Apicularen A
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| Category | Mycotoxins |
| Catalog number | BBF-00059 |
| CAS | 220757-04-0 |
| Molecular Weight | 441.52 |
| Molecular Formula | C25H31NO6 |
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Description
Apicularen A is a macrolide antibiotic produced by Chondromyces robustus Cma 13. Apicularen A has no antibacterial activity, but for human and animal tumor cells such as KB-3-1, KB-V1, K-562, HL-60, U-937, A-498, A-549, PC-3 and SK-OV -3 grade has strong cytotoxicity.
Specification
| IUPAC Name | (2Z,4Z)-N-[(E)-3-[(1S,11S,13R,15R)-7,15-dihydroxy-9-oxo-10,17-dioxatricyclo[11.3.1.03,8]heptadeca-3(8),4,6-trien-11-yl]prop-1-enyl]hepta-2,4-dienamide |
| Canonical SMILES | CCC=CC=CC(=O)NC=CCC1CC2CC(CC(O2)CC3=C(C(=CC=C3)O)C(=O)O1)O |
| InChI | InChI=1S/C25H31NO6/c1-2-3-4-5-11-23(29)26-12-7-9-19-16-21-15-18(27)14-20(31-21)13-17-8-6-10-22(28)24(17)25(30)32-19/h3-8,10-12,18-21,27-28H,2,9,13-16H2,1H3,(H,26,29)/b4-3-,11-5-,12-7+/t18-,19+,20+,21-/m1/s1 |
| InChI Key | MVOORUCGKRDJFW-ZZBSXQHZSA-N |
Properties
| Appearance | Colorless Crystal |
Reference Reading
1. A synthetic study toward the core structure of (-)-apicularen A
Tapas R Pradhan, Debendra K Mohapatra Org Biomol Chem. 2018 Nov 21;16(45):8810-8818. doi: 10.1039/c8ob02301h.
A concise synthetic strategy towards the core structure of (-)-apicularen A has been described in an 11-step synthetic sequence from a known intermediate. The key steps include tandem isomerization followed by C-O and C-C bond-forming reactions and iodocyclization strategies for the synthesis of a bicyclic ether embedded in the macrolactone ring. The applied reagent-controlled Keck-Maruoka allylation, Lin Pu alkynylation and Ricket-Diels-Alder reactions were used to simplify the synthetic sequence of related natural products. An intramolecular Yamaguchi lactonization constructed the macrolactone core, while the attempt to install the C11 hydroxyl chiral centre either under catalytic hydrogenation conditions or oxidative conditions was not successful.
2. PMA synergistically enhances apicularen A-induced cytotoxicity by disrupting microtubule networks in HeLa cells
Kang-Sik Seo, Jong-Seok Kim, Ji-Hoon Park, Kyoung-Sub Song, Eun-Jin Yun, Jong-Il Park, Gi Ryang Kweon, Wan-Hee Yoon, Kyu Lim, Byung-Doo Hwang BMC Cancer. 2014 Jan 22;14:36. doi: 10.1186/1471-2407-14-36.
Background: Combination therapy is key to improving cancer treatment efficacy. Phorbol 12-myristate 13-acetate (PMA), a well-known PKC activator, increases the cytotoxicity of several anticancer drugs. Apicularen A induces cytotoxicity in tumor cells through disrupting microtubule networks by tubulin down-regulation. In this study, we examined whether PMA increases apicularen A-induced cytotoxicity in HeLa cells. Methods: Cell viability was examined by thiazolyl blue tetrazolium (MTT) assays. To investigate apoptotic potential of apicularen A, DNA fragmentation assays were performed followed by extracting genomic DNA, and caspase-3 activity assays were performed by fluorescence assays using fluorogenic substrate. The cell cycle distribution induced by combination with PMA and apicularen A was examined by flow cytometry after staining with propidium iodide (PI). The expression levels of target proteins were measured by Western blotting analysis using specific antibodies, and α-tubulin mRNA levels were assessed by reverse transcription polymerase chain reaction (RT-PCR). To examine the effect of combination of PMA and apicularen A on the microtubule architecture, α-tubulin protein and nuclei were visualized by immunofluorescence staining using an anti-α-tubulin antibody and PI, respectively. Results: We found that apicularen A induced caspase-dependent apoptosis in HeLa cells. PMA synergistically increased cytotoxicity and apoptotic sub-G1 population induced by apicularen A. These effects were completely blocked by the PKC inhibitors Ro31-8220 and Go6983, while caspase inhibition by Z-VAD-fmk did not prevent cytotoxicity. RNA interference using siRNA against PKCα, but not PKCβ and PKCγ, inhibited cytotoxicity induced by combination PMA and apicularen A. PMA increased the apicularen A-induced disruption of microtubule networks by further decreasing α- and β-tubulin protein levels in a PKC-dependent manner. Conclusions: These results suggest that the synergy between PMA and apicularen A is involved by PKCα activation and microtubule disruption, and that may inform the development of novel approaches to treat cancer.
3. Correction: A synthetic study toward the core structure of (-)-apicularen A
Tapas R Pradhan, Debendra K Mohapatra Org Biomol Chem. 2019 Jan 2;17(2):397. doi: 10.1039/c8ob90184h.
Correction for 'A synthetic study toward the core structure of (-)-apicularen A' by Tapas R. Pradhan et al., Org. Biomol. Chem., 2018, 16, 8810-8818.
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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 ╳
