Demecolcine

Quality 0.50 · 1 view · Updated 2 months ago

Chemical compound

title: "Demecolcine" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["pyrogallol-ethers", "microtubule-inhibitors", "benzodihydroheptalenes", "tropolones", "secondary-amines", "enol-ethers"] description: "Chemical compound" topic_path: "general/pyrogallol-ethers" source: "https://en.wikipedia.org/wiki/Demecolcine" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| Watchedfields = changed | verifiedrevid = 414414817 | IUPAC_name = (S)-1,2,3,10-Tetramethoxy-7-methylamino-6,7-dihydro-5H-benzo[a]heptalen-9-one | image = Demecolcine.png | image_class = skin-invert-image | alt = Skeletal formula of demecolcine | image2 = Demecolcine 3D ball.png | image_class2 = bg-transparent | alt2 = Ball-and-stick model of the demecolcine molecule | tradename = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration = | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion = | CAS_number_Ref = | CAS_number = 477-30-5 | ATC_prefix = L01 | ATC_suffix = CC01 | PubChem = 220401 | DrugBank_Ref = | DrugBank = | ChemSpiderID_Ref = | ChemSpiderID = 191135 | UNII_Ref = | UNII = Z01IVE25KI | ChEMBL_Ref = | ChEMBL = 312862 | KEGG_Ref = | KEGG = C11250 | synonyms = Colcemid | C=21 | H=25 | N=1 | O=5 | smiles = O=C/1C(\OC)=C/C=C2\C(=C\1)C@@HCCc3c2c(OC)c(OC)c(OC)c3 | StdInChI_Ref = | StdInChI = 1S/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 | StdInChIKey_Ref = | StdInChIKey = NNJPGOLRFBJNIW-HNNXBMFYSA-N

Demecolcine (INN; also known as colcemid) is a drug used in chemotherapy. It is closely related to the natural alkaloid colchicine with the replacement of the acetyl group on the amino moiety with methyl, but it is less toxic. It depolymerises microtubules and limits microtubule formation (inactivates spindle fibre formation), thus arresting cells in metaphase and allowing cell harvest and karyotyping to be performed.

During cell division, demecolcine inhibits mitosis at metaphase by inhibiting spindle formation. Medically, demecolcine has been used to improve the results of cancer radiotherapy by synchronising tumour cells at metaphase, the radiosensitive stage of the cell cycle.

In animal cloning procedures, demecolcine makes an ovum eject its nucleus, creating space for insertion of a new nucleus.

Mechanism of action

Demecolcine is a microtubule-depolymerizing drug like vinblastine. It acts by two distinct mechanisms. At very low concentration it binds to microtubule plus end to suppress microtubule dynamics. Recent study has found at higher concentration demecolcine can promote microtubule detachment from microtubule organizing center. Detached microtubules with unprotected minus end depolymerize with time. Cytotoxicity of the cells seems to correlate better with microtubule detachment. Lower concentration affects microtubule dynamics and cell migration.

Research use

Demecolcine is used for scientific research in cells. It is used in a variety of ways, however, until recently, was used mostly for the study of mitosis in cells. For example, microtubules are necessary for the splitting of cells. More importantly, the movement of chromosomes during the M phase. Demecolcine inhibition of microtubules causes aneuploidy in mitotic cells where the microtubules fall apart or are suppressed before they can complete their function of pulling chromosomes into the daughter cell, also known as nondisjunction of chromosomes. Demecolcine, depending on dose, has also been found to cause DNA fragmentation of chromosomes in micronuclei when nondisjunction occurs.

References

References

  1. (February 1965). "Superior Mediastinal Obstruction Treated with Demecolcine Followed by Radiotherapy". British Medical Journal.
  2. (2006). "Demecolcine-induced enucleation of sheep meiotically maturing oocytes". Reproduction, Nutrition, Development.
  3. (April 2004). "Microtubules as a target for anticancer drugs". Nature Reviews. Cancer.
  4. (October 2010). "Inhibition of cell migration and cell division correlates with distinct effects of microtubule inhibiting drugs". The Journal of Biological Chemistry.
  5. (July 2013). "Mitotic slippage underlies the relationship between p53 dysfunction and the induction of large micronuclei by colcemid". Mutagenesis.
  6. (April 2014). "Chromosome loss caused by DNA fragmentation induced in main nuclei and micronuclei of human lymphoblastoid cells treated with colcemid". Mutation Research.

::callout[type=info title="Wikipedia Source"] This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page. ::

pyrogallol-ethersmicrotubule-inhibitorsbenzodihydroheptalenestropolonessecondary-aminesenol-ethers