477-30-5 Usage
Description
DEMECOLCINE, also known as Colcemid, is a secondary amino compound derived from the autumn crocus, Colchicum autumnale. It is a colchicine derivative that inhibits tubulin polymerization, acting as an antimitotic agent. DEMECOLCINE is less toxic than colchicine and is used for various applications in the medical and scientific fields.
Uses
Used in Anticancer Applications:
DEMECOLCINE is used as an antineoplastic agent for its ability to disrupt microtubules by binding to tubulin and preventing its polymerization. It stimulates the intrinsic GTPase activity of tubulin, induces apoptosis in several normal and tumor cell lines, and activates the JNK/SAPK signaling pathway.
Used in Cell Biology Research:
DEMECOLCINE is used as an inhibitor of spindle fiber formation for its ability to block microtubule assembly, which arrests cells in metaphase. This property makes it a valuable tool for cell synchronization, chromosome visualization, and inducing oocyte enucleation for somatic cell cloning.
Used in Cytogenetic Studies:
DEMECOLCINE is used as a cell synchronization agent for karyotyping, as its mitotic block allows for the study of chromosomes in a controlled manner. Prolonged exposure to DEMECOLCINE can activate p53, leading to apoptosis, which is useful for studying cell death mechanisms.
Biochem/physiol Actions
Often in karyotyping and cell cycle research it is desirable to increase the yield of mitotic cells in a particular phase of the cell cycle. This can be achieved in a variety of ways with the most popular being the use of a cell cycle synchronizing agent such as demecolcine. Demecolcine will arrest cells in metaphase with no remarkable effect on the biochemical events in mitotic cells or in synchronized G1 and S phase cells. White blood cells are often treated with demecolcine to arrest cells in metaphase.
Safety Profile
Poison by ingestion,
intraperitoneal, parenteral, intravenous, and
intramuscular routes. Human systemic
effects by ingestion: (skin and appendages)
hair effects. Human mutation data reported.
An experimental teratogen. Experimental
reproductive effects. When heated to
decomposition it emits toxic fumes of NOx.
Purification Methods
Colcemide is purified by chromatography on silica and eluting with CHCl3/MeOH (9:1), and by recrystallisation from EtOAc/Et2O to form yellow prisms. UV in EtOH has max 243nm ( 30,200) and 350nm ( 16,3000). [Synthesis, IR, NMR, MS: Capraro & Brossi Helv Chim Acta 62 965 1979, Beilstein 8 IV 3319.]
Check Digit Verification of cas no
The CAS Registry Mumber 477-30-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,7 and 7 respectively; the second part has 2 digits, 3 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 477-30:
(5*4)+(4*7)+(3*7)+(2*3)+(1*0)=75
75 % 10 = 5
So 477-30-5 is a valid CAS Registry Number.
InChI:InChI=1/C21H25NO5/c1-22-15-8-6-12-10-18(25-3)20(26-4)21(27-5)19(12)13-7-9-17(24-2)16(23)11-14(13)15/h7,9-11,15,22H,6,8H2,1-5H3/t15-/m0/s1
477-30-5Relevant articles and documents
Biosynthesis. Part 28.1,2 Colchicine: Definition of intermediates between O-methylandrocymbine and colchicine and studies on speciosine
Barker, Alan C.,Julian, David R.,Ramage, Robert,Woodhouse, Robert N.,Hardy, Gilbert,McDonald, Edward,Battersby, Alan R.
, p. 2989 - 2994 (2007/10/03)
Labelled samples are prepared of demecolcine 3, colchicine 4, N-formyl-N-deacetylcolchlcine 6 and N-deacetylcolchicine 7, the last depending on a new method for its preparation from colchicine. Incorporation experiments with these compounds and with specifically labelled autumnaline 1 support the pathway 2→5→3→6→7→4 as the terminal sequence for the biosynthesis of colchicine. The key intermediate O-methylandrocymbine 2 is isolated from Colchicum autumnale plants together with speciosine 14 and its O-acetyl derivative 15; all three are first isolations from this plant. Speciosine 14 and N-methyldemecolcine 8 are shown to be formed in vivo largely from demecolcine 3 whereas N-formyldemecolcine 5 is the precursor of demecolcine and its N-formyl group is derived from C-3 of autumnaline. This discovery of a tropolone alkaloid which retains both carbons of the ethanamine bridge of 2 is important for future stereochemical work on the ring-expansion process.
