Leucinostatin | CAS# 39405-64-6 | Antibiotic

MedKoo Cat#: 571081 | Name: Leucinostatin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Leucinostatin is a class of peptide mycotoxins that have some potent effects on liver cells after oral administration, and are used as both antimicrobial and antitumor agents through interactions with the membrane phospholipids. Leucinostatin has shown effects against prostate cancer cell growth and leukemia cell growth.

Chemical Structure

Leucinostatin

CAS#39405-64-6

Theoretical Analysis

MedKoo Cat#: 571081

Name: Leucinostatin

CAS#: 39405-64-6

Chemical Formula: C58H102N10O13

Exact Mass: 1146.7628

Molecular Weight: 1147.51

Elemental Analysis: C, 60.71; H, 8.96; N, 12.21; O, 18.13

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

No Data

Synonym

Leucinostatin A; A 20668; A-20668; A20668

IUPAC/Chemical Name

(2S)-N-((13S,16S,22S,25S)-1-amino-29-hydroxy-22-(1-hydroxy-2-methylpropyl)-13,16-diisobutyl-7,7,10,10,19,19,27-heptamethyl-1,6,9,12,15,18,21,24,31-nonaoxo-5,8,11,14,17,20,23-heptaazatritriacontan-25-yl)-4-methyl-1-((S,E)-4-methylhex-2-enoyl)pyrrolidine-2-carboxamide

InChi Key

GWAKUJDAJHEQBU-CXMBYJBLSA-N

InChi Code

InChI=1S/C58H102N10O13/c1-18-35(9)22-23-45(72)68-31-37(11)29-43(68)51(77)62-42(28-36(10)27-39(70)30-38(69)19-2)49(75)64-46(47(73)34(7)8)52(78)66-57(14,15)54(80)63-40(25-32(3)4)48(74)61-41(26-33(5)6)50(76)65-58(16,17)55(81)67-56(12,13)53(79)60-24-20-21-44(59)71/h22-23,32-37,39-43,46-47,70,73H,18-21,24-31H2,1-17H3,(H2,59,71)(H,60,79)(H,61,74)(H,62,77)(H,63,80)(H,64,75)(H,65,76)(H,66,78)(H,67,81)/b23-22+/t35-,36?,37?,39?,40-,41-,42-,43-,46-,47?/m0/s1

SMILES Code

CC[C@H](C)/C=C/C(=O)N1CC(C[C@H]1C(=O)N[C@@H](CC(C)CC(CC(=O)CC)O)C(=O)N[C@@H](C(C(C)C)O)C(=O)NC(C)(C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)NC(C)(C)C(=O)NC(C)(C)C(=O)NCCCC(=O)N)C

