Tetracycline
Tetracycline is a polyketide antibiotic originally produced by Streptomyces that exhibits antibacterial and neuroprotective activities. Tetracycline binds the 30S subunit of the bacterial ribosome, preventing aminoacyl-tRNA from binding to the ribosomal A site and inhibiting protein synthesis. Tetracycline is clinically used to treat acne, rosacea, Lyme disease, and various bacterial infections. Tetracycline binds amyloid-β (Aβ) peptides, increasing their solubility and decreasing their neurotoxicity in vitro. Tetracycline may also inhibit matrix metalloproteinases (MMPs). Additionally, tetracycline inhibits mammalian RNA splicing.
References PubMed ID：:http://www.ncbi.nlm.nih.gov/pubmed/18975906
| Cas No. |
60-54-8 |
|---|---|
| Purity |
≥90% |
| Formula |
C22H24N2O8 |
| Formula Wt. |
444.43 |
| Chemical Name |
[4S-(4α,4aα,5aα,6b,12aα)]-4-(Dimethylamino)-1,4,4a,-5,5a,6-11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide |
| IUPAC Name |
4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide |
| Synonym |
Deschlorobiomycin; Ambramycin; Liquamycin |
| Melting Point |
170-175°C(dec) |
| Solubility |
Soluble in methanol or ethanol (20 mg/mL). Slightly soluble in water (0.4 mg/mL). |
| Appearance |
Yellow Crystal Powder |
Kennedy R, Alibhai M, Shakib K. Tetracycline: a cure all? Br J Oral Maxillofac Surg. 2014 Apr;52(4):382-3. PMID: 24613100.
Mahajan GB, Balachandran L. Antibacterial agents from actinomycetes – a review. Front Biosci (Elite Ed). 2012 Jan 1;4:240-53. PMID: 22201868.
Airoldi C, Colombo L, Manzoni C, et al. Tetracycline prevents Aβ oligomer toxicity through an atypical supramolecular interaction. Org Biomol Chem. 2011 Jan 21;9(2):463-72. PMID: 21063627.
Griffin MO, Fricovsky E, Ceballos G, et al. Tetracyclines: a pleitropic family of compounds with promising therapeutic properties. Review of the literature. Am J Physiol Cell Physiol. 2010 Sep;299(3):C539-48. PMID: 20592239.
Hertweck M, Hiller R, Mueller MW. Inhibition of nuclear pre-mRNA splicing by antibiotics in vitro. Eur J Biochem. 2002 Jan;269(1):175-83. PMID: 11784311.
