A cyclic depsipeptide with diverse biological activities
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Aureobasidin A

Item No. 39722

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
cyclo[L-alloisoleucyl-N-methyl-L-valyl-L-leucyl-N,3-dimethyl-L-threonyl-(2R,3R)-2-hydroxy-3-methylpentanoyl-N-methyl-L-valyl-L-phenylalanyl-N-methyl-L-phenylalanyl-L-prolyl]
CAS Number
127785-64-2
Synonyms
  • Antibiotic R 106I
  • Basifungin
  • LY295337
  • NK 204
  • R 106-1
Molecular Formula
C60H92N8O11
Formula Weight
1101.4
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Methanol: Soluble
SMILES
[H][C@@]12CCCN1C([C@@H](N(C([C@@H](NC([C@@H](N(C([C@@]([C@@H](CC)C)(OC([C@@H](N(C([C@@H](NC([C@@H](N(C([C@@]([H])(NC2=O)[C@H](C)CC)=O)C)C(C)C)=O)CC(C)C)=O)C)C(C)(C)O)=O)[H])=O)C)C(C)C)=O)CC3=CC=CC=C3)=O)C)CC4=CC=CC=C4)=O
InChi Code
InChI=1S/C60H92N8O11/c1-17-38(9)46-57(75)65(14)47(36(5)6)52(70)61-42(32-35(3)4)55(73)67(16)50(60(11,12)78)59(77)79-49(39(10)18-2)58(76)66(15)48(37(7)8)53(71)62-43(33-40-26-21-19-22-27-40)54(72)64(13)45(34-41-28-23-20-24-29-41)56(74)68-31-25-30-44(68)51(69)63-46/h19-24,26-29,35-39,42-50,78H,17-18,25,30-34H2,1-16H3,(H,61,70)(H,62,71)(H,63,69)/t38-,39-,42+,43+,44+,45+,46+,47+,48+,49-,50-/m1/s1
InChi Key
RLMLFADXHJLPSQ-QKCBWMAHSA-N
Origin
Synthetic; originally from Aureobasidium pullulans
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    10 mg

    $180

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    50 mg

    $808

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    100 mg

    $1,346

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    Product Description

    Aureobasidin A is a cyclic depsipeptide that has been found in A. pullulans and has diverse biological activities.1,2,3 It inhibits inositol phosphorylceramide synthase, an enzyme involved in sphingolipid biosynthesis (Kis = 0.18 and 0.23 for the C. albicans and S. cerevisiae enzymes, respectively).1 Aureobasidin A also inhibits P-glycoprotein (P-gp), also known as multidrug resistance protein 1 (MDR1; IC50 = 2.27 µM).2 It is active against various mammalian pathogenic fungi, including Candida and Cryptococcus (MICs = <0.04-0.16 and 0.31-0.63 µg/ml, respectively), and the plant pathogenic fungus S. cerevisiae (MIC = 0.4 µg/ml).3,2 Aureobasidin A (80 mg/kg, p.o.) increases survival in a mouse model of candidiasis induced by C. albicans.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Aeed, P.A., Young, C.L., Nagiec, M.M., et al. Inhibition of inositol phosphorylceramide synthase by the cyclic peptide aureobasidin A. Antimicrob. Agents Chemother. 53(2), 496-504 (2009).

    2. Tiberghien, F., Kurome, T., Takesako, K., et al. Aureobasidins: Structure-activity relationships for the inhibition of the human MDR1 P-glycoprotein ABC-transporter. J. Med. Chem 43(13), 2547-2556 (2000).

    3. Takesako, K., Kuroda, H., Inoue, T., et al. Biological properties of aureobasidin A, a cyclic depsipeptide antifungal antibiotic. J. Antibiot. (Tokyo) 46(9), 1414-1420 (1993).