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Spiramycin

CAS# 8025-81-8

Spiramycin

2D Structure

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3D structure

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Spiramycin

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Chemical Properties of Spiramycin

Cas No. 8025-81-8 SDF Download SDF
PubChem ID 6419898 Appearance Powder
Formula C43H74N2O14 M.Wt 843.058
Type of Compound N/A Storage Desiccate at -20°C
Solubility DMSO : ≥ 100 mg/mL (118.62 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name 2-[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-6-[5-(4,5-dihydroxy-4,6-dimethyloxan-2-yl)oxy-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-10-[5-(dimethylamino)-6-methyloxan-2-yl]oxy-4-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-1-oxacyclohexadeca-11,13-dien-7-yl]acetaldehyde
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)OC4CCC(C(O4)C)N(C)C
Standard InChIKey ACTOXUHEUCPTEW-JMRHEKERSA-N
Standard InChI InChI=1S/C43H74N2O14/c1-24-21-29(19-20-46)39(59-42-37(49)36(45(9)10)38(27(4)56-42)58-35-23-43(6,51)41(50)28(5)55-35)40(52-11)31(47)22-33(48)53-25(2)15-13-12-14-16-32(24)57-34-18-17-30(44(7)8)26(3)54-34/h12-14,16,20,24-32,34-42,47,49-51H,15,17-19,21-23H2,1-11H3/b13-12+,16-14+/t24-,25-,26?,27?,28?,29+,30?,31-,32+,34?,35?,36?,37?,38?,39+,40+,41?,42?,43?/m1/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Spiramycin Dilution Calculator

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Preparing Stock Solutions of Spiramycin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.1862 mL 5.9308 mL 11.8616 mL 23.7232 mL 29.654 mL
5 mM 0.2372 mL 1.1862 mL 2.3723 mL 4.7446 mL 5.9308 mL
10 mM 0.1186 mL 0.5931 mL 1.1862 mL 2.3723 mL 2.9654 mL
50 mM 0.0237 mL 0.1186 mL 0.2372 mL 0.4745 mL 0.5931 mL
100 mM 0.0119 mL 0.0593 mL 0.1186 mL 0.2372 mL 0.2965 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Spiramycin

Spiramycin is a 16-membered ring macrolide (antibiotic).

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References on Spiramycin

iTRAQ-based quantitative proteomic analysis of Microcystis aeruginosa exposed to spiramycin at different nutrient levels.[Pubmed:28236765]

Aquat Toxicol. 2017 Apr;185:193-200.

Research on the combined effects of antibiotic contaminants and environmental factors in cyanobacteria is still limited. This study focused on the action and its mechanism of Spiramycin combined with changes in nitrogen and phosphorus level in Microcystis aeruginosa at environmentally relevant concentrations. Though photosynthetic activity was stimulated by Spiramycin at a high nutrient level, no significant correlation (p>0.05) was found between photosynthesis-related proteins and growth-related proteins, and the growth rate was inhibited by 200ngL(-1) of Spiramycin. At low nitrogen and low phosphorus levels, up-regulated photosynthesis-related proteins were closely correlated with (p<0.05) stress response-related, transcription-related and cell division-related proteins, which consequently led to stimulated growth of M. aeruginosa under Spiramycin exposure. Spiramycin exposure also regulated the production of microcystins (MCs) and the expression of two microcystin synthetases (mcyB and mcyC). The Spiramycin-induced protein secretion process and the up-regulation of ATP binding cassette transporters might contribute to the increased MC release. Enolase, superoxide dismutase, protein GrpE, DNA-directed RNA polymerase subunit alpha and serine protease were candidate target proteins of Spiramycin in M. aeruginosa under different nutrient conditions. Coexisting Spiramycin mitigated the threat of cyanobacteria to aquatic environments at a high nutrient level but aggravated cyanobacterial bloom at a low nitrogen level.

Influence of Al(3+) on the titer of spiramycin and effective components in fermentor.[Pubmed:28278108]

Prep Biochem Biotechnol. 2017 May 28;47(5):481-488.

Spiramycin is a multicomponent antibiotic, and different components have different antibacterial activities. In Streptomyces spiramyceticus 16-10-2, Spiramycin II and Spiramycin III (SPMII and SPMIII) are the main components, while Spiramycin I (SPMI) needs to be controlled below 12%. Based on this, the influences of Al(3+) on total Spiramycin titer and components were investigated in this work. Those experiments were mainly performed in 15 L fermentor and Al(3+) made a great improvement in Spiramycin titer. The optimal adding concentration and adding time of Al(3+) were 0.32 g/L at 12 hr. Under this condition, Spiramycin titer was increased by 19.51% compared with the control. Moreover, the percentage of SPMII and SPMIII was increased by 7.14%. At the same time, the time of mycelia autolysis was lengthened. In addition, the specific activities of acetyl-CoA synthetase, acetate kinase, acetylphosphotransferase, and acylating enzyme were much higher than those of control. The content of acetic acid and succinic acid was beyond 3 and 4.5 times than that of control, respectively.

Anaerobic biodegradation of spiramycin I and characterization of its new metabolites.[Pubmed:28095730]

Biosci Biotechnol Biochem. 2017 May;81(5):1051-1054.

Activated sludge was used to treat the wastewater containing Spiramycin I. Three new metabolites were isolated and identified, which produced by oxidation of C6-aldehyde, hydrolysis of C5-mycaminose-mycarose and macrolactone ring-open reaction of Spiramycin I in anaerobic digestion. And their antimicrobial activities were inactivated. Our results indicated that anaerobic biodegradation metabolites of Spiramycin I could not induce bacterial resistance in environment.

Description

Spiramycin (Rovamycin) is a macrolide antibiotic produced by Streptomyces ambofaciens with against bacteria and Toxoplasma gondii activities, and also has antiparasitic effect. Spiramycin is composed of a 16-member lactone ring, on which three sugars (mycaminose, forosamine, and mycarose) are attached.

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