Gramicidin S TFA| CAS#113-73-5

MedKoo Cat#: 333082 | Name: Gramicidin S TFA

Description:

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

Gramicidin S (GS), also known as Gramicidin soviet, is an antibiotic. GS reduces the cell number of planktonic cells within 20-40 min at a concentration of 40-80 μg/mL. GS kills the cells of pre-grown biofilms at concentrations of 100-200 μg/mL, such that no re-growth is possible. The translocation of the peptide into the cell interior and its complexation with intracellular nucleotides, including the alarmon ppGpp, can explain its anti-biofilm effect. The successful treatment of persistently infected root canals of two volunteers confirms the high effectiveness of GS. The broad GS activity towards resistant, biofilm-forming E. faecalis suggests its applications for approval in root canal medication.

Chemical Structure

Gramicidin S TFA

CAS#113-73-5 (free base)

Theoretical Analysis

MedKoo Cat#: 333082

Name: Gramicidin S TFA

CAS#: 113-73-5 (free base)

Chemical Formula: C64H94F6N12O14

Exact Mass: 0.0000

Molecular Weight: 1369.52

Elemental Analysis: C, 56.13; H, 6.92; F, 8.32; N, 12.27; O, 16.36

Price and Availability

Size	Price	Availability
5mg	USD 150.00	Ready to ship
10mg	USD 250.00	Ready to ship
25mg	USD 450.00	Ready to ship
50mg	USD 750.00	Ready to ship
100mg	USD 1,250.00	Ready to ship
200mg	USD 2,050.00	Ready to ship
1g	USD 4,650.00	Ready to ship
2g	USD 7,650.00	Ready to ship

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Related CAS #

113-73-5 (free base) 15207-30-4 (HCl)

Synonym

Gramicidin S; Gramicidin S TFA salt; Gramicidin S 1; Gramicidin S-1; Gramicidin S1; Gramicidin S-A;

IUPAC/Chemical Name

(6R,9S,12S,15S,17aS,23R,26S,29S,32S,34aS)-12,29-bis(3-aminopropyl)-6,23-dibenzyl-9,26-diisobutyl-15,32-diisopropyldocosahydro-1H,5H-dipyrrolo[1,2-a:1',2'-p][1,4,7,10,13,16,19,22,25,28]decaazacyclotriacontine-5,8,11,14,17,22,25,28,31,34(34aH)-decaone bis(2,2,2-trifluoroacetate)

InChi Key

TWKUVBDWZULHEV-MZFDKZDRSA-N

InChi Code

InChI=1S/C60H92N12O10.2C2HF3O2/c1-35(2)31-43-53(75)67-45(33-39-19-11-9-12-20-39)59(81)71-29-17-25-47(71)55(77)70-50(38(7)8)58(80)64-42(24-16-28-62)52(74)66-44(32-36(3)4)54(76)68-46(34-40-21-13-10-14-22-40)60(82)72-30-18-26-48(72)56(78)69-49(37(5)6)57(79)63-41(23-15-27-61)51(73)65-43;2*3-2(4,5)1(6)7/h9-14,19-22,35-38,41-50H,15-18,23-34,61-62H2,1-8H3,(H,63,79)(H,64,80)(H,65,73)(H,66,74)(H,67,75)(H,68,76)(H,69,78)(H,70,77);2*(H,6,7)/t41-,42-,43-,44-,45+,46+,47-,48-,49-,50-;;/m0../s1

SMILES Code

O=C1N2[C@](CCC2)([H])C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@@H](C(N3[C@](CCC3)([H])C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@@H]1CC4=CC=CC=C4)=O)CC(C)C)=O)CCCN)=O)C(C)C)=O)=O)CC5=CC=CC=C5)=O)CC(C)C)=O)CCCN)=O)C(C)C)=O.O=C(O)C(F)(F)F.O=C(O)C(F)(F)F

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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

Cyclo(L-valyl-L-ornithyl-L-leucyl-D-phenylalanyl-L-prolyl-L-valyl-L-ornithyl-L-leucyl-D-phenylalanyl-L-prolyl) 1H,5H-Dipyrrolo[1,2-a:1′,2′-p][1,4,7,10,13,16,19,22,25,28]decaazacyclotriacontine, cyclic peptide deriv. (ZCI) Cyclo(L-leucyl-D-phenylalanyl-L-prolyl-L-valyl-L-ornithyl-L-leucyl-D-phenylalanyl-L-prolyl-L-valyl-L-ornithyl)

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot# A23T11K07

QC Data

View QC data: current batch, Lot# A23T11K07

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

GS is active against Gram-negative and Gram-positive bacteria by perturbing integrity of the bacterial membranes. GS inhibits cytochrome bd quinol oxidase.

