Neoxaline
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| Category | Enzyme inhibitors |
| Catalog number | BBF-05692 |
| CAS | 909900-78-3 |
| Molecular Weight | 435.47 |
| Molecular Formula | C23H25N5O4 |
| Purity | >95% by HPLC |
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Description
Neoxaline is an alkaloid fungal metabolite originally isolated from Aspergillus japonicus. It inhibits the proliferation of Jurkat cells and induces cell cycle arrest at the G(2)/M phase.
Specification
| Related CAS | 71812-10-7 |
| Synonyms | (3E,6S,7aR,12aS)-7a-(1,1-dimethyl-2-propen-1-yl)-6,7,7a,12-tetrahydro-6-hydroxy-3-(1H-imidazol-5-ylmethylene)-12-methoxy-1H,5H-imidazo[1',2':1,2]pyrido[2,3-b]indole-2,5(3H)-dione; Epi-neoxaline; (6S,7aR,12aS,E)-3-((1H-imidazol-5-yl)methylene)-6-hydroxy-12-methoxy-7a-(2-methylbut-3-en-2-yl)-6,7,7a,12-tetrahydro-1H,5H-imidazo[1',2':1,2]pyrido[2,3-b]indole-2,5(3H)-dione |
| Storage | Store at 2-8°C for short term (days to weeks) or -20°C for long term (months to years) |
| IUPAC Name | (1S,9R,11S,14E)-11-hydroxy-14-(1H-imidazol-5-ylmethylidene)-2-methoxy-9-(2-methylbut-3-en-2-yl)-2,13,16-triazatetracyclo[7.7.0.01,13.03,8]hexadeca-3,5,7-triene-12,15-dione |
| Canonical SMILES | CC(C)(C=C)C12CC(C(=O)N3C1(NC(=O)C3=CC4=CN=CN4)N(C5=CC=CC=C25)OC)O |
| InChI | InChI=1S/C23H25N5O4/c1-5-21(2,3)22-11-18(29)20(31)27-17(10-14-12-24-13-25-14)19(30)26-23(22,27)28(32-4)16-9-7-6-8-15(16)22/h5-10,12-13,18,29H,1,11H2,2-4H3,(H,24,25)(H,26,30)/b17-10+/t18-,22-,23-/m0/s1 |
| InChI Key | HHLNXXASUKFCCX-FUNOPTADSA-N |
Properties
| Appearance | Needles |
| Melting Point | 202°C (dec.) |
| Density | 1.443 g/cm3 |
| Solubility | Soluble in Chloroform, DMSO, Methanol |
Reference Reading
1. Aspergillus labruscus sp. nov., a new species of Aspergillus section Nigri discovered in Brazil
Maria Helena P Fungaro, Larissa S Ferranti, Fernanda P Massi, Josué J da Silva, Daniele Sartori, Marta H Taniwaki, Jens C Frisvad, Beatriz T Iamanaka Sci Rep. 2017 Jul 24;7(1):6203. doi: 10.1038/s41598-017-06589-y.
A novel fungal species, Aspergillus labruscus sp. nov., has been found in Brazil during an investigation of the fungal species present on the surface of grape berries (Vitis labrusca L.) for use in the production of concentrated grape juice. It seems to be associated to V. labrusca, and has never been recovered from Vitis vinifera. This new species belonging to Aspergillus subgenus Circumdati section Nigri is described here using morphological characters, extrolite profiling, partial sequence data from the BenA and CaM genes, and internal transcribed spacer sequences of ribosomal DNA. Phenotypic and molecular data enabled this novel species to be clearly distinguished from other black aspergilli. A. labruscus sp. nov. is uniseriate, has yellow mycelium, poor sporulation on CYA at 25 °C, abundant salmon to pink sclerotia and rough conidia. Neoxaline and secalonic acid D were consistently produced by isolates in this taxon. The type strain of A. labruscus sp. nov. is CCT 7800 (T) = ITAL 22.223 (T) = IBT 33586 (T).
2. Asymmetric Total Synthesis of Indole Alkaloids Containing an Indoline Spiroaminal Framework
Takeshi Yamada, Tetsuya Ideguchi-Matsushita, Tomoyasu Hirose, Tatsuya Shirahata, Rei Hokari, Aki Ishiyama, Masato Iwatsuki, Akihiro Sugawara, Yoshinori Kobayashi, Kazuhiko Otoguro, Satoshi Ōmura, Toshiaki Sunazuka Chemistry. 2015 Aug 10;21(33):11855-64. doi: 10.1002/chem.201501150. Epub 2015 Jul 6.
The total synthesis of the indole alkaloids, neoxaline, oxaline and meleagrin A, all containing a unique indoline spiroaminal framework, was accomplished through the stereoselective introduction of a reverse prenyl group to the congested benzylic carbon of furoindoline, a two-pot transformation of indoline (containing three nitrogen atoms at appropriate positions) to the featured indoline spiroaminal framework, and elimination of carbonate assisted by the adjacent imidazole moiety to construct the (E)-dehydrohistidine. The absolute stereochemistry of neoxaline was elucidated through our total synthesis. In addition, we evaluated the bioactivity, especially the anti-infectious properties, of neoxaline and oxaline, and of some synthetic intermediates.
3. Evolutionary formation of gene clusters by reorganization: the meleagrin/roquefortine paradigm in different fungi
Juan F Martín, Paloma Liras Appl Microbiol Biotechnol. 2016 Feb;100(4):1579-1587. doi: 10.1007/s00253-015-7192-y. Epub 2015 Dec 15.
The biosynthesis of secondary metabolites in fungi is catalyzed by enzymes encoded by genes linked in clusters that are frequently co-regulated at the transcriptional level. Formation of gene clusters may take place by de novo assembly of genes recruited from other cellular functions, but also novel gene clusters are formed by reorganization of progenitor clusters and are distributed by horizontal gene transfer. This article reviews (i) the published information on the roquefortine/meleagrin/neoxaline gene clusters of Penicillium chrysogenum (Penicillium rubens) and the short roquefortine cluster of Penicillium roqueforti, and (ii) the correlation of the genes present in those clusters with the enzymes and metabolites derived from these pathways. The P. chrysogenum roq/mel cluster consists of seven genes and includes a gene (roqT) encoding a 12-TMS transporter protein of the MFS family. Interestingly, the orthologous P. roquefortine gene cluster has only four genes and the roqT gene is present as a residual pseudogene that encodes only small peptides. Two of the genes present in the central region of the P. chrysogenum roq/mel cluster have been lost during the evolutionary formation of the short cluster and the order of the structural genes in the cluster has been rearranged. The two lost genes encode a N1 atom hydroxylase (nox) and a roquefortine scaffold-reorganizing oxygenase (sro). As a consequence P. roqueforti has lost the ability to convert the roquefortine-type carbon skeleton to the glandicoline/meleagrin-type scaffold and is unable to produce glandicoline B, meleagrin and neoxaline. The loss of this genetic information is not recent and occurred probably millions of years ago when a progenitor Penicillium strain got adapted to life in a few rich habitats such as cheese, fermented cereal grains or silage. P. roqueforti may be considered as a "domesticated" variant of a progenitor common to contemporary P. chrysogenum and related Penicillia.
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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
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g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
