Albocycline
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| Category | Antibiotics |
| Catalog number | BBF-00403 |
| CAS | 25129-91-3 |
| Molecular Weight | 308.41 |
| Molecular Formula | C18H28O4 |
| Purity | 95% |
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Description
It is produced by the strain of Streptomyces bruneoriseus and Str. roseocinereus. It was mainly resistant to gram-positive bacteria, and the MIC of S. aureus Sitajima strain was 1.56-3.12 ㎍/mL. The mice were not killed by intraperitoneal injection of 1000 mg/kg.
Specification
| Synonyms | Albocycline; Ingramycin; CHEMBL4128170; BDBM50274417; MFCD01674465; LS-16246; J-015824; Oxacyclotetradeca-3,6,9-trien-2-one,5-hydroxy-8-methoxy-5,9,13,14-tetramethyl-, (3E,5R,6E,8S,9E,13S,14R)- |
| IUPAC Name | (3E,5R,6E,8S,9E,13S,14R)-5-hydroxy-8-methoxy-5,9,13,14-tetramethyl-1-oxacyclotetradeca-3,6,9-trien-2-one |
| Canonical SMILES | CC1CCC=C(C(C=CC(C=CC(=O)OC1C)(C)O)OC)C |
| InChI | InChI=1S/C18H28O4/c1-13-7-6-8-14(2)16(21-5)9-11-18(4,20)12-10-17(19)22-15(13)3/h8-13,15-16,20H,6-7H2,1-5H3/b11-9+,12-10+,14-8+/t13-,15+,16-,18+/m0/s1 |
| InChI Key | BYWWNDLILWPPJP-REXWONOSSA-N |
Properties
| Appearance | Colorless Flake Crystals |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 465.7 °C at 760 mmHg |
| Melting Point | 83-84 °C |
| Density | 1.040 g/cm3 |
| Solubility | Soluble in Chloroform, Methanol |
Reference Reading
1. Staphylococcus aureus resistance to albocycline can be achieved by mutations that alter cellular NAD/PH pools
Tyler Scherzi, Elizabeth A D'Ambrosio, Samer S Daher, Catherine L Grimes, Paul M Dunman, Rodrigo B Andrade Bioorg Med Chem. 2021 Feb 15;32:115995. doi: 10.1016/j.bmc.2021.115995. Epub 2021 Jan 7.
Small molecule target identification is a critical step in modern antibacterial drug discovery, particularly against multi-drug resistant pathogens. Albocycline (ALB) is a macrolactone natural product with potent activity against methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant S. aureus (VRSA) whose mechanism of action has been elusive to date. Herein, we report biochemical and genomic studies that reveal ALB does not target bacterial peptidoglycan biosynthesis or the ribosome; rather, it appears to modulate NADPH ratios and upregulate redox sensing in the cell consistent with previous studies at Upjohn. Owing to the complexity inherent in biological pathways, further genomic assays are needed to identify the true molecular target(s) of albocycline.
2. Synthesis and biological evaluation of semi-synthetic albocycline analogs
Samer S Daher, Kevin P Franklin, Tyler Scherzi, Paul M Dunman, Rodrigo B Andrade Bioorg Med Chem Lett. 2020 Nov 1;30(21):127509. doi: 10.1016/j.bmcl.2020.127509. Epub 2020 Aug 19.
Albocycline (ALB) is a unique macrolactone natural product with potent, narrow-spectrum activity against methicillin-resistant Staphylococcus aureus (MRSA), vancomycin-intermediate (VISA), and vancomycin-resistant S. aureus (VRSA) strains (MIC = 0.5-1.0 μg/mL). Described herein is the synthesis and evaluation of a novel series analogs derived from albocycline by functionalization at three specific sites: the C2-C3 enone, the tertiary carbinol at C4, and the allylic C16 methyl group. Exploration of the structure-activity relationships (SAR) by means of minimum inhibitory concentration assays (MICs) revealed that C4 ester analog 6 was twice as potent as ALB, which represents a class of lead compound that can be further studied to address multi-drug resistant pathogens.
3. Albocycline-type Macrolides with Antibacterial Activities from Streptomyces sp. 4205
Cheng-Zhen Gu, Sheng-Hao Yuan, Jing Lü, Yi-Jun Qiao, Yuan-Yuan Song, Mohammed Esmail Abdalla Elzaki, Chong-Ren Yang, Ying-Jun Zhang, Ren-Sen Zeng Chem Biodivers. 2019 Jan;16(1):e1800344. doi: 10.1002/cbdv.201800344. Epub 2018 Dec 17.
The actinomycete genus Streptomyces is characterized by producing bioactive secondary metabolites, including antibiotics. In this study, chemical and biological investigations were carried out on Streptomyces strain 4205 isolated from the paddy soil, leading to the identification and characterization of 10 albocycline-type macrolides, among which 4 compounds were new, namely albocyclines A-D (1-4). The structures of 1-10 were identified according to the 1D- and 2D-NMR spectroscopic data. Furthermore, compounds 1-10 were evaluated for antimicrobial activity. Compounds 5-7 displayed antimicrobial activities against Candidaalbicans ATCC 90028 with the same MIC value of 10.0 mg/mL and the IC50 values of 1.5, 1.0, and 1.0 mg/mL, respectively. Thus, the research on Streptomyces sp. is of vital significance for developing new antibiotic agents.
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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 ╳