In vitro activity:

GS outperformed temporin L (TL) and innate-defense regulator IDR-1018 (IDR) against clinical strains of Staphylococcus aureus, Enterococcus faecalis, and Enterococcus faecium, displaying superior potency and effectiveness in killing cells. GS demonstrated the lowest minimal biofilm inhibiting concentrations, particularly against strains with substantial biofilm biomass, and exhibited robust bactericidal, antipersister, and antibiofilm activities. Reference: Sci Rep. 2019 Nov 29;9(1):17938. https://pubmed.ncbi.nlm.nih.gov/31784584/

In vivo activity:

GS has potential in anticancer treatments. A daily intraperitoneal injection of GS exhibited a high inhibitory effect on the growth of subcutaneously implanted allotransplantable sarcoma 180 in ICR mice, and on the growth of subcutaneously implanted syngeneic Meth A in BALB/c mice. Reference: Oncology. 1984;41(1):43-8. https://pubmed.ncbi.nlm.nih.gov/6199707/

Preparing Stock Solutions

The following data is based on the product molecular weight 1,369.52 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:

1. Berditsch M, Afonin S, Reuster J, Lux H, Schkolin K, Babii O, Radchenko DS, Abdullah I, William N, Middel V, Strähle U, Nelson A, Valko K, Ulrich AS. Supreme activity of gramicidin S against resistant, persistent and biofilm cells of staphylococci and enterococci. Sci Rep. 2019 Nov 29;9(1):17938. doi: 10.1038/s41598-019-54212-z. PMID: 31784584; PMCID: PMC6884456. 2. Mogi T, Kita K. Gramicidin S and polymyxins: the revival of cationic cyclic peptide antibiotics. Cell Mol Life Sci. 2009 Dec;66(23):3821-6. doi: 10.1007/s00018-009-0129-9. Epub 2009 Aug 23. PMID: 19701717. 3. Chen D, Qin W, Wen G, Shi B, Liu Z, Wang Y, Zhou Q, Quan J, Zhou B, Bu X. Dissociation of haemolytic and oligomer-preventing activities of gramicidin S derivatives targeting the amyloid-β N-terminus. Chem Commun (Camb). 2017 Dec 14;53(100):13340-13343. doi: 10.1039/c7cc08180d. PMID: 29188836. 4. Okamoto K, Tomita Y, Yonezawa H, Hirohata T, Ogura R, Izumiya N. Inhibitory effect of gramicidin S on the growth of murine tumor cells in vitro and in vivo. Oncology. 1984;41(1):43-8. doi: 10.1159/000225789. PMID: 6199707.

In vitro protocol:

In vivo protocol:

1. Chen D, Qin W, Wen G, Shi B, Liu Z, Wang Y, Zhou Q, Quan J, Zhou B, Bu X. Dissociation of haemolytic and oligomer-preventing activities of gramicidin S derivatives targeting the amyloid-β N-terminus. Chem Commun (Camb). 2017 Dec 14;53(100):13340-13343. doi: 10.1039/c7cc08180d. PMID: 29188836. 2. Okamoto K, Tomita Y, Yonezawa H, Hirohata T, Ogura R, Izumiya N. Inhibitory effect of gramicidin S on the growth of murine tumor cells in vitro and in vivo. Oncology. 1984;41(1):43-8. doi: 10.1159/000225789. PMID: 6199707.

