Demecycline
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| Category | Antibiotics |
| Catalog number | BBF-03478 |
| CAS | 987-02-0 |
| Molecular Weight | 430.41 |
| Molecular Formula | C21H22N2O8 |
| Purity | ≥95% |
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Description
Demecycline is a tetracycline antibiotic produced by the strain of Streptomyces aureofaciens var. 38-2-14 that is a C6-demethylated derivative of tetracycline and is used to treat bacterial infections including pneumonia and other respiratory tract infections.
Specification
| Synonyms | 6-Demethyltetracycline; Antibiotic 38-2-14 B; Demethyltetracycline; Antibiotic RP-6798; Demeclocycline EP impurity A; (4S-(4a,4aa,5aa,6b,12aa))-4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-1,11-dioxo-2-naphthacenecarboxamide |
| Storage | Store at-20°C |
| IUPAC Name | (4S,4aS,5aS,6S,12aR)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide |
| Canonical SMILES | CN(C)C1C2CC3C(C4=C(C(=CC=C4)O)C(=C3C(=O)C2(C(=C(C1=O)C(=O)N)O)O)O)O |
| InChI | InChI=1S/C21H22N2O8/c1-23(2)14-9-6-8-12(16(26)11-7(15(8)25)4-3-5-10(11)24)18(28)21(9,31)19(29)13(17(14)27)20(22)30/h3-5,8-9,14-15,24-26,29,31H,6H2,1-2H3,(H2,22,30)/t8-,9-,14-,15+,21-/m0/s1 |
| InChI Key | RMVMLZHPWMTQGK-SOUFLCLCSA-N |
Properties
| Appearance | Pale Grey to Brown Solid |
| Boiling Point | 776.2±60.0°C (Predicted) |
| Melting Point | >148°C (dec.) |
| Density | 1.69±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in Methanol, DMSO |
Reference Reading
1. The construction of cloned Sika deer embryos (Cervus nippon hortulorum) by demecolcine auxiliary enucleation
M Mei, Z Li, Y Yin, H Zhou, D Zhang, S Zhang, A Fan Reprod Domest Anim . 2014 Feb;49(1):164-9. doi: 10.1111/rda.12246.
The objective of our study was to establish the feasibility of experimental protocols for cloning sika deer. We performed auxiliary enucleation to improve the efficiency of nuclear transfer operation by optimizing the demecolcine concentration to induce cytoplasmic protrusions in the sika deer oocytes. In the present study,we had studied the impact of different demecolcine concentrations on cytoplasmic protrusions and enucleation rates. We determined that 95.9% of the sika deer oocytes formed cytoplasmic protrusions when treated for 1 h with 0.8 μg/ml demecolcine. The lowest observed rate of protrusion was 19.3% after overnight treatment with demecolcine. When the oocytes aged or had a poor cumulus expansion, they exhibited a significant decrease in the ability to form cytoplasmic protrusions. The rates of enucleation (94.9% vs 85.8%, p < 0.05), cell fusion (84.6% vs 70.1%, p < 0.05) and blastocyst formation (15.4% vs 10.9%, p < 0.05) using demecolcine auxiliary enucleation were significantly higher than those after blind enucleation. These results demonstrated that sika deer oocytes could be enucleated quickly and effectively using demecolcine auxiliary enucleation, which could enhance the enucleation rate, cell fusion rate and blastocyst rate of cloned embryos in vitro.
2. Apoptosis by demecolcine in V79 cells
K Teraoka, Z P Zong, K Fujikawa-Yamamoto, H Yamagishi, S Odashima Cell Struct Funct . 1994 Dec;19(6):391-6. doi: 10.1247/csf.19.391.
Demecolcine (Colcemid), an inhibitor of spindle fiber formation in M phase, induced apoptosis in V79 cells. At a concentration of 0.01 microgram/ml demecolcine, V79 cells proliferated exponentially as well as controls, although temporal M phase accumulation occurred 6 h after the addition of demecolcine. At 0.1 microgram/ml, the cells became hyperploid after remaining in the M phase for some time. Apoptosis occurred in V79 cells exposed to demecolcine at a concentration of 0.03 microgram/ml. Apoptosis was defined as the appearance of a sub-G1 peak in DNA histograms and a ladder pattern of fragmented DNA in gelelectrophoresis.
3. Demecolcine-induced enucleation of sheep meiotically maturing oocytes
Lei Liu, Xiaorong An, Tinghua Lei, Jian Hou, Xiuhong Cui, Yongfu Chen Reprod Nutr Dev . 2006 Mar-Apr;46(2):219-26. doi: 10.1051/rnd:2006002.
The objective of this study was to investigate the possible effect of demecolcine, a microtubule-disrupting reagent, on induced enucleation (IE) of sheep meiotically maturing oocytes. Immunofluorescent staining with anti-tubulin antibodies was used to examine the spindle status of the oocytes. When the oocytes with intact germinal vesicles (GV) were cultured in the medium containing various concentrations of demecolcine (0.01 to 0.4 microg.mL-1) for 20 to 22 h, the spindle microtubule organization and first polar body (PB1) extrusion were inhibited by demecolcine in a dose-dependent manner. The highest IE rate (58.1%) was from the treatment with 0.04 microg.mL-1 demecolcine. Demecolcine treatment applied after germinal vesicle breakdown (GVBD) or at metaphase (M) yielded a PB1 extrusion rate and IE efficiency similar to the treatment applied at the onset of maturation. Analysis by immunofluorescence showed that both nonspindle microtubules and spindle microtubules were significantly disorganized by demecolcine. Combination treatment with demecolcine and cycloheximide (CHX) or 6-dimethylaminopurine (6-DMAP) led to single pronuclear formation rather than PB1 extrusion. When demecolcine-treated oocytes were transferred into demecolcine-free medium, the ability to extrude PB1 was quickly restored and a 72.1% IE rate was obtained following such treatment. These results demonstrate that demecolcine can be used as a potential reagent for induced enucleation of sheep meiotically maturing oocytes and may greatly facilitate research in nuclear transfer.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
