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| | A 54556A Basic information |
| Product Name: | A 54556A | | Synonyms: | PubChem ID: 24767779;A 54556A (~90%);A 54556A;Antibiotic A-54556A;L-Proline, N-[(2E,4E,6E)-1-oxo-2,4,6-octatrien-1-yl]-L-phenylalanyl-L-seryl-L-prolyl-N-methyl-L-alanyl-L-alanyl-4-methyl-, (6→2)-lactone, (4R)- | | CAS: | 95398-45-1 | | MF: | C38H50N6O8 | | MW: | 718.839 | | EINECS: | | | Product Categories: | | | Mol File: | 95398-45-1.mol |  |
| | A 54556A Chemical Properties |
| Melting point | >180oC (dec.) | | Boiling point | 1086.9±65.0 °C(Predicted) | | density | 1.28±0.1 g/cm3(Predicted) | | storage temp. | Amber Vial, Refrigerator | | solubility | Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly) | | form | Solid | | pka | 12.80±0.46(Predicted) | | color | Pale Yellow to Light Brown | | Stability: | Light Sensitive |
| | A 54556A Usage And Synthesis |
| Description | A-54556A is an acyldepsipeptide (ADEP) antibiotic that has been found in Streptomyces hawaiiensis. It is active against B. subtilis, S. pyogenes, and E. faecalis, as well as penicillin-resistant S. pneumoniae, vancomycin-resistant E. faecium, and methicillin-resistant S. aureus (MRSA; IC50s = 0.2, 0.4, 0.4, 1.6, 0.4, and 6.3 μg/ml, respectively). It binds to and activates caseinolytic protease P (ClpP), inducing degradation of β-casein by the B. subtilis ClpP in an ATPase-independent manner when used at concentrations of 2.5 and 5 μg/ml. | | Uses | A 54556A is an unusual depsipeptide isolated from Streptomyces hawaiiensis by researchers at Eli Lilly in 1985, featuring a trienone side chain. A 54556A is potently active against Gram positive and Gram negative bacteria, including MRSA. A 54556A was the original lead structure of the recently re-discovered acyldepsipeptide (ADEP) antibiotics that act by activating and disregulating Clp-family proteins. ADEPs are considered important leads in the development of new generations of antibiotics against resistant bacteria. | | in vitro | previous study found that the treatment of b. subtilis with 1.6 mg/ml of a-54556a reduced the number of viable cells by 2 log units. in addition, the biosynthesis of dna, rna, protein, cell wall and fatty acid proceeded unhindered for 1 h at 2 mg/ml a-54556a, whereas classical antibiotics were clearly distinguished by preferential inhibition of their target pathway. microscopic examination showed that after addition of a-54556a at concentrations as low as 0.4 mg/ml, b. subtilis started to form filaments [1]. | | in vivo | two a-54556a analogs, adep 2 and adep 4, were proven to be active in the treatment of bacterial infections in rodents. when mice were challenged with a lethal systemic infection of e. faecalis, 1 mg/kg adep 2 or 0.5 mg/kg adep 4 were sufficient for 100% survival. in lethal sepsis caused by s. aureus, 12.5 mg/kg adep 4 rescued 80% of the mice and reduced the bacterial loads in liver, spleen and lung by 2–3 log units compared to an untreated control [1]. | | IC 50 | 0.2 μg/ml for bacillus subtilis 168 | | references | [1] h. brtz-oesterhelt, d. beyer, h. p. kroll, et al. dysregulation of bacterial proteolytic machinery by a new class of antibiotics. nature medicine 11(10), 1082-1087 (2005). |
| | A 54556A Preparation Products And Raw materials |
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