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Daptomycin

Daptomycin

Catalog No.

A1206

Calcium-dependent antibiotic

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Grouped product items
Size	Price	Stock
10mM (in 1mL DMSO)	$50.00	In stock
25mg	$50.00	In stock
100mg	$180.00	In stock

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Background
Product Citation
Chemical Properties
Protocol
Quality Control

Background

Daptomycin is a bactericidal antibiotic which works against a broad spectrum of Gram-positive bacteria and it can work both in-vitro and in-vivo. It is a cyclic lipopeptide and many antibiotic resistant strains can be inhibited by daptomycin, such as meticillin-resistant S. aureus (MRSA), vancomycin-intermediate S. aureus (VISA) and vancomycin-resistant S. aureus (VRSA).[1, 2]

The mode of action of Daptomycin would be through a calcium-dependent interaction with the cytoplasmic membrane, thus leading to the cell membrane depolarisation, ion loss and cell death.[2] Daptomycin can bind to the lipid tail of cell membrane of Gram-positive cells, then the following Ca2+ dependent insertion of daptomycin and oligomerization can cause a damage to the bacterial membrane potential, thus kills the cell very fast.[3]

References:
[1] Feng Wang, Ni-Ni Ren, Shuai Luo, Xiao-Xia Chen, Xu-Ming Mao, Yong-Quan Li. DptR2, a DeoR-type auto-regulator, is required for daptomycin production in Streptomyces roseosporus. Gene. 10 July 2014. 544(2): 208-215.
[2] Diixa Patel, Mashkur Husain, Celine Vidaillac, Molly E. Steed, Michael J. Rybak, Susan M. Seo, Glenn W. Kaatz. Mechanisms of in-vitro-selected daptomycin-non-susceptibility in Staphylococcus aureus. International Journal of Antimicrobial Agents. November 2011. 38(5): 442-446.
[3] Yong He, Jing Li, Nin Yin, Prudencio S. Herradura, Larry Martel, Yanzhi Zhang, Andre L. Pearson, Vidya Kulkarni, Carmela Mascio. Reduced pulmonary surfactant interaction of daptomycin analogs via tryptophan replacement with alternative amino acids. Bioorganic & Medicinal Chemistry Letters. 1 October 2012. 22(19): 6248-6251.

Product Citation

1. Brennan-Krohn T, Pironti A, Kirby JE. "Synergistic Activity of Colistin-Containing Combinations against Colistin-Resistant Enterobacteriaceae."Antimicrob Agents Chemother. 2018 Jul 30. pii: AAC.00873-18. PMID:30061285

Chemical Properties

Physical Appearance	A solid
Storage	Store at -20°C
M.Wt	1620.67
Cas No.	103060-53-3
Formula	C₇₂H₁₀₁N₁₇O₂₆
Solubility	≥81.05mg/mL in DMSO or H2O
SDF	Download SDF
Canonical SMILES	CCCCCCCCCC(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)NC(CC(=O)N)C(=O)NC(CC(=O)O)C(=O)NC3C(OC(=O)C(NC(=O)C(NC(=O)C(NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)CNC3=O)CCCN)CC(=O)O)C)CC(=O)O)CO)C(C)CC(=O)O)CC(=O)C4=CC=CC=C4N)C
Shipping Condition	Evaluation sample solution: ship with blue ice. All other available sizes: ship with RT, or blue ice upon request.
General tips	For obtaining a higher solubility, please warm the tube at 37°C and shake it in the ultrasonic bath for a while. Stock solution can be stored below -20°C for several months.

Protocol

Cell experiment [1]:
Cell lines	Methicillin susceptible S. aureus (ATCC #29213)
Preparation method	The solubility of this compound in DMSO is >81.1mg/mL. General tips for obtaining a higher concentration: Please warm the tube at 37℃ for 10 minutes and/or shake it in the ultrasonic bath for a while. Stock solution can be stored below -20℃ for several months.
Reacting condition	MIC: l μg/mL
Applications	In methicillin susceptible S. aureus (ATCC #29213), Daptomycin (DAP) maintained good antibacterial activities against S. auerus in Mueller-Hinton Broth supplemented with 50 mg/L calcium (MHBc).
Animal experiment [2]:
Animal models	murine model of enterococcal experimental peritonitis
Dosage form	50 mg/kg; q24h, intravenous (i.v.); 2 h after enterococcal inoculation for 48 h
Application	In mice injected intraperitoneally with 4 × 1010 colony-forming units of Enterococcus faecium, Daptomycin (DAP) significantly prolonged the mean time until death. DAP or DAP plus AMP significantly decreased the viable bacteria counts of the peritoneal fluid 6 h after inoculation.
Other notes	Please test the solubility of all compounds indoor, and the actual solubility may slightly differ with the theoretical value. This is caused by an experimental system error and it is normal.
References: [1] Yong He, Jing Li, Nin Yin, Prudencio S. Herradura, Larry Martel, Yanzhi Zhang, Andre L. Pearson, Vidya Kulkarni, Carmela Mascio. Reduced pulmonary surfactant interaction of daptomycin analogs via tryptophan replacement with alternative amino acids. Bioorganic & Medicinal Chemistry Letters. 1 October 2012. 22(19): 6248-6251. [2] Kajihara T1, Nakamura S2, Iwanaga N3, et al. Comparative efficacies of daptomycin, vancomycin, and linezolid in experimental enterococcal peritonitis. J Infect Chemother. 2017 Jul;23(7):498-501.