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SBR00014

Sigma-Aldrich

Daptomycin Ready Made Solution

1 mg/mL in DMSO

Synonyme(s) :

N-decanoyl-L-tryptophyl-L-asparaginyl-L-aspartyl-L-threonylglycyl-L-ornithyl-L-aspartyl-D-alanyl-L-aspartylglycyl-D-seryl-threo-3-methyl-L-glutamyl-3-anthraniloyl-L-alanine[egr]1-lactone

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About This Item

Formule empirique (notation de Hill):
C72H101N17O26
Numéro CAS:
Poids moléculaire :
1620.67
Numéro MDL:
Code UNSPSC :
51102829
Nomenclature NACRES :
NA.76

Source biologique

Streptomyces roseosporus

Niveau de qualité

Description

Ready Made Solution

Forme

liquid

Conditions de stockage

(Keep container tightly closed in a dry and well-ventilated place.)

Concentration

1 mg/mL in DMSO

Couleur

colorless to faint yellow

Spectre d'activité de l'antibiotique

Gram-positive bacteria

Mode d’action

DNA synthesis | interferes
protein synthesis | interferes

Conditions d'expédition

dry ice

Température de stockage

−20°C

Chaîne SMILES 

O=C(NCC(N[C@H](CCCN)C(N[C@@H](CC(O)=O)C(N[C@H](C)C(N[C@@H](CC(O)=O)C(NC1)=O)=O)=O)=O)=O)[C@@H](NC([C@H](CC(O)=O)NC([C@@H](CC(N)=O)NC([C@H](CC2=CNC3=C2C=CC=C3)NC(CCCCCCCCC)=O)=O)=O)=O)[C@@H](C)OC([C@H](CC(C4=C(N)C=CC=C4)=O)NC([C@@]([C@H](C)CC(O)=O)([H])NC(

InChI

1S/C72H101N17O26/c1-5-6-7-8-9-10-11-22-53(93)81-44(25-38-31-76-42-20-15-13-17-39(38)42)66(108)84-45(27-52(75)92)67(109)86-48(30-59(102)103)68(110)89-61-37(4)115-72(114)49(26-51(91)40-18-12-14-19-41(40)74)87-71(113)60(35(2)24-56(96)97)88-69(111)50(34-90)82-55(95)32-77-63(105)46(28-57(98)99)83-62(104)36(3)79-65(107)47(29-58(100)101)85-64(106)43(21-16-23-73)80-54(94)33-78-70(61)112/h12-15,17-20,31,35-37,43-50,60-61,76,90H,5-11,16,21-30,32-34,73-74H2,1-4H3,(H2,75,92)(H,77,105)(H,78,112)(H,79,107)(H,80,94)(H,81,93)(H,82,95)(H,83,104)(H,84,108)(H,85,106)(H,86,109)(H,87,113)(H,88,111)(H,89,110)(H,96,97)(H,98,99)(H,100,101)(H,102,103)/t35?,36-,37?,43+,44+,45+,46+,47+,48+,49+,50-,60+,61?/m1/s1

Clé InChI

DOAKLVKFURWEDJ-OFNKPWESSA-N

Actions biochimiques/physiologiques

Daptomycin is a natural cyclic lipopeptide antibiotic found in Streptomyces roseosporus. It is has been found to be effective in treating infections caused by aerobic Gram-positive bacteria. Daptomycin inhibits many antibiotic resistant strains such as methicillin-resistant S. aureus (MRSA), vancomycin-intermediate S. aureus (VISA) and vancomycin-resistant S. aureus (VRSA).

The mode of action of daptomycin is quite different from that of any other antibiotic. Daptomycin binds to bacterial membranes and causes a rapid depolarization of membrane potential. This loss of membrane potential causes inhibition of protein, DNA, and RNA synthesis, which results in bacterial cell death.

Conditionnement

0.5ML

Notes préparatoires

The 1 mg/mL solution may be further diluted in an appropriate buffer prior to use. It is recommended that a fresh dilution be made on the day of use.

Autres remarques

Keep container tightly closed in a dry and well-ventilated place.

Code de la classe de stockage

10 - Combustible liquids

Classe de danger pour l'eau (WGK)

WGK 1

Point d'éclair (°F)

188.6 °F

Point d'éclair (°C)

87 °C


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Consulter la Bibliothèque de documents

[Daptomycin: revitalizing a former drug due to the need of new active agents against grampositive multiresistant bacterias].
Hernandez Marti V, et al.
Revista Espanola de Quimioterapia : Publicacion Oficial de la Sociedad Espanola de Quimioterapia, 20, 261-276 (2007)
Reduced pulmonary surfactant interaction of daptomycin analogs via tryptophan replacement with alternative amino acids.
He Y, et al.
Bioorganic & Medicinal Chemistry Letters, 22, 6248-6251 (2012)
Feng Wang et al.
Gene, 544(2), 208-215 (2014-04-29)
Daptomycin, a novel cyclic lipopeptide antibiotic against Gram-positive bacteria, is produced by Streptomyces roseosporus. Though its biosynthetic mechanism, structural shuffling and fermentation optimization have been extensively studied, little is understood about its production regulation at the transcriptional levels. Here we
Diixa Patel et al.
International journal of antimicrobial agents, 38(5), 442-446 (2011-08-16)
Daptomycin is highly active against Staphylococcus aureus, including multidrug-resistant strains and those with reduced susceptibility to vancomycin. However, daptomycin-non-susceptible (Dap(NS)) strains [minimum inhibitory concentration (MIC) >1mg/L] have been derived clinically and in vitro. The mechanism(s) by which this occurs is

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