Dorrigocin A
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-01170 |
| CAS | 158446-29-8 |
| Molecular Weight | 507.61 |
| Molecular Formula | C27H41NO8 |
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Description
It is produced by the strain of Streptomyces platensis subsp. rosaceus AB-1981F-75. It has weak anti-tumor cell activity and moderate anti-aspergillus and fusarium activity, but has no effect on yeast. Dorrigocin B has stronger antitumor and antifungal activities than Dorrigocin A. It can restore the morphology of RAS-deformed NIH/3T3 cells from the deformed phenotype to the normal phenotype.
Specification
| IUPAC Name | (2E,6E,8S,9S,10R,11E,13R,14S)-18-(2,6-dioxopiperidin-4-yl)-9,13-dihydroxy-8-methoxy-10,12,14-trimethyl-15-oxooctadeca-2,6,11-trienoic acid |
| Canonical SMILES | CC(C=C(C)C(C(C)C(=O)CCCC1CC(=O)NC(=O)C1)O)C(C(C=CCCC=CC(=O)O)OC)O |
| InChI | InChI=1S/C27H41NO8/c1-17(14-18(2)27(35)22(36-4)12-7-5-6-8-13-25(32)33)26(34)19(3)21(29)11-9-10-20-15-23(30)28-24(31)16-20/h7-8,12-14,18-20,22,26-27,34-35H,5-6,9-11,15-16H2,1-4H3,(H,32,33)(H,28,30,31)/b12-7+,13-8+,17-14+/t18-,19-,22+,26+,27+/m1/s1 |
| InChI Key | HJCZOTBHYAPUHT-LPYGBFRZSA-N |
Properties
| Appearance | Oily Matter |
| Antibiotic Activity Spectrum | Neoplastics (Tumor); Fungi |
| Solubility | Soluble in Methanol, Ethyl Acetate |
Reference Reading
1. Stereoselective synthesis of the C1-C13 fragment of 2,3-dihydrodorrigocin A
Jean-Yves Le Brazidec, Charles A Gilson rd, Marcus F Boehm J Org Chem. 2005 Sep 30;70(20):8212-5. doi: 10.1021/jo050942s.
[Chemical reaction: see text] The first synthesis of the C1-C13 fragment of 2,3-dihydrodorrigocin A has been achieved from 6-bromohexanoic acid in 14 linear steps and an overall yield of 2%. The configurations of the stereogenic centers C8, C9, and C10 have been determined to be the same as for migrastatin.
2. Evaluation of new migrastatin and dorrigocin congeners unveils cell migration inhibitors with dramatically improved potency
Jianhua Ju, Scott R Rajski, Si-Kyu Lim, Jeong-Woo Seo, Noël R Peters, F Michael Hoffmann, Ben Shen Bioorg Med Chem Lett. 2008 Nov 15;18(22):5951-4. doi: 10.1016/j.bmcl.2008.07.072. Epub 2008 Jul 24.
Lactimidomycin (LTM, 1), iso-migrastatin (iso-MGS, 2) and migrastatin (MGS, 3) are macrolide antitumor antibiotics differing in macrolide ring size but all bearing a glutarimide side chain. To further develop these natural products and related analogs as drug candidates we have produced and evaluated the biological activities of a small library of iso-MGS and LTM-derived agents; congeners evaluated bear either the MGS scaffold or related acyclic (dorrigocin) scaffolds. Scratch wound-healing (SWH) assays with 4T1 mouse and MDA-MB-231 human mammary tumor cell lines, respectively, reveal structural elements crucial to inhibition of cell migration by these compounds. Moreover, two substances, 14 and 17, with activity far superior to that of MGS are unveiled by SWH assays.
3. Synthesis of novel migrastatin and dorrigocin A analogues from D-glucal
Guillaume Anquetin, Sarah L Rawe, Kevin McMahon, Evelyn P Murphy, Paul V Murphy Chemistry. 2008;14(5):1592-600. doi: 10.1002/chem.200701033.
The synthesis of a range of analogues of the migrastatin macrolide core has been achieved from tri-O-acetyl-D-glucal in order to facilitate structure-activity studies. Efficient macrolactone formation was achieved in the presence of a reactive olefin, by increasing steric hindrance in the olefin environment. Acyclic analogues of migrastatin, structurally related to dorrigocin A, have also been prepared from D-glucal. The dorrigocin A analogues were prepared using the combination of the cross metathesis of ethyl 6-heptenoate with a glycal derivative and a subsequent allylic rearrangement-alkene isomerisation reaction (Perlin reaction). A synthetic route is thus provided that will enable dorrigocin A analogues to be prepared in parallel to migrastatin analogues in the search for novel anti-cancer and anti-arthritic therapeutics. Biological evaluation of one migrastatin and one dorrigocin A sugar derived analogue show that they inhibit proliferation and serum-induced migration of tumour and synovial cells at higher concentrations than evodiamine. Dorrigocin A analogues displayed similar potency to analogues of the migrastatin core.
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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 ╳
