Tridecaptin A
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| Category | Antibiotics |
| Catalog number | BBF-02715 |
| CAS | 67922-28-5 |
| Molecular Weight | 1550.79 |
| Molecular Formula | C73H115N17O20 |
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Description
It is an antibiotic with antimicrobial properties produced by the strain of Bacillus polymyxa AR-110.
Specification
| Synonyms | D-2,4-diaminobutanoylglycyl-Dseryl-D-tryptophyl-L-seryl-L-2,4-diaminobutanoyl-D-2,4-diaminobutanoyl-L-phenylalanyl-L-r-glutamyl-L-valyl-Dalloisoleucyl |
| IUPAC Name | (4S)-4-[[(2S)-2-[[(2R)-4-amino-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2R)-2-[[(2R)-2-[[2-[[(2R)-4-amino-2-[[(2R)-2-(3-hydroxynonanoylamino)-3-methylbutanoyl]amino]butanoyl]amino]acetyl]amino]-3-hydroxypropanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-3-hydroxypropanoyl]amino]butanoyl]amino]butanoyl]amino]-3-phenylpropanoyl]amino]-5-[[(2S)-1-[[(2R,3S)-1-[[(1S)-1-carboxyethyl]amino]-3-methyl-1-oxopentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-5-oxopentanoic acid |
| Canonical SMILES | CCCCCCC(CC(=O)NC(C(C)C)C(=O)NC(CCN)C(=O)NCC(=O)NC(CO)C(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)NC(CO)C(=O)NC(CCN)C(=O)NC(CCN)C(=O)NC(CC3=CC=CC=C3)C(=O)NC(CCC(=O)O)C(=O)NC(C(C)C)C(=O)NC(C(C)CC)C(=O)NC(C)C(=O)O)O |
| InChI | InChI=1S/C73H115N17O20/c1-9-11-12-16-21-45(93)34-56(94)88-59(39(3)4)70(106)84-49(26-29-74)62(98)78-36-57(95)80-54(37-91)68(104)86-53(33-44-35-77-47-23-18-17-22-46(44)47)67(103)87-55(38-92)69(105)83-50(27-30-75)63(99)82-51(28-31-76)64(100)85-52(32-43-19-14-13-15-20-43)66(102)81-48(24-25-58(96)97)65(101)89-60(40(5)6)71(107)90-61(41(7)10-2)72(108)79-42(8)73(109)110/h13-15,17-20,22-23,35,39-42,45,48-55,59-61,77,91-93H,9-12,16,21,24-34,36-38,74-76H2,1-8H3,(H,78,98)(H,79,108)(H,80,95)(H,81,102)(H,82,99)(H,83,105)(H,84,106)(H,85,100)(H,86,104)(H,87,103)(H,88,94)(H,89,101)(H,90,107)(H,96,97)(H,109,110)/t41-,42-,45?,48-,49+,50-,51+,52-,53+,54+,55-,59+,60-,61+/m0/s1 |
| InChI Key | QETFUGBMXLKUFY-RUKUHQBXSA-N |
Properties
| Melting Point | 192-197°C |
Reference Reading
1. A novel family of non-secreted tridecaptin lipopeptide produced by Paenibacillus elgii
Rosiane Andrade da Costa, Isadora Emanoela Pereira Costa Andrade, Otávio Henrique Bezerra Pinto, et al. Amino Acids. 2022 Nov;54(11):1477-1489. doi: 10.1007/s00726-022-03187-9. Epub 2022 Jul 21.
