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MedKoo Cat#: 598698 | Name: Lucimycin

Description:

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

Lucimycin is a macrolide antibiotic isolated from cultures of Streptomyces lucensis.

Chemical Structure

Lucimycin
Lucimycin
CAS#13058-67-8

Theoretical Analysis

MedKoo Cat#: 598698

Name: Lucimycin

CAS#: 13058-67-8

Chemical Formula: C36H53NO13

Exact Mass: 707.3517

Molecular Weight: 707.81

Elemental Analysis: C, 61.09; H, 7.55; N, 1.98; O, 29.38

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
Lucimycin; FI 1163; FI-1163; FI1163; Antibiotic 1163 F.I.; NSC 143257; NS0-143257; NSC143257; Leusensomycin;
IUPAC/Chemical Name
(1R,3S,5R,7R,8E,14E,16E,18E,20E,22R,24S,25R,26S)-22-(((2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-12-butyl-1,3,26-trihydroxy-10-oxo-6,11,28-trioxatricyclo[22.3.1.05,7]octacosa-8,14,16,18,20-pentaene-25-carboxylic acid
InChi Key
MUAOHYJGHYFDSA-YZMLMZOASA-N
InChi Code
InChI=1S/C36H53NO13/c1-3-4-12-23-13-10-8-6-5-7-9-11-14-24(48-35-33(42)31(37)32(41)21(2)46-35)18-28-30(34(43)44)25(39)20-36(45,50-28)19-22(38)17-27-26(49-27)15-16-29(40)47-23/h5-11,14-16,21-28,30-33,35,38-39,41-42,45H,3-4,12-13,17-20,37H2,1-2H3,(H,43,44)/b6-5+,9-7+,10-8+,14-11+,16-15+/t21-,22+,23?,24+,25+,26-,27-,28+,30-,31+,32-,33+,35+,36-/m1/s1
SMILES Code
CCCCC1C/C=C/C=C/C=C/C=C/[C@H](O[C@@H]2O[C@@H]([C@H]([C@@H]([C@@H]2O)N)O)C)C[C@@H]3O[C@](C[C@H](C[C@H]4O[C@@H]4/C=C/C(O1)=O)O)(C[C@@H]([C@H]3C(O)=O)O)O
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
>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 707.81 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: Pöppel AK, Koch A, Kogel KH, Vogel H, Kollewe C, Wiesner J, Vilcinskas A. Lucimycin, an antifungal peptide from the therapeutic maggot of the common green bottle fly Lucilia sericata. Biol Chem. 2014 Jun;395(6):649-56. doi: 10.1515/hsz-2013-0263. PubMed PMID: 24622788. 2: Baumann A, Lehmann R, Beckert A, Vilcinskas A, Franta Z. Selection and Evaluation of Tissue Specific Reference Genes in Lucilia sericata during an Immune Challenge. PLoS One. 2015 Aug 7;10(8):e0135093. doi: 10.1371/journal.pone.0135093. eCollection 2015. PubMed PMID: 26252388; PubMed Central PMCID: PMC4529112. 3: Nedeau P, Gruda I, Medoff G, Brajtburg J. Relative avidity of etruscomycin to cholesterol and ergosterol. Antimicrob Agents Chemother. 1982 Apr;21(4):545-50. PubMed PMID: 7044302; PubMed Central PMCID: PMC181938. 4: Salerno C, Capuozzo E, Cucco C, Crifo C. Interaction of lucensomycin with membranes: the role of non-steroidal components. Biochimie. 1989 Jan;71(1):63-6. PubMed PMID: 2497799. 5: Pöppel AK, Vogel H, Wiesner J, Vilcinskas A. Antimicrobial peptides expressed in medicinal maggots of the blow fly Lucilia sericata show combinatorial activity against bacteria. Antimicrob Agents Chemother. 2015 May;59(5):2508-14. doi: 10.1128/AAC.05180-14. Epub 2015 Feb 9. PubMed PMID: 25666157; PubMed Central PMCID: PMC4394815. 6: Capuozzo E, Bolard J. Interaction of the polyene antibiotic etruscomycin with large unilamellar lipid vesicles: binding and proton permeability inducement. Biochim Biophys Acta. 1985 Oct 24;820(1):63-73. PubMed PMID: 2996598. 