Tropolone
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| Category | Antibiotics |
| Catalog number | BBF-03897 |
| CAS | 533-75-5 |
| Molecular Weight | 122.12 |
| Molecular Formula | C7H6O2 |
| Purity | ≥ 99 % |
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Description
A bactericidal antibiotic composed of a seven membered aromatic ring.
Specification
| Synonyms | Purpurocatechol |
| Storage | Store at 2-8 ℃ |
| IUPAC Name | 2-hydroxycyclohepta-2,4,6-trien-1-one |
| Canonical SMILES | C1=CC=C(C(=O)C=C1)O |
| InChI | InChI=1S/C7H6O2/c8-6-4-2-1-3-5-7(6)9/h1-5H,(H,8,9) |
| InChI Key | MDYOLVRUBBJPFM-UHFFFAOYSA-N |
Properties
| Appearance | Off-white solid |
| Antibiotic Activity Spectrum | fungi |
| Boiling Point | 290.1±33.0 ℃ at 760 mmHg |
| Melting Point | 49-52 ℃ |
| Flash Point | >230°F |
| Density | 1.278 g/cm3 |
| Solubility | Soluble in Chloroform, Ethanol |
| LogP | 0.75240 |
Toxicity
| Toxicity | The acute oral toxicity LD50 in rats was 459 mg / kg (female) , 223 mg / kg (male) and (662 mg / kg, rat). The acute dermal toxicity LD(50) in rabbit was no less than 2000mg/kg. There was mild irritation to the eye of rabbits. LC50 in Japanese carp is 0.5mg / L (48h) . An improved test and hamster ovary test, done by Ames, showed no mutations had been caused. Japanese carp LC50 is 0.5mg / L (48h) |
Reference Reading
1.2-Hetaryl-1,3-tropolones based on five-membered nitrogen heterocycles: synthesis, structure and properties.
Sayapin YA1, Tupaeva IO2, Kolodina AA2, Gusakov EA2, Komissarov VN2, Dorogan IV2, Makarova NI2, Metelitsa AV2, Tkachev VV3, Aldoshin SM3, Minkin VI1. Beilstein J Org Chem. 2015 Nov 12;11:2179-88. doi: 10.3762/bjoc.11.236. eCollection 2015.
A series of derivatives of 2-hetaryl-1,3-tropolone (β-tropolone) was prepared by the acid-catalyzed reaction of 2-methylbenzoxazoles, 2-methylbenzothiazoles and 2,3,3-trimethylindoline with 3,4,5,6-tetrachloro-1,2-benzoquinone. The molecular structures of the three representative compounds were determined by X-ray crystallography. In crystal and (as shown by the DFT PBE0/6-311+G** calculations) in solution, 2-hetaryl-4,5,6,7-tetrachloro- and 2-hetaryl-5,6,7-trichloro-1,3-tropolones exist in the NH-tautomeric form with a strong resonance-assisted intramolecular N-H···O hydrogen bond. The mechanism of the formation of 1,3-tropolones in the reaction of methylene-active five-membered heterocycles with o-chloranil in acetic acid solution has been studied using density functional theory (DFT) methods. The reaction of 2-(2-benzoxa(thia)zolyl)-5,6,7-trichloro(4,5,6,7-tetrachloro)-1,3-tropolones with alcohols leads to the contraction of the seven-membered tropone ring with the formation of 2-(2-benzoxa(thia)zolyl)-6-alkoxycarbonylphenols.
2.Hinokitiol inhibits vasculogenic mimicry activity of breast cancer stem/progenitor cells through proteasome-mediated degradation of epidermal growth factor receptor.
Tu DG1, Yu Y2, Lee CH3, Kuo YL4, Lu YC5, Tu CW6, Chang WW7. Oncol Lett. 2016 Apr;11(4):2934-2940. Epub 2016 Mar 2.
Hinokitiol, alternatively known as β-thujaplicin, is a tropolone-associated natural compound with antimicrobial, anti-inflammatory and antitumor activity. Breast cancer stem/progenitor cells (BCSCs) are a subpopulation of breast cancer cells associated with tumor initiation, chemoresistance and metastatic behavior, and may be enriched by mammosphere cultivation. Previous studies have demonstrated that BCSCs exhibit vasculogenic mimicry (VM) activity via the epidermal growth factor receptor (EGFR) signaling pathway. The present study investigated the anti-VM activity of hinokitiol in BCSCs. At a concentration below the half maximal inhibitory concentration, hinokitiol inhibited VM formation of mammosphere cells derived from two human breast cancer cell lines. Hinokitiol was additionally indicated to downregulate EGFR protein expression in mammosphere-forming BCSCs without affecting the expression of messenger RNA. The protein stability of EGFR in BCSCs was also decreased by hinokitiol.
3.Discovery and characterization of natural tropolones as inhibitors of the antibacterial target CapF from Staphylococcus aureus.
Nakano K1, Chigira T2, Miyafusa T3,4, Nagatoishi S5, Caaveiro JM5, Tsumoto K1,2,3,5. Sci Rep. 2015 Oct 16;5:15337. doi: 10.1038/srep15337.
The rapid spread of antibiotic-resistance among pathogenic bacteria poses a serious risk for public health. The search for novel therapeutic strategies and antimicrobial compounds is needed to ameliorate this menace. The bifunctional metalloenzyme CapF is an antibacterial target produced by certain pathogenic bacteria essential in the biosynthetic route of capsular polysaccharide, a mucous layer on the surface of bacterium that facilitates immune evasion and infection. We report the first inhibitor of CapF from Staphylococcus aureus, which was identified by employing fragment-based methodologies. The hit compound 3-isopropenyl-tropolone inhibits the first reaction catalyzed by CapF, disrupting the synthesis of a key precursor of capsular polysaccharide. Isothermal titration calorimetry demonstrates that 3-isopropenyl-tropolone binds tightly (KD = 27 ± 7 μM) to the cupin domain of CapF. In addition, the crystal structure of the enzyme-inhibitor complex shows that the compound engages the essential Zn(2+) ion necessary for the first reaction catalyzed by the enzyme, explaining its inhibitory effect.
4.Indole-3-Acetic Acid Produced by Burkholderia heleia Acts as a Phenylacetic Acid Antagonist to Disrupt Tropolone Biosynthesis in Burkholderia plantarii.
Wang M1,2, Tachibana S1, Murai Y1,3, Li L1, Lau SY1, Cao M2, Zhu G2, Hashimoto M1, Hashidoko Y1. Sci Rep. 2016 Mar 3;6:22596. doi: 10.1038/srep22596.
Burkholderia heleia PAK1-2 is a potent biocontrol agent isolated from rice rhizosphere, as it prevents bacterial rice seedling blight disease caused by Burkholderia plantarii. Here, we isolated a non-antibacterial metabolite from the culture fluid of B. heleia PAK1-2 that was able to suppress B. plantarii virulence and subsequently identified as indole-3-acetic acid (IAA). IAA suppressed the production of tropolone in B. plantarii in a dose-dependent manner without any antibacterial and quorum quenching activity, suggesting that IAA inhibited steps of tropolone biosynthesis. Consistent with this, supplementing cultures of B. plantarii with either L-[ring-(2)H5]phenylalanine or [ring-(2)H2~5]phenylacetic acid revealed that phenylacetic acid (PAA), which is the dominant metabolite during the early growth stage, is a direct precursor of tropolone. Exposure of B. plantarii to IAA suppressed production of both PAA and tropolone. These data particularly showed that IAA produced by B.
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Bio Calculators
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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
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