Phosmidosine
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| Category | Antibiotics |
| Catalog number | BBF-02412 |
| CAS | 134966-01-1 |
| Molecular Weight | 473.38 |
| Molecular Formula | C16H24N7O8P |
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Description
It is produced by the strain of Str. sp. RK-16. It can inhibit the cell cycle progression and cell morphology recovery of srcts-NRK cells. It has antifungal effect.
Specification
| Synonyms | Phosmidosine A; Adenosine, 7,8-dihydro-8-oxo-, 5'-(methyl(2-pyrrolidinylcarbonyl)phosphoramidate), (S)-; 5'-O-[Methoxy[[[(2S)-pyrrolidin-2α-yl]carbonyl]amino]phosphinyl]-7,8-dihydro-8-oxoadenosine; Adenosine, 7,8-dihydro-8-oxo-, 5'-[methyl N-[(2S)-2-pyrrolidinylcarbonyl]phosphoramidate] |
| IUPAC Name | (2S)-N-[[(2R,3S,4R,5R)-5-(6-amino-8-oxo-7H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-methoxyphosphoryl]pyrrolidine-2-carboxamide |
| Canonical SMILES | COP(=O)(NC(=O)C1CCCN1)OCC2C(C(C(O2)N3C4=NC=NC(=C4NC3=O)N)O)O |
| InChI | InChI=1S/C16H24N7O8P/c1-29-32(28,22-14(26)7-3-2-4-18-7)30-5-8-10(24)11(25)15(31-8)23-13-9(21-16(23)27)12(17)19-6-20-13/h6-8,10-11,15,18,24-25H,2-5H2,1H3,(H,21,27)(H2,17,19,20)(H,22,26,28)/t7-,8+,10+,11+,15+,32?/m0/s1 |
| InChI Key | HBJDRXMCLFRSGN-CRDJCKMPSA-N |
Properties
| Antibiotic Activity Spectrum | Fungi |
| Melting Point | 230°C (dec.) |
| Density | 1.618 g/cm3 |
| Solubility | Soluble in Water |
Reference Reading
1. Discovery and applications of nucleoside antibiotics beyond polyoxin
Hiroyuki Osada J Antibiot (Tokyo). 2019 Dec;72(12):855-864. doi: 10.1038/s41429-019-0237-1. Epub 2019 Sep 25.
Nucleoside antibiotics possess various biological activities such as antibacterial, antifungal, anticancer, and herbicidal activities. RIKEN scientists contributed to this area of research with two representative antifungal nucleoside antibiotics, blasticidin S and polyoxin. Blasticidin S was the first antibiotic exploited in agriculture worldwide. Meanwhile, the polyoxins discovered by Isono and Suzuki are still used globally as an agricultural antibiotic. In this review article, the research on nucleoside antibiotics mainly done by Isono and his collaborators is summarized from the discovery of polyoxin to subsequent investigations.
2. Structure-activity relationship of phosmidosine: importance of the 7,8-dihydro-8-oxoadenosine residue for antitumor activity
Mitsuo Sekine, Kazuhisa Okada, Kohji Seio, Hideaki Kakeya, Hiroyuki Osada, Takuma Sasaki Bioorg Med Chem. 2004 Oct 1;12(19):5193-201. doi: 10.1016/j.bmc.2004.07.021.
To study the structure-activity relationship of phosmidosine, a variety of phosmidosine derivatives 9a-g were synthesized by condensation of N-diisopropyl N'-(N-tritylprolyl)phosphorodiamidite 6 with appropriately protected nucleoside derivatives 7a-g. As the result, replacement of the 7,8-dihydro-8-oxoadenine base by adenine and 6-N-acetyladenine did not affect the antitumor activity. However, phosmidosine derivatives containing uracil, cytosine, and guanine in place of the 7,8-dihydro-8-oxoadenine base did not show significant activity. A plausible explanation for the selective expression of phosmidosine compared with that of phosmidosine analogs having other amino acids in place of proline is also discussed. These results suggest that phosmidosine serves as an inhibitor of prolyl adenosine 5'-phosphate (prolyl-AMP) to inhibit the peptide synthesis in cancer-related cells.
3. Synthesis and biological properties of new phosmidosine analogs having an N-acylsulfamate linkage
Haruhiko Taguchi, Akihiro Ohkubo, Mitsuo Sekine, Kohji Seio, Hideaki Kakeya, Hiroyuki Osada, Takuma Sasaki Nucleosides Nucleotides Nucleic Acids. 2006;25(4-6):647-54. doi: 10.1080/15257770600686360.
A new phosmidosine analog 10, in which the proline and 8-oxoadenosine moieties were linked by an N-acyl sulfamate linkage, was successfully synthesized by the sulfamoylation of an 8-oxoadenosine derivative 5 followed by coupling with an L-proline derivative 8. An L-alanine-substituted derivative 13 and its derivative 14 without the alanyl residue were also synthesized. The morphological reversion activity of these synthetic compounds in v-src(ts) NRK cells and their antitumor activity in L1210 and KB cells were studied. As the result, neither L-proline- nor L-alanine-substituted phosmidosine analogs 10 and 13 showed any antitumor activity. Contrary to these results, the derivative 14 lacking the amino acid residue showed potent antitumor activities against cancer cells.
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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 ╳
