Pristinamycin IC
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| Category | Antibiotics |
| Catalog number | BBF-02062 |
| CAS | 28979-74-0 |
| Molecular Weight | 852.93 |
| Molecular Formula | C44H52N8O10 |
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Description
Pristinamycin IC is an ester peptide antibiotic produced by Str. pristinaespiralis 5647 (NRRL 2958). Activity against gram-positive bacteria.
Specification
| Synonyms | Vernamycin B gamma |
| IUPAC Name | N-[3-[[4-(dimethylamino)phenyl]methyl]-4,12,16-trimethyl-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 |
| Canonical SMILES | CC1C(C(=O)NC(C(=O)N2CCCC2C(=O)N(C(C(=O)N3CCC(=O)CC3C(=O)NC(C(=O)O1)C4=CC=CC=C4)CC5=CC=C(C=C5)N(C)C)C)C)NC(=O)C6=C(C=CC=N6)O |
| InChI | InChI=1S/C44H52N8O10/c1-25-41(58)51-21-10-13-31(51)42(59)50(5)33(23-27-15-17-29(18-16-27)49(3)4)43(60)52-22-19-30(53)24-32(52)38(55)48-36(28-11-7-6-8-12-28)44(61)62-26(2)35(39(56)46-25)47-40(57)37-34(54)14-9-20-45-37/h6-9,11-12,14-18,20,25-26,31-33,35-36,54H,10,13,19,21-24H2,1-5H3,(H,46,56)(H,47,57)(H,48,55) |
| InChI Key | BYRKDHSWMQLYJB-UHFFFAOYSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 1201.6°C at 760 mmHg |
| Melting Point | 198°C |
| Density | 1.4 g/cm3 |
| Solubility | Soluble in Chloroform, ethyl acetate, acetone |
Reference Reading
1. IMB-XMA0038, a new inhibitor targeting aspartate-semialdehyde dehydrogenase of Mycobacterium tuberculosis
Xiao Wang, Ruifang Yang, Sihan Liu, Yan Guan, Chunling Xiao, Chuanyou Li, Jianzhou Meng, Yu Pang, Yishuang Liu Emerg Microbes Infect. 2021 Dec;10(1):2291-2299. doi: 10.1080/22221751.2021.2006578.
The emergence of drug-resistant tuberculosis (TB) constitutes a major challenge to TB control programmes. There is an urgent need to develop effective anti-TB drugs with novel mechanisms of action. Aspartate-semialdehyde dehydrogenase (ASADH) is the second enzyme in the aspartate metabolic pathway. The absence of the pathway in humans and the absolute requirement of aspartate in bacteria make ASADH a highly attractive drug target. In this study, we used ASADH coupled with Escherichia coli type III aspartate kinase (LysC) to establish a high-throughput screening method to find new anti-TB inhibitors. IMB-XMA0038 was identified as an inhibitor of MtASADH with an IC50 value of 0.59 μg/mL through screening. The interaction between IMB-XMA0038 and MtASADH was confirmed by surface plasmon resonance (SPR) assay and molecular docking analysis. Furthermore, IMB-XMA0038 was found to inhibit various drug-resistant MTB strains potently with minimal inhibitory concentrations (MICs) of 0.25-0.5 μg/mL. The conditional mutant strain MTB::asadh cultured with different concentrations of inducer (10-5 or 10-1 μg/mL pristinamycin) resulted in a maximal 16 times difference in MICs. At the same time, IMB-XMA0038 showed low cytotoxicity in vitro and vivo. In mouse model, it encouragingly declined the MTB colony forming units (CFU) in lung by 1.67 log10 dosed at 25 mg/kg for 15 days. In conclusion, our data demonstrate that IMB-XMA0038 is a promising lead compound against drug-resistant tuberculosis.
