WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H574123
CAS#: 164802-68-0
Description: Siamycin I is a tricyclic peptide with antiviral and antibacterial activities. It is active against HIV-1 and CBL-20 strain of HIV-2. Siamycin I inhibits HIV-induced fusion of C8166 T cells with HIV-1-infected CEM-SS cells. It is also active against B. subtilis, M. luteus, and S. aureus. Siamycin I inhibits autophosphorylation of the E. faecalis quorum sensing kinase FsrC induced by gelatinase biosynthesis-activating pheromone (GBAP).
Hodoodo Cat#: H574123
Name: Siamycin I
CAS#: 164802-68-0
Chemical Formula: C97H131N23O26S4
Exact Mass: 2,161.85
Molecular Weight: 2,163.490
Elemental Analysis: C, 53.85; H, 6.10; N, 14.89; O, 19.23; S, 5.93
Synonym: BMY 29304, FR 901724, Siamycin I
IUPAC/Chemical Name: ((1S,4S,7S,13R,19S,22S,25S,28S,31R,36R,39S,45S,51S,54R,60S)-60-(2-amino-2-oxoethyl)-4-benzyl-25-((S)-sec-butyl)-19-(4-hydroxybenzyl)-39-(hydroxymethyl)-51-isobutyl-28,45-diisopropyl-7,22-dimethyl-2,5,8,11,14,17,20,23,26,29,38,41,44,47,50,53,56,59,62-nonadecaoxo-33,34,64,65-tetrathia-3,6,9,12,15,18,21,24,27,30,37,40,43,46,49,52,55,58,61-nonadecaazatricyclo[34.21.5.413,54]hexahexacontane-31-carbonyl)-L-phenylalanyl-L-tryptophan
InChi Key: TXYRKTDGDMHVHR-NEKRQKPVSA-N
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
SMILES Code: 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
Appearance: Solid powder
Purity: >85% (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: 2934.99.9001
More Info:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
The following data is based on the product molecular weight 2,163.49 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 |
| Formulation protocol: | |
| In vitro protocol: | |
| In vivo protocol: |
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).
