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MedKoo Cat#: 574123 | Name: Siamycin I
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Description:

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

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).

Chemical Structure

Siamycin I
Siamycin I
CAS#164802-68-0

Theoretical Analysis

MedKoo Cat#: 574123

Name: Siamycin I

CAS#: 164802-68-0

Chemical Formula: C97H131N23O26S4

Exact Mass: 2161.8518

Molecular Weight: 2163.49

Elemental Analysis: C, 53.85; H, 6.10; N, 14.89; O, 19.23; S, 5.93

Price and Availability

Size Price Availability Quantity
1mg USD 550.00 2 weeks
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Related CAS #
No Data
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
To be determined
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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Siamycin I 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. 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.
In vitro activity:
Siamycin-I is the first lasso peptide that has been shown to inhibit cell wall biosynthesis. Siamycin-I interacts with lipid II, the central building block of the major cell wall component peptidoglycan, which is readily accessible on the outside of the cell. This interaction compromises cell wall biosynthesis in a manner that activates the liaI stress response. Reference: ACS Chem Biol. 2019 May 17;14(5):966-974. https://pubmed.ncbi.nlm.nih.gov/31026131/
In vivo activity:
Siamycin I prevented Helicobacter pylori infection by inhibiting the futalosine pathway of menaquinone biosynthesis. Daily administration of siamycin I (2.5 μM) in drinking water reduced the H. pylori SS1 colonization in the gastric mucosa of C57BL/6 mice by 68%. Reference: J Infect Chemother. 2016 Sep;22(9):587-92. https://pubmed.ncbi.nlm.nih.gov/27346378/

Preparing Stock Solutions

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.