2. Dual-regulated expression of C/EBP-alpha and BMP-2 enables differential differentiation of C2C12 cells into adipocytes and osteoblasts
Cornelia Fux, Barbara Mitta, Beat P Kramer, Martin Fussenegger Nucleic Acids Res. 2004 Jan 2;32(1):e1. doi: 10.1093/nar/gnh001.
CCAAT/enhancer-binding proteins (C/EBPs) as well as bone morphogenic proteins (BMPs) play essential roles in mammalian cell differentiation in shaping adipogenic and osteoblastic lineages in particular. Recent evidence suggested that adipocytes and osteoblasts share a common mesenchymal precursor cell phenotype. Yet, the molecular details underlying the decision of adipocyte versus osteoblast differentiation as well as the involvement of C/EBPs and BMPs remains elusive. We have engineered C2C12 cells for dual-regulated expression of human C/EBP-alpha and BMP-2 to enable independent transcription control of both differentiation factors using clinically licensed antibiotics of the streptogramin (pristinamycin) and tetracycline (tetracycline) classes. Differential as well as coordinated expression of C/EBP-alpha and BMP-2 revealed that (i) C/EBP-alpha may differentiate C2C12 myoblasts into adipocytes as well as osteoblasts, (ii) BMP-2 prevents myotube differentiation, (iii) is incompetent in differentiating C2C12 into osteoblasts and (iv) even decreases C/EBP-alpha's osteoblast-specific differentiation potential but (v) cooperates with C/EBP-alpha on adipocyte differentiation, (vi) osteoblast formation occurs at low C/EBP-alpha levels while adipocyte-specific differentiation requires maximum C/EBP-alpha expression and that (vii) BMP-2 may bias the C/EBP-alpha-mediated adipocyte versus osteoblast differentiation switch towards fat cell formation. Dual-regulated expression technology enabled precise insight into combinatorial effects of two key differentiation factors involved in adipocyte/osteoblast lineage control which could be implemented in rational reprogramming of multipotent cells into desired cell phenotypes tailored for gene therapy and tissue engineering.
3. [Drug interactions with colchicine, are the contraindications well respected? A descriptive study of prescriptions in Brittany based on data from the French National Health Data System]
Marion Girard de Courtilles, Frédéric Balusson, Claudine Queric, Stéphanie Bouric, Dominique Carlhant-Kowalski, Lucie-Marie Scailteux, Elisabeth Polard Therapie. 2020 Nov-Dec;75(6):675-679. doi: 10.1016/j.therap.2020.06.003. Epub 2020 Jun 20.
Although the French Health Authority "ANSM" widely informed healthcare professionals about the risk factors for colchicine overdose, its impact and suitable dosages, cases of potentially fatal preventable overdose continue to be reported in France. Using the French National Health Insurance of the Brittany area, we quantified the proportion of prescriptions presenting an absolute drug contraindication (CI) to colchicine (according to the ANSM Drug Interactions "Thesaurus") and its impact in terms of hospitalisation. Between 2013 and 2016, nearly 77,000 patients (mean age, 66±15 years) were reimbursed for at least one colchicine-based drug (Colchimax®, Colchicine Opocalcium®), representing nearly 205,000 prescriptions. General practitioners were the main prescribers (93%). Among the prescriptions, 0.5% had absolute IC with colchicine: in 51% of cases with pristinamycin, followed by azithromycin (15.6%), clarithromycin (15.2%) and roxithromycin (11.9%). In the 15 days following the simultaneous prescription of colchicine and a contraindicated drug, 53 hospital stays were recorded. However, using only the primary diagnosis of hospitalization was not sufficiently relevant to conclude that there was no potential overdose of colchicine. Over the study period, the Thesaurus contained inconsistencies that confused clinicians: mention of absolute IC with colchicine in the "macrolide" and "pristinamycin" sections but not in the sections of 'potent CYP inhibitors' or macrolide class molecules. Overall, very few prescriptions included absolute IC with colchicine. Regular training and information of healthcare professionals remains essential to limit the risk of colchicine overdose and to remind them of the potentially fatal consequences.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
