Size | Price | Stock | Qty |
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5mg |
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10mg |
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25mg |
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50mg |
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Other Sizes |
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ln Vitro |
Pyrrolobenzodiazepines (PBDs) are DNA alkylating agents that are selective for certain sequences and exhibit notable anti-tumor activity.
Anthramycin, sibiromycin, and tomaymycin all alkylate DNA in a sequence-specific manner, with the following trend for binding preference. 5′–Pu–G–Pu>5′–Py–G–Pu>5′–Pu–G–Py>5′–Py–G–Py.
Sibiromycin demonstrates cytotoxicity with IC50s ranging from 0.000017 to 0.0029 μM against ADJ/PC6 (plasmacytoma), L1210 (leukemia), and CH1 (ovarian) cells[1].
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References |
Molecular Formula |
C24H33N3O7
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Molecular Weight |
475.5347
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Exact Mass |
475.23
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Elemental Analysis |
C, 60.62; H, 6.99; N, 8.84; O, 23.55
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CAS # |
12684-33-2
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Appearance |
Solid powder
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SMILES |
O=C1N2[C@](CC(/C=C/C)=C2)([H])[C@@H](O)NC3=C(O)C(C)=C(O[C@H]4[C@@H]([C@]([C@@H](NC)[C@H](C)O4)(C)O)O)C=C13
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InChi Key |
RAGFPHFDFVNLCG-INYQBOQCSA-N
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InChi Code |
InChI=1S/C24H33N3O7/c1-6-7-13-8-15-21(30)26-17-14(22(31)27(15)10-13)9-16(11(2)18(17)28)34-23-20(29)24(4,32)19(25-5)12(3)33-23/h6-7,9-10,12,15,19-21,23,25-26,28-30,32H,8H2,1-5H3/b7-6+/t12-,15-,19-,20-,21+,23-,24+/m0/s1
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Chemical Name |
5H-Pyrrolo[2,1-c][1,4]benzodiazepin-5-one,7-[[4,6-dideoxy-3-C-methyl-4-(methylamino)-a-L-mannopyranosyl]oxy]-1,10,11,11a-tetrahydro-9,11-dihydroxy-8-methyl-2-(1E)-1-propen-1-yl-,(11R,11aS)-
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Synonyms |
Sibiromycin
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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 Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 :Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400  (Please use freshly prepared in vivo formulations for optimal results.) |
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Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
1 mM | 2.1029 mL | 10.5146 mL | 21.0292 mL | |
5 mM | 0.4206 mL | 2.1029 mL | 4.2058 mL | |
10 mM | 0.2103 mL | 1.0515 mL | 2.1029 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.
(A) Pyrrolobenzodiazepine common ring system. (B) Metabolic precursors and chemical structures of sibiromycin, anthramycin, tomaymycin, and lincomycin A. [2]. Appl Environ Microbiol. 2009;75(9):2869-2878. td> |
td> |
HPLC-ESI and bioassay analyses of the secondary metabolites produced by wild-type and ΔsibC strains, and by chemical complementation of ΔsibC strains with l-kynurenine, 3-hydroxy-l-kynurenine, 3-hydroxyanthranilic acid, and 3-hydroxy-4-methylanthranilic acid. [2]. Appl Environ Microbiol. 2009;75(9):2869-2878. td> |
Proposed pathway for the biosynthesis of the 3,5-hydroxy-4-methylanthranilic acid moiety in sibiromycin, which is the suggested substrate for the NRPS enzymes catalyzing diazepine ring formation. . [2]. Appl Environ Microbiol. 2009;75(9):2869-2878. td> |
(A) HPLC analyses of the secondary metabolites produced by wild-type and ΔsibG strains. Isolation of the metabolites was carried out by ethyl acetate extractions. (B) ESI spectrum of the HPLC peak eluting at 20.1 min and the chemical structure of the 7-deoxyaglycone of sibiromycin. . [2]. Appl Environ Microbiol. 2009;75(9):2869-2878. td> |