Leucomycin V

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Leucomycin V
Category Antibiotics
Catalog number BBF-02650
CAS 22875-15-6
Molecular Weight 701.84
Molecular Formula C35H59NO13
Purity 97%

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Description

It is produced by the strain of Str. kitasatoensis. It's a macrolide antibiotic. It has strong anti-gram-positive bacterial effect, and also has an effect on spirochetes, rickettsium and Chlamydia. After the C3 position on the lactone ring in the structure is acetylated, the activity in vitro is reduced, but the activity in vivo is enhanced, and the toxicity is also reduced. The antibacterial activity of Leucomycin group A is stronger than group B. It has been used in clinical and the indications are the same as erythromycin.

Specification

Synonyms Selectomycin; Turimycin; Antibiotic A 6599; Antibiotic JA-6599; Stereomycine; 4''-Deacylturimycin H; Deacylleucomycin A1; Deisovaleryl leucomycin A1
IUPAC Name 2-[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-6-[(2S,3R,4R,5S,6R)-5-[(2S,4R,5S,6S)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-4,10-dihydroxy-5-methoxy-9,16-dimethyl-2-oxo-1-oxacyclohexadeca-11,13-dien-7-yl]acetaldehyde
Canonical SMILES CC1CC=CC=CC(C(CC(C(C(C(CC(=O)O1)O)OC)OC2C(C(C(C(O2)C)OC3CC(C(C(O3)C)O)(C)O)N(C)C)O)CC=O)C)O
InChI InChI=1S/C35H59NO13/c1-19-16-23(14-15-37)31(32(44-8)25(39)17-26(40)45-20(2)12-10-9-11-13-24(19)38)49-34-29(41)28(36(6)7)30(21(3)47-34)48-27-18-35(5,43)33(42)22(4)46-27/h9-11,13,15,19-25,27-34,38-39,41-43H,12,14,16-18H2,1-8H3/b10-9+,13-11+/t19-,20-,21-,22+,23+,24+,25-,27+,28-,29-,30-,31+,32+,33+,34+,35-/m1/s1
InChI Key XYJOGTQLTFNMQG-KJHBSLKPSA-N

Properties

Antibiotic Activity Spectrum Gram-positive bacteria; Mycoplasma
Boiling Point 851.7°C at 760 mmHg
Density 1.25 g/cm3
Solubility Soluble in Methanol, Chloroform

Reference Reading

1. Electrochemical study of spiramycin and its determination in pharmaceutical preparation
Rasha M Youssef, Hadir M Maher Drug Test Anal. 2010 Aug;2(8):392-6. doi: 10.1002/dta.137.
Spiramycin (SPY) is a medium-spectrum antibiotic with high effectiveness against Gram-positive bacteria. The voltammetric behaviour of spiramycin was studied using differential pulse polarography (DPP) and square wave polarography (SWP). The drug in Britton-Robinson buffer (pH 11.5) is reduced at - 1.45 V, giving rise to a well-defined cathodic peak using hanging mercury drop electrode (HMDE) versus Ag/AgCl electrode. This peak is attributed to the reduction of the aldehyde group. The results proved that the reduction of SPY is an irreversible diffusion-controlled process. The diffusion current-concentration relationship was shown to be rectilinear over the range of 20-80 and 0.8-80 µg ml(-1) using DPP and SWP modes, respectively, with detection limit of 8.5 µg ml(-1) (1.01 × 10(-5) M) and 0.46 µg ml(-1) (5.46 × 10(-7) M) for DPP and SWP modes, respectively. A mechanism is postulated for the reduction of SPY. The proposed techniques were successfully applied to the determination of the studied compound either in pure form or in its formulation.
2. Improved liquid chromatographic method for quality control of spiramycin using superficially porous particles
Qi Lin, Getu Kahsay, Tom de Waal, Peixi Zhu, Minh Tam, Roel Teughels, Wenhua Wang, Ann Van Schepdael, Erwin Adams J Pharm Biomed Anal. 2018 Feb 5;149:57-65. doi: 10.1016/j.jpba.2017.10.041. Epub 2017 Oct 31.
This article describes the development and validation of a liquid chromatographic method for spiramycin using a column with superficially porous particles. Gradient elution was applied and the mobile phase consisted of phosphate buffer (0.2M; pH 8.3) - H2O - acetonitrile in a ratio 10:60:30 (v/v/v) for mobile phase A and 10:30:60 (v/v/v) for mobile phase B. UV detection was performed at 232nm. Compared to previous methods, the analysis time was about two times faster and impurities were better separated. Furthermore, impurities which were present above 0.25% were characterized using liquid chromatography coupled with mass spectrometry (LC/MS).
3. Spiramycin adsorption behavior on activated bentonite, activated carbon and natural phosphate in aqueous solution
Yassine El Maataoui, Mohamadine El M'rabet, Abdelkrim Maaroufi, Abdelmalek Dahchour Environ Sci Pollut Res Int. 2019 Jun;26(16):15953-15972. doi: 10.1007/s11356-019-05021-4. Epub 2019 Apr 8.
Efficacy of activated bentonite, activated carbon, and natural phosphate under experimental conditions was tested as low-cost adsorbents for spiramycin antibiotic removal from aqueous solution. Equilibrium kinetic and isotherm adsorption process are well described by pseudo-second order and Langmuir isotherm models for activated bentonite and activated carbon, while natural phosphate follows pseudo-first order and Freundlich models, respectively. Obtained results revealed that activated bentonite has the highest adsorption capacity (260.3 mg/g) as compared to activated carbon (80.3 mg/g) and natural phosphate (1.7 mg/g). The adsorption capacity decreases for all adsorbents in the presence of NaCl. The adsorption processes are facilitated in the alkaline pH range for activated bentonite and activated carbon, whereas, for natural phosphate, the acidic pH range is favorable. They are involving ion exchange and hydrogen bond mechanisms as well as Van der Waals forces and also π interactions for activated carbon. Thermodynamic calculation shows that spiramycin adsorption is endothermic and spontaneous on all adsorbents. The activated bentonite reusability is more efficient by more than 95% in two-step desorption using NaOH and HCl eluents compared to activated carbon. Thus, activated bentonite is a promising adsorbent for spiramycin removal from aqueous solution.

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