Lasalocid B

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Category Antibiotics
Catalog number BBF-02238
CAS 55051-86-0
Molecular Weight 604.81
Molecular Formula C35H56O8

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Description

It is produced by the strain of Str. lasaliensis. It has anti-gram-positive bacteria and protozoa activity. It is added to feed to prevent coccidiosis in chickens.

Specification

Synonyms 3-Ethyl-6-[(3R,4S,5S,7R)-7-[(2S,3S,5S)-5-ethyl-5-[(2R,5R)-tetrahydro-5-ethyl-5-hydroxy-6α-methyl-2H-pyran-2-yl]tetrahydro-3-methylfuran-2-yl]-4-hydroxy-3,5-dimethyl-6-oxononyl]-2-hydroxybenzoic acid
IUPAC Name 3-ethyl-6-[(3R,4S,5S,7R)-7-[(2S,3S,5S)-5-ethyl-5-[(2R,5R,6S)-5-ethyl-5-hydroxy-6-methyloxan-2-yl]-3-methyloxolan-2-yl]-4-hydroxy-3,5-dimethyl-6-oxononyl]-2-hydroxybenzoic acid
Canonical SMILES CCC1=C(C(=C(C=C1)CCC(C)C(C(C)C(=O)C(CC)C2C(CC(O2)(CC)C3CCC(C(O3)C)(CC)O)C)O)C(=O)O)O
InChI InChI=1S/C35H56O8/c1-9-24-15-16-25(28(31(24)38)33(39)40)14-13-20(5)29(36)22(7)30(37)26(10-2)32-21(6)19-35(12-4,43-32)27-17-18-34(41,11-3)23(8)42-27/h15-16,20-23,26-27,29,32,36,38,41H,9-14,17-19H2,1-8H3,(H,39,40)/t20-,21+,22+,23+,26+,27-,29+,32+,34-,35+/m1/s1
InChI Key BBZNPMRJIHRUOP-REKREQLFSA-N

Properties

Appearance Colorless Crystal
Antibiotic Activity Spectrum Gram-positive bacteria; Parasites
Melting Point 168-174°C
Solubility Soluble in Chloroform

Reference Reading

1. Revisiting Old Ionophore Lasalocid as a Novel Inhibitor of Multiple Toxins
Nassim Mahtal, Yu Wu, Jean-Christophe Cintrat, Julien Barbier, Emmanuel Lemichez, Daniel Gillet Toxins (Basel). 2020 Jan 1;12(1):26. doi: 10.3390/toxins12010026.
The ionophore lasalocid is widely used as a veterinary drug against coccidiosis. We found recently that lasalocid protects cells from two unrelated bacterial toxins, the cytotoxic necrotizing factor-1 (CNF1) from Escherichia. coli and diphtheria toxin. We evaluated lasalocid's capacity to protect cells against other toxins of medical interest comprising toxin B from Clostridium difficile, Shiga-like toxin 1 from enterohemorrhagic E. coli and exotoxin A from Pseudomonas aeruginosa. We further characterized the impact of lasalocid on the endolysosomal and the retrograde pathways and organelle integrity, especially the Golgi apparatus. We found that lasalocid protects cells from all toxins tested and impairs the drop of vesicular pH along the trafficking pathways that are required for toxin sorting and translocation to the cytoplasm. Lasalocid also has an impact on the cellular distribution of GOLPH4 and GOLPH2 Golgi markers. Other intracellular trafficking compartments positive for EEA1 and Rab9A display a modified cellular pattern. In conclusion, lasalocid protects cells from multiple deadly bacterial toxins by corrupting vesicular trafficking and Golgi stack homeostasis.
2. Efficacy of treatments with toltrazuril 7.5% and lasalocid sodium in sheep naturally infected with Eimeria spp
Fernando de Souza Rodrigues, Luiz Eduardo Roland Tavares, Fernando Paiva Rev Bras Parasitol Vet. 2016 Jul-Sep;25(3):293-8. doi: 10.1590/S1984-29612016048. Epub 2016 Aug 25.
The objective of this study was to evaluate the efficacy of an experimental formulation of toltrazuril 7.5% + Trimix™ on a naturally acquired infection of Eimeria spp. in suckling lambs kept on pasture and, in another trial, evaluate the comparative efficacy between lasalocid and toltrazuril 7.5% + Trimix™ in newly weaned sheep under feedlot conditions that had been naturally infected with Eimeria spp. In the first experiment, 30 suckling lambs were divided into two groups: A - treated with toltrazuril 7.5% + Trimix™ and B- control. In experiment 2, 30 weaned sheep were divided into three groups: I - treated with toltrazuril 7.5% + Trimix™, II - treated with lasalocid and III - control. Treatment group A showed an efficacy of 90, 99.4 and 87.3% on days 5, 10 and 20, respectively. Treatment group I had an efficacy of 98.2, 92.6 and 94.5%, while group II had an efficacy of 72.7, 81.6 and 95.9% on days 7, 21 and 42, respectively. Eight Eimeria species were identified; E. ovinoidalis was the most common. Treatment with the toltrazuril 7.5% +Trimix ™ formulation was effective against Eimeria spp. in suckling lambs in field conditions and lambs weaned in under feedlot conditions.
3. Polyether ionophores residues in Minas Frescal cheese by UHPLC-MS/MS
Felipe R N Silva, Andrea R Bortolotte, Patricia A de C Braga, Felix G R Reyes, Adriana P Arisseto-Bragotto Food Addit Contam Part B Surveill. 2020 Jun;13(2):130-138. doi: 10.1080/19393210.2020.1739149. Epub 2020 Mar 24.
An analytical method was developed and validated for the determination of three polyether ionophores (monensin, lasalocid, and salinomycin) in 60 samples of Brazilian Minas Frescal cheese by UHPLC-MS/MS. Linearity ranged from 1 to 8 μg kg-1 for monensin and salinomycin, and from 0.50 to 4 μg kg-1 for lasalocid. Limits of detection and quantitation were 0.50 μg kg-1 and 1 μg kg-1, respectively, for both monensin and salinomycin, and 0.25 μg kg-1 and 0.50 μg kg-1, respectively, for lasalocid. Recoveries were between 69% and 84% with coefficients of variation up to 16.28% for repeatability and 13.79% for intermediate precision. A total of 60 samples of Minas Frescal cheese were analysed and only monensin residues were found. Monensin was detected in 55% of the samples and quantified in 5 of them at mean levels varying from 1.00 to 1.73 μg kg-1. The proposed method demonstrated the suitability for monitoring these substances in cheese.

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