Name: Colcemide
Brand: BOC Sciences
Rating: 5 (1 reviews)

Synonyms

Demecolcine; colcemid; (-)-Demecolcine; Colchamine; Demecolcin; Reichstein's F; Colcemide; Desmecolcine; Substance F; Santavy's substance F; (-)-Colchamine; Kolchamin; Kolkamin; Omain; Omaine; Methylcolchicine; N-Deacetyl-N-methylcolchicine; N-Methyl-N-deacetylcolchicine; Deacetylmethylcolchicine; N-Desacetyl-N-methylcolchicine; N-Methyl-N-desacetylcolchicine; Desacetylmethylcolchicine; Demecolcina; Demecolcinum; Deacetyl-N-methylcolchicine; Kolchicin; N-Desacetylmethylcolchicine; Colchicine, N-deacetyl-N-methyl-; (S)-1,2,3,10-Tetramethoxy-7-(methylamino)-6,7-dihydrobenzo[a]heptalen-9(5H)-one; Colchamin

IUPAC Name

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

Canonical SMILES

CNC1CCC2=CC(=C(C(=C2C3=CC=C(C(=O)C=C13)OC)OC)OC)OC

InChI

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

InChIKey

NNJPGOLRFBJNIW-HNNXBMFYSA-N

Melting Point

73-75°C

Appearance

Crystalline powder

Shipping

Room temperature

Storage

Store at room temperature.

In Vivo

The increased cell size in response to SP600125 was detected even in P19 cells treated with colcemide, an inhibitor of cell cycle progression at the metaphase. C-metaphase plates were obtained from the bone marrow lymphocytes synchronized by the addition of 0.25 microg/ml colcemide. No significant difference in chromosomal aneuploidy between transgenic (61%) and non-transgenic (51.27%) rabbits of line I was observed.

Colcemide, also known by its chemical name demecolcine, is a semi-synthetic analog of colchicine that functions as an ADC cytotoxin. It is utilized as a payload in the development of antibody-drug conjugates for targeted cancer therapy. As a compound with a well-characterized mechanism, Colcemide is integrated into an ADC construct to enable the delivery of its cytotoxic activity directly to tumor cells. This approach leverages its inherent potency while aiming to improve the therapeutic index of the final product. Colcemide's suitability for bioconjugation makes it a component for developing targeted therapeutics.

The cytotoxic activity of Colcemide stems from its mechanism as a tubulin polymerization inhibitor. When this ADC cytotoxin is released inside the target cell, it binds to tubulin heterodimers, preventing their assembly into microtubules. This disruption of microtubule formation leads to the disorganization of the mitotic spindle, resulting in mitotic arrest. By arresting cells in the metaphase of mitosis, Colcemide induces apoptosis, primarily affecting rapidly proliferating cancer cells. This specific antimitotic agent mechanism targets a fundamental process of cell division, which is a key characteristic of many cytotoxic payload classes.

Colcemide is a compound used in bioconjugation research and tumor therapy. Its chemical properties, including its ability to be conjugated to various linkers, support its application in constructing stable and effective antibody-drug conjugates. For researchers and companies focused on developing targeted therapeutics, Colcemide serves as a payload with established cytotoxic activity. The compound’s mechanism of action is a factor in its use for targeting cell proliferation, a hallmark of malignant cells.

1. Effect of cadmium and colcemide on the mitoses of a human epithelial cell line with high content of cytoplasmic metallothionein

A Bakka, V Digernes Acta Pharmacol Toxicol (Copenh) . 1984 Sep;55(3):242-6. doi: 10.1111/j.1600-0773.1984.tb02044.x.

Cultures of cell strains with and without metallothionein were exposed to CdCl2 in doses ranging from 10 mu mol/l to 200 mu mol/l . Cell growth parameters were monitored by flow cytometric DNA-measurements, cell counts and counting of mitoses during the first two days after exposure. CdCl2 inhibited cell growth in a dose dependent way. The cadmium resistant cells were inhibited with concentrations above 100 mu mol/l, the concentration which the metallothionein-containing cells had previously been adjusted to. Microscopy of the cell cultures showed a dose dependent accumulation of cells in the mitotic prophase, whereas the other phases of the cell cycle were unaffected as measured by flow cytometry. When exposed to colcemide, however, the two cell strains showed identical responsiveness.

2. LIFE CYCLE ANALYSIS OF MAMMALIAN CELLS. I. A METHOD FOR LOCALIZING METABOLIC EVENTS WITHIN THE LIFE CYCLE, AND ITS APPLICATION TO THE ACTION OF COLCEMIDE AND SUBLETHAL DOSES OF X-IRRADIATION

J STEFFEN, T T PUCK Biophys J . 1963 Sep;3(5):379-97. doi: 10.1016/s0006-3495(63)86828-9.

Equations are presented describing the accumulation of cells at any part of the life cycle as a result of addition of specific blocking agents. An experimental methodology using these relationships is described which makes possible analysis with relatively high resolution of the distribution of cells throughout the life cycle in normal cultures or those treated with various agents. The action of colcemide on S3 HeLa cells studied by this method revealed that colcemide has no effect on the G1, S, or G2 stages; it blocks cells quantitatively at the metaphase-anaphase region; but it accumulates mitotic figures only from the cells which have not yet entered mitosis at the time of its addition. The technique was also applied to study the efficiency of x-irradiation in delaying the entrance of G2 cells into mitosis. A definite lag was found at the lowest dose studied which was 9 rads. Only the cells confined to a central region of G2 at the time of irradiation are affected by this dose.

3. Sister chