Demecolcine | Colcemid | CAS#477-30-5 | microtubule polymerization inhibitor

MedKoo Cat#: 540102 | Name: Demecolcine

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Demecolcine, also known as colcemid, is a chemotherapeutic agent that disrupts microtubule dynamics by binding to tubulin, thereby inhibiting spindle fiber formation and arresting cells in metaphase. This property is utilized in cytogenetics to facilitate chromosome analysis. Additionally, demecolcine has applications in animal cloning procedures, where it induces enucleation of oocytes to prepare them for nuclear transfer.

Chemical Structure

Demecolcine

CAS#477-30-5 (free base)

Theoretical Analysis

MedKoo Cat#: 540102

Name: Demecolcine

CAS#: 477-30-5 (free base)

Chemical Formula: C21H25NO5

Exact Mass: 371.1733

Molecular Weight: 371.43

Elemental Analysis: C, 67.91; H, 6.78; N, 3.77; O, 21.54

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 400.00	2 Weeks
10mg	USD 650.00	2 Weeks

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Related CAS #

477-30-5 (free base) 1246817-95-7 (HBr)

Synonym

Demecolcine; Demecolcin; Colcemid; Colcemide; Colchamine; (-)-Demecolcine; Kolchicin; NSC-3096; NSC 3096; NSC3096;

IUPAC/Chemical Name

(S)-1,2,3,10-tetramethoxy-7-(methylamino)-6,7-dihydrobenzo[a]heptalen-9(5H)-one

InChi Key

NNJPGOLRFBJNIW-HNNXBMFYSA-N

InChi Code

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

SMILES Code

O=C1C=C2[C@@H](NC)CCC3=CC(OC)=C(OC)C(OC)=C3C2=CC=C1OC

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Colcemid (Demecolcine), a derivative of colchicine, is a potent mitotic inhibitor that binds to the protein tubulin and arrest cells in metaphase for karyotyping assays.

In vitro activity:

The level of MPF and the distribution of cyclin B1 were assessed in porcine oocytes following DEM (demecolcine) treatment. MPF was uniformly distributed in oocytes that had been treated with 0.4 μg/ml DEM for 1 h. Immunofluorescence microscopy showed that in untreated oocytes, cyclin B1, the regulatory subunit of MPF, accumulated around the spindle, and was lowly detected in the cytoplasm. DEM treatment disrupted spindle microtubules, induced chromosome condensation, and reduced the level of cyclin B1 in the nuclear region. Cyclin B1 was uniformly distributed in DEM-treated oocytes and the level of MPF was increased. Reference: PLoS One. 2014 Mar 13;9(3):e91483. https://pubmed.ncbi.nlm.nih.gov/24626152/

In vivo activity:

Mice were given Colcemid intraperitoneally (i.p.) according to the following schecules: Group I, 2 mg/kg i.p., single injection; Group II, 14 mg/kg i.p., single injection; Group III, 2 mg/kg i.p. q.2h. x 4; Group IV, 2 mg/kg i.p. q.2h. x 7. In Group I (Colcemid 2 mg/kg, single injection), the number of megakaryocytes/mm2 changed little during the first 8 h (Fig. 1A). A sharp rise in megakaryocytes/mm2 occurred between 8 and 12 h. This increase in megakaryocytes persisted through day four, (66% above control maximum). On comparing the effects of Colcemid on Groups I and IV the rise in megakaryocytes can be resolved into early and late components (Figs. 1A and 1B). The early component of the rise (8-48 h) was most apparent in Group I and was blunted in Group IV. The late component (days 3 and 4) was more pronounced in Group IV. A fall in marrow cellularity was observed in both Groups I and IV, beginning with the 4-h time point, and reaching a nadir at 24 h. In Groups I and II an increase in peripheral platelet count was apparent between 12 and 24 h (Fig. 2A and B). The maximum increase was observed on day 6. In contrast, peripheral leukocyte counts fell on all the Colcemid schedules employed (Fig. 3). Reference: J Clin Invest. 1976 Nov;58(5):1280-5. https://pubmed.ncbi.nlm.nih.gov/993346/

