Aminocoumarin Dyes

Aminocoumarin is a class of antibiotics and is a chemical with a molecular weight of 175.18. Its role is to inhibit the DNA gyrase involved in bacterial cell division. They are derived from the species streptomyces, its most famous representative-coelicolor Streptomyces-which was sequenced in 2002.

Structure

The core of the aminocoumarin antibiotic consists of a 3-amino-4,7-dihydroxycoumarin ring, which is linked, for example, to a sugar at the 7-position and a benzoic acid derivative at the 3-position. Clorobiocin is a natural antibiotic isolated from several Streptomyces strains and is different from neomycin in the methyl neomycin at position 8 of the coumarin ring is replaced by a chlorine atom and at the 3 'position of noviose sugar. The carbamoyl group is substituted by 5-methyl-2-pyrrolylcarbonyl.

Figure 1. Chemical structure of Aminocoumarin.

Applications

Fluorescent labeling reagent for enzyme trace determination; suitable as a laser dye; as a matrix for monosulfated disaccharide analysis, and as a co-matrix with 6-aza2-thiothymine for analysis of sulfate Sexual and salivated trisaccharides and tetrasaccharides; reagents for the preparation of new AMC-based fluorescent substrates for cystine aminopeptidase (and other hydrolases); used as reference compounds in enzyme identification

Mechanism

Aminocoumarin antibiotics are known inhibitors of DNA gyrase. The aminocoumarin family of antibiotics inhibits this essential enzyme by exerting its therapeutic activity by tightly binding to the B subunit of bacterial DNA gyrase. They compete with ATP for binding to the B subunit of the enzyme and inhibit the ATP-dependent DNA supercoil catalyzed by gyrase. X-ray crystallographic studies have confirmed that ATP binding sites on the gyrB subunit of DNA gyrase have binding effects. Their affinity for gyrase is much higher than that of modern fluoroquinolones. It also targets DNA gyrase, but is located in the gyrA subunit.

Conclusions

Coumarin and its derivatives are one of the first fluorescent dyes found in plants. It is widely distributed in many plants. So far, more than 100 natural coumarin compounds have been discovered. Later, heterocyclic compounds such as quinoxaline derivatives, anthranilic acid amide derivatives, xanthene derivatives, cyclic dextrin derivatives, and pyrrole derivatives were discovered successively. Good fluorescent material. Therefore, many natural and synthetic coumarin derivatives are used in fluorescent whitening agents, laser dyes, and fluorescent dyes.

References:

1. Du, Lupei.; et al. Rational design of a fluorescent hydrogen peroxide probe based on the umbelliferone fluorophore. Tetrahedron Letters. 2008, 49 (19): 3045–3048.
2. Bye, A.; et al. The biosynthesis of 4-hydroxycoumarin and dicoumarol by Aspergillus fumigatus Fresenius. Biochemical Journal. 1970, 117 (2): 237–245.
3. Bentley.; et al. Complete genome sequence of the model actinomycete "Streptomyces coelicolor" A3(2)". Nature. 2002, 417 (6885): 141–147.