Polymyxin D2
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-02042 |
| CAS | 34167-45-8 |
| Molecular Weight | 1130.33 |
| Molecular Formula | C49H91N15O15 |
| Purity | >98% |
Online Inquiry
Description
Polymyxin D2 is a cyclic peptide antibiotic of Bacillus polymyxa. The effect of anti-gram-negative bacteria is greater than that of anti-gram-positive bacteria.
Specification
| Storage | Store at -20°C |
| IUPAC Name | N-[(2S)-4-amino-1-[[(2S,3R)-3-hydroxy-1-[[(2R)-3-hydroxy-1-oxo-1-[[(3S,6S,9S,12S,15R,18S,21S)-6,9,18-tris(2-aminoethyl)-3,12-bis[(1R)-1-hydroxyethyl]-15-(2-methylpropyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptazacyclotricos-21-yl]amino]propan-2-yl]amino]-1-oxobutan-2-yl]amino]-1-oxobutan-2-yl]-6-methylheptanamide |
| Canonical SMILES | CC(C)CCCCC(=O)NC(CCN)C(=O)NC(C(C)O)C(=O)NC(CO)C(=O)NC1CCNC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC1=O)CCN)CC(C)C)C(C)O)CCN)CCN)C(C)O |
| InChI | InChI=1S/C49H91N15O15/c1-24(2)10-8-9-11-36(69)55-29(12-17-50)43(73)63-39(28(7)68)49(79)61-35(23-65)46(76)58-33-16-21-54-47(77)37(26(5)66)62-44(74)32(15-20-53)57-40(70)31(14-19-52)59-48(78)38(27(6)67)64-45(75)34(22-25(3)4)60-41(71)30(13-18-51)56-42(33)72/h24-35,37-39,65-68H,8-23,50-53H2,1-7H3,(H,54,77)(H,55,69)(H,56,72)(H,57,70)(H,58,76)(H,59,78)(H,60,71)(H,61,79)(H,62,74)(H,63,73)(H,64,75)/t26-,27-,28-,29+,30+,31+,32+,33+,34-,35-,37+,38+,39+/m1/s1 |
| InChI Key | AMOWTOQDROFIIR-ALESKEBOSA-N |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Boiling Point | 1583.4±65.0°C at 760 mmHg |
| Melting Point | 228-230°C (dec.) |
| Density | 1.3±0.1 g/cm3 |
| Solubility | Soluble in DMSO |
Reference Reading
1. Mast cells partially contribute to mucosal adjuvanticity of surfactin in mice
Naoto Yoshino, Ryosuke Takeshita, Hanae Kawamura, Yutaka Sasaki, Masahiro Kagabu, Toru Sugiyama, Yasushi Muraki, Shigehiro Sato Immun Inflamm Dis. 2018 Mar;6(1):117-127. doi: 10.1002/iid3.204. Epub 2017 Nov 3.
Introduction: Surfactin (SF) is a cyclic lipopeptide that has potent mucosal adjuvant properties. However, immunological mechanisms of SF adjuvant action have not yet been elucidated. As some cyclic lipopeptides, such as polymyxin, can stimulate histamine release from mast cells, we hypothesized that mast cell activation is critical for SF adjuvanticity. Methods/results: We observed that following intranasal immunization with ovalbumin (OVA) plus SF, the titers of the OVA-specific antibody (Ab) in the mucosal secretions and plasma of mast cell-deficient mice were significantly lower than those in congenic normal mice, although OVA-specific Ab did not entirely disappear from mast cell-deficient mice. SF induced degranulation of mast cells and release of histamine in vitro. To investigate whether SF stimulated mast cells in vivo, we measured body temperature of mice immunized intranasally with OVA plus SF because histamine level affects body temperature. Following immunizations, body temperature of immunized congenic normal mice transiently decreased, whereas body temperature of mast cell-deficient mice did not change. Plasma levels of OVA-specific IgE Ab were not significantly different in mast cell-deficient and congenic normal mice. These findings suggest that SF directly affected mast cells in an IgE Ab-independent fashion. Furthermore, we analyzed the effects of SF on MC/9 mast cells cultured in vitro. MC/9 cells stimulated by SF released not only histamine but also leukotriene B4 and prostaglandin D2 . Moreover, SF up-regulated mRNA expression levels of Tnf, Ccr5, and Il4 genes in mast cells. These cytokines may play a facilitating role in OVA-specific immune responses in mice. Conclusion: Overall, our results showed that mast cell activation partially mediated SF adjuvanticity.
