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MedKoo Cat#: 574450 | Name: Bacitracin F

Description:

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

Bacitracin F is a major Bacitracin analog -- a peptide antibiotic used as an inhibitor of protein disulfide isomerase (PDI).

Chemical Structure

Bacitracin F
Bacitracin F
CAS#22601-63-4

Theoretical Analysis

MedKoo Cat#: 574450

Name: Bacitracin F

CAS#: 22601-63-4

Chemical Formula: C66H98N16O17S

Exact Mass: 1418.7017

Molecular Weight: 1419.66

Elemental Analysis: C, 55.84; H, 6.96; N, 15.79; O, 19.16; S, 2.26

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Synonym
Bacitracin F
IUPAC/Chemical Name
5-(((2S,3R)-1-(((6R,12R,18R,21S)-9-((1H-imidazol-5-yl)methyl)-3-(2-amino-2-oxoethyl)-18-(3-aminopropyl)-12-benzyl-15-(sec-butyl)-6-(carboxymethyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptaazacyclopentacosan-21-yl)amino)-3-methyl-1-oxopentan-2-yl)amino)-4-((S)-4-methyl-2-(2-((S)-2-methylbutanoyl)thiazole-4-carboxamido)pentanamido)-5-oxopentanoic acid
InChi Key
FCLQHQCOKGKLHR-GRGWNPLCSA-N
InChi Code
InChI=1S/C66H98N16O17S/c1-9-35(6)52(82-58(92)42(22-23-50(84)85)73-59(93)43(26-34(4)5)75-63(97)48-32-100-66(80-48)54(88)37(8)11-3)64(98)74-40-20-15-16-25-70-55(89)46(29-49(68)83)77-62(96)47(30-51(86)87)78-61(95)45(28-39-31-69-33-71-39)76-60(94)44(27-38-18-13-12-14-19-38)79-65(99)53(36(7)10-2)81-57(91)41(21-17-24-67)72-56(40)90/h12-14,18-19,31-37,40-47,52-53H,9-11,15-17,20-30,67H2,1-8H3,(H2,68,83)(H,69,71)(H,70,89)(H,72,90)(H,73,93)(H,74,98)(H,75,97)(H,76,94)(H,77,96)(H,78,95)(H,79,99)(H,81,91)(H,82,92)(H,84,85)(H,86,87)/t35-,36?,37+,40+,41-,42?,43+,44-,45?,46?,47-,52+,53?/m1/s1
SMILES Code
CCC(C1C(N[C@H](CC2=CC=CC=C2)C(NC(CC3=CN=CN3)C(N[C@H](CC(O)=O)C(NC(CC(N)=O)C(NCCCC[C@H](NC([C@@H](NC(C(NC([C@@H](NC(C4=CSC(C([C@H](CC)C)=O)=N4)=O)CC(C)C)=O)CCC(O)=O)=O)[C@@H](CC)C)=O)C(N[C@H](CCCN)C(N1)=O)=O)=O)=O)=O)=O)=O)C
Appearance
Pale Yellow Solid
Purity
>75% (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
Aqueous Acid (Slightly), Acidic Methanol (Slightly), Methanol (Slightly)
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:
Bacitracin functions as an inhibitor of cell wall biosynthesis through its binding to the undecaprenyl pyrophosphate.
In vitro activity:
To investigate the effect of Bacitracin (Bac) on the intoxication of cells with the binary actin ADP-ribosylating C2 toxin, HeLa cells were incubated with recombinantly expressed C2 toxin in the absence and presence of Bac. After different incubation periods, the number of round cells was determined as a specific and highly sensitive endpoint for the C2 toxin–mediated destruction of the actin cytoskeleton of the cells. As shown in Fig. 1A, the number of round cells was significantly reduced in the presence of Bac, indicating that Bac protects cells from the intoxication with recombinant C2 toxin. Reference: FASEB J. 2019 Apr;33(4):5755-5771. https://faseb.onlinelibrary.wiley.com/doi/10.1096/fj.201802453R
In vivo activity:
The effects of protease inhibitor bacitracin on brain beta-endorphin content and analgesia, were examined in vivo. Male Sprague-Dawley rats were injected with bacitracin intracerebroventricularly and sacrificed by microwave irradiation 15 and 30 min after injection. Brain beta-endorphin levels were 27% higher in bacitracin treated rats than in controls. A second group of bacitracin injected rats was subjected to continuous intermittent 55 degrees C hot plate exposure. Bacitracin-injected rats exhibited total analgesia 15 min after bacitracin injection. At 30 min, this analgesic effect subsided. Control rats exhibited no analgesia. These results suggest that bacitracin induced analgesia might be due to the elevated levels of brain beta-endorphin caused by a decrease in its breakdown by bacitracin. Reference: Brain Res. 1982 Jun 17;242(1):119-23. https://www.sciencedirect.com/science/article/abs/pii/0006899382905017?via%3Dihub
Solvent mg/mL mM
Solubility
Water 53.3 37.49
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 1,419.66 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. Schnell L, Felix I, Müller B, Sadi M, von Bank F, Papatheodorou P, Popoff MR, Aktories K, Waltenberger E, Benz R, Weichbrodt C, Fauler M, Frick M, Barth H. Revisiting an old antibiotic: bacitracin neutralizes binary bacterial toxins and protects cells from intoxication. FASEB J. 2019 Apr;33(4):5755-5771. doi: 10.1096/fj.201802453R. Epub 2019 Jan 30. PMID: 30699302. 2. Zhu Z, Schnell L, Müller B, Müller M, Papatheodorou P, Barth H. The Antibiotic Bacitracin Protects Human Intestinal Epithelial Cells and Stem Cell-Derived Intestinal Organoids from Clostridium difficile Toxin TcdB. Stem Cells Int. 2019 Aug 5;2019:4149762. doi: 10.1155/2019/4149762. PMID: 31467562; PMCID: PMC6701344. 3. Sikand G, Havlicek V. Bacitracin produces analgesia by increasing brain immunoreactive beta-endorphin (beta-E) content. Brain Res. 1982 Jun 17;242(1):119-23. doi: 10.1016/0006-8993(82)90501-7. PMID: 7104723.
In vitro protocol:
1. Schnell L, Felix I, Müller B, Sadi M, von Bank F, Papatheodorou P, Popoff MR, Aktories K, Waltenberger E, Benz R, Weichbrodt C, Fauler M, Frick M, Barth H. Revisiting an old antibiotic: bacitracin neutralizes binary bacterial toxins and protects cells from intoxication. FASEB J. 2019 Apr;33(4):5755-5771. doi: 10.1096/fj.201802453R. Epub 2019 Jan 30. PMID: 30699302. 2. Zhu Z, Schnell L, Müller B, Müller M, Papatheodorou P, Barth H. The Antibiotic Bacitracin Protects Human Intestinal Epithelial Cells and Stem Cell-Derived Intestinal Organoids from Clostridium difficile Toxin TcdB. Stem Cells Int. 2019 Aug 5;2019:4149762. doi: 10.1155/2019/4149762. PMID: 31467562; PMCID: PMC6701344.
In vivo protocol:
1. Sikand G, Havlicek V. Bacitracin produces analgesia by increasing brain immunoreactive beta-endorphin (beta-E) content. Brain Res. 1982 Jun 17;242(1):119-23. doi: 10.1016/0006-8993(82)90501-7. PMID: 7104723.

View History

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