Lavendamycin
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| Category | Antibiotics |
| Catalog number | BBF-02243 |
| CAS | 81645-09-2 |
| Molecular Weight | 398.38 |
| Molecular Formula | C22H14N4O4 |
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Description
It is produced by the strain of Str. lavendulae C-22030. It's a quinone antibiotic. It has anti-bacterial and fungal effect, but the anti-bacterial effect is weaker than Streptonigrin, while the anti-fungal effect is stronger than Streptonigrin.
Specification
| Synonyms | 9H-Pyrido(3,4-b)indole-3-carboxylic acid, 1-(7-amino-5,8-dihydro-5,8-dioxo-2-quinolinyl)-4-methyl-; Antibiotic K 82A |
| IUPAC Name | 1-(7-amino-5,8-dioxoquinolin-2-yl)-4-methyl-9H-pyrido[3,4-b]indole-3-carboxylic acid |
| Canonical SMILES | CC1=C2C3=CC=CC=C3NC2=C(N=C1C(=O)O)C4=NC5=C(C=C4)C(=O)C=C(C5=O)N |
| InChI | InChI=1S/C22H14N4O4/c1-9-16-10-4-2-3-5-13(10)24-20(16)19(26-17(9)22(29)30)14-7-6-11-15(27)8-12(23)21(28)18(11)25-14/h2-8,24H,23H2,1H3,(H,29,30) |
| InChI Key | IGQJRDIREIWBQP-UHFFFAOYSA-N |
Properties
| Antibiotic Activity Spectrum | Fungi |
| Boiling Point | 790.0°C at 760 mmHg |
| Melting Point | >300°C (dec.) |
| Density | 1.56 g/cm3 |
| Solubility | Soluble in Methanol, Methanol-Hydrochloric acid, Methanol-Sodium hydroxide |
Reference Reading
1. Synthesis, metabolism and in vitro cytotoxicity studies on novel lavendamycin antitumor agents
Wen Cai, Mary Hassani, Rajesh Karki, Ervin D Walter, Katherine H Koelsch, Hassan Seradj, Jayana P Lineswala, Hamid Mirzaei, Jeremy S York, Fatemeh Olang, Minoo Sedighi, Jennifer S Lucas, Thomas J Eads, Anthony S Rose, Sahba Charkhzarrin, Nicholas G Hermann, Howard D Beall, Mohammad Behforouz Bioorg Med Chem. 2010 Mar 1;18(5):1899-909. doi: 10.1016/j.bmc.2010.01.037. Epub 2010 Jan 25.
A series of lavendamycin analogues with two, three or four substituents at the C-6, C-7 N, C-2', C-3' and C-11' positions were synthesized via short and efficient methods and evaluated as potential NAD(P)H:quinone oxidoreductase (NQO1)-directed antitumor agents. The compounds were prepared through Pictet-Spengler condensation of the desired 2-formylquinoline-5,8-diones with the required tryptophans followed by further needed transformations. Metabolism and toxicity studies demonstrated that the best substrates for NQO1 were also the most selectively toxic to NQO1-rich tumor cells compared to NQO1-deficient tumor cells.
2. Methyl 1-(7-acetamido-5,8-dimeth-oxy-quinolin-2-yl)-4-methyl-β-carboline-3-carboxyl-ate
Felix Nissen, Dieter Schollmeyer, Heiner Detert Acta Crystallogr Sect E Struct Rep Online. 2011 Jun 1;67(Pt 6):o1497-8. doi: 10.1107/S1600536811018794. Epub 2011 May 25.
The title compound, C(27)H(24)N(4)O(5), is an inter-mediate in the synthesis of lavendamycin via a ruthenium-catalysed [2 + 2 + 2] cyclo-addition. An intra-molecular hydrogen-bond bridge from the carboline to the quinoline stabilizes a highly planar geometry [maximum deviation = 0.065 (6) Å] for the two rigid units. This hydrogen-bond-stabilized coplanarity has a very close analogy in the structure of the anti-tumor anti-biotic streptonigrin in the solid state and in solution. Inter-molecular hydrogen-bond bridges of amides groups along the a axis and π-π stacking inter-actions [centroid-centroid distance = 3.665 (9) Å] connect mol-ecules arranged in a parallel manner.
3. Significance of agitation-induced shear stress on mycelium morphology and lavendamycin production by engineered Streptomyces flocculus
Xue Xia, Shuangjun Lin, Xiao-Xia Xia, Feng-Song Cong, Jian-Jiang Zhong Appl Microbiol Biotechnol. 2014 May;98(10):4399-407. doi: 10.1007/s00253-014-5555-4. Epub 2014 Feb 13.
Lavendamycin methyl ester (LME) is a derivative of a highly functionalized aminoquinone alkaloid lavendamycin and could be used as a scaffold for novel anticancer agent development. This work demonstrated LME production by cultivation of an engineered strain of Streptomyces flocculus CGMCC4.1223 ΔstnB1, while the wild-type strain did not produce. To enhance its production, the effect of shear stress and oxygen supply on ΔstnB1 strain cultivation was investigated in detail. In flask culture, when the shaking speed increased from 150 to 220 rpm, the mycelium was altered from a large pellet to a filamentous hypha, and the LME production was almost doubled, while no significant differences were observed among varied filling volumes, which implied a crucial role of shear stress in the morphology and LME production. To confirm this suggestion, experiments with agitation speed ranging from 400 to 1,000 rpm at a fixed aeration rate of 1.0 vvm were conducted in a stirred tank bioreactor. It was found that the morphology became more hairy with reduced pellet size, and the LME production was enhanced threefolds when the agitation speed increased from 400 to 800 rpm. Further experiments by varying initial k L a value at the same agitation speed indicated that oxygen supply only slightly affected the physiological status of ΔstnB1 strain. Altogether, shear stress was identified as a major factor affecting the cell morphology and LME production. The work would be helpful to the production of LME and other secondary metabolites by filamentous microorganism cultivation.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
