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SML0188 Sigma-Aldrich

Ikarugamycin

≥98% (HPLC), from Streptomyces sp.

Synonym: 14,17-Metheno-17H-as-indaceno[3,2-k][1,6]diazacycloheptadecine-9,16,18(1H)-trione, 3-Ethyl-2,3,3a,5a,5b,6,10,11,12,13,14,15,20a,21,21a,21b-hexadecahydro-22-hydroxy-2-methyl-, (2R,3R,3aS,5aR,5bS,7Z,14S,19E,20aS,21aR,21bR)-, IKA, TU-6239 C3

  • CAS Number 36531-78-9

  • Empirical Formula (Hill Notation) C29H38N2O4

  • Molecular Weight 478.62

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Properties

Related Categories Antibiotics, Antibiotics A to Z, Antibiotics G-M, Apoptosis Inducers, Apoptosis and Cell Cycle,
biological source   Streptomyces sp.
assay   ≥98% (HPLC)
solubility   chloroform: 1 mg/mL (requires heating and sonication)
  methanol: 1 mg/mL (requires heating and sonication)
  DMSO: 5 mg/mL (requires heating and sonication)
Mode of action   protein synthesis | interferes
antibiotic activity spectrum   Gram-positive bacteria
  parasites
storage temp.   −20°C

Description

Biochem/physiol Actions

Ikarugamycin, an unusual pentacyclic tetramic acid produced by Streptomyces sp., has a potent activity against the protozoan Trichomonas vaginalis with IC50 of 0.3-1.25 μg/mL. Ikarugamycin also demonstrates selective Gram positive antibacterial activity and exhibits anti-ulcer activity possibly through inhibition of Helicobacter. Ikarugamycin-induced inhibition of cholesteryl-ester accumulation reduced uptake of oxidized low-density lipoprotein (LDL) in mouse macrophages J774. Moreover, Ikarugamycin inhibits Nef-induced degradation of CD4 on Human Immunodeficiency Virus type 1 (HIV) infected T cells, thus increasing its half-life and possibly restoring some normal functions lost in the infected cells. Ikarugamycin inhibition of clathrin-coated pit-mediated endocytosis indicates it as a useful agent for studying the process of endocytosis. Ikarugamycin inhibit HL-60 cell proliferation through genotoxicity and apoptosis induction and to activated caspase by induction of intracellular rise in calcium levels and activation of p38 MAP kinase.

Features and Benefits

This compound is featured on the Caspases page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Safety & Documentation

Safety Information

Symbol 
GHS06  GHS06
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
UN 2811 6.1 / PGIII
WGK Germany 
3

Documents

Certificate of Analysis

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Milli-Q® Water Purification Solutions
Protocols & Articles

Articles

Caspases

Caspases (Cysteine dependant Aspartate Specific Proteases) form a family of closely related enzymes (family C14; clan CD) involved in regulating a type of cell death known as apoptosis, inflammatory ...
Keywords: Alkylations, Alzheimer Disease, Apoptosis, Cancer, Catalysis, Clinical, Diseases, Gene expression, Huntington Disease, Inflammation, Ligands, Oncology, Parkinson Disease, Polymorphisms

Peer-Reviewed Papers
15

References

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