Eupenifeldin
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Mycotoxins |
| Catalog number | BBF-03519 |
| CAS | 151803-45-1 |
| Molecular Weight | 548.66 |
| Molecular Formula | C33H40O7 |
Online Inquiry
Description
Ekoenifelden is a bis-heptanol (Bistropolone) compound produced by Eupenicillum brefeldianum. It is cytotoxic to HCT-116 cell line (IC50 = 0.005 μg/mL), and has anti-tumor effect on P388 leukemia model.
Specification
| Synonyms | (6aR*,8E,11aS*,18aR*,19R*,20aR*)-6a,7,10,11,11a,18a,19,20,20a,21-Decahydro-4,16,19-trihydroxy-1,6a,10,13,18a-hexamethyl-3H-dicyclohepta(e,e')cycloundeca(1,2-b:5,6-b')dipyran-3,15(12H)-dione |
| IUPAC Name | (17E)-3,9,25-trihydroxy-4,11,16,16,20,27-hexamethyl-5,21-dioxapentacyclo[18.9.0.04,14.06,12.022,28]nonacosa-6,9,11,17,22,25,27-heptaene-8,24-dione |
| Canonical SMILES | CC1=C2CC3CC(C4(C(CC5=C(C=C(C(=O)C=C5O4)O)C)CC(C=CCC3(OC2=CC(=O)C(=C1)O)C)(C)C)C)O |
| InChI | InChI=1S/C33H40O7/c1-18-10-24(34)26(36)15-28-22(18)12-20-14-30(38)33(6)21(17-31(3,4)8-7-9-32(20,5)39-28)13-23-19(2)11-25(35)27(37)16-29(23)40-33/h7-8,10-11,15-16,20-21,30,38H,9,12-14,17H2,1-6H3,(H,34,36)(H,35,37)/b8-7+ |
| InChI Key | BWTQHPFSWXJOGP-BQYQJAHWSA-N |
Properties
| Antibiotic Activity Spectrum | neoplastics (Tumor) |
| Boiling Point | 748°C at 760 mmHg |
| Density | 1.28 g/cm3 |
Reference Reading
1. Delivery of eupenifeldin via polymer-coated surgical buttresses prevents local lung cancer recurrence
Zeinab Y Al Subeh, Ngoc-Quynh Chu, Jeremy T Korunes-Miller, Lillian L Tsai, Tyler N Graf, Yin P Hung, Cedric J Pearce, Mark W Grinstaff, Aaron H Colby, Yolonda L Colson, Nicholas H Oberlies J Control Release. 2021 Mar 10;331:260-269. doi: 10.1016/j.jconrel.2021.01.026. Epub 2021 Jan 21.
Lung cancer is the leading cause of cancer deaths worldwide. Unfortunately, high recurrence rates and poor survival remain despite surgical resection and conventional chemotherapy. Local drug delivery systems are a promising intervention for lung cancer treatment with the potential for improved efficacy with reduced systemic toxicity. Here, we describe the development of a chemotherapy-loaded polymer buttress, to be implanted along the surgical margin at the time of tumor resection, for achieving local and prolonged release of a new anticancer agent, eupenifeldin. We prepared five different formulations of buttresses with varying amounts of eupenifeldin, and additional external empty polymer coating layers (or thicknesses) to modulate drug release. The in vitro eupenifeldin release profile depends on the number of external coating layers with the formulation of the greatest thickness demonstrating a prolonged release approaching 90 days. Similarly, the long-term cytotoxicity of eupenifeldin-loaded buttress formulations against murine Lewis lung carcinoma (LLC) and human lung carcinoma (A549) cell lines mirrors the eupenifeldin release profiles and shows a prolonged cytotoxic effect. Eupenifeldin-loaded buttresses significantly decrease local tumor recurrence in vivo and increase disease-free survival in a lung cancer resection model.
2. Meroterpenoids from Neosetophoma sp.: A Dioxa[4.3.3]propellane Ring System, Potent Cytotoxicity, and Prolific Expression
Tamam El-Elimat, Huzefa A Raja, Sloan Ayers, Steven J Kurina, Joanna E Burdette, Zachary Mattes, Robert Sabatelle, Jeffrey W Bacon, Aaron H Colby, Mark W Grinstaff, Cedric J Pearce, Nicholas H Oberlies Org Lett. 2019 Jan 18;21(2):529-534. doi: 10.1021/acs.orglett.8b03769. Epub 2019 Jan 8.
Six fungal metabolites, of which five were new, including one (1) with a dioxa[4.3.3]propellane ring system, were discovered, identified, and structurally elucidated from Neosetophoma sp. (strain MSX50044); these compounds are similar to the bis-tropolone, eupenifeldin. Three of the meroterpenoids are potent cytotoxic agents against breast, ovarian, mesothelioma, and lung cancer cells with nanomolar IC50 values while not inducing mitochondrial toxicity at 12.5 μM.
3. Synthetic Biology Driven Biosynthesis of Unnatural Tropolone Sesquiterpenoids
Carsten Schotte, Lei Li, Daniel Wibberg, Jörn Kalinowski, Russell J Cox Angew Chem Int Ed Engl. 2020 Dec 21;59(52):23870-23878. doi: 10.1002/anie.202009914. Epub 2020 Oct 26.
Tropolone sesquiterpenoids (TS) are an intriguing family of biologically active fungal meroterpenoids that arise through a unique intermolecular hetero Diels-Alder (hDA) reaction between humulene and tropolones. Here, we report on the combinatorial biosynthesis of a series of unprecedented analogs of the TS pycnidione 1 and xenovulene A 2. In a systematic synthetic biology driven approach, we recombined genes from three TS biosynthetic gene clusters (pycnidione 1, xenovulene A 2 and eupenifeldin 3) in the fungal host Aspergillus oryzae NSAR1. Rational design of the reconstituted pathways granted control over the number of hDA reactions taking place, the chemical nature of the fused polyketide moiety (tropolono- vs. monobenzo-pyranyl) and the degree of hydroxylation. Formation of unexpected monobenzopyranyl sesquiterpenoids was investigated using isotope-feeding studies to reveal a new and highly unusual oxidative ring contraction rearrangement.
Recommended Products
| BBF-01829 | Deoxynojirimycin | Inquiry |
| BBF-01825 | Loganin | Inquiry |
| BBF-01826 | Deoxymannojirimycin | Inquiry |
| BBF-01693 | Doxorubicin EP Impurity A (Daunorubicin) | Inquiry |
| BBF-03755 | Actinomycin D | Inquiry |
| BBF-00764 | Cerebroside C | Inquiry |
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 ╳
