Dalfopristin
Dalfopristin is a streptogramin antibiotic and a 50S ribosome inhibitor [1][2].
Streptogramins are produced by a variety of Streptomyces sp as a mixture (ratio of 7:3) of two chemically unrelated compounds, type A and B. Dalfopristin, the type A Streptogramin, is often combined with type B streptogramin antibiotic, quinupristin, to produce Quinupristin-Dalfopristin Complex, known commercially as Synercid. Synercid is used to treat skin infections, and is also active against some Gram-negative and anaerobic bacteria [2][3].
The ribosome is composed of two ribonucleoprotein subunits, the 50S and 30S. The 50S ribosome inhibitors inhibited protein synthesis [2].
Dalfopristin is a cyclic polyunsaturated macrolactone that interferes with binding of tRNA substrates to both A- and P-sites [2]. Dalfopristin blocked the access of peptidyl-tRNAs to the ribosome and peptidyltransferase elongation reaction in bacteria [1]. quinupristin and dalfopristin acted synergistically to kill Gram-positive bacteria, as well as some Gram-negative and anaerobic bacteria [2][3]. Dalfopristin hydrolyzed rapidly to virginiamycin M under physiological conditions.
References:
[1].? Kohanski MA, Dwyer DJ, Collins JJ. How antibiotics kill bacteria: from targets to networks. Nat Rev Microbiol. 2010 Jun;8(6):423-35.
[2].? Wilson DN. The A-Z of bacterial translation inhibitors. Crit Rev Biochem Mol Biol. 2009 Nov-Dec;44(6):393-433.
[3].? Noeske J, Huang J, Olivier NB, et al. Synergy of streptogramin antibiotics occurs independently of their effects on translation. Antimicrob Agents Chemother. 2014 Sep;58(9):5269-79.
| Physical Appearance | A solid |
| Storage | Store at -20°C |
| M.Wt | 690.85 |
| Cas No. | 112362-50-2 |
| Formula | C34H50N4O9S |
| Synonyms | RP 54476 |
| Solubility | ≥50.3 mg/mL in DMSO; ≥51.8 mg/mL in EtOH; insoluble in H2O |
| Chemical Name | (12Z,32S,33R,6S,7R,8E,13Z,15E,17S)-33-((2-(diethylamino)ethyl)sulfonyl)-17-hydroxy-6-isopropyl-7,15-dimethyl-5-oxa-11-aza-1(4,2)-oxazola-3(1,2)-pyrrolidinacycloicosaphane-8,13,15-triene-2,4,10,19-tetraone |
| Canonical SMILES | O=C(N(CC[C@H]1S(CCN(CC)CC)(=O)=O)[C@@]1([H])C(O[C@@H](C(C)C)[C@H](C)/C=C/C2=O)=O)C3=COC(CC(C[C@H](O)/C=C(C)/C=C\CN2)=O)=N3 |
| Shipping Condition | Small Molecules with Blue Ice, Modified Nucleotides with Dry Ice. |
| General tips | We do not recommend long-term storage for the solution, please use it up soon. |
Quality Control & MSDS
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Chemical structure
