Chondramide C
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| Category | Antibiotics |
| Catalog number | BBF-00324 |
| CAS | |
| Molecular Weight | 616.75 |
| Molecular Formula | C35H44N4O6 |
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Description
It is produced by the strain of Chondromyces crocatus. Chondramide C has anti-candida, Henson yeast, lipids yeast, ball-like yeast and other fungal activities, but has no anti-gram positive and negative bacteria activities.
Specification
| Synonyms | CHEBI:84382 |
| IUPAC Name | (4R,7R,10S,13S,15E,17R,18R)-4-(4-hydroxyphenyl)-7-(1H-indol-3-ylmethyl)-8,10,13,15,17,18-hexamethyl-1-oxa-5,8,11-triazacyclooctadec-15-ene-2,6,9,12-tetrone |
| Canonical SMILES | CC1CC(=CC(C(OC(=O)CC(NC(=O)C(N(C(=O)C(NC1=O)C)C)CC2=CNC3=CC=CC=C32)C4=CC=C(C=C4)O)C)C)C |
| InChI | InChI=1S/C35H44N4O6/c1-20-15-21(2)24(5)45-32(41)18-30(25-11-13-27(40)14-12-25)38-34(43)31(17-26-19-36-29-10-8-7-9-28(26)29)39(6)35(44)23(4)37-33(42)22(3)16-20/h7-15,19,21-24,30-31,36,40H,16-18H2,1-6H3,(H,37,42)(H,38,43)/b20-15+/t21-,22+,23+,24-,30-,31-/m1/s1 |
| InChI Key | NCRSWJPOFRASIF-HPUNWYTPSA-N |
Properties
| Antibiotic Activity Spectrum | fungi |
Reference Reading
1. Total synthesis of (-)-doliculide, structure-activity relationship studies and its binding to F-actin
Kiran Matcha, Ashoka V R Madduri, Sayantani Roy, Slava Ziegler, Herbert Waldmann, Anna K H Hirsch, Adriaan J Minnaard Chembiochem. 2012 Nov 26;13(17):2537-48. doi: 10.1002/cbic.201200512. Epub 2012 Nov 5.
Actin, an abundant protein in most eukaryotic cells, is one of the targets in cancer research. Recently, a great deal of attention has been paid to the synthesis and function of actin-targeting compounds and their use as effective molecular probes in chemical biology. In this study, we have developed an efficient synthesis of (-)-doliculide, a very potent actin binder with a higher cell-membrane permeability than phalloidin. Actin polymerization assays with (-)-doliculide and two analogues on HeLa and BSC-1 cells, together with a prediction of their binding mode to F-actin by unbiased computational docking, show that doliculide stabilizes F-actin in a similar way to jasplakinolide and chondramide C.
2. Selective chemical imaging of static actin in live cells
Lech-Gustav Milroy, Stefano Rizzo, Abram Calderon, Bernhard Ellinger, Silke Erdmann, Justine Mondry, Peter Verveer, Philippe Bastiaens, Herbert Waldmann, Leif Dehmelt, Hans-Dieter Arndt J Am Chem Soc. 2012 May 23;134(20):8480-6. doi: 10.1021/ja211708z. Epub 2012 May 14.
We have characterized rationally designed and optimized analogues of the actin-stabilizing natural products jasplakinolide and chondramide C. Efficient actin staining was achieved in fixed permeabilized and non-permeabilized cells using different combinations of dye and linker length, thus highlighting the degree of molecular flexibility of the natural product scaffold. Investigations into synthetically accessible, non-toxic analogues have led to the characterization of a powerful cell-permeable probe to selectively image static, long-lived actin filaments against dynamic F-actin and monomeric G-actin populations in live cells, with negligible disruption of rapid actin dynamics.
3. Myxobacterial depsipeptide chondramides interrupt SARS-CoV-2 entry by targeting its broad, cell tropic spike protein
Rey Arturo Fernandez, Mark Tristan Quimque, Kin Israel Notarte, Joe Anthony Manzano, Delfin Yñigo Pilapil th, Von Novi de Leon, John Jeric San Jose, Omar Villalobos, Nisha Harur Muralidharan, M Michael Gromiha, Simone Brogi, Allan Patrick G Macabeo J Biomol Struct Dyn. 2022;40(22):12209-12220. doi: 10.1080/07391102.2021.1969281. Epub 2021 Aug 31.
The severity of the COVID-19 pandemic has necessitated the search for drugs against SARS-CoV-2. In this study, we explored via in silico approaches myxobacterial secondary metabolites against various receptor-binding regions of SARS-CoV-2 spike which are responsible in recognition and attachment to host cell receptors mechanisms, namely ACE2, GRP78, and NRP1. In general, cyclic depsipeptide chondramides conferred high affinities toward the spike RBD, showing strong binding to the known viral hot spots Arg403, Gln493 and Gln498 and better selectivity compared to most host cell receptors studied. Among them, chondramide C3 (1) exhibited a binding energy which remained relatively constant when docked against most of the spike variants. Chondramide C (2) on the other hand exhibited strong affinity against spike variants identified in the United Kingdom (N501Y), South Africa (N501Y, E484K, K417N) and Brazil (N501Y, E484K, K417T). Chondramide C6 (9) showed highest BE towards GRP78 RBD. Molecular dynamics simulations were also performed for chondramides 1 and 2 against SARS-CoV-2 spike RBD of the Wuhan wild-type and the South African variant, respectively, where resulting complexes demonstrated dynamic stability within a 120-ns simulation time. Protein-protein binding experiments using HADDOCK illustrated weaker binding affinity for complexed chondramide ligands in the RBD against the studied host cell receptors. The chondramide derivatives in general possessed favorable pharmacokinetic properties, highlighting their potential as prototypic anti-COVID-19 drugs limiting viral attachment and possibly minimizing viral infection.Communicated by Ramaswamy H. Sarma.
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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 ╳
