Mer-A2026B
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-03647 |
| CAS | |
| Molecular Weight | 385.54 |
| Molecular Formula | C24H35NO3 |
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Description
It is originally isolated from Streptomyces pactum. Mer-A2026B has the function of vasodilator and hypotension.
Specification
| Synonyms | Mer-A-2026B |
| IUPAC Name | 2-[(2E,5E,7E,11E)-10-hydroxy-3,7,9,11-tetramethyltrideca-2,5,7,11-tetraenyl]-6-methoxy-3-methyl-1H-pyridin-4-one |
| Canonical SMILES | CC=C(C)C(C(C)C=C(C)C=CCC(=CCC1=C(C(=O)C=C(N1)OC)C)C)O |
| InChI | InChI=1S/C24H35NO3/c1-8-18(4)24(27)19(5)14-17(3)11-9-10-16(2)12-13-21-20(6)22(26)15-23(25-21)28-7/h8-9,11-12,14-15,19,24,27H,10,13H2,1-7H3,(H,25,26)/b11-9+,16-12+,17-14+,18-8+ |
| InChI Key | RESCEXRHBPSAAM-AUTRRBDOSA-N |
Properties
| Appearance | Yellow Oily Matter |
| Boiling Point | 551.5±50.0°C at 760 mmHg |
| Density | 1.0±0.1 g/cm3 |
Reference Reading
1. An NF-κB-based high-throughput screen identifies piericidins as inhibitors of the Yersinia pseudotuberculosis type III secretion system
Miles C Duncan, Weng Ruh Wong, Allison J Dupzyk, Walter M Bray, Roger G Linington, Victoria Auerbuch Antimicrob Agents Chemother. 2014;58(2):1118-26. doi: 10.1128/AAC.02025-13. Epub 2013 Dec 2.
The type III secretion system (T3SS) is a bacterial appendage used by dozens of Gram-negative pathogens to subvert host defenses and cause disease, making it an ideal target for pathogen-specific antimicrobials. Here, we report the discovery and initial characterization of two related natural products with T3SS-inhibitory activity that were derived from a marine actinobacterium. Bacterial extracts containing piericidin A1 and the piericidin derivative Mer-A 2026B inhibited Yersinia pseudotuberculosis from triggering T3SS-dependent activation of the host transcription factor NF-κB in HEK293T cells but were not toxic to mammalian cells. As the Yersinia T3SS must be functional in order to trigger NF-κB activation, these data indicate that piericidin A1 and Mer-A 2026B block T3SS function. Consistent with this, purified piericidin A1 and Mer-A 2026B dose-dependently inhibited translocation of the Y. pseudotuberculosis T3SS effector protein YopM inside CHO cells. In contrast, neither compound perturbed bacterial growth in vitro, indicating that piericidin A1 and Mer-A 2026B do not function as general antibiotics in Yersinia. In addition, when Yersinia was incubated under T3SS-inducing culture conditions in the absence of host cells, Mer-A 2026B and piericidin A1 inhibited secretion of T3SS cargo as effectively as or better than several previously described T3SS inhibitors, such as MBX-1641 and aurodox. This suggests that Mer-A 2026B and piericidin A1 do not block type III secretion by blocking the bacterium-host cell interaction, but rather inhibit an earlier stage, such as T3SS needle assembly. In summary, the marine-derived natural products Mer-A 2026B and piericidin A1 possess previously uncharacterized activity against the bacterial T3SS.
2. Enantioselective total syntheses and absolute configuration of JBIR-02 and Mer-A2026B
Johannes Hoecker, Karl Gademann Org Lett. 2013 Feb 1;15(3):670-3. doi: 10.1021/ol303502a. Epub 2013 Jan 18.
The first total syntheses of the piericidin related natural products Mer-A2026B and JBIR-02 are reported. Key features of the synthetic approach involve an Ir-catalyzed one-pot C-H activation/oxidation procedure for the preparation of the hydroxypyridine, a vinylogous Mukaiyama aldol reaction, and a final Negishi cross-coupling of an advanced pyridine derivative with an allylic side chain precursor. In addition, the absolute configuration of Mer-A2026B (9R,10R) and JBIR-02 (9R,10R) was established.
3. Antifungal compounds from Streptomyces associated with attine ants also inhibit Leishmania donovani
Humberto E Ortega, Leonardo L G Ferreira, Weilan G P Melo, Ana Ligia L Oliveira, René F Ramos Alvarenga, Norberto P Lopes, Tim S Bugni, Adriano D Andricopulo, Mônica T Pupo PLoS Negl Trop Dis. 2019 Aug 5;13(8):e0007643. doi: 10.1371/journal.pntd.0007643. eCollection 2019 Aug.
Bacterial strains isolated from attine ants showed activity against the insect specialized fungal pathogen Escovopsis and also against the human protozoan parasite Leishmania donovani. The bioassay guided fractionation of extracts from cultures of Streptomyces sp. ICBG292, isolated from the exoskeleton of Cyphomyrmex workers, led to the isolation of Mer-A2026B (1), piericidin-A1 (2) and nigericin (3). Nigericin (3) presented high activity against intracellular amastigotes of L. donovani (IC50 0.129 ± 0.008 μM). Streptomyces puniceus ICBG378, isolated from workers of Acromyrmex rugosus rugosus, produced dinactin (4) with potent anti-L. donovani activity against intracellular amastigotes (IC50 0.018 ± 0.003 μM). Compounds 3 and 4 showed good selectivity indexes, 88.91 and 656.11 respectively, and were more active than positive control, miltefosine. Compounds 1-4 were also active against some Escovopsis strains. Compounds 1 and 2 were also produced by Streptomyces sp. ICBG233, isolated from workers of Atta sexdens, and detected in ants' extracts by mass spectrometry, suggesting they are produced in the natural environment as defensive compounds involved in the symbiotic interaction.
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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 ╳
