CINNAMYCIN Chemical Properties

Density 

1.59±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

acetonitrile: water: 5 mg/mL

form 

solid

pka

3.15±0.11(Predicted)

color 

brown

biological source

Streptomyces cinnamoneus

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

RTECS 

GE1745000

CINNAMYCIN Usage And Synthesis

Uses

Cinnamycin has been used in cinnamycin senstivity assay in mouse embryonic fibroblasts (MEFs).

Uses

Cinnamycin (lanthiopeptin) is a high molecular weight tricyclic antibiotic produced by several species of Streptoverticillium. Cinnamycin is a potent indirect inhibitor of phospholipase A2, acting by specifically sequestering phosphatidylethanolamine (PE), a major component of the mammalian plasma cell membrane. Cinnamycin induces trans-bilayer phospholipid movement in cell membranes to expose internally bound PE. At high surface concentrations of PE, cinnamycin induces membrane re-organisation including membrane fusion and alteration of gross morphology.

Definition

ChEBI: Cinnamycin is a type B lantibiotic consisting of a 19 amino acid tetracyclic polypeptide produced by Streptomyces cinnamoneus. It is a heterodetic cyclic peptide, a macrocycle, a type B lantibiotic and a L-cysteine thioether.

Biosynthesis

Ayşe Ökesli and colleagues investigated the biosynthetic machinery using both in vitro studies and heterologous expression in Escherichia coli. CinX is an α-ketoglutarate/iron(II)-dependent hydroxylase that carries out the hydroxylation of aspartate 15 of the precursor peptide CinA. In addition, CinM catalyzes dehydration of four Ser and Thr residues and subsequent cyclization of Cys residues to form the three (Me)Lan bridges.

General Description

Cinnamycin is synthesized after proteolytic cleavage from core peptide and takes up a compact globular structure.

Biological Activity

cinnamycin is a tricyclic antibiotic.cinnamycin, a tetracyclic lantibiotic, is produced from s. cinnamoneus containing four unusual amino acids: mesolanthionine, erythro-β-hydroxyaspartic acid, threo-β-methyllanthionine and lysinoalanine.

Biochem/physiol Actions

Cinnamycin is a tetracyclic polypeptide antibiotic containing 19 amino acids. The polypeptide has the unusual amino acids threo-3-methyl-lanthionine, meso-lanthionine, lysinoalanine and 3-hydroxyaspartic acid. It is produced by Streptomyces cinnamoneus and belongs to the duramycin-type l antibiotics. Lantibiotics are synthesized in the ribosome and undergo extensive post-translational modifications to attain their active antimicrobial form. The unique receptor for Cinnamycin, phosphatidylethanolamine (PE), is located on the inner leaflet of the plasma membrane. Cinnamycin induces transbilayer lipid movement leading to the exposure of PE to the outer leaflet of the plasma membrane. The interaction of Cinnamycin with PE provides a tool for PE monitoring. Cinnamycin is active against Gram-positive rods such as Bacilli, Clostyridium and Mycobacterium, causing cell wall biosynthesis stress.Cinnamycin, like other lantibiotics, was also reported to inhibit phospholipase A2 (PLA2). It was suggested as an alternative treatment for atherosclerosis through its ability to inhibit PLA2 by binding to its substrate PE. Moreover, Cinnamycin was found to inhibit Herpes simplex virus (HSV-1) activity.

in vitro

a previous study indicated that cinnamycin could exclusively bind to ethanolamine phospholipids, such as pe and ethanolamine plasmalogen. model membrane study showed that the binding of cinnamycin to pe-containing liposomes was dependent on membrane curvature. the binding of cinnamycin to multilamellar liposomes induced tubulation of membranes, as demonstrated by electron microscopy and small-angle x-ray scattering [1].

References

[1] iwamoto k, hayakawa t, murate m, makino a, ito k, fujisawa t, kobayashi t. curvature-dependent recognition of ethanolamine phospholipids by duramycin and cinnamycin. biophys j. 2007 sep 1;93(5):1608-19.
[2] wilson dh. clindamycin in the treatment of soft tissue infections: a review of 15 019 patients. br j surg. 1980 feb;67(2):93-6.

CINNAMYCIN(110655-58-8)Related Product Information

• TRIS(2,2,6,6-TETRAMETHYL-3,5-HEPTANEDIONATO)DYSPROSIUM(III)
• Ethyl isocyanoacetate
• Ferric acetylacetonate
• Aluminum acetylacetonate
• SALCOMINE
• Cupric acetylacetonate
• TERT-BUTYL ISOCYANIDE
• Benzyl isocyanide
• COBALT(II) ACETYLACETONATE
• METHYL ISOCYANOACETATE
• N-BUTYLISOCYANIDE
• PHENYLSELENOL
• 1,1,3,3-TETRAMETHYLBUTYL ISOCYANIDE
• DICHLORO(ETHYLENEDIAMINE)PLATINUM(II)
• 2,4-PENTANEDIONE, SILVER DERIVATIVE
• Tosylmethyl isocyanide
• TRIS(2,2,6,6-TETRAMETHYL-3,5-HEPTANEDIONATO)EUROPIUM(III)
• Tris(2,4-pentanedionato)chroMiuM(III)