Skip to Content
Merck

5.06291

Sigma-Aldrich

Lactimidomycin

≥98% (HPLC), powder, ribosome inhibitor, Calbiochem®

Synonym(s):

Lactimidomycin, LTM

Sign Into View Organizational & Contract Pricing

Select a Size

All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C26H35NO6
CAS Number:
134869-15-1
Molecular Weight:
457.56
MDL number:
MFCD30533614
UNSPSC Code:
12352200
NACRES:
NA.77

Product Name

Lactimidomycin,

Assay

≥98% (HPLC)

Quality Level

100

form

powder

potency

37.8 nM IC50

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

white

solubility

DMSO: soluble

storage temp.

−20°C

SMILES string

N1C(=O)CC(CC1=O)CC(O)CC(=O)C(C)\C=C(/C2OC(=O)\C=C/CC\C=C/C=C\C2C)\C

InChI

1S/C26H35NO6/c1-17-10-8-6-4-5-7-9-11-25(32)33-26(17)19(3)12-18(2)22(29)16-21(28)13-20-14-23(30)27-24(31)15-20/h4,6,8-12,17-18,20-21,26,28H,5,7,13-16H2,1-3H3,(H,27,30,31)/b6-4-,10-8-,11-9-,19-12-

InChI key

OYOKHBHOTQDIPM-YVQSYIHDSA-N

Related Categories

General description

A glutarimide based 12-membered macrolide antibiotic with antifungal properties. Acts as a potent inhibitor of cell migration, cell proliferation, and protein synthesis (IC50 = 37.82 nM), but does not affect RNA synthesis even at high concentrations (IC50 >10 µM). Acts as a potent inhibitor of translation and appears to block the first translocation step without affecting tRNA binding or peptide bond formation. It exhibits about 10-fold greater potency than cycloheximide (Cat. No. 239763 and 239764). Binds to the same site on the 60S ribosomal subunit with high affinity (Kd = 500 nM vs 15 µM for cycloheximide). Shown to extend the survival of mice bearing P388 lymphoma by blocking cell growth, however, it does not significantly affect non-tumorigenic MCF10A breast cell lines. Also shown to retard the growth of MDA MB231 cells in nude mice (~0.6 /mg/kg).
Lactimidomycin, CAS 134869-15-1, inhibits cell migration, proliferation, & protein synthesis (IC₅₀ = 37.8 nM). Blocks the first translocation step and has no effect on tRNA binding.

Biochem/physiol Actions

Primary Target
Ribosome
Reversible: yes

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Other Notes

Schneider-Poetsch, T., et al. 2010. Nat. Chem. Biol.6, 209.
Micoine, K., et al. 2010. J. Am. Chem. Soc.132, 14064.
Ju, J., et al. 2009. J. Am. Chem. Soc.131, 1370.
Sugawara, K., et al. 1992. J. Antibiot.45, 1433.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Standard Handling (A)

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Related Content

New Products Flyer- Feb 2014 - Vol 1

"Apoptosis & Autophagy in Cancer: Cell Survival by Eluding Cell Death The ability of tumor cells to elude programmed cell death, also known as apoptosis, is a hallmark of most types of cancer. Similary, autophagy is a highly regulated, homeostatic degradative process where cells destroy their own components via the lysosomal machinery and recycle them for prolonged cell survival. Via extensive crosstalk with pro-apoptotic signaling pathways, autophagy can also contribute to cell death and greatly influence general cell health. Elucidating the correlation between autophagy and apoptotic cell death has become the focus of a great deal of research, particularly in tumor biology. On one hand, autophagy may induce cell death by degrading essential components; on the other hand, it may facilitate survival of cancer cells under unfavorable metabolic conditions."

Global Trade Item Number

SKUGTIN
5.06291.000104055977243215

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service