	Solvent	mg/mL	mM
Solubility
	DMSO	25.0	67.31

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 371.43 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Li S, Kang JD, Jin JX, Hong Y, Zhu HY, Jin L, Gao QS, Yan CG, Cui CD, Li WX, Yin XJ. Effect of demecolcine-assisted enucleation on the MPF level and cyclin B1 distribution in porcine oocytes. PLoS One. 2014 Mar 13;9(3):e91483. doi: 10.1371/journal.pone.0091483. PMID: 24626152; PMCID: PMC3953396. 2. Fujikawa-Yamamoto K, Teraoka K, Zong ZP, Yamagishi H, Odashima S. Apoptosis by demecolcine in V79 cells. Cell Struct Funct. 1994 Dec;19(6):391-6. doi: 10.1247/csf.19.391. PMID: 7720099. 3. Li GP, White KL, Aston KI, Bunch TD, Hicks B, Liu Y, Sessions BR. Colcemid-treatment of heifer oocytes enhances nuclear transfer embryonic development, establishment of pregnancy and development to term. Mol Reprod Dev. 2009 Jul;76(7):620-8. doi: 10.1002/mrd.21004. PMID: 19170231. 4. Bunn PA Jr, Shackney SE, Ford SS. The effects of colcemid on hematopoiesis in the mouse. J Clin Invest. 1976 Nov;58(5):1280-5. doi: 10.1172/JCI108583. PMID: 993346; PMCID: PMC333298.

In vitro protocol:

In vivo protocol:

1. Li GP, White KL, Aston KI, Bunch TD, Hicks B, Liu Y, Sessions BR. Colcemid-treatment of heifer oocytes enhances nuclear transfer embryonic development, establishment of pregnancy and development to term. Mol Reprod Dev. 2009 Jul;76(7):620-8. doi: 10.1002/mrd.21004. PMID: 19170231. 2. Bunn PA Jr, Shackney SE, Ford SS. The effects of colcemid on hematopoiesis in the mouse. J Clin Invest. 1976 Nov;58(5):1280-5. doi: 10.1172/JCI108583. PMID: 993346; PMCID: PMC333298.