1: Enayathullah MG, Parekh Y, Banu S, Ram S, Nagaraj R, Kumar BK, Idris MM. Gramicidin S and melittin: potential anti-viral therapeutic peptides to treat SARS-CoV-2 infection. Sci Rep. 2022 Mar 2;12(1):3446. doi: 10.1038/s41598-022-07341-x. PMID: 35236909; PMCID: PMC8891299. 2: Hu C, Wen Q, Huang S, Xie S, Fang Y, Jin Y, Campagne R, Alezra V, Miclet E, Zhu J, Wan Y. Corrigendum: Gramicidin-S-Inspired Cyclopeptidomimetics as Potent Membrane-Active Bactericidal Agents with Therapeutic Potential. ChemMedChem. 2022 Feb 4;17(3):e202100765. doi: 10.1002/cmdc.202100765. Epub 2022 Jan 10. Erratum for: ChemMedChem. 2021 Jan 19;16(2):368-376. PMID: 35014188. 3: Asano A, Minami C, Matsuoka S, Kato T, Doi M. An Ornithine-Free Gramicidin S Analogue Using Norleucine, Cyclo(Val-Nle-Leu-D-Phe-Pro)2, Forms Helically Aligned β-Sheets. Chem Pharm Bull (Tokyo). 2021;69(11):1097-1103. doi: 10.1248/cpb.c21-00548. PMID: 34719592. 4: Ashrafuzzaman M. The Antimicrobial Peptide Gramicidin S Enhances Membrane Adsorption and Ion Pore Formation Potency of Chemotherapy Drugs in Lipid Bilayers. Membranes (Basel). 2021 Mar 30;11(4):247. doi: 10.3390/membranes11040247. PMID: 33808204; PMCID: PMC8067072. 5: Hu C, Wen Q, Huang S, Xie S, Fang Y, Jin Y, Campagne R, Alezra V, Miclet E, Zhu J, Wan Y. Gramicidin-S-Inspired Cyclopeptidomimetics as Potent Membrane- Active Bactericidal Agents with Therapeutic Potential. ChemMedChem. 2021 Jan 19;16(2):368-376. doi: 10.1002/cmdc.202000568. Epub 2020 Oct 16. Erratum in: ChemMedChem. 2022 Feb 4;17(3):e202100765. PMID: 33026182. 6: Rathman BM, Allen JL, Shaw LN, Del Valle JR. Synthesis and biological evaluation of backbone-aminated analogues of gramicidin S. Bioorg Med Chem Lett. 2020 Aug 1;30(15):127283. doi: 10.1016/j.bmcl.2020.127283. Epub 2020 May 22. PMID: 32527462. 7: Guan Q, Chen K, Chen Q, Hu J, Cheng K, Hu C, Zhu J, Jin Y, Miclet E, Alezra V, Wan Y. Development of Therapeutic Gramicidin S Analogues Bearing Plastic β,γ-Diamino Acids. ChemMedChem. 2020 Jun 17;15(12):1089-1100. doi: 10.1002/cmdc.202000097. Epub 2020 May 20. PMID: 32233075. 8: Yamamura H, Isshiki K, Fujita Y, Kato H, Katsu T, Masuda K, Osawa K, Miyagawa A. Gramicidin S-inspired antimicrobial cyclodextrin to disrupt gram-negative and gram-positive bacterial membranes. Medchemcomm. 2019 Jul 17;10(8):1432-1437. doi: 10.1039/c9md00229d. PMID: 31803397; PMCID: PMC6836745. 9: Berditsch M, Afonin S, Reuster J, Lux H, Schkolin K, Babii O, Radchenko DS, Abdullah I, William N, Middel V, Strähle U, Nelson A, Valko K, Ulrich AS. Supreme activity of gramicidin S against resistant, persistent and biofilm cells of staphylococci and enterococci. Sci Rep. 2019 Nov 29;9(1):17938. doi: 10.1038/s41598-019-54212-z. PMID: 31784584; PMCID: PMC6884456. 10: Asano A, Matsuoka S, Minami C, Kato T, Doi M. [Leu2]Gramicidin S preserves the structural properties of its parent peptide and forms helically aligned β-sheets. Acta Crystallogr C Struct Chem. 2019 Oct 1;75(Pt 10):1336-1343. doi: 10.1107/S2053229619011872. Epub 2019 Sep 6. PMID: 31589149. 