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MedKoo Cat#: 598639 | Name: Leucinostatin A
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Description:

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

Leucinostatin A, a hydrophobic nonapeptide antibiotic isolated from the fungus Acremonium sp., assumes an alpha-helical secondary structure in nonpolar environments. 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.

Chemical Structure

Leucinostatin A
Leucinostatin A
CAS#76600-38-9

Theoretical Analysis

MedKoo Cat#: 598639

Name: Leucinostatin A

CAS#: 76600-38-9

Chemical Formula: C62H111N11O13

Exact Mass: 1217.8363

Molecular Weight: 1218.63

Elemental Analysis: C, 61.11; H, 9.18; N, 12.64; O, 17.07

Price and Availability

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500µg USD 385.00 2 Weeks
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Synonym
CC 1014; CC-1014; CC1014; NSC 356885; NSC-356885; NSC356885; Paecilotoxin A; P-168; Leucinostatin A
IUPAC/Chemical Name
(2S,4S)-N-((4S,17S,20S,26S,29S,31S,33S)-33-hydroxy-26-((R)-1-hydroxy-2-methylpropyl)-17,20-diisobutyl-2,4,11,11,14,14,23,23,31-nonamethyl-6,10,13,16,19,22,25,28,35-nonaoxo-2,5,9,12,15,18,21,24,27-nonaazaheptatriacontan-29-yl)-4-methyl-1-((R,E)-4-methylhex-2-enoyl)pyrrolidine-2-carboxamide
InChi Key
FOAIGCPESMNWQP-FXTHJUADSA-N
InChi Code
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
SMILES Code
CN(C)C[C@H](C)NC(CCNC(C(C)(C)NC(C(C)(C)NC([C@H](CC(C)C)NC([C@H](CC(C)C)NC(C(C)(C)NC([C@H]([C@H](O)C(C)C)NC([C@H](C[C@H](C)C[C@H](O)CC(CC)=O)NC([C@@H]1C[C@H](C)CN1C(/C=C/[C@H](C)CC)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O
Appearance
Solid powder
Purity
>95% (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
>3 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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 1,218.63 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.

Recalculate based on batch purity %
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: Watanabe T, Abe H, Shibasaki M. Catalytic Asymmetric Total Synthesis of Leucinostatin A. Chem Rec. 2021 Jan;21(1):175-187. doi: 10.1002/tcr.202000108. Epub 2020 Oct 27. PMID: 33107684. 2: Lyu Q, Ludwig IS, Kooten PJS, Sijts AJAM, Rutten VPMG, van Eden W, Broere F. Leucinostatin acts as a co-inducer for heat shock protein 70 in cultured canine retinal pigment epithelial cells. Cell Stress Chaperones. 2020 Mar;25(2):235-243. doi: 10.1007/s12192-019-01066-z. Epub 2020 Jan 15. PMID: 31940135; PMCID: PMC7058576. 3: Kiss C, Gall FM, Dreier B, Adams M, Riedl R, Plückthun A, Mittl PRE. Structure of a hydrophobic leucinostatin derivative determined by host lattice display. Acta Crystallogr D Struct Biol. 2022 Dec 1;78(Pt 12):1439-1450. doi: 10.1107/S2059798322010762. Epub 2022 Nov 29. PMID: 36458615. 4: Csermely P, Radics L, Rossi C, Szamel M, Ricci M, Mihály K, Somogyi J. The nonapeptide leucinostatin A acts as a weak ionophore and as an immunosuppressant on T lymphocytes. Biochim Biophys Acta. 1994 Mar 31;1221(2):125-32. doi: 10.1016/0167-4889(94)90004-3. PMID: 8148389. 5: Abe H, Ouchi H, Sakashita C, Kawada M, Watanabe T, Shibasaki M. Catalytic Asymmetric Total Synthesis and Stereochemical Revision of Leucinostatin A: A Modulator of Tumor-Stroma Interaction. Chemistry. 2017 Sep 4;23(49):11792-11796. doi: 10.1002/chem.201703239. Epub 2017 Aug 10. PMID: 28703358. 6: 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. PMID: 19795463. 7: 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. doi: 10.1016/s1074-5521(97)90325-2. PMID: 9263641. 8: 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. doi: 10.1016/j.ijpharm.2004.01.030. PMID: 15081138. 9: 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. doi: 10.1208/pt010102. PMID: 14727851; PMCID: PMC2784834. 10: 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]. PMID: 19407848. 11: Mori Y, Tsuboi M, Suzuki M, Fukushima K, Arai T. Isolation of leucinostatin A and one of its constituents, the new amino acid, 4-methyl-6-(2-oxobutyl)-2-piperidinecarboxylic acid, from Paecilomyces lilacinus A-267. J Antibiot (Tokyo). 1982 Apr;35(4):543-4. doi: 10.7164/antibiotics.35.543. PMID: 7201464. 12: 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. doi: 10.1002/bip.360280138. PMID: 2720117. 13: 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. doi: 10.7164/antibiotics.49.1119. PMID: 8982341. 14: 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. doi: 10.7164/antibiotics.48.254. PMID: 7730161. 15: Ishiguro K, Arai T. Action of the peptide antibiotic leucinostatin. Antimicrob Agents Chemother. 1976 Jun;9(6):893-8. doi: 10.1128/AAC.9.6.893. PMID: 945714; PMCID: PMC429646. 16: Brand M, Wang L, Agnello S, Gazzola S, Gall FM, Raguž L, Kaiser M, Schmidt RS, Ritschl A, Jelk J, Hemphill A, Mäser P, Bütikofer P, Adams M, Riedl R. Antiprotozoal Structure-Activity Relationships of Synthetic Leucinostatin Derivatives and Elucidation of their Mode of Action. Angew Chem Int Ed Engl. 2021 Jul 5;60(28):15613-15621. doi: 10.1002/anie.202102153. Epub 2021 May 10. PMID: 33730410; PMCID: PMC8360131. 17: Kil YS, Risinger AL, Petersen CL, Mooberry SL, Cichewicz RH. Leucinostatins from Ophiocordyceps spp. and Purpureocillium spp. Demonstrate Selective Antiproliferative Effects in Cells Representing the Luminal Androgen Receptor Subtype of Triple Negative Breast Cancer. J Nat Prod. 2020 Jun 26;83(6):2010-2024. doi: 10.1021/acs.jnatprod.0c00404. Epub 2020 Jun 8. PMID: 32510949; PMCID: PMC7704123. 18: 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. doi: 10.7164/antibiotics.36.1613. PMID: 6662805. 19: Jiao Y, Li Y, Li Y, Cao H, Mao Z, Ling J, Yang Y, Xie B. Functional genetic analysis of the leucinostatin biosynthesis transcription regulator lcsL in Purpureocillium lilacinum using CRISPR-Cas9 technology. Appl Microbiol Biotechnol. 2019 Aug;103(15):6187-6194. doi: 10.1007/s00253-019-09945-2. Epub 2019 Jun 7. PMID: 31175427. 20: Watanabe T. Chemical Studies on Bioactive Natural Products Directed toward Development of Novel Antiinfective and Anticancer Medicines. Chem Pharm Bull (Tokyo). 2019;67(7):620-631. doi: 10.1248/cpb.c19-00215. PMID: 31257316.

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AS604872

AS604872