1: Gao Y, Ren J, Zhang L, Zhang Y, Wu X, Jiang H, Xu F, Yuan B, Yu X, Zhang J. The effects of demecolcine, alone or in combination with sucrose on bovine oocyte protrusion rate, MAPK1 protein level and c-mos gene expression level. Cell Physiol Biochem. 2014;34(6):1974-82. doi: 10.1159/000366393. Epub 2014 Nov 25. PubMed PMID: 25500918. 2: Yin Y, Mei M, Zhang D, Zhang S, Fan A, Zhou H, Li Z. The construction of cloned Sika deer embryos (Cervus nippon hortulorum) by demecolcine auxiliary enucleation. Reprod Domest Anim. 2014 Feb;49(1):164-9. doi: 10.1111/rda.12246. Epub 2013 Oct 21. PubMed PMID: 24138424. 3: Meng Q, Wu X, Bunch TD, White K, Sessions BR, Davies CJ, Rickords L, Li GP. Enucleation of demecolcine-treated bovine oocytes in cytochalasin-free medium: mechanism investigation and practical improvement. Cell Reprogram. 2011 Oct;13(5):411-8. doi: 10.1089/cell.2011.0012. Epub 2011 Jul 8. PubMed PMID: 21740270. 4: Saraiva NZ, Perecin F, Méo SC, Ferreira CR, Tetzner TA, Garcia JM. Demecolcine effects on microtubule kinetics and on chemically assisted enucleation of bovine oocytes. Cloning Stem Cells. 2009 Mar;11(1):141-52. doi: 10.1089/clo.2008.0044. PubMed PMID: 19226217. 5: Wang Q, An ZX, Gu L, Ma LB, Zheng YM, Zhang Y. [Demecolcine-induced enucleation of Kunming mouse oocyte]. Yi Chuan. 2004 Sep;26(5):653-7. Chinese. PubMed PMID: 15640080. 6: Miyoshi K, Mori H, Yamamoto H, Kishimoto M, Yoshida M. Effects of demecolcine and sucrose on the incidence of cytoplasmic protrusions containing chromosomes in pig oocytes matured in vitro. J Reprod Dev. 2008 Apr;54(2):117-21. Epub 2008 Jan 30. PubMed PMID: 18239352. 7: Hou J, Lei T, Liu L, Cui X, An X, Chen Y. Demecolcine-induced enucleation of sheep meiotically maturing oocytes. Reprod Nutr Dev. 2006 Mar-Apr;46(2):219-26. Epub 2006 Apr 6. PubMed PMID: 16597428. 8: Lan GC, Wu YG, Han D, Ge L, Liu Y, Wang HL, Wang JZ, Tan JH. Demecolcine-assisted enucleation of goat oocytes: protocol optimization, mechanism investigation, and application to improve the developmental potential of cloned embryos. Cloning Stem Cells. 2008 Jun;10(2):189-202. doi: 10.1089/clo.2007.0088. PubMed PMID: 18373477. 9: Tani T, Shimada H, Kato Y, Tsunoda Y. Demecolcine-assisted enucleation for bovine cloning. Cloning Stem Cells. 2006;8(1):61-6. PubMed PMID: 16571078. 10: Fujikawa-Yamamoto K, Teraoka K, Zong ZP, Yamagishi H, Odashima S. Apoptosis by demecolcine in V79 cells. Cell Struct Funct. 1994 Dec;19(6):391-6. PubMed PMID: 7720099. 11: Alali FQ, Tawaha K, El-Elimat T. Determination of (-)-demecolcine and (-)-colchicine content in selected Jordanian Colchicum species. Pharmazie. 2007 Oct;62(10):739-42. PubMed PMID: 18236776. 12: Russell DF, Ibáñez E, Albertini DF, Overström EW. Activated bovine cytoplasts prepared by demecolcine-induced enucleation support development of nuclear transfer embryos in vitro. Mol Reprod Dev. 2005 Oct;72(2):161-70. PubMed PMID: 16007680. 13: Saraiva NZ, Oliveira CS, Leal CL, de Lima MR, Del Collado M, Vantini R, Monteiro FM, Niciura SC, Garcia JM. Chemically induced enucleation of activated bovine oocytes: chromatin and microtubule organization and production of viable cytoplasts. Zygote. 2015 Dec;23(6):852-62. doi: 10.1017/S0967199414000537. Epub 2014 Oct 16. PubMed PMID: 25318529. 14: Fujikawa-Yamamoto K, Miyagoshi M, Luo X, Yamagishi H. DNA-unstable decaploid mouse H1 (ES) cells established from DNA-stable pentaploid H1 (ES) cells polyploidized using demecolcine. Cell Prolif. 2011 Apr;44(2):111-9. doi: 10.1111/j.1365-2184.2011.00734.x. PubMed PMID: 21401752. 15: Wang L, Jiang H, Su L, Tang B, Li D, Li Z. Effects of colchicine or demecolcine on cytoplasmic protrusions and assisted enucleation of golden hamster oocytes. Cell Biol Int. 2009 Dec;33(12):1274-9. doi: 10.1016/j.cellbi.2009.08.010. Epub 2009 Sep 2. PubMed PMID: 19732847. 16: Kawakami M, Tani T, Yabuuchi A, Kobayashi T, Murakami H, Fujimura T, Kato Y, Tsunoda Y. Effect of demecolcine and nocodazole on the efficiency of chemically assisted removal of chromosomes and the developmental potential of nuclear transferred porcine oocytes. Cloning Stem Cells. 2003;5(4):379-87. PubMed PMID: 14733755. 17: Li Z, Chen X, Sun X, Zhou Q, Chen J, Leno GH, Engelhardt JF. Nuclear transfer of M-phase ferret fibroblasts synchronized with the microtubule inhibitor demecolcine. J Exp Zool A Comp Exp Biol. 2005 Dec 1;303(12):1126-34. PubMed PMID: 16254916. 18: Iuso D, Czernik M, Zacchini F, Ptak G, Loi P. A simplified approach for oocyte enucleation in mammalian cloning. Cell Reprogram. 2013 Dec;15(6):490-4. doi: 10.1089/cell.2013.0051. Epub 2013 Nov 12. PubMed PMID: 24219576; PubMed Central PMCID: PMC3848443. 19: Ibáñez E, Albertini DF, Overström EW. Demecolcine-induced oocyte enucleation for somatic cell cloning: coordination between cell-cycle egress, kinetics of cortical cytoskeletal interactions, and second polar body extrusion. Biol Reprod. 2003 Apr;68(4):1249-58. Epub 2002 Oct 30. PubMed PMID: 12606412. 20: Nomura T, Plager JE. Action of demecolcine (colcemid) in the murine sarcoma 180 tumor. Cancer Treat Rep. 1981 Mar-Apr;65(3-4):283-90. PubMed PMID: 7237451.