, normal tissue concentrations of [111In]4b were similar to those obtained using the standard reagents (1 and [111In]3b), except that the blood and liver concentrations were slightly higher with the new reagents. While the reasons for the higher blood and liver concentrations are unknown, the differences in the galactose structures of the clearance agents 1 and 2 may play a role.

Water soluble multi-biotin-containing compounds

Water-soluble discrete multi-biotin-containing compounds with at least three (3) biotin moieties are disclosed. The water-soluble biotin-containing compounds may additionally comprise one or more moieties that confer resistance to cleavage by biotinidase or that is cleavable in vitro or in vivo. The discrete multi-biotin-containing compounds may include a reactive moiety that provides a site for reaction with yet another moiety, such as a targeting, diagnostic or therapeutic functional moiety. Biotinylation reagents comprising water-soluble linker moieties are also disclosed and may additionally comprise a biotinidase protective group. Methods for amplifying the number of sites for binding biotin-binding proteins at a selected target using multi-biotin compounds also are disclosed.

POLYBIOTIN COMPOUNDS FOR MAGNETIC RESONANCE IMAGINING AND DRUG DELIVERY

The invention relates generally to biotin-containing compounds that are useful as imaging agents and drug-delivery agents. Another aspect of the invention relates to the aforementioned compounds chelated to a metal atom. In a preferred embodiment, the metal atom is a gadolinium. Another aspect of the invention relates to a compound comprising three biotin moieties and a pharmaceutical agent covalently bound to a heterocyclic core. In certain embodiments, the pharmaceutical agent is an antibiotic, antiviral, or radionuclide. Another aspect of the present invention relates to a method of treating disease involving administering the compounds of the invention to a mammal. Another aspect of the present invention relates to a method of acquiring a magnetic resonance image using the compounds of the invention.