53130-71-5

Upstream product

• 108-24-7 acetic anhydride 
• 13123-37-0 10-L-arabitol-5-yl-7,8-dimethyl-10H-benzo[g]pteridine-2,4-dione 
• 33210-89-8 arabinoflavin 
• 83-88-5 riboflavin 
• 752-13-6 7,8-dimethyl-10-(tetra-O-acetyl-L-arabitol-1-yl)-10H-benzo[g]pteridine-2,4-dione 
• 5978-88-1 Tetraacetyl-D-arabinoflavin 
• 113473-93-1 5-(4,5-dimethyl-2-phenylazo-anilino)-5-deoxy-L-arabitol 
• 64598-64-7 5-(2-amino-4,5-dimethyl-anilino)-5-deoxy-L-arabitol 

Downstream Products

• 752-13-6 7,8-dimethyl-10-(tetra-O-acetyl-DL-arabitol-1-yl)-10H-benzo[g]pteridine-2,4-dione 
• 21066-33-1 3-Methyl-tetra-O-acetyl-riboflavin 

Relevant academic research and scientific papers

Dynamically modified, biospecific optical fiber sensor for riboflavin binding protein based on hydrophobically associated 3-octylriboflavin

A new approach to the production of optical fiber sensors Is described which Is based on a dynamic modification procedure. In this approach, the optical fiber surface is rendered Hydrophobic through the covalent attachment of a C18 moiety. Specific sensing ligands are then associated with this surface through either their inherent or designed hydrophobicity. To investigate the feasibility of the approach, an optical fiber sensor has been constructed for riboflavin binding protein in which 3-octylriboflavin is associated with the fiber surface. Fluorescence quenching occurs upon binding of the protein to the immobilized riboflavin derivative. The sensor possesses a minimum measurable quantity of 7.3 pmol of binding protein in a probe volume which is less than 10 μL. With this approach, the sensing surface was repetitively regenerated 15 times over a 1-h period with less than a 5% variation in sensor-to-sensor performance. The approach is general, and with minor variations it can be used in a variety of sensing situations.

(Trifluoromethylselenyl)methylchalcogenyl as Emerging Fluorinated Groups: Synthesis under Photoredox Catalysis and Determination of the Lipophilicity

The synthesis of molecules bearing (trifluoromethylselenyl)methylchalcogenyl groups is described via an efficient two-step strategy based on a metal-free photoredox catalyzed decarboxylative trifluoromethylselenolation with good yields up to 88 %, which raised to 98 % in flow chemistry conditions. The flow methods allowed also to scale up the reaction. The mechanism of this key reaction was studied. The physicochemical characterization of these emerging groups was performed by determining their Hansch–Leo lipophilicity parameters with high values up to 2.24. This reaction was also extended to perfluoroalkylselenolation with yields up to 95 %. Finally, this method was successfully applied to the functionalization of relevant bioactive molecules such as tocopherol or estrone derivatives.

Synthesis and evaluation of antimycobacterial activity of riboflavin derivatives

The riboflavin biosynthetic pathway is a promising target for the development of novel antimycobacterial drugs given the lack of riboflavin transporter in M. tuberculosis. Herein, a series of riboflavin derivatives was designed, synthesized and screened for their antimycobacterial and antibacterial activity. The compounds 1a, 1b, 2a, 3a and 5a displayed noticeable antitubercular activity against M. tuberculosis with minimum inhibitory concentration (MIC99) in the range of 6.25 to 25 μM. The lead compound 5a had a selectivity index of 10.7 in the present study. The compounds 2a, 2b, 2c, 4c and 4d showed relatively low to moderate antibacterial activity (MIC = 100–200 μM) against gram-positive strains. Notably, the compounds do not show any inhibition against gram-negative strains even at 200 μM concentration. Further, molecular docking and binding experiments with representative flavin mononucleotide (FMN) riboswitch suggested that the riboflavin analogs exhibited antimycobacterial activity plausibly through FMN riboswitch-mediated repression of riboflavin biosynthesis. In addition to FMN riboswitch, flavoproteins involved in the flavin biosynthesis could also be target of riboflavin derivatives. In conclusion, the potency and low toxicity of riboflavin analogs particularly 5a (MIC99 = 6.25) make it a lead compound for the synthesis of new analogs for antimycobacterial therapy.

A low-molecular-weight supramolecular hydrogel of riboflavin bolaamphiphile for VEGF-siRNA delivery

A low-molecular-weight hydrogel derived from riboflavin (vitamin B 2) that self-assembles to provide supramolecular nanofibers, biocompatible material, can be used to deliver VEGF-siRNA efficiently into human cells by the endocytosis pathway, where the siRNA is functionalized.

Redox reaction between m-thiocresol and riboflavin glycosides with 2:1 complex formation; regulation by the steric effect of sugar in the side chain

We investigated the reduction of riboflavin-2′, 3′, 4′, 5′-tetra-acetate (AcB2), riboflavin-1″-glucoside- 2″, 3″, 4″, 6″, 2′, 3′, 4′, 5′-hepta-acetate (AcB2gl) and lumiflavin using m-thiocresol (mTc) in the presence of tetrabutylammonium hydroxide. The series of rate constants for AcB2 and AcB2gl reductions indicated that modified Lineweaver-Burk plots were best fit by assuming a 1:2 complex formation. The complex formation in the reaction was supported by the 2-D nuclear Overhauser enhancement spectroscopy and circular dichroism spectra. The modified Michaelis-Menten constants (Km) for AcB2 and AcB2gl with mTc were 1.32 and 0.86 × 10-3M 2, respectively, and the maximum rate constant k2 were 4.45 and 4.35 × 10-2M-1s-1, respectively. The E1/2 values of AcB2 and AcB2gl were - 331 and - 341mV, respectively, which indicated that their reduction activities were almost the same. It was established that the redox function depended on the formation of the complex and was regulated by the steric effect of the sugar in the side chain.