21066-33-1Relevant articles and documents
Riboflavin derivatives for enhanced photodynamic activity against Leishmania parasites
Silva, Alexandre Vieira,López-Sánchez, Almudena,Junqueira, Helena Couto,Rivas, Luis,Baptista, Mauricio S.,Orellana, Guillermo
, p. 457 - 462 (2015)
Riboflavin derivatives with various substituents (O-acyl, N-methyl, N-alkylcarboxyalkyl or N-alkyl(trialkyl)ammonium) have been prepared and spectroscopically characterized (absorption, emission and fluorescence quantum yields). Their quantum yields of photosensitized singlet molecular oxygen production (ΦΔ 0.24-0.58) and octanol/water partition coefficients (Pow ≤0.01-11) were measured. Preliminary studies indicate that all derivatives display higher phototoxicity against the human protozoan parasite Leishmania than the parent riboflavin, with negligible toxicity in the absence of light. Their photodynamic action shows a higher correlation with P;bsubesub& than with Φbsubesub&, opening up their potential application to cutaneous diseases treatment.
Synthesis and evaluation of antimycobacterial activity of riboflavin derivatives
Chouhan, Dwarika Kumar,Harale, Bhaiyyasaheb,Khedkar, Vijay,Kidwai, Saqib,Ojha, Divya,Rode, Ambadas B.,Singh, Manisha,Singh, Ramandeep
supporting information, (2021/07/16)
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.
Photocatalytic esterification under Mitsunobu reaction conditions mediated by flavin and visible light
M?rz,Chudoba,Kohout,Cibulka
supporting information, p. 1970 - 1975 (2017/03/11)
The usefulness of flavin-based aerial photooxidation in esterification under Mitsunobu reaction conditions was demonstrated, providing aerial dialkyl azodicarboxylate recycling/generation from the corresponding dialkyl hydrazine dicarboxylate. Simultaneously, activation of triphenylphosphine (Ph3P) by photoinduced electron transfer from flavin allows azo-reagent-free esterification. An optimized system with 3-methylriboflavin tetraacetate (10%), oxygen (terminal oxidant), visible light (450 nm), Ph3P, and dialkyl hydrazine dicarboxylate (10%) has been shown to provide efficient and stereoselective coupling of various alcohols and acids to esters with retention of configuration.
