A tricyclic peptide with antiviral and antibacterial activities
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Siamycin I

Item No. 27783

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
CAS Number
164802-68-0
Synonyms
  • BMY 29304
  • FR 901724
Molecular Formula
C97H131N23O26S4
Formula Weight
2163.5
Purity
≥85%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: SolubleMethanol: Soluble
SMILES
OC([C@@H](NC([C@H](CC1=CC=CC=C1)NC([C@H](CSSC[C@@](NC([C@@H](NC(CNC([C@@H](NC(CNC2=O)=O)C(C)C)=O)=O)CO)=O)([H])C(N[C@H](C(N[C@](CC(N[C@](CSSC[C@]3([H])NC4=O)([H])C(N[C@H]2CC(C)C)=O)=O)([H])C(N[C@@H](CC5=CC=CC=C5)C(N[C@H](C(NC4)=O)C)=O)=O)=O)CC(N)=O)=O)NC([C@@H](NC([C@](NC([C@@H](NC([C@@H](NC(CNC3=O)=O)CC6=CC=C(O)C=C6)=O)C)=O)([H])[C@@H](C)CC)=O)C(C)C)=O)=O)=O)CC7=CNC8=C7C=CC=C8)=O
InChi Code
InChI=1S/C97H131N23O26S4/c1-11-50(8)80-96(144)119-79(49(6)7)95(143)117-71(93(141)112-63(32-54-22-16-13-17-23-54)87(135)115-66(97(145)146)34-56-37-99-59-25-19-18-24-58(56)59)46-150-149-45-70-92(140)113-64(35-72(98)123)88(136)114-65-36-73(124)108-69(91(139)110-60(30-47(2)3)83(131)101-41-77(128)118-78(48(4)5)94(142)103-40-75(126)107-67(42-121)90(138)116-70)44-148-147-43-68(109-76(127)38-100-81(129)51(9)104-86(134)62(111-89(65)137)31-53-20-14-12-15-21-53)84(132)102-39-74(125)106-61(33-55-26-28-57(122)29-27-55)85(133)105-52(10)82(130)120-80/h12-29,37,47-52,60-71,78-80,99,121-122H,11,30-36,38-46H2,1-10H3,(H2,98,123)(H,100,129)(H,101,131)(H,102,132)(H,103,142)(H,104,134)(H,105,133)(H,106,125)(H,107,126)(H,108,124)(H,109,127)(H,110,139)(H,111,137)(H,112,141)(H,113,140)(H,114,136)(H,115,135)(H,116,138)(H,117,143)(H,118,128)(H,119,144)(H,120,130)(H,145,146)/t50-,51-,52-,60-,61-,62-,63-,64-,65-,66-,67-,68-,69-,70-,71-,78-,79-,80-/m0/s1
InChi Key
TXYRKTDGDMHVHR-NEKRQKPVSA-N
Origin
Bacterium/Streptomyces sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    Siamycin I is a tricyclic peptide originally isolated from Streptomyces and has antiviral and antibacterial activities.1,2 It is active against laboratory strains and clinical isolates of HIV-1 (ED50s = 0.05-0.45 and 0.89-5.7 μM, respectively), as well as the CBL-20 strain of HIV-2 (ED50 = 0.45 μM), in vitro.1 Siamycin I inhibits HIV-induced fusion of C8166 T cells with HIV-1-infected CEM-SS cells with an ED50 value of 0.08 μM. It is also active against B. subtilis, M. luteus, and S. aureus (MICs = 1.6-6.3 μg/ml).2 Siamycin I inhibits autophosphorylation of the E. faecalis quorum sensing kinase FsrC induced by gelatinase biosynthesis-activating pheromone (GBAP).3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lin, P.F., Samanta, H., Bechtold, C.M., et al. Characterization of siamycin I, a human immunodeficiency virus fusion inhibitor. Antimicrob. Agents Chemother. 40(1), 133-138 (1996).

    2. Tsunakawa, M., Hu, S.L., Hoshino, Y., et al. Siamycins I and II, new anti-HIV peptides: I. Fermentation, isolation, biological activity and initial characterization. J. Antibiot. (Tokyo) 48(5), 433-434 (1995).

    3. Ma, P., Nishiguchi, K., Yuille, H.M., et al. Anti-HIV siamycin I directly inhibits autophosphorylation activity of the bacterial FsrC quorum sensor and other ATP-dependent enzyme activities. FEBS Lett. 585(17), 2660-2664 (2011).