146-14-5 Usage
Description
FLAVIN ADENINE DINUCLEOTIDE, also known as FAD, is a coenzyme derived from the vitamin riboflavin, which plays a crucial role in various biological processes. It is an adenine nucleotide containing two phosphate groups esterified to the sugar moiety at the 5′-position. FAD is a vital component in the structure and function of certain flavoproteins, which are involved in redox reactions and electron transport processes.
Uses
1. Used in Enzymatic Reactions:
FLAVIN ADENINE DINUCLEOTIDE is used as a prosthetic group for certain flavoproteins, such as D-amino acid oxidase, glucose oxidase, glycine oxidase, fumaric hydrogenase, histaminase, and xanthine oxidase. It facilitates redox reactions and electron transport processes in these enzymes, playing a vital role in cellular metabolism.
2. Used in Signal Transduction:
FLAVIN ADENINE DINUCLEOTIDE is used as a component in the activation of riboflavin kinase tumor necrosis factor receptor 1 and NADPH oxidase. These proteins are involved in signal transduction pathways, which are essential for cellular communication and response to external stimuli.
3. Used in Diagnostic Applications:
Labelled Flavine Adenine Dinucleotide is used in various diagnostic assays and techniques, such as enzyme-linked immunosorbent assays (ELISA) and fluorescence-based assays, to detect and measure the activity of flavoproteins and other related enzymes.
4. Used in Pharmaceutical Industry:
FLAVIN ADENINE DINUCLEOTIDE is used as a key component in the development of drugs targeting flavoproteins and their associated pathways. This can be particularly relevant in the treatment of diseases related to redox imbalances and oxidative stress.
5. Used in Research and Development:
FLAVIN ADENINE DINUCLEOTIDE is used as a research tool to study the structure, function, and mechanisms of flavoproteins and their role in various biological processes. This knowledge can be applied to develop new therapeutic strategies and improve our understanding of cellular metabolism and redox regulation.
Purification Methods
Small quantities of FAD are purified by paper chromatography using tert-butyl alcohol/water, cutting out the main spot and eluting with water. Larger amounts can be precipitated from water as the uranyl complex by adding a slight excess of uranyl acetate to a solution at pH 6.0, dropwise and with gentle stirring. The solution is set aside overnight in the cold, and the precipitate is centrifuged off, washed with small portions of cold EtOH, then with cold peroxide-free diethyl ether. It is dried in the dark under vacuum over P2O5 at 50-60o. The uranyl complex is suspended in water, and, after adding sufficient 0.01M NaOH to adjust the pH to 7, the precipitate of uranyl hydroxide is removed by centrifugation [Huennekens & Felton Methods Enzymol 3 954 1957]. It can also be crystallised from water. It should be kept in the dark. More recently it was purified by elution from a DEAE-cellulose (Whatman DE 23) column with 0.1M phosphate buffer pH 7, and the purity was checked by TLC. [Holt & Cotton, J Am Chem Soc 109 1841 1987, Beilstein 26 III/IV 3632.]
Check Digit Verification of cas no
The CAS Registry Mumber 146-14-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,4 and 6 respectively; the second part has 2 digits, 1 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 146-14:
(5*1)+(4*4)+(3*6)+(2*1)+(1*4)=45
45 % 10 = 5
So 146-14-5 is a valid CAS Registry Number.
146-14-5Relevant articles and documents
Methylene Homologues of Artemisone: An Unexpected Structure–Activity Relationship and a Possible Implication for the Design of C10-Substituted Artemisinins
Wu, Yuet,Wu, Ronald Wai Kung,Cheu, Kwan Wing,Williams, Ian D.,Krishna, Sanjeev,Slavic, Ksenija,Gravett, Andrew M.,Liu, Wai M.,Wong, Ho Ning,Haynes, Richard K.
, p. 1469 - 1479 (2016)
We sought to establish if methylene homologues of artemisone are biologically more active and more stable than artemisone. The analogy is drawn with the conversion of natural O- and N-glycosides into more stable C-glycosides that may possess enhanced biological activities and stabilities. Dihydroartemisinin was converted into 10β-cyano-10-deoxyartemisinin that was hydrolyzed to the α-primary amide. Reduction of the β-cyanide and the α-amide provided the respective methylamine epimers that upon treatment with divinyl sulfone gave the β- and α-methylene homologues, respectively, of artemisone. Surprisingly, the compounds were less active in vitro than artemisone against P. falciparum and displayed no appreciable activity against A549, HCT116, and MCF7 tumor cell lines. This loss in activity may be rationalized in terms of one model for the mechanism of action of artemisinins, namely the cofactor model, wherein the presence of a leaving group at C10 assists in driving hydride transfer from reduced flavin cofactors to the peroxide during perturbation of intracellular redox homeostasis by artemisinins. It is noted that the carba analogue of artemether is less active in vitro than the O-glycoside parent toward P. falciparum, although extrapolation of such activity differences to other artemisinins at this stage is not possible. However, literature data coupled with the leaving group rationale suggest that artemisinins bearing an amino group attached directly to C10 are optimal compounds.
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Huennekens,Kilgour
, p. 6716 (1955)
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Synthesis of nucleotide coenzymes via nucleoside 5'-phosphorothioate intermediates.
Hata,Nakagawa
, p. 5516 - 5516 (2007/10/09)
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