デメコルチン
- 関
- colcemid
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2016/10/04 02:11:37」(JST)
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Demecolcine
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Systematic (IUPAC) name |
(S)-1,2,3,10-Tetramethoxy-7-methylamino-6,7-dihydro-5H-benzo[a]heptalen-9-one
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Identifiers |
CAS Number |
477-30-5 Y |
ATC code |
L01CC01 (WHO) |
PubChem |
CID 2832 |
ChemSpider |
191135 Y |
UNII |
Z01IVE25KI Y |
ChEMBL |
CHEMBL312862 Y |
Chemical data |
Formula |
C21H25NO5 |
Molar mass |
371.43 g/mol |
SMILES
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O=C/1C(\OC)=C/C=C2\C(=C\1)[C@@H](NC)CCc3c2c(OC)c(OC)c(OC)c3
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InChI
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InChI=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 Y
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Key:NNJPGOLRFBJNIW-HNNXBMFYSA-N Y
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Demecolcine, 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.[1]
In animal cloning procedures, demecolcine makes an ovum eject its nucleus, creating space for insertion of a new nucleus.[2]
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.[3] Recent study has found at higher concentration Colcemid can promote microtubule detachment from microtubule organizing center. Detached microtubules with unprotected minus end depolymerizes with time. Cytotoxicity of the cells seems to correlate better with microtubule detachment.[4] Lower concentration affects microtubule dynamics and cell migration.[4]
References
- ^ Brit med J., 1965, 1, 495 – 496
- ^ Reprod Nutr Dev. 2006 Mar-Apr;46(2):219-26
- ^ Jordan, Mary Ann; Wilson, Leslie (2004). "Microtubules as a target for anticancer drugs". Nature reviews. Cancer. 4 (4): 253–65. doi:10.1038/nrc1317. PMID 15057285.
- ^ a b Yang, Hailing; Ganguly, Anutosh; Cabral, Fernando (2010). "Inhibition of cell migration and cell division correlate with distinct effects of microtubule inhibiting drugs". The Journal of Biological Chemistry. 285 (42): 32242–50. doi:10.1074/jbc.M110.160820. PMC 2952225. PMID 20696757.
English Journal
- Chemically induced enucleation of activated bovine oocytes: chromatin and microtubule organization and production of viable cytoplasts.
- Saraiva NZ1, Oliveira CS2, Leal CL3, de Lima MR4, Del Collado M4, Vantini R4, Monteiro FM5, Niciura SC6, Garcia JM4.
- Zygote (Cambridge, England).Zygote.2015 Dec;23(6):852-62. doi: 10.1017/S0967199414000537. Epub 2014 Oct 16.
- As the standard enucleation method in mammalian nuclear transfer is invasive and damaging to cytoplast spatial organization, alternative procedures have been developed over recent years. Among these techniques, chemically induced enucleation (IE) is especially interesting because it does not employ
- PMID 25318529
- Chemically assisted somatic cell nuclear transfer without micromanipulator in the goat: effects of demecolcine, cytochalasin-B, and MG-132 on the efficiency of a manual method of oocyte enucleation using a pulled Pasteur pipette.
- Hosseini SM1, Hajian M2, Forouzanfar M2, Ostadhosseini S2, Moulavi F2, Ghanaei HR2, Gourbai H3, Shahverdi AH4, Vosough AD5, Nasr-Esfahani MH6.
- Animal reproduction science.Anim Reprod Sci.2015 Jul;158:11-8. doi: 10.1016/j.anireprosci.2015.04.002. Epub 2015 Apr 15.
- The present study aimed to facilitate widespread application of a previously described manual method of somatic cell nuclear transfer (SCNT) by investigating the effects of demecolcine (a microtubule-depolymerizing chemical), cytochalasin-B (a microfilament-depolymerizing chemical: 2.5μg/ml for 15m
- PMID 25956201
- Recurrent micronucleation through cell cycle progression in the presence of microtubule inhibitors.
- Nakayama Y1, Uno N, Uno K, Mizoguchi Y, Komoto S, Kazuki Y, Nanba E, Inoue T, Oshimura M.
- Cell structure and function.Cell Struct Funct.2015;40(1):51-9. doi: 10.1247/csf.14005. Epub 2015 Jan 9.
- Although most cell lines undergo mitotic arrest after prolonged exposure to microtubule inhibitors, some cells subsequently exit this state and become tetraploid. Among these cells, limited numbers of rodent cells are known to undergo multinucleation to generate multiple small independent nuclei, or
- PMID 25736016
Japanese Journal
- Unstable Chromosome Aberrations Do Not Accumulate in Normal Human Fibroblast after Fractionated X-Irradiation
- The Establishment of Tetraploid Human Embryonic Cells Using Demecolcine
- Effects of Demecolcine and Sucrose on the Incidence of Cytoplasmic Protrusions Containing Chromosomes in Pig Oocytes Matured In Vitro
- The Journal of reproduction and development 54(2), 117-121, 2008-04-01
- NAID 10021218892
Related Links
- Demecolcine 販売元 和光純薬工業(株) 販売元コード 045-16963,049-16961 製造元 製造元コード CAS.NO 477-30-5 分子式 C21H25NO5 分子量 371.43 保存条件 冷蔵 (氷冷輸送) 適用法規 危険有害性 等級 生化学用 for Biochemistry ...
- Sigma-Aldrich offers Sigma-D7385, Demecolcine for your research needs. Find product specific information including CAS, MSDS, protocols and references. ... Biochem/physiol Actions Depolymerizes microtubules; blocks ...
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