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
Formulation protocol:
1. Tan S, Ludwig KC, Müller A, Schneider T, Nodwell JR. The Lasso Peptide Siamycin-I Targets Lipid II at the Gram-Positive Cell Surface. ACS Chem Biol. 2019 May 17;14(5):966-974. doi: 10.1021/acschembio.9b00157. Epub 2019 May 3. PMID: 31026131. 2. Nakayama J, Tanaka E, Kariyama R, Nagata K, Nishiguchi K, Mitsuhata R, Uemura Y, Tanokura M, Kumon H, Sonomoto K. Siamycin attenuates fsr quorum sensing mediated by a gelatinase biosynthesis-activating pheromone in Enterococcus faecalis. J Bacteriol. 2007 Feb;189(4):1358-65. doi: 10.1128/JB.00969-06. Epub 2006 Oct 27. PMID: 17071762; PMCID: PMC1797363. 3. Yamamoto T, Matsui H, Yamaji K, Takahashi T, Øverby A, Nakamura M, Matsumoto A, Nonaka K, Sunazuka T, Ōmura S, Nakano H. Narrow-spectrum inhibitors targeting an alternative menaquinone biosynthetic pathway of Helicobacter pylori. J Infect Chemother. 2016 Sep;22(9):587-92. doi: 10.1016/j.jiac.2016.05.012. Epub 2016 Jun 23. PMID: 27346378.
In vitro protocol:
1. Tan S, Ludwig KC, Müller A, Schneider T, Nodwell JR. The Lasso Peptide Siamycin-I Targets Lipid II at the Gram-Positive Cell Surface. ACS Chem Biol. 2019 May 17;14(5):966-974. doi: 10.1021/acschembio.9b00157. Epub 2019 May 3. PMID: 31026131. 2. Nakayama J, Tanaka E, Kariyama R, Nagata K, Nishiguchi K, Mitsuhata R, Uemura Y, Tanokura M, Kumon H, Sonomoto K. Siamycin attenuates fsr quorum sensing mediated by a gelatinase biosynthesis-activating pheromone in Enterococcus faecalis. J Bacteriol. 2007 Feb;189(4):1358-65. doi: 10.1128/JB.00969-06. Epub 2006 Oct 27. PMID: 17071762; PMCID: PMC1797363.
In vivo protocol:
1. Yamamoto T, Matsui H, Yamaji K, Takahashi T, Øverby A, Nakamura M, Matsumoto A, Nonaka K, Sunazuka T, Ōmura S, Nakano H. Narrow-spectrum inhibitors targeting an alternative menaquinone biosynthetic pathway of Helicobacter pylori. J Infect Chemother. 2016 Sep;22(9):587-92. doi: 10.1016/j.jiac.2016.05.012. Epub 2016 Jun 23. PMID: 27346378.
1: Tan S, Ludwig KC, Müller A, Schneider T, Nodwell JR. The Lasso Peptide Siamycin-I Targets Lipid II at the Gram-Positive Cell Surface. ACS Chem Biol. 2019 May 17;14(5):966-974. doi: 10.1021/acschembio.9b00157. Epub 2019 May 3. PMID: 31026131. 2: Kaweewan I, Hemmi H, Komaki H, Harada S, Kodani S. Isolation and structure determination of a new lasso peptide specialicin based on genome mining. Bioorg Med Chem. 2018 Dec 15;26(23-24):6050-6055. doi: 10.1016/j.bmc.2018.11.007. Epub 2018 Nov 9. PMID: 30448257. 3: Daniel-Ivad M, Hameed N, Tan S, Dhanjal R, Socko D, Pak P, Gverzdys T, Elliot MA, Nodwell JR. An Engineered Allele of afsQ1 Facilitates the Discovery and Investigation of Cryptic Natural Products. ACS Chem Biol. 2017 Mar 17;12(3):628-634. doi: 10.1021/acschembio.6b01002. Epub 2017 Jan 19. PMID: 28075554. 4: Yamamoto T, Matsui H, Yamaji K, Takahashi T, Øverby A, Nakamura M, Matsumoto A, Nonaka K, Sunazuka T, Ōmura S, Nakano H. Narrow-spectrum inhibitors targeting an alternative menaquinone biosynthetic pathway of Helicobacter pylori. J Infect Chemother. 2016 Sep;22(9):587-92. doi: 10.1016/j.jiac.2016.05.012. Epub 2016 Jun 23. PMID: 27346378. 5: Phillips-Jones MK, Patching SG, Edara S, Nakayama J, Hussain R, Siligardi G. Interactions of the intact FsrC membrane histidine kinase with the tricyclic peptide inhibitor siamycin I revealed through synchrotron radiation circular dichroism. Phys Chem Chem Phys. 2013 Jan 14;15(2):444-7. doi: 10.1039/c2cp43722h. Epub 2012 Nov 26. PMID: 23183669. 6: Ma P, Nishiguchi K, Yuille HM, Davis LM, Nakayama J, Phillips-Jones MK. Anti- HIV siamycin I directly inhibits autophosphorylation activity of the bacterial FsrC quorum sensor and other ATP-dependent enzyme activities. FEBS Lett. 2011 Sep 2;585(17):2660-4. doi: 10.1016/j.febslet.2011.07.026. Epub 2011 Jul 26. PMID: 21803040. 7: Nakayama J, Tanaka E, Kariyama R, Nagata K, Nishiguchi K, Mitsuhata R, Uemura Y, Tanokura M, Kumon H, Sonomoto K. Siamycin attenuates fsr quorum sensing mediated by a gelatinase biosynthesis-activating pheromone in Enterococcus faecalis. J Bacteriol. 2007 Feb;189(4):1358-65. doi: 10.1128/JB.00969-06. Epub 2006 Oct 27. PMID: 17071762; PMCID: PMC1797363. 8: De Clercq E. Current lead natural products for the chemotherapy of human immunodeficiency virus (HIV) infection. Med Res Rev. 2000 Sep;20(5):323-49. doi: 10.1002/1098-1128(200009)20:5<323::aid-med1>3.0.co;2-a. PMID: 10934347. 9: Lin PF, Samanta H, Bechtold CM, Deminie CA, Patick AK, Alam M, Riccardi K, Rose RE, White RJ, Colonno RJ. Characterization of siamycin I, a human immunodeficiency virus fusion inhibitor. Antimicrob Agents Chemother. 1996 Jan;40(1):133-8. doi: 10.1128/AAC.40.1.133. PMID: 8787894; PMCID: PMC163071. 10: Yano K, Toki S, Nakanishi S, Ochiai K, Ando K, Yoshida M, Matsuda Y, Yamasaki M. MS-271, a novel inhibitor of calmodulin-activated myosin light chain kinase from Streptomyces sp.--I. Isolation, structural determination and biological properties of MS-271. Bioorg Med Chem. 1996 Jan;4(1):115-20. doi: 10.1016/0968-0896(95)00175-1. PMID: 8689231. 11: Detlefsen DJ, Hill SE, Volk KJ, Klohr SE, Tsunakawa M, Furumai T, Lin PF, Nishio M, Kawano K, Oki T, et al. Siamycins I and II, new anti-HIV-1 peptides: II. Sequence analysis and structure determination of siamycin I. J Antibiot (Tokyo). 1995 Dec;48(12):1515-7. doi: 10.7164/antibiotics.48.1515. PMID: 8557614. 12: Tsunakawa M, Hu SL, Hoshino Y, Detlefson DJ, Hill SE, Furumai T, White RJ, Nishio M, Kawano K, Yamamoto S, et al. Siamycins I and II, new anti-HIV peptides: I. Fermentation, isolation, biological activity and initial characterization. J Antibiot (Tokyo). 1995 May;48(5):433-4. doi: 10.7164/antibiotics.48.433. PMID: 7797448. 13: Constantine KL, Friedrichs MS, Detlefsen D, Nishio M, Tsunakawa M, Furumai T, Ohkuma H, Oki T, Hill S, Bruccoleri RE, et al. High-resolution solution structure of siamycin II: novel amphipathic character of a 21-residue peptide that inhibits HIV fusion. J Biomol NMR. 1995 Apr;5(3):271-86. doi: 10.1007/BF00211754. PMID: 7787424.