Bacteria from the genus Paenibacillus make a variety of antimicrobial compounds, including lipopeptides produced by a non-ribosomal synthesis mechanism (NRPS). In the present study, we show the genomic and phenotypical characterization of Paenibacillus elgii AC13 which makes three groups of small molecules: the antimicrobial pelgipeptins and two other families of peptides that have not been described in P. elgii. A family of lipopeptides with [M + H]+ 1664, 1678, 1702, and 1717 m/z was purified from the culture cell fraction. Partial characterization revealed that they are similar to tridecaptin from P. terrae. However, they present amino acid chain modifications in positions 3, 7, and 10. These new variants were named tridecaptin G1, G2, G3, and G4. Furthermore, a gene cluster was identified in P. elgii AC13 genome, revealing high similarity to the tridecaptin-NRPS gene cluster from P. terrae. Tridecaptin G1 and G2 showed in vitro antimicrobial activity against Escherichia coli, Klebsiella pneumonia (including a multidrug-resistant strain), Staphylococcus aureus, and Candida albicans. Tri G3 did not show antimicrobial activity against S. aureus and C. albicans at all tested concentrations. An intriguing feature of this family of lipopeptides is that it was only observed in the cell fraction of the P. elgii AC13 culture, which could be a result of the amino acid sequence modifications presented in these variants.
2. Tridecaptin M, a New Variant Discovered in Mud Bacterium, Shows Activity against Colistin- and Extremely Drug-Resistant Enterobacteriaceae
Manoj Jangra, Manpreet Kaur, Rushikesh Tambat, Rohit Rana, Sushil K Maurya, Neeraj Khatri, Abdul Ghafur, Hemraj Nandanwar Antimicrob Agents Chemother. 2019 May 24;63(6):e00338-19. doi: 10.1128/AAC.00338-19. Print 2019 Jun.
The World Health Organization has categorized the Gram-negative superbugs, which are inherently impervious to many antibiotics, as critical priority pathogens due to the lack of effective treatments. The breach in our last-resort antibiotic (i.e., colistin) by extensively drug-resistant and pan-drug-resistant Enterobacteriaceae strains demands the immediate development of new therapies. In the present study, we report the discovery of tridecaptin M, a new addition to the family, and its potential against colistin-resistant Enterobacteriaceae in vitro and in vivo Also, we performed mode-of-action studies using various fluorescent probes and studied the hemolytic activity and mammalian cytotoxicity in two cell lines. Tridecaptin M displayed strong antibacterial activity (MICs of 2 to 8 μg ml-1) against clinical strains of Klebsiella pneumoniae (which were resistant to colistin, carbapenems, third- and fourth-generation cephalosporins, fluoroquinolones, fosfomycin, and other antibiotics) and mcr-1-positive Escherichia coli strains. Unlike polymyxins, tridecaptin M did not permeabilize the outer membrane or cytoplasmic membrane. It blocked ATP synthesis in bacteria by dissipating the proton motive force. The compound exhibited negligible acquired resistance, low in vitro cytotoxicity and hemolytic activity, and no significant acute toxicity in mice. It also showed promising efficacy in a thigh infection model of colistin-resistant K. pneumoniae Altogether, these results demonstrate the future prospects of this class of antibiotics to address the unmet medical need to circumvent colistin resistance in extensively drug-resistant Enterobacteriaceae infections. The work also emphasizes the importance of natural products in our shrunken drug discovery pipeline.
3. A Chemical-Intervention Strategy To Circumvent Peptide Hydrolysis by d-Stereoselective Peptidases
Samantha J Bann, Ross D Ballantine, Conor E McCallion, Pei-Yuan Qian, Yong-Xin Li, Stephen A Cochrane J Med Chem. 2019 Nov 27;62(22):10466-10472. doi: 10.1021/acs.jmedchem.9b01078. Epub 2019 Nov 8.
d-Stereoselective peptidases that degrade nonribosomal peptides (NRPs) were recently discovered and could have serious implications for the future of NRPs as antibiotics. Herein, we report chemical modifications that can be used to impart resistance to the d-peptidases BogQ and TriF. New tridecaptin A analogues were synthesized that retain strong antimicrobial activity and have significantly enhanced d-peptidase stability. In vitro assays confirmed that synthetic analogues retain the ability to bind to their cellular receptor, peptidoglycan intermediate lipid II.
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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 ╳
