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lavendamycin
Sign in to saveLavendamycin is a naturally occurring chemical compound discovered in fermentation broth of the soil bacterium Streptomyces lavendulae. Lavendamycin has antibiotic properties and anti-proliferative effects against several cancer cell lines. The use of lavendamycin as a cytotoxic agent in cancer therapy failed due to poor water solubility and non-specific cytotoxicity. The study of lavendamycin-based analogs designed to overcome these liabilities has been an area of research.
Chemical data
- Formula
- C22H14N4O4
- Molecular weight
- 398.4 g/mol
- IUPAC name
- 1-(7-amino-5,8-dioxoquinolin-2-yl)-4-methyl-9H-pyrido[3,4-b]indole-3-carboxylic acid
- SMILES
- CC1=C2C3=CC=CC=C3NC2=C(N=C1C(=O)O)C4=NC5=C(C=C4)C(=O)C=C(C5=O)N
- InChIKey
- IGQJRDIREIWBQP-UHFFFAOYSA-N
- XLogP
- 2.6
- Polar surface area
- 139 Ų
- H-bond donors
- 3
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 398.101505
Show 2 more facts
- chemical formula
- C₂₂H₁₄N₄O₄
- canonical SMILES
- CC1=C2C3=CC=CC=C3NC2=C(N=C1C(=O)O)C4=NC5=C(C=C4)C(=O)C=C(C5=O)N
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
3 sectionsContents
- Discovery
- Total syntheses
- References
Lavendamycin is a naturally occurring chemical compound discovered in fermentation broth of the soil bacterium Streptomyces lavendulae. Lavendamycin has antibiotic properties and anti-proliferative effects against several cancer cell lines. The use of lavendamycin as a cytotoxic agent in cancer therapy failed due to poor water solubility and non-specific cytotoxicity. The study of lavendamycin-based analogs designed to overcome these liabilities has been an area of research.
__TOC__ == Discovery == Lavendamycin was first discovered in 1981 by Doyle et al., who isolated it from Streptomyces lavendulae. As the compound failed to crystallize, a direct characterization of the molecular structure with X-ray crystallography was not possible. Careful analysis using NMR, IR, and UV-VIS spectroscopy and mass spectrometry allowed the assignment of the pentacyclic structure consisting of a β-carboline unit and a quinolinequinone unit.
Excerpted from Wikipedia’s “lavendamycin” article, available under the CC BY-SA 4.0 licence.