TL-119
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| Category | Antibiotics |
| Catalog number | BBF-02514 |
| CAS | 55599-68-3 |
| Molecular Weight | 803.9 |
| Molecular Formula | C42H57N7O9 |
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Description
TL-119 is an antibiotic isolated from Bacillus subtilis. It is effective against gram-positive bacteria and fungi.
Specification
| Synonyms | Antibiotic TL-119; TL 119 |
| IUPAC Name | (2R)-2-[[(2R)-2-acetamido-3-phenylpropanoyl]amino]-N-[(2S)-1-[[(3Z,6S,9S,12S,13R)-3-ethylidene-6,13-dimethyl-2,5,8,11-tetraoxo-9-propan-2-yl-1-oxa-4,7,10-triazacyclotridec-12-yl]amino]-1-oxo-3-phenylpropan-2-yl]-4-methylpentanamide |
| Canonical SMILES | CC=C1C(=O)OC(C(C(=O)NC(C(=O)NC(C(=O)N1)C)C(C)C)NC(=O)C(CC2=CC=CC=C2)NC(=O)C(CC(C)C)NC(=O)C(CC3=CC=CC=C3)NC(=O)C)C |
| InChI | InChI=1S/C42H57N7O9/c1-9-30-42(57)58-26(7)35(41(56)48-34(24(4)5)40(55)43-25(6)36(51)45-30)49-39(54)33(22-29-18-14-11-15-19-29)47-37(52)31(20-23(2)3)46-38(53)32(44-27(8)50)21-28-16-12-10-13-17-28/h9-19,23-26,31-35H,20-22H2,1-8H3,(H,43,55)(H,44,50)(H,45,51)(H,46,53)(H,47,52)(H,48,56)(H,49,54)/b30-9-/t25-,26+,31+,32+,33-,34-,35-/m0/s1 |
| InChI Key | SGGJJTTZBRPIKP-GGQKFFLHSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; fungi |
| Boiling Point | 1231°C at 760 mmHg |
| Melting Point | >332°C (dec.) |
| Density | 1.24 g/cm3 |
Reference Reading
1. Synthesis and reactivity of dimeric Ar'TlTlAr' and trimeric (Ar"T1)3 (Ar', Ar" = bulky terphenyl group) thallium(I) derivatives: Tl(I)-Tl(I) bonding in species ligated by monodentate ligands
Robert J Wright, Andrew D Phillips, Shirley Hino, Philip P Power J Am Chem Soc. 2005 Apr 6;127(13):4794-9. doi: 10.1021/ja0432259.
The synthesis and characterization of three new organothallium(I) compounds are reported. Reaction of (Ar'Li)(2) (Ar' = C(6)H(3)-2,6-(C(6)H(3)-2,6-Pr(i)(2))(2)) and Ar"Li (Ar" = C(6)H(3)-2,6-(C(6)H(3)-2,6-Me(2))(2)) with TlCl in Et(2)O afforded (Ar'Tl)(2) (1) and (Ar' 'Tl)(3) (2). The "dithallene" 1 is the heaviest group 13 dimetallene and features a planar, trans-bent structure with Ar'Tl-Tl = 119.74(14) degrees and Tl-Tl = 3.0936(8) A. Compound 2 is the first structurally characterized neutral, three-membered ring species of formula c-(MR)(3) (M = Al-Tl; R = organo group). The Tl(3) ring has Tl-Tl distances in the range ca. 3.21-3.37 A as well as pyramidal Tl geometries. The Tl-Tl bonds in 1 and 2 are outside the range (2.88-2.97 A) of Tl-Tl single bonds in R(2)TlTlR(2) compounds. The weak Tl-Tl bonding in 1 and 2 leads to their dissociation into Ar'Tl and Ar' 'Tl monomers in hexane. The Ar'Tl monomer behaves as a Lewis base and readily forms a 1:1 donor-acceptor complex with B(C(6)F(5))(3) to give Ar'TlB(C(6)F(5))(3), 3. Adduct 3 features an almost linear thallium C(ipso)-Tl-B angle of 174.358(7) degrees and a Tl-B distance of 2.311(2) A, which indicates strong association. Treatment of 1 with a variety of reagents resulted in no reactions. The lower reactivity of 1 is in accord with the reluctance of Tl(I) to undergo oxidation to Tl(III) due to the unreactive character of the 6s(2) electrons.
