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100mg |
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Purity: ≥98%
Spiramycin (HSDB7027; HSDB-7027; Rovamycin) is naturally occurring and clinically important 16-member macrolide antibiotic isolated from Streptomyces ambofaciens. It has activity against bacteria and Toxoplasma gondii, and also has antiparasitic effect. Spiramycin is composed of a 16-member lactone ring, on which three sugars (mycaminose, forosamine, and mycarose) are attached. Biosynthetic studies have established that the earliest lactonic intermediate in spiramycin biosynthesis, the macrolactone platenolide I, is synthesized by a type I modular polyketide synthase (PKS). Platenolide I then undergoes a series of post-PKS tailoring reactions yielding the final products, spiramycins I, II, and III.
Targets |
Macrolide;Toxoplasma
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ln Vitro |
Treatment with spiramycin (24 hours; 1-1000 μM; T. gondii-infected HeLa cells and HeLa cells) decreases the cytotoxicity and exhibits anti-Toxoplasma gondii activity, with IC50 values of 189 μM for HeLa cells and 262 μM for T. gondii-infected HeLa cells[3].
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ln Vivo |
Treatment with spiramycin (100 mg/kg; intraperitoneal injection; daily; for 4 days; female KM mice) decreases tachyzoites, hepatotoxicity, and greatly increases antioxidative effects. Treatment with piramycin also lessens the liver's granulomatous inflammation[3].
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Cell Assay |
Cell Line: T. gondii infected HeLa cells and HeLa cells
Concentration: 1-1000 μM Incubation Time: 24 hours Result: Reduced the cytotoxicity. |
Animal Protocol |
Animal Model: 36 female KM mice with T.gondii[3]
Dosage: 100 mg/kg Administration: Intraperitoneal injection; every day; for 4 days Result: Tachyzoites were considerably fewer in number. decreased hepatotoxicity and markedly increased antioxidative benefits. Formation of cysts and granulomas was inhibited. |
References |
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Molecular Formula |
C43H74N2O14
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Molecular Weight |
843.0527
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Exact Mass |
842.51
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Elemental Analysis |
C, 61.26; H, 8.85; N, 3.32; O, 26.57
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CAS # |
8025-81-8
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Related CAS # |
8025-81-8;24916-52-7 (III);67724-08-7 (Embonate);68880-55-7 (adipate);
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Appearance |
Solid powder
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SMILES |
O=CC[C@@H]1[C@H](O[C@@H]2O[C@H](C)[C@@H](O[C@@H]3O[C@@H](C)[C@H](O)C(C)(O)C3)[C@H](N(C)C)[C@H]2O)[C@@H](OC)[C@H](O)CC(O[C@H](C)C/C=C/C=C/[C@H](O[C@@H]4O[C@H](C)[C@@H](N(C)C)CC4)[C@H](C)C1)=O
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InChi Key |
ACTOXUHEUCPTEW-AQKFJFIXSA-N
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InChi Code |
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
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Chemical Name |
2-[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-6-{[(2S,3R,4R,5S,6R)-5-{[(2S,5S,6S)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy}-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-10-{[(2R,5S,6R)-5-(dimethylamino)-6-methyloxan-2-yl]oxy}-4-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-1-oxacyclohexadeca-11,13-dien-7-yl]acetaldehyde
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Synonyms |
HSDB-7027; Rovamycin; HSDB7027; HSDB 7027
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HS Tariff Code |
2934.99.9001
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Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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Solubility (In Vitro) |
DMSO : 100~157 mg/mL ( 118.62~186.22 mM )
Ethanol : ~157 mg/mL |
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Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (2.97 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. Solubility in Formulation 2: ≥ 2.5 mg/mL (2.97 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in 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 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (2.97 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. Solubility in Formulation 4: 10% DMSO+40% PEG300+5% Tween-80+45% Saline: ≥ 2.5 mg/mL (2.97 mM) |
Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
1 mM | 1.1862 mL | 5.9308 mL | 11.8617 mL | |
5 mM | 0.2372 mL | 1.1862 mL | 2.3723 mL | |
10 mM | 0.1186 mL | 0.5931 mL | 1.1862 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration: mg/mL;
Method for preparing DMSO stock solution: mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation::Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
Spiramycin biosynthesis. (A) Spiramycin biosynthetic cluster with the three putative reductase genes srm26, srm42, and srm43 represented by blue arrows and srm13 represented by a red arrow. (B) Proposed biosynthetic pathway for the post-PKS tailoring steps.[1].Antimicrob Agents Chemother. 2013 Aug;57(8):3836-42. td> |
LC and LC-MS analyses of culture supernatants of the wild-type strain (OSC2) and the Δsrm13 deletion mutant (SPM513). [1].Antimicrob Agents Chemother. 2013 Aug;57(8):3836-42. td> |
Identification of the gene catalyzing the reduction of the C-9 keto group of platenolide I by LC-MS analyses. [1].Antimicrob Agents Chemother. 2013 Aug;57(8):3836-42. td> |