7: Capuozzo E, Salerno C, Strom R, Crifò C. Kinetics of binding of lucensomycin to natural and artificial membranes. Eur J Biochem. 1987 Aug 17;167(1):59-64. PubMed PMID: 3622509. 8: Crifó C, Oratore A, Rossi Fanelli F, Cangiano C, Equizi S, Strom R. Concentration of "available" unesterified cholesterol in human plasma as evaluated from inhibition of hemolysis by lucensomycin. Experientia. 1976 Feb 15;32(2):239-40. PubMed PMID: 1269625. 9: Capuozzo E, Crifo C, Salerno C, Strom R. Interaction of lucensomycin with cholesterol in membranes: kinetic and structural studies. Drugs Exp Clin Res. 1986;12(6-7):619-26. PubMed PMID: 3743374. 10: Grabowski MW, Rottem S, Barile MF. Cholesterol requirement of mycoplasmas as determined by microtiter test using polyene antibiotics. J Clin Microbiol. 1976 Feb;3(2):110-2. PubMed PMID: 1254708; PubMed Central PMCID: PMC274244. 11: Capuozzo E, Salvi S, Salerno C, Crifò C. Combined effects exerted by amphotericin B and lucensomycin on cation permeability in a unilamellar vesicle system. Biochimie. 1989 Jan;71(1):57-61. PubMed PMID: 2497798. 12: Capuozzo E, Jullien S, Salerno C, Crifò C. Inhibition of erythrocyte ghost ATPase by polyene antibiotics. Biochem Int. 1990;20(6):1135-9. PubMed PMID: 2164397. 13: Pierce AM, Pierce HD Jr, Unrau AM, Oehlschlager AC. Lipid composition and polyene antibiotic resistance of Candida albicans mutants. Can J Biochem. 1978 Feb;56(2):135-42. PubMed PMID: 343892. 14: BIGGIO P, LOSTIA A. [On the antimycotic activity in vitro of a new antibiotic (etruscomycin) isolated from Streptomyces lucensis n. sp]. Rass Med Sarda. 1962 Nov-Dec;64:585-8. Italian. PubMed PMID: 13971116. 15: Podo F, Di Blasi R, Crifò C, Strom R. PMR studies of phosphatidylcholine-cholesterol vesicles interacting with lucensomycin. Physiol Chem Phys. 1979;11(2):125-33. PubMed PMID: 482384. 16: Strom R, Blumberg WE, Dale RE, Crifo C. The interaction of the polyene antibiotic lucensomycin with cholesterol in erythrocyte membranes and in model systems. III. Characterization of spectral parameters. Biophys J. 1976 Nov;16(11):1297-314. PubMed PMID: 974222; PubMed Central PMCID: PMC1334959. 17: Bossa R, Dasdia T, Galatulas I, Zunino F. Sensitivity to anthracyclines in P388/dx leukaemia cells. Anticancer Res. 1986 Sep-Oct;6(5):1037-9. PubMed PMID: 3099628. 18: Strom R, Crifò C, Eusebi F, Sabetta F, Oratore A. Stoichiometry of hemolysis by the polyene antibiotic lucensomycin. Biochim Biophys Acta. 1976 Dec 14;455(3):961-72. PubMed PMID: 999947. 19: Bolard J. How do the polyene macrolide antibiotics affect the cellular membrane properties? Biochim Biophys Acta. 1986 Dec 22;864(3-4):257-304. Review. PubMed PMID: 3539192. 20: Pandey RC, Rinehart KL Jr. Polyene antibiotics. VII. Carbon-13 nuclear magnetic resonance evidence for cyclic hemiketals in the polyene antibiotics amphotericin B, nystatin A1, tetrin A, tetrin B, lucensomycin, and pimaricin1,2. J Antibiot (Tokyo). 1976 Oct;29(10):1035-42. PubMed PMID: 1086913.

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