1-Alaninechlamydocin
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| Category | Antibiotics |
| Catalog number | BBF-04199 |
| CAS | 141446-96-0 |
| Molecular Weight | 512.61 |
| Molecular Formula | C27H36N4O6 |
| Purity | >95% by HPLC |
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Description
It is a cyclic tetrapeptide antibiotic containing a single β-amino acid, which was isolated from diheterospora chlamydosporia in 1992. It is less widely characterised than the related chlamydocin. It exhibits potent antitumor activity and acts by inhibiting histone deacetylase.
Specification
| Synonyms | Cyclo[L-alanyl-L-phenylalanyl-D-prolyl-(αS,2S)-α-amino-η-oxooxiraneoctanoyl]; (S)-Cyclo(L-alanyl-L-phenylalanyl-D-prolyl-η-oxo-L-α-aminooxiraneoctanoyl) |
| Storage | Store at -20°C |
| IUPAC Name | (3S,6S,9S,12S)-3-benzyl-6-methyl-9-[6-(oxiran-2-yl)-6-oxohexyl]-1,4,7,10-tetrazabicyclo[10.3.0]pentadecane-2,5,8,11-tetrone |
| Canonical SMILES | CC1C(=O)NC(C(=O)N2CCCC2C(=O)NC(C(=O)N1)CCCCCC(=O)C3CO3)CC4=CC=CC=C4 |
| InChI | InChI=1S/C27H36N4O6/c1-17-24(33)30-20(15-18-9-4-2-5-10-18)27(36)31-14-8-12-21(31)26(35)29-19(25(34)28-17)11-6-3-7-13-22(32)23-16-37-23/h2,4-5,9-10,17,19-21,23H,3,6-8,11-16H2,1H3,(H,28,34)(H,29,35)(H,30,33)/t17-,19-,20-,21-,23?/m0/s1 |
| InChI Key | QMNUPNOLDLHVTB-UKAZWLHKSA-N |
| Source | Unidentified fungus |
Properties
| Appearance | White Solid |
| Antibiotic Activity Spectrum | Neoplastics (Tumor) |
| Boiling Point | 871.9±65.0°C at 760 mmHg |
| Density | 1.3±0.1 g/cm3 |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO; Poorly soluble in Water |
Reference Reading
1. A potent HDAC inhibitor, 1-alaninechlamydocin, from a Tolypocladium sp. induces G2/M cell cycle arrest and apoptosis in MIA PaCa-2 cells
Jarrod B King, April L Risinger, Lin Du, Douglas R Powell, Robert H Cichewicz J Nat Prod . 2014 Jul 25;77(7):1753-7. doi: 10.1021/np500387h.
The cyclic tetrapeptide 1-alaninechlamydocin was purified from a Great Lakes-derived fungal isolate identified as a Tolypocladium sp. Although the planar structure was previously described, a detailed analysis of its spectroscopic data and biological activity are reported here for the first time. Its absolute configuration was determined using a combination of spectroscopic ((1)H-(1)H ROESY, ECD, and X-ray diffraction) and chemical (Marfey's analysis) methods. 1-Alaninechlamydocin showed potent antiproliferative/cytotoxic activities in a human pancreatic cancer cell line (MIA PaCa-2) at low-nanomolar concentrations (GI50 5.3 nM, TGI 8.8 nM, LC50 22 nM). Further analysis revealed that 1-alaninechlamydocin induced G2/M cell cycle arrest and apoptosis. Similar to other cyclic epoxytetrapeptides, the inhibitory effects of 1-alaninechlamydocin are proposed to be produced primarily via inhibition of histone deacetylase (HDAC) activity.
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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 ╳
