Chlamydocin
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| Category | Others |
| Catalog number | BBF-00304 |
| CAS | 53342-16-8 |
| Molecular Weight | 526.62 |
| Molecular Formula | C28H38N4O6 |
| Purity | 95% |
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Description
Chlamydocin is a highly potent HDAC inhibitor produced by the strain of Diheterospora chlamydosporia. The inhibitory activity of mouse mast cell cancer cells was stronger than that of actinomycin D, but it could be inactivated by plasma, so the anti-tumor effect in vivo was low.
Specification
| Synonyms | Cyclo[2-methylalanyl-L-phenylalanyl-D-prolyl-(aS,2S)-a-amino-h-oxo-2-oxiraneoctanoyl] |
| IUPAC Name | (3S,9S,12R)-3-benzyl-6,6-dimethyl-9-[6-(oxiran-2-yl)-6-oxohexyl]-1,4,7,10-tetrazabicyclo[10.3.0]pentadecane-2,5,8,11-tetrone |
| Canonical SMILES | CC1(C(=O)NC(C(=O)N2CCCC2C(=O)NC(C(=O)N1)CCCCCC(=O)C3CO3)CC4=CC=CC=C4)C |
| InChI | InChI=1S/C28H38N4O6/c1-28(2)27(37)30-20(16-18-10-5-3-6-11-18)26(36)32-15-9-13-21(32)25(35)29-19(24(34)31-28)12-7-4-8-14-22(33)23-17-38-23/h3,5-6,10-11,19-21,23H,4,7-9,12-17H2,1-2H3,(H,29,35)(H,30,37)(H,31,34)/t19-,20-,21+,23?/m0/s1 |
| InChI Key | SGYJGGKDGBXCNY-ZDIDWYTNSA-N |
Properties
| Boiling Point | 861.8ºC at 760mmHg |
| Density | 1.27g/cm3 |
Reference Reading
1. Divergent Access to Histone Deacetylase Inhibitory Cyclopeptides via a Late-Stage Cyclopropane Ring Cleavage Strategy. Short Synthesis of Chlamydocin
Gábor Zoltán Elek, Kaur Koppel, Dzmitry M Zubrytski, Nele Konrad, Ivar Järving, Margus Lopp, Dzmitry G Kananovich Org Lett. 2019 Oct 18;21(20):8473-8478. doi: 10.1021/acs.orglett.9b03305. Epub 2019 Oct 9.
A unified step-economical strategy for accessing histone deacetylase inhibitory peptides is proposed, based on the late-stage installation of multiple zinc-binding functionalities via the cleavage of the strained cyclopropane ring in the common pluripotent cyclopropanol precursor. The efficacy of the proposed diversity-oriented approach has been validated by short stereoselective synthesis of natural product chlamydocin, containing a challenging-to-install fragment of (2S,9S)-2-amino-8-oxo-9,10-epoxydecanoic acid (Aoe) and a range of its analogues, derivatives of 2-amino-8-oxodecanoic and 2-aminosuberic acids.
2. Improved development of mouse somatic cell nuclear transfer embryos by chlamydocin analogues, class I and IIa histone deacetylase inhibitors†
Satoshi Kamimura, Kimiko Inoue, Eiji Mizutani, Jin-Moon Kim, Hiroki Inoue, Narumi Ogonuki, Kei Miyamoto, Shunya Ihashi, Nobuhiko Itami, Teruhiko Wakayama, Akihiro Ito, Norikazu Nishino, Minoru Yoshida, Atsuo Ogura Biol Reprod. 2021 Aug 3;105(2):543-553. doi: 10.1093/biolre/ioab096.
In mammalian cloning by somatic cell nuclear transfer (SCNT), the treatment of reconstructed embryos with histone deacetylase (HDAC) inhibitors improves efficiency. So far, most of those used for SCNT are hydroxamic acid derivatives-such as trichostatin A-characterized by their broad inhibitory spectrum. Here, we examined whether mouse SCNT efficiency could be improved using chlamydocin analogues, a family of newly designed agents that specifically inhibit class I and IIa HDACs. Development of SCNT-derived embryos in vitro and in vivo revealed that four out of five chlamydocin analogues tested could promote the development of cloned embryos. The highest pup rates (7.1-7.2%) were obtained with Ky-9, similar to those achieved with trichostatin A (7.2-7.3%). Thus, inhibition of class I and/or IIa HDACs in SCNT-derived embryos is enough for significant improvements in full-term development. In mouse SCNT, the exposure of reconstructed oocytes to HDAC inhibitors is limited to 8-10 h because longer inhibition with class I inhibitors causes a two-cell developmental block. Therefore, we used Ky-29, with higher selectivity for class IIa than class I HDACs for longer treatment of SCNT-derived embryos. As expected, 24-h treatment with Ky-29 up to the two-cell stage did not induce a developmental block, but the pup rate was not improved. This suggests that the one-cell stage is a critical period for improving SCNT cloning using HDAC inhibitors. Thus, chlamydocin analogues appear promising for understanding and improving the epigenetic status of mammalian SCNT-derived embryos through their specific inhibitory effects on HDACs.
3. Discovery of potent HDAC inhibitors based on chlamydocin with inhibitory effects on cell migration
Shimiao Wang, Xiaohui Li, Yingdong Wei, Zhilong Xiu, Norikazu Nishino ChemMedChem. 2014 Mar;9(3):627-37. doi: 10.1002/cmdc.201300372. Epub 2013 Nov 27.
The histone deacetylase (HDAC) family is a promising drug target class owing to the importance of these enzymes in a variety of cellular processes. Docking studies were conducted to identify novel HDAC inhibitors. Subtle modifications in the recognition domain were introduced into a series of chlamydocin analogues, and the resulting scaffolds were combined with various zinc binding domains. Remarkably, cyclo(L-Asu(NHOH)-L-A3mc6c-L-Phe-D-Pro, compound 1 b), with a methyl group at positions 3 or 5 on the aliphatic ring, exhibited better antiproliferative effects than trichostatin A (TSA) against MCF-7 and K562 cell lines. In addition to cell-cycle arrest and apoptosis, cell migration inhibition was observed in cells treated with compound 1 b. Subsequent western blot analysis revealed that the balance between matrix metalloproteinase 2 (MMP2) and tissue inhibitors of metalloproteinase 1 (TIMP1) determines the degree of metalloproteinase activity in MCF-7 cells, thereby regulating cell migration. The improved inhibitory activity imparted by altering the hydrophobic substitution pattern at the bulky cap group is a valuable approach in the development of novel HDAC inhibitors.
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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 ╳