2. Purification and characterisation of a novel antistaphylococcal peptide (ASP-1) from Bacillus sp. URID 12.1
Ajay Ghosh Chalasani, Utpal Roy, Sushma Nema Int J Antimicrob Agents. 2018 Jan;51(1):89-97. doi: 10.1016/j.ijantimicag.2017.08.030. Epub 2017 Sep 5.
A strong antistaphylococcal peptide (ASP-1) from Bacillus subtilis URID 12.1 strain that is active against cefoxitin- and methicillin-resistant Staphylococcus aureus clinical isolates was purified to homogeneity by solvent extraction, silica gel-based adsorption chromatography and reversed-phase high-performance liquid chromatography. The peptide sequence of ASP-1 as determined by MALDI-TOF/MS and ESI-FTICR-MS was acetylated Phe-Thr-Ala-Val-Dhb-Phe-Ile/Leu. The peptide was further analysed by alkaline hydrolysis, ESI-Q-TOF-MS and an ion mobility assay, which detected the presence of a lactone ring in the intact peptide and a cyclic nature, subsequently revealing the linearised peptide sequence as acPhe-Leu-Phe-Thr-Val-Ala-Dhb. Based on the molecular mass (804.5 Da), peptide sequence and amino acid composition, ASP-1 was identified as a lactone ring-containing peptide similar to TL-119, a poorly studied cyclic depsipeptide. Circular dichroism spectroscopy revealed its predominantly random structure in aqueous solution and its β-sheet conformation in methanol. Minimum inhibitory concentrations (MICs) of the purified peptide against S. aureus and methicillin-resistant S. aureus (MRSA) ranged from 2 µg/mL to 64 µg/mL. At sub-MICs and 1× MIC, ASP-1 showed a strong antibiofilm characteristic. ASP-1 at a concentration of 128 µg/mL did not show haemolytic activity, and no cytotoxicity was observed against hepatic carcinoma and breast carcinoma cell lines at the same concentration. Peptide ASP-1 with anti-MRSA and antibiofilm abilities and non-haemolytic and non-cytotoxic properties has not been reported previously. These findings suggest that it may serve as a lead molecule for developing alternative topical antibacterial agents.
3. Marine Depsipeptide Nobilamide I Inhibits Cancer Cell Motility and Tumorigenicity via Suppressing Epithelial-Mesenchymal Transition and MMP2/9 Expression
Tu Cam Le, Sultan Pulat, Jihye Lee, Geum Jin Kim, Haerin Kim, Eun-Young Lee, Prima F Hillman, Hyukjae Choi, Inho Yang, Dong-Chan Oh, Hangun Kim, Sang-Jip Nam, William Fenical ACS Omega. 2022 Jan 3;7(2):1722-1732. doi: 10.1021/acsomega.1c04520. eCollection 2022 Jan 18.
A cyclic depsipeptide, nobilamide I (1), along with the known peptide A-3302-B/TL-119 (2), was isolated from the saline cultivation of the marine-derived bacterium Saccharomonospora sp., strain CNQ-490. The planar structure of 1 was elucidated by interpretation of 1D and 2D NMR and MS spectroscopic data. The absolute configurations of the amino acids in 1 were assigned by using the C3 Marfey's analysis and comparing them with those of 2 based on their biosynthetic pathways. Nobilamide I (1) decreased cell motility by inhibiting epithelial-mesenchymal transition markers in A549 (lung cancer), AGS (gastric cancer), and Caco2 (colorectal cancer) cell lines. In addition, 1 modulated the expression of the matrix metalloproteinase (MMP) family (MMP2 and MMP9) in the three cell lines.
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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 ╳
