Antibacterial; coccidiostat; feed additives

The cell wall is one major determinant of plant cell morphology, and is an attractive bioresource. Here, we report a novel strategy to modify plant cell wall property by small molecules. Lasalocid sodium (LS) was isolated by chemical screening to identify molecules that affect the cell morphology of tobacco BY-2 cells. LS treatment led to an increase in cell wall thickness, whilst the quantity and sugar composition of the cell wall remained unchanged in BY-2 cells. The chemical also disordered the cellular arrangement of hypocotyls of Arabidopsis plants, resulting in a decrease in hypocotyl length. LS treatment enhanced enzymatic saccharification efficiency in both BY-2 cells and Arabidopsis plants. Microarray analysis on Arabidopsis showed that exposure to LS upregulated type III peroxidase genes, of which some are involved in lignin biogenesis, and jasmonic acid response genes, and phloroglucinol staining supported the activation of lignification by the LS treatment. As jasmonic acid-mediated lignification is a typical reaction to cell wall damage, it is possible that LS induces cell wall loosening, which can trigger cell wall damage response. Thus, LS is a unique chemical for modification of cell wall and morphology through changes in cell wall architecture.[1]

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It is thought that monensin increases the efficiency of feed utilization by cattle by altering the rumen fermentation. We studied the effect of monensin and the related ionophore antibiotic Lasalocid sodium (Hoffman-LaRoche) on the growth of methanogenic and rumen saccharolytic bacteria in a complex medium containing rumen fluid. Ruminococcus albus, Ruminococcus flavefaciens, and Butyrivibrio fibrisolvens were inhibited by 2.5 mug of monensin or lasalocid per ml. Growth of Bacteroides succinogenes and Bacteroides ruminicola was delayed by 2.5 mug of monensin or lasalocid per ml. Populations of B. succinogenes and B. ruminicola that were resistant to 20 mug of either drug per ml were rapidly selected by growth in the presence of each drug at 5.0 mug/ml. Selenomonas ruminantium was insensitive to 40 mug of monensin or lasalocid per ml. Either antibiotic (10 mug/ml) inhibited Methanobacterium MOH, Methanobacterium formicicum, and Methanosarcina barkeri MS. Methanobacterium ruminantium PS was insensitive to 40 mug of monensin or 20 mug of lasalocid per ml. The methanogenic strain 442 was insensitive to 40 mug of monensin but sensitive to 10 mug of lasalocid per ml. The results suggest that monensin or lasalocid acts in the rumen by selecting for succinate-forming Bacteroides and for S. ruminantium, a propionate producer that decarboxylates succinate to propionate. The selection could lead to an increase in rumen propionate formation. Selection against H(2) and formate producers, e.g. R. albus, R. flavefaciens, and B. fibrisolvens, could lead to a depression of methane production in the rumen[2].

The oral LD50 for mice was 146 mg/kg. (Kirk-Osmer Encyclopedia of Chemical Technology, 3rd Edition, edited by M. Grayson and D. Eckroth, New York: John Wiley & Sons, 1978, Vol. 3, No. 47). The intraperitoneal LD50 for mice was 64 mg/kg. (Kirk-Osmer Encyclopedia of Chemical Technology, 3rd Edition, edited by M. Grayson and D. Eckroth, New York: John Wiley & Sons, 1978, Vol. 3, No. 47).

[1]. Sci Rep. 2016 Oct 3:6:34602. doi: 10.1038/srep34602.
[2]. Appl Environ Microbiol . 1979 Jul;38(1):72-7. doi: 10.1128/aem.38.1.72-77.1979.

Lasalocid is a polyether antibiotic used for the prevention and treatment of coccidiosis in poultry. It possesses multiple functions, including anticoccidiosis, action against bacterial metabolites, and ion carrier activity. It is a monohydroxybenzoic acid, β-hydroxy ketone, secondary alcohol, oxacyclopentane compound, monocarboxylic acid, oxacycloalkane compound, tertiary alcohol, and polyether antibiotic. It is the conjugate acid of lasalloxicillin (1-). Lasalocid is a drug with antibacterial and anticoccidioidal activity. It is produced by certain strains of the genus Streptomyces lasaliensis. There are reports and data regarding the presence of lasalloxicillin in Streptomyces. This cationic ion carrier antibiotic, extracted from Streptomyces lasaliensis, can, among other effects, block the flow of calcium ions in muscle fibers. It is used as an anticoccidial drug, particularly suitable for poultry. See also: Lasaloxine Sodium (in salt form); Bacitracin Zinc; Lasaloxine (ingredient); Banbemycin; Lasaloxine (ingredient)... See more...

C34H53NAO8

612.77

612.364

C, 66.64; H, 8.72; Na, 3.75; O, 20.89

25999-20-6

Lasalocid;25999-31-9

5360807

Typically exists as White to yellow solid at room temperature

1.119g/cm3

735.7ºC at 760mmHg

180ºC (dec.)(lit.)

224.8ºC

1.01E-22mmHg at 25°C

1.528

4.507

4

8

13

42

910

10

O=C([O-])C1=C(CC[C@@H](C)[C@H](O)[C@H](C)C([C@@H]([C@H]2O[C@@]([C@H]3CC[C@](O)(CC)[C@H](C)O3)(CC)C[C@@H]2C)CC)=O)C=CC(C)=C1O.[Na+]

BBMULGJBVDDDNI-OWKLGTHSSA-N

InChI=1S/C34H54O8/c1-9-25(31-21(6)18-34(11-3,42-31)26-16-17-33(40,10-2)23(8)41-26)30(37)22(7)28(35)19(4)12-14-24-15-13-20(5)29(36)27(24)32(38)39/h13,15,19,21-23,25-26,28,31,35-36,40H,9-12,14,16-18H2,1-8H3,(H,38,39)/t19-,21+,22+,23+,25+,26-,28+,31+,33-,34+/m1/s1

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-hydroxy-3-methylbenzoic acid

NSC-243046; NSC 243046; Lasalocid A sodium salt; 25999-20-6; Bovatec; Lasalocid A Sodium; Sodium lasalocid; Avatec; Lasalocid sodium salt; Lasalocid sodium

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: Please store this product in a sealed and protected environment, avoid exposure to moisture.

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

DMSO : ~100 mg/mL (~163.19 mM)

Solubility in Formulation 1: ≥ 2.5 mg/mL (4.08 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

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Solubility in Formulation 2: ≥ 2.5 mg/mL (4.08 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

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 (Please use freshly prepared in vivo formulations for optimal results.)