11: Guan Q, Huang S, Jin Y, Campagne R, Alezra V, Wan Y. Recent Advances in the Exploration of Therapeutic Analogues of Gramicidin S, an Old but Still Potent Antimicrobial Peptide. J Med Chem. 2019 Sep 12;62(17):7603-7617. doi: 10.1021/acs.jmedchem.9b00156. Epub 2019 Apr 17. PMID: 30938996. 12: Wenzel M, Rautenbach M, Vosloo JA, Siersma T, Aisenbrey CHM, Zaitseva E, Laubscher WE, van Rensburg W, Behrends JC, Bechinger B, Hamoen LW. The Multifaceted Antibacterial Mechanisms of the Pioneering Peptide Antibiotics Tyrocidine and Gramicidin S. mBio. 2018 Oct 9;9(5):e00802-18. doi: 10.1128/mBio.00802-18. PMID: 30301848; PMCID: PMC6178620. 13: Wan Y, Stanovych A, Gori D, Zirah S, Kouklovsky C, Alezra V. β,γ-diamino acids as building blocks for new analogues of Gramicidin S: Synthesis and biological activity. Eur J Med Chem. 2018 Apr 10;149:122-128. doi: 10.1016/j.ejmech.2018.02.053. Epub 2018 Feb 21. PMID: 29499484. 14: Chen D, Qin W, Wen G, Shi B, Liu Z, Wang Y, Zhou Q, Quan J, Zhou B, Bu X. Dissociation of haemolytic and oligomer-preventing activities of gramicidin S derivatives targeting the amyloid-β N-terminus. Chem Commun (Camb). 2017 Dec 14;53(100):13340-13343. doi: 10.1039/c7cc08180d. PMID: 29188836. 15: Priem C, Wuttke A, Berditsch M, Ulrich AS, Geyer A. Scaling the Amphiphilic Character and Antimicrobial Activity of Gramicidin S by Dihydroxylation or Ketal Formation. J Org Chem. 2017 Dec 1;82(23):12366-12376. doi: 10.1021/acs.joc.7b02177. Epub 2017 Nov 7. PMID: 29077406. 16: Rautenbach M, Vlok NM, Eyéghé-Bickong HA, van der Merwe MJ, Stander MA. An Electrospray Ionization Mass Spectrometry Study on the "In Vacuo" Hetero- Oligomers Formed by the Antimicrobial Peptides, Surfactin and Gramicidin S. J Am Soc Mass Spectrom. 2017 Aug;28(8):1623-1637. doi: 10.1007/s13361-017-1685-0. Epub 2017 May 30. PMID: 28560564. 17: Berditsch M, Trapp M, Afonin S, Weber C, Misiewicz J, Turkson J, Ulrich AS. Antimicrobial peptide gramicidin S is accumulated in granules of producer cells for storage of bacterial phosphagens. Sci Rep. 2017 Mar 15;7:44324. doi: 10.1038/srep44324. PMID: 28295017; PMCID: PMC5353757. 18: Laskin J, Hu Q. Reactive Landing of Gramicidin S and Ubiquitin Ions onto Activated Self-Assembled Monolayer Surfaces. J Am Soc Mass Spectrom. 2017 Jul;28(7):1304-1312. doi: 10.1007/s13361-017-1614-2. Epub 2017 Mar 13. PMID: 28290125. 19: Berditsch M, Lux H, Babii O, Afonin S, Ulrich AS. Therapeutic Potential of Gramicidin S in the Treatment of Root Canal Infections. Pharmaceuticals (Basel). 2016 Sep 7;9(3):56. doi: 10.3390/ph9030056. PMID: 27618065; PMCID: PMC5039509. 20: Swierstra J, Kapoerchan V, Knijnenburg A, van Belkum A, Overhand M. Structure, toxicity and antibiotic activity of gramicidin S and derivatives. Eur J Clin Microbiol Infect Dis. 2016 May;35(5):763-9. doi: 10.1007/s10096-016-2595-y. Epub 2016 Feb 17. PMID: 26886453; PMCID: PMC4840228