Leucinostatin A

Leucinostatin A

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Leucinostatin A
Category Antibiotics
Catalog number BBF-02646
CAS 76600-38-9
Molecular Weight 1218.61
Molecular Formula C62H111N11O13
Purity >95% by HPLC

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Description

It is produced by the strain of Paecilomyces lilacinus A-267. It's a peptide antibiotic. It has a strong anti-pathogenic and non-pathogenic yeast and fungi activity, but also has a medium anti-bacterial effect. It was previously reported that Leucinostatin A and B mixtures inhibited HeLa cells. 0.05 μg/mL of Leucinostatin A for a week (0.25 mg/kg・d) has inhibitory effect on the airy ascites carcinoma entity type, and for ascites type is invalid.

Specification

Related CAS 78149-02-7 (hydrochloride)
Synonyms Antibiotic 1907-VIII; Antibiotic CC 1014; Paecilotoxin A; Antibiotic P-168; beta-Alaninamide, cis-4-methyl-1-(4-methyl-1-oxo-2-hexenyl)-L-prolyl-(4S,6S)-6-hydroxy-4-methyl-8-oxo-L-2-aminodecanoyl-threo-3-hydroxy-L-leucyl-2-methylalanyl-L-leucyl-L-leucyl-2-methylalanyl-2-methylalanyl-N-(2-(dimethylamino)-1-methylethyl)-, (1(S-(E)),9(S))-; Tryanocidin
Storage Store at -20°C
IUPAC Name (2S,4S)-N-[(2S,4S)-1-[[(2S,3R)-1-[[1-[[(2S)-1-[[(2S)-1-[[1-[[1-[[3-[[(2S)-1-(dimethylamino)propan-2-yl]amino]-3-oxopropyl]amino]-2-methyl-1-oxopropan-2-yl]amino]-2-methyl-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-2-methyl-1-oxopropan-2-yl]amino]-3-hydroxy-4-methyl-1-oxopentan-2-yl]amino]-6-hydroxy-4-methyl-1,8-dioxodecan-2-yl]-4-methyl-1-[(E,4R)-4-methylhex-2-enoyl]pyrrolidine-2-carboxamide
Canonical SMILES CCC(C)C=CC(=O)N1CC(CC1C(=O)NC(CC(C)CC(CC(=O)CC)O)C(=O)NC(C(C(C)C)O)C(=O)NC(C)(C)C(=O)NC(CC(C)C)C(=O)NC(CC(C)C)C(=O)NC(C)(C)C(=O)NC(C)(C)C(=O)NCCC(=O)NC(C)CN(C)C)C
InChI InChI=1S/C62H111N11O13/c1-21-38(9)23-24-49(77)73-33-40(11)31-47(73)55(82)66-46(30-39(10)29-43(75)32-42(74)22-2)53(80)68-50(51(78)37(7)8)56(83)70-61(15,16)58(85)67-44(27-35(3)4)52(79)65-45(28-36(5)6)54(81)69-62(17,18)59(86)71-60(13,14)57(84)63-26-25-48(76)64-41(12)34-72(19)20/h23-24,35-41,43-47,50-51,75,78H,21-22,25-34H2,1-20H3,(H,63,84)(H,64,76)(H,65,79)(H,66,82)(H,67,85)(H,68,80)(H,69,81)(H,70,83)(H,71,86)/b24-23+/t38-,39-,40+,41+,43?,44+,45+,46+,47+,50+,51-/m1/s1
InChI Key FOAIGCPESMNWQP-QJMNAQKNSA-N
Source Paecilomyces sp.

