GR 135402
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| Category | Antibiotics |
| Catalog number | BBF-03586 |
| CAS | 204199-15-5 |
| Molecular Weight | 600.74 |
| Molecular Formula | C34H48O9 |
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Description
A novel antifungal antibiotic GR 135402 has been isolated from a Graphium putredinis which inhibited protein synthesis in Candida albicans but not rabbit reticulocytes.
Specification
| Synonyms | Antibiotic GR135402; GR135402 |
| IUPAC Name | (1R,2S,4R,5R,8R,9S,11S)-9-formyl-2-[[(2R,3S,4S,5R,6R)-3-hydroxy-5-methoxy-6-methyl-4-[(2Z,4E)-2-methylhexa-2,4-dienoyl]oxyoxan-2-yl]oxymethyl]-5-methyl-13-propan-2-yltetracyclo[7.4.0.02,11.04,8]tridec-12-ene-1-carboxylic acid |
| Canonical SMILES | CC=CC=C(C)C(=O)OC1C(C(OC(C1OC)C)OCC23CC4C(CCC4C5(C2(C(=CC3C5)C(C)C)C(=O)O)C=O)C)O |
| InChI | InChI=1S/C34H48O9/c1-8-9-10-20(5)29(37)43-28-26(36)30(42-21(6)27(28)40-7)41-17-33-15-23-19(4)11-12-24(23)32(16-35)14-22(33)13-25(18(2)3)34(32,33)31(38)39/h8-10,13,16,18-19,21-24,26-28,30,36H,11-12,14-15,17H2,1-7H3,(H,38,39)/b9-8+,20-10-/t19-,21-,22-,23-,24-,26+,27-,28+,30-,32+,33+,34+/m1/s1 |
| InChI Key | YJGMLBISALRTRW-OOKLOIGGSA-N |
Properties
| Antibiotic Activity Spectrum | fungi |
| Boiling Point | 699.6°C at 760 mmHg |
| Density | 1.23 g/cm3 |
Reference Reading
1. Sordarins: A new class of antifungals with selective inhibition of the protein synthesis elongation cycle in yeasts
J M Domínguez, V A Kelly, O S Kinsman, M S Marriott, F Gómez de las Heras, J J Martín Antimicrob Agents Chemother. 1998 Sep;42(9):2274-8. doi: 10.1128/AAC.42.9.2274.
GR135402, a sordarin derivative, was isolated in an antifungal screening program. GR135402, sordarin, and derivatives of both compounds were evaluated for their ability to inhibit cell-free translational systems from five different pathogenic fungi (Candida albicans, Candida glabrata, Candida krusei, Candida parapsilosis, and Cryptococcus neoformans). The activity profile of GR135402 is extended to other chemical compounds derived from sordarin. Experimental results indicate that sordarin analogs exert their antifungal effects by specifically inhibiting the protein synthesis elongation cycle in yeasts but do not affect protein synthesis machinery in mammalian systems. Intrinsically resistant strains owe their resistance to differences in the molecular target of sordarins in these strains. Preliminary studies performed to elucidate the mode of action of this new class of antifungal agents have shown that the putative target of sordarins is one of the protein synthesis elongation factors.
2. Novel inhibitors of fungal protein synthesis produced by a strain of Graphium putredinis. Isolation, characterisation and biological properties
T C Kennedy, G Webb, R J Cannell, O S Kinsman, R F Middleton, P J Sidebottom, N L Taylor, M J Dawson, A D Buss J Antibiot (Tokyo). 1998 Nov;51(11):1012-8. doi: 10.7164/antibiotics.51.1012.
The isolation and structure determination of 6 analogues of the fungal protein synthesis inhibitor GR135402, from Graphium putredinis, is described. The relative potencies of the compounds as protein synthesis inhibitors and as in vitro antifungal agents provide interesting insights into the structure-activity relationships in this series.
3. Antifungal agents: mode of action in yeast cells
A J Carrillo-Muñoz, G Giusiano, P A Ezkurra, G Quindós Rev Esp Quimioter. 2006 Jun;19(2):130-9.
Different kinds of mycoses, especially invasive, have become an important public health problem as their incidence has increased dramatically in the last decades in relation to AIDS, hematological malignancies, transplant recipients and other immunosuppressed individuals. Management of fungal infections is markedly limited by problems of drug safety, resistance and effectiveness profile. Current therapy for invasive mycoses uses a relatively reduced number of antifungal drugs, such as amphotericin B, fluconazole and itraconazole. Other new antifungal agents from old and new chemical families, like voriconazole, posaconazole, ravuconazole, caspofungin and micafungin, have been introduced into the armamentarium for fungal infections management. This review is focused on the mode of action of those antifungal drugs used against pathogenic yeasts. The interaction of amphotericin B with ergosterol and other membrane sterols results in the production of aqueous pores of drug and the ergosterol biosynthetic pathway is the target of the allylamines, phenylmorpholines and azole antifungal agents. The main molecular target of azole antifungals is the cytochrome P-450 protein Erg11p/Cyp51p. Echinocandins, a new class of antifungal drugs, are fungal secondary metabolites that act against beta-1-3-D-glucan synthesis. The phenylmorpholines, of which amorolfine is the sole representative in human therapy, affect two targets in the ergosterol pathway: Erg24p (delta 14 reductase) and Erg2p (delta 8-delta 7 isomerase). The sordarins group are protein synthesis inhibitors that work by blocking the function of fungal translation elongation factor 2. Other protein inhibitors are zofimarin, BE31045, SCH57504, xylarin, hypoxysordarin and GR135402. In order to overcome the problems derived from the exploitation of azole drugs, macrolides and echinocandins, novel targets were explored. Proposed antifungal drugs have been developed against potential targets like the N-myristylation of fungal proteins, with inhibitors like myristate and histidine analogues or myristoylpeptide derivatives, aminobenzothiazoles, quinolines and benzofurans. Polymerization of cell wall carbohydrates from uridine di-phospho sugars is another potential target.
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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 ╳
