Meclocycline sulfosalicylate
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| Category | Antibiotics |
| Catalog number | BBF-03938 |
| CAS | 73816-42-9 |
| Molecular Weight | 695.05 |
| Molecular Formula | C29H27ClN2O14S |
| Purity | >98% by HPLC |
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Description
Mecycline sulfosalicylate is a kind of tetracycline antibiotic, which shows broad-spectrum antibacterial and protozoal activity by combining 30S and 50S ribosomal subunits, preventing protein synthesis.
Specification
| Synonyms | Mecloderm; Meclan; Meclutin |
| Storage | Store at -20°C |
| IUPAC Name | (4S,4aR,5S,5aR,12aR)-7-chloro-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methylidene-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide;2-hydroxy-5-sulfobenzoic acid |
| Canonical SMILES | CN(C)C1C2C(C3C(=C)C4=C(C=CC(=C4C(=C3C(=O)C2(C(=C(C1=O)C(=O)N)O)O)O)O)Cl)O.C1=CC(=C(C=C1S(=O)(=O)O)C(=O)O)O |
| InChI | InChI=1S/C22H21ClN2O8.C7H6O6S/c1-6-9-7(23)4-5-8(26)11(9)16(27)12-10(6)17(28)14-15(25(2)3)18(29)13(21(24)32)20(31)22(14,33)19(12)30;8-6-2-1-4(14(11,12)13)3-5(6)7(9)10/h4-5,10,14-15,17,26-28,31,33H,1H2,2-3H3,(H2,24,32);1-3,8H,(H,9,10)(H,11,12,13)/t10-,14-,15+,17+,22+;/m1./s1 |
| InChI Key | WVJKUGVVYXCLFV-CCHMMTNSSA-N |
| Source | Semi-synthetic |
Properties
| Appearance | Yellow to Orange Solid |
| Boiling Point | 716.4°C at 760 mmHg |
| Solubility | Soluble in ethanol, methanol, DMF, DMSO; Good water solubility. |
Reference Reading
1. [Effect of propyl gallate on the antibacterial activity of meclocycline sulfosalicylate]
A Retico, A Torosantucci, V Strippoli, N Simonetti Farmaco Sci . 1981 Sep;36(9):817-26.
Propyl gallate shows little antibacterial activity however it markedly potentiates the activity of meclocycline against Pseudomonas, Proteus, Serratia, Escherichia coli and Klebsiella strains. The potentiating effect of propyl gallate is seen especially with resistant strains whereas sensitive strains of Salmonella do not manifest a potentiating effect on meclocycline by propyl gallate. The mechanism of action of propyl gallate is discussed.
2. 13C-NMR spectroscopy of three tetracycline antibiotics: minocycline hydrochloride, meclocycline, and rolitetracycline
L G Wayland, J A Melin, E P Mazzola J Pharm Sci . 1980 Feb;69(2):229-30. doi: 10.1002/jps.2600690236.
13C-NMR data and spectral assignments are presented for tetracycline antibiotics minocycline hydrochloride, meclocycline, and rolitetracycline.
3. Tetracyclines as Inhibitors of Pre-microRNA Maturation: A Disconnection between RNA Binding and Inhibition
Tanpreet Kaur, Amanda L Garner, Jorge Sandoval, Arya Menon, Daniel A Lorenz, Erin E Gallagher, Samuel A Kerk ACS Med Chem Lett . 2019 Apr 22;10(5):816-821. doi: 10.1021/acsmedchemlett.9b00091.
In a high-throughput screening campaign, we recently discovered the rRNA-binding tetracyclines, methacycline and meclocycline, as inhibitors of Dicer-mediated processing of microRNAs. Herein, we describe our biophysical and biochemical characterization of these compounds. Interestingly, although direct, albeit weak, binding to the pre-microRNA hairpins was observed, the inhibitory activity of these compounds was not due to RNA binding. Through additional biochemical and chemical studies, we revealed that metal chelation likely plays a principle role in their mechanism of inhibition. By exploring the activity of other known RNA-binding scaffolds, we identified additional disconnections between direct RNA interaction and inhibition of Dicer processing. Thus, the results presented within provide a valuable case study in the complexities of targeting RNA with small molecules, particularly with weak binding and potentially promiscuous scaffolds.
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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 ╳
