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1-Alaninechlamydocin

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1-Alaninechlamydocin
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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Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

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Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product 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.

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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
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
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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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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