2. Synthesis and Bioactivity Investigation of the Individual Components of Cyclic Lipopeptide Antibiotics
A-Long Cui, Xin-Xin Hu, Yan Gao, Jie Jin, Hong Yi, Xiu-Kun Wang, Tong-Ying Nie, Yang Chen, Qi-Yang He, Hui-Fang Guo, Jian-Dong Jiang, Xue-Fu You, Zhuo-Rong Li J Med Chem. 2018 Mar 8;61(5):1845-1857. doi: 10.1021/acs.jmedchem.7b01367. Epub 2018 Feb 15.
In this paper, 26 natural polymyxin components and a new derivative S2 were synthesized, and their differences in efficacy and toxicity have been investigated. Almost all of the synthesized components showed strong activity against both susceptible and resistant strains of E. coli, K. pneumoniae, P. aeruginosa, and A. baumannii. The toxicities were obviously different between the components. Only some of the components were tested for toxicity in vivo. Compounds E2, E2-Val, A2, M2, D2, and S2 showed obviously lower renal cytotoxicity and acute toxicity than polymyxins B and E. The in vivo nephrotoxicity of E2, M2, and S2 was similar to that of polymyxin E. Compound S2, with four positive charges, was especially interesting as it possessed both increased efficacy and decreased toxicity. The SAR and toxicity studies indicated that further structural modification could concentrate on polymyxin S. The results also indicated that S2 could be a new drug candidate.
3. Synergistic antimicrobial activity of a novel cationic micelle L/D2 and imipenem against multidrug-resistant Acinetobacter baumannii
Guansheng Zhong, Yingjiao Zhang, Kun Yu, Li Wen, Hongjiang Lu, Yang Zheng Front Biosci (Landmark Ed). 2021 Nov 30;26(11):977-987. doi: 10.52586/5002.
Background: The multidrug-resistant (MDR) Acinetobacter baumannii (A. baumannii) has become one of the most important pathogens of nosocomial infection due to widespread use of broad spectrum antimicrobial drugs and immunosuppressor therapy. As polymyxins resistance emerges, developing novel effective antibacterial agents capable of overcoming multidrug resistance is urgently needed. Methods: In this study, biodegradable triblock copolymers of polyethylene glycol (PEG), guanidinium-functionalized polycarbonate and polylactide, PEG-PGC20-PLLA20 (L2) and PEG-PGC20-PDLA20 (D2), were utilized as antibacterial agents. Results: The copolymers self-assemble into micellar nanoparticles (L/D2), and exhibit broad-spectrum antibacterial activity against 20 clinically isolated multidrug-resistant A. baumannii strains. L/D2 had more rapid killing kinetics than conventional antibiotics imipenem and ceftazidime, and exhibited potent anti-biofilm activity. Repeated use of L/D2 did not induce drug resistance. From scanning electron microscopy and nucleic acid release analyses, L/D2 showed membrane-lytic mechanism. We also demonstrated that L/D2 was synergistically active with imipenem against MDR A. baumannii strains. Additionally, strong synergistic antibacterial activity was also observed for the combined use of L/D2 and imipenem in a MDR A. baumannii abdominal infection mouse model. Conclusions: Therefore, the combination of L/D2 and imipenem might be an alternative option for the prevention of nosocomial infection caused by A. baumannii.
Recommended Products
| BBF-01826 | Deoxymannojirimycin | Inquiry |
| BBF-00764 | Cerebroside C | Inquiry |
| BBF-02642 | Lactonamycin | Inquiry |
| BBF-01829 | Deoxynojirimycin | Inquiry |
| BBF-03753 | Baicalin | Inquiry |
| BBF-00677 | 3-Amino-3-deoxy-D-glucose | Inquiry |
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 ╳
