Conglobatin
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-01736 |
| CAS | 72263-05-9 |
| Molecular Weight | 498.61 |
| Molecular Formula | C28H38N2O6 |
| Purity | >98% by HPLC |
Online Inquiry
Description
Conglobatin is produced by the strain of Streptomyces conglobatus. It has a unusual, dimeric, macrolide dilactone structure with pendant oxazole groups. It exhibits an IC50 of 0.63 μg/mL in a NFAT-dependant transcription assay. It has no antifungal, bacterial, protozoan and tumor activity.
Specification
| Synonyms | (-)-Conglobatin; Conglobatin A; FW-04-806 |
| Storage | -20 °C |
| IUPAC Name | (3E,5R,7S,8S,11E,13R,15S,16S)-3,5,7,11,13,15-Hexamethyl-8,16-bis(5-oxazolylmethyl)-1,9-dioxacyclohexadeca-3,11-diene-2,10-dione |
| Canonical SMILES | CC1CC(C(OC(=O)C(=CC(CC(C(OC(=O)C(=C1)C)CC2=CN=CO2)C)C)C)CC3=CN=CO3)C |
| InChI | InChI=1S/C28H38N2O6/c1-17-7-19(3)25(11-23-13-29-15-33-23)35-28(32)22(6)10-18(2)8-20(4)26(12-24-14-30-16-34-24)36-27(31)21(5)9-17/h9-10,13-20,25-26H,7-8,11-12H2,1-6H3/b21-9+,22-10+/t17-,18-,19+,20+,25+,26+/m1/s1 |
| InChI Key | LAJRJVDLKYGLOO-MUIZUDCYSA-N |
| Source | Streptomyces conglobatus |
Properties
| Appearance | White to Off-White Solid |
| Boiling Point | 673.4 °C at 760 mmHg |
| Melting Point | 125 °C |
| Density | 1.06 g/cm3 |
| Solubility | Soluble in Ethanol, Methanol, Chloroform, DMF, DMSO; Poorly soluble in Water |
Reference Reading
1. Conglobatin, a novel macrolide dilactone from Streptomyces conglobatus ATCC 31005
J F Blount, R H Evans, C M Liu, J W Westley J Antibiot (Tokyo) . 1979 Sep;32(9):874-7. doi: 10.7164/antibiotics.32.874.
Fermentation of deposited cultures of Streptomyces conglobatus, known to produce the polyether antibiotic, ionomycin has resulted in the isolation and characterization of a second metabolite, conglobatin (C28H38N2O6). X-Ray analysis revealed a dimeric macrolide dilactone structure for conglobatin, similar to the structures of the mold metabolites vermiculin and pyrenophorin, from which the absolute configuration of conglobatin has been inferred. The dimer consists of two molecules of 7-hydroxy-8-oxazoyl-2,4,6-trimethyl-2-octenoic acid joined by two ester linkages.
2. Conglobatins B-E: cytotoxic analogues of the C2-symmetric macrodiolide conglobatin
Peter J Rutledge, Andrew M Piggott, Ernest Lacey, Yit-Heng Chooi, Heather J Lacey, Daniel Vuong, Thomas J Booth J Antibiot (Tokyo) . 2020 Nov;73(11):756-765. doi: 10.1038/s41429-020-0332-3.
Chemical investigation of a previously unreported indigenous Australian Streptomyces strain MST-91080 has identified six novel analogues related to the oxazole-pendanted macrodiolide, conglobatin. Phylogenetic analysis of the 16S rRNA gene sequence identified MST-91080 as a species of Streptomyces, distinct from reported conglobatin producer, Streptomyces conglobatus ATCC 31005. Conglobatins B-E diverge from conglobatin through differing patterns of methylation on the macrodiolide skeleton. The altered methyl positions suggest a deviation from the published biosynthetic pathway, which proposed three successive methylmalonyl-CoA extender unit additions to the conglobatin monomer. Conglobatins B1, C1 and C2 exhibited more potent cytotoxic activity selectively against the NS-1 myeloma cell line (IC500.084, 1.05 and 0.45 µg ml-1, respectively) compared with conglobatin (IC501.39 µg ml-1).
3. Panowamycins A and B, new antitrypanosomal isochromans produced by Streptomyces sp. K07-0010
Junko Hashida, Mihoko Mori, Miyuki Namatame, Aki Nishihara-Tsukashima, Kazuro Shiomi, Satoshi Omura, Megumi Niitsuma, Masato Iwatsuki, Aki Ishiyama, Atsuko Matsumoto, Ismet Ara, Haruki Yamada, Kazuhiko Otoguro, Yoko Takahashi J Antibiot (Tokyo) . 2012 Apr;65(4):197-202. doi: 10.1038/ja.2011.139.
Two new isochromans, panowamycins A and B, were purified by solvent extraction, silica gel and octadecylsilyl silica gel (ODS) column chromatography followed by preparative HPLC, from a culture broth of Streptomyces sp. K07-0010, together with the known compounds NFAT-133, conglobatin, piericidin C series and dinactin. Structures of panowamycins were elucidated as new analogs of NFAT-133 by spectroscopic studies including various NMR experiments. Panowamycins A and B showed moderate antitrypanosomal activity, with IC(50) values of 0.40 and 3.30 μg ml(-1), respectively.
Recommended Products
| BBF-01825 | Loganin | Inquiry |
| BBF-01826 | Deoxymannojirimycin | Inquiry |
| BBF-02642 | Lactonamycin | Inquiry |
| BBF-03755 | Actinomycin D | Inquiry |
| BBF-03754 | Castanospermine | Inquiry |
| BBF-05862 | Epirubicin | 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 ╳
