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Purity: ≥98%
Pristinamycin IA (also known as Mikamycin B; Mikamycin IA), a naturally occuring and biologically active decapeptide isolated from the skin of the Australian frog Hyla caerulea, is a novel and potent cholecystokinetic agent which acts as a cholecystokinin receptor agonist.
| Targets |
Ribosome (specifically induces transient ribosome stalling) [2]
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|---|---|
| ln Vitro |
Pristinamycin IA (100 μM, 0–4 h) suppresses the disruption of [3H]vinblastine in Caco-2 cells [1]. Pristinamycin IA (4.614 μM) stimulates the ribosome-supporting ribose regulatory factor (LRR), and Pristinamycin IA (100 μM) and [3H]vinblastine rescue in Caco-2 cell monolayers [2].
Pristinamycin IA (Pnm) was identified as one of the ribosome-targeting antibiotics that can markedly induce the "on" state of the LRR attenuator in Bacillus thuringiensis BMB171. In an assay measuring β-galactosidase activity (LacZ reporter), treatment with Pristinamycin IA at 4 µg/mL (4.614 µM) significantly increased LacZ expression compared to the no-antibiotic control, indicating it can effectively activate the LRR-mediated gene expression switch. [2] The fold-change in LacZ expression induced by Pristinamycin IA (4 µg/mL) was reported, although the exact numerical fold-change from this specific antibiotic is not separately listed in the provided figures/tables; it is grouped among other effective inducers like retapamulin, virginiamycin, chloramphenicol, and linezolid. [2] The activity of Pristinamycin IA (as well as other antibiotics like retapamulin, chloramphenicol, tetracycline, and virginiamycin) in activating the LRR attenuator was also tested in Escherichia coli using an RFP reporter system. The expression level of RFP increased when Pristinamycin IA was added, demonstrating that LRR (and thus the ribosome-stalling mechanism) functions in this Gram-negative bacterium as well. [2] |
| Cell Assay |
For antibiotic-induction experiments in B. thuringiensis, strains carrying the reporter plasmid (e.g., pB-PLR with lacZ) were grown overnight, diluted, and then treated with Pristinamycin IA (at 4 µg/mL final concentration) for a specified period (e.g., 6 hours). Cells were harvested, and β-galactosidase activity was measured to quantify gene expression. The assay involved cell disruption, incubation with ONPG substrate, and measurement of absorbance at 420 nm to calculate Miller units. [2]
For testing in E. coli, the strain BL21 harboring plasmid pET-LRR-RFP was cultured with or without Pristinamycin IA (4 µg/mL) at 37°C for 10 hours. Cells were collected, washed, and resuspended in PBS. Fluorescence intensity (excitation 584 nm, emission 607 nm) was measured and normalized to cell density (OD600) to determine RFP expression levels. [2] |
| References | |
| Additional Infomation |
Prilistatin IA is a cyclic condensate that (along with Prilistatin IIA) is a component of prilistatin. Prilistatin is an oral streptomycin antibiotic produced by Streptomyces pristinaespiralis. Prilistatin has bactericidal activity against Gram-positive bacteria, including methicillin-resistant Staphylococcus aureus (MRSA). It is an antibacterial agent, an antimicrobial agent, and a bacterial metabolite. Prilistatin IA has been reported in Streptomyces pristinaespiralis, and relevant data are available. Prilistatin IA is a specific group B streptomycin antibiotic produced by Streptomyces graminofaciens and other bacteria. Prilistatin IA is a ribosome-targeting antibiotic. [2]
Prilistatin IA is one of several antibiotics that can induce transient ribosome arrest (others include methylparine, virginiamycin, chloramphenicol, and linezolid). It causes a conformational change in LRR attenuating RNA, transforming it from a terminator structure to an antiterminator structure, thereby upregulating the expression of downstream genes. [2] This study focuses on the use of prilistatin IA as an inducer of synthetic biology tools (LRR attenuators) to control gene expression in a variety of bacterial hosts, including Bacillus thuringiensis, Bacillus subtilis, Bacillus cereus, Bacillus amyloliquefaciens, and Escherichia coli. [2] The concentration used for induction in Bacillus thuringiensis was 4 µg/mL (4.614 µM). [2] |
| Molecular Formula |
C45H54N8O10
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|---|---|
| Molecular Weight |
866.957860000001
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| Exact Mass |
866.396
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| CAS # |
3131-03-1
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| Related CAS # |
Pristinamycin;270076-60-3
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| PubChem CID |
11136668
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| Appearance |
Light yellow to yellow solid powder
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| Density |
1.38g/cm3
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| Boiling Point |
1202.1ºC at 760mmHg
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| Flash Point |
680.8ºC
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| LogP |
2.132
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
12
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| Rotatable Bond Count |
7
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| Heavy Atom Count |
63
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| Complexity |
1700
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| Defined Atom Stereocenter Count |
7
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| InChi Key |
YGXCETJZBDTKRY-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C45H54N8O10/c1-6-31-42(59)52-22-11-14-32(52)43(60)51(5)34(24-27-16-18-29(19-17-27)50(3)4)44(61)53-23-20-30(54)25-33(53)39(56)49-37(28-12-8-7-9-13-28)45(62)63-26(2)36(40(57)47-31)48-41(58)38-35(55)15-10-21-46-38/h7-10,12-13,15-19,21,26,31-34,36-37,55H,6,11,14,20,22-25H2,1-5H3,(H,47,57)(H,48,58)(H,49,56)
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| Chemical Name |
N-[3-[[4-(dimethylamino)phenyl]methyl]-12-ethyl-4,16-dimethyl-2,5,11,14,18,21,24-heptaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentazatricyclo[20.4.0.06,10]hexacosan-15-yl]-3-hydroxypyridine-2-carboxamide
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| Synonyms |
Mikamycin B; Mikamycin IA
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~33.33 mg/mL (~38.44 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 3 mg/mL (3.46 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 30.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 3 mg/mL (3.46 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 30.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 3 mg/mL (3.46 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.1535 mL | 5.7673 mL | 11.5346 mL | |
| 5 mM | 0.2307 mL | 1.1535 mL | 2.3069 mL | |
| 10 mM | 0.1153 mL | 0.5767 mL | 1.1535 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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