Properties

Appearance White Ribbed Crystal
Antibiotic Activity Spectrum Neoplastics (Tumor); Fungi; Yeast
Boiling Point 1408.0±65.0°C (Predicted)
Melting Point 98-101°C
Density 1.116±0.06 g/cm3 (Predicted)
Solubility Soluble in Methanol, Ethanol, DMF, DMSO; Poorly soluble in Water

Reference Reading

1. The nonapeptide leucinostatin A acts as a weak ionophore and as an immunosuppressant on T lymphocytes
L Radics, P Csermely, K Mihály, C Rossi, J Somogyi, M Ricci, M Szamel Biochim Biophys Acta . 1994 Mar 31;1221(2):125-32. doi: 10.1016/0167-4889(94)90004-3.
Earlier studies have disclosed that leucinostatin A, a hydrophobic nonapeptide antibiotic, assumes an alpha-helical secondary structure in nonpolar environments. The present report demonstrates that the peptide acts as a weak ionophore facilitating the transport of mono-and divalent cations through the plasma membrane of T lymphocytes and through artificial membranes. Leucinostatin A does not change the thymidine uptake of both resting mouse thymocytes and peripheral blood lymphocytes but dose-dependently prevents the activation of T lymphocytes by tetradecanoyl-phorbol-acetate and by anti-T cell receptor antibody.
2. Leucinostatin acts as a co-inducer for heat shock protein 70 in cultured canine retinal pigment epithelial cells
Peter J S Kooten, Femke Broere, Victor P M G Rutten, Alice J A M Sijts, Willem van Eden, Irene S Ludwig, Qingkang Lyu Cell Stress Chaperones . 2020 Mar;25(2):235-243. doi: 10.1007/s12192-019-01066-z.
Dysregulation of retinal pigment epithelium (RPE) cells is the main cause of a variety of ocular diseases. Potentially heat shock proteins, by preventing molecular and cellular damage and modulating inflammatory disease, may exert a protective role in eye disease. In particular, the inducible form of heat shock protein 70 (Hsp70) is widely upregulated in inflamed tissues, and in vivo upregulation of Hsp70 expression by HSP co-inducing compounds has been shown to be a potential therapeutic strategy for inflammatory diseases. In order to gain further understanding of the potential protective effects of Hsp70 in RPE cells, we developed a method for isolation and culture of canine RPE cells. Identity of RPE cells was confirmed by detection of its specific marker, RPE65, in qPCR, flow cytometry, and immunocytochemistry analysis. The ability of RPE cells to express Hsp70 upon experimental induction of cell stress, by arsenite, was analyzed by flow cytometry. Finally, in search of a potential Hsp70 co-inducer, we investigated whether the compound leucinostatin could enhance Hsp70 expression in stressed RPE cells. Canine RPE cells were isolated and cultured successfully. Purity of cells that strongly expressed RPE65 was over 90%. Arsenite-induced stress led to a time- and dose-dependent increase in Hsp70 expression in canine RPE cells in vitro. In addition, leucinostatin, which enhanced heat shock factor-1-induced transcription from the heat shock promoter in DNAJB1-luc-O23 reporter cell line, also enhanced Hsp70 expression in arsenite-stressed RPE cells, in a dose-dependent fashion. These findings demonstrate that leucinostatin can boost Hsp70 expression in canine RPE cells, most likely by activating heat shock factor-1, suggesting that leucinostatin might be applied as a new co-inducer for Hsp70 expression.
3. In vitro and in vivo antitrypanosomal activities of three peptide antibiotics: leucinostatin A and B, alamethicin I and tsushimycin
Miyuki Namatame, Kazuro Shiomi, Yuta Kinoshita, Satoshi Omura, Masato Iwatsuki, Rokuro Masuma, Aki Ishiyama, Aki Nishihara, Haruki Yamada, Kenichi Nonaka, Kazuhiko Otoguro, Yoko Takahashi J Antibiot (Tokyo) . 2009 Jun;62(6):303-8. doi: 10.1038/ja.2009.32.
In the course of our screening for antitrypanosomal compounds from soil microorganisms, as well as from the antibiotics library of the Kitasato Institute for Life Sciences, we found three peptide antibiotics, leucinostatin (A and B), alamethicin I and tsushimycin, which exhibited potent or moderate antitrypanosomal activity. We report here the in vitro and in vivo antitrypanosomal properties and cytotoxicities of leucinostatin A and B, alamethicin I and tsushimycin compared with suramin. We also discuss their possible mode of action. This is the first report of in vitro and in vivo trypanocidal activity of leucinostatin A and B, alamethicin I and tsushimycin.

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