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 1,147.51 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Wang G, Liu Z, Lin R, Li E, Mao Z, Ling J, Yang Y, Yin WB, Xie B. Biosynthesis of Antibiotic Leucinostatins in Bio-control Fungus Purpureocillium lilacinum and Their Inhibition on Phytophthora Revealed by Genome Mining. PLoS Pathog. 2016 Jul 14;12(7):e1005685. doi: 10.1371/journal.ppat.1005685. eCollection 2016 Jul. PubMed PMID: 27416025; PubMed Central PMCID: PMC4946873. 2: Martinez AF, Moraes LA. Liquid chromatography-tandem mass spectrometry characterization of five new leucinostatins produced by Paecilomyces lilacinus CG-189. J Antibiot (Tokyo). 2015 Mar;68(3):178-84. doi: 10.1038/ja.2014.120. Epub 2014 Sep 3. PubMed PMID: 25182486. 3: Mikami Y, Fukushima K, Arai T, Abe F, Shibuya H, Ommura Y. Leucinostatins, peptide mycotoxins produced by Paecilomyces lilacinus and their possible roles in fungal infection. Zentralbl Bakteriol Mikrobiol Hyg A. 1984 Jul;257(2):275-83. PubMed PMID: 6485630. 4: Fukushima K, Arai T, Mori Y, Tsuboi M, Suzuki M. Studies on peptide antibiotics, leucinostatins. I. Separation, physico-chemical properties and biological activities of leucinostatins A and B. J Antibiot (Tokyo). 1983 Dec;36(12):1606-12. PubMed PMID: 6662804. 5: Kawada M, Inoue H, Ohba S, Masuda T, Momose I, Ikeda D. Leucinostatin A inhibits prostate cancer growth through reduction of insulin-like growth factor-I expression in prostate stromal cells. Int J Cancer. 2010 Feb 15;126(4):810-8. doi: 10.1002/ijc.24915. PubMed PMID: 19795463. 6: Fukushima K, Arai T, Mori Y, Tsuboi M, Suzuki M. Studies on peptide antibiotics, leucinostatins. II. The structures of leucinostatins A and B. J Antibiot (Tokyo). 1983 Dec;36(12):1613-30. PubMed PMID: 6662805. 7: Shima A, Fukushima K, Arai T, Terada H. Dual inhibitory effects of the peptide antibiotics leucinostatins on oxidative phosphorylation in mitochondria. Cell Struct Funct. 1990 Feb;15(1):53-8. PubMed PMID: 2140298. 8: Park JO, Hargreaves JR, McConville EJ, Stirling GR, Ghisalberti EL, Sivasithamparam K. Production of leucinostatins and nematicidal activity of Australian isolates of Paecilomyces lilacinus (Thom) Samson. Lett Appl Microbiol. 2004;38(4):271-6. PubMed PMID: 15214724. 9: Ishiyama A, Otoguro K, Iwatsuki M, Namatame M, Nishihara A, Nonaka K, Kinoshita Y, Takahashi Y, Masuma R, Shiomi K, Yamada H, Omura S. In vitro and in vivo antitrypanosomal activities of three peptide antibiotics: leucinostatin A and B, alamethicin I and tsushimycin. J Antibiot (Tokyo). 2009 Jun;62(6):303-8. doi: 10.1038/ja.2009.32. Epub 2009 May 1. Erratum in: J Antibiot (Tokyo). 2009 Jun;62(6):343. Iwatsuki, Masahito [corrected to Iwatsuki, Masato]. PubMed PMID: 19407848. 10: Strobel GA, Hess WM. Glucosylation of the peptide leucinostatin A, produced by an endophytic fungus of European yew, may protect the host from leucinostatin toxicity. Chem Biol. 1997 Jul;4(7):529-36. PubMed PMID: 9263641. 11: Muroi M, Suehara K, Wakusawa H, Suzuki K, Sato T, Nishimura T, Otake N, Takatsuki A. Novel blockade of cell surface expression of virus glycoproteins by leucinostatin A. J Antibiot (Tokyo). 1996 Nov;49(11):1119-26. PubMed PMID: 8982341. 12: Ishiguro K, Arai T. Action of the peptide antibiotic leucinostatin. Antimicrob Agents Chemother. 1976 Jun;9(6):893-8. PubMed PMID: 945714; PubMed Central PMCID: PMC429646. 13: Rossi C, Tuttobello L, Ricci M, Casinovi CG, Radics L. Leucinostatin D, a novel peptide antibiotic from Paecilomyces marquandii. J Antibiot (Tokyo). 1987 Jan;40(1):130-3. PubMed PMID: 3558114. 14: Crebelli R, Carere A, Conti G, Conti L, Rossi C, Tuttobello L. Evaluation of the mutagenic activity of leucinostatins, a novel class of antibiotic peptides produced by Paecilomyces marquandii, in the modul Aspergillus nidulans. Microbiologica. 1988 Oct;11(4):299-305. PubMed PMID: 3063923. 15: Cerrini S, Lamba D, Scatturin A, Ughetto G. The crystal and molecular structure of the alpha-helical nonapeptide antibiotic leucinostatin A. Biopolymers. 1989 Jan;28(1):409-20. PubMed PMID: 2720117. 16: Ricci M, Sassi P, Nastruzzi C, Rossi C. Liposome-based formulations for the antibiotic nonapeptide Leucinostatin A: Fourier transform infrared spectroscopy characterization and in vivo toxicologic study. AAPS PharmSciTech. 2000 Mar 3;1(1):E2. PubMed PMID: 14727851; PubMed Central PMCID: PMC2784834. 17: Ricci M, Blasi P, Giovagnoli S, Perioli L, Vescovi C, Rossi C. Leucinostatin-A loaded nanospheres: characterization and in vivo toxicity and efficacy evaluation. Int J Pharm. 2004 May 4;275(1-2):61-72. PubMed PMID: 15081138. 18: Mori Y, Suzuki M, Fukushima K, Arai T. Structure of leucinostatin B, an uncoupler on mitochondria. J Antibiot (Tokyo). 1983 Aug;36(8):1084-6. PubMed PMID: 6630061. 19: Arai T, Mikami Y, Fukushima K, Utsumi T, Yazawa K. A new antibiotic, leucinostatin, derived from Penicillium lilacinum. J Antibiot (Tokyo). 1973 Mar;26(3):157-61. PubMed PMID: 4783199. 20: Vertuani G, Boggian M, Scatturin A, Ricci M, Meli Balbocchino B, Tuttobello L, Rossi C. Structure activity studies on chemically modified homologues of the antibiotic phytotoxic leucinostatin A. J Antibiot (Tokyo). 1995 Mar;48(3):254-60. PubMed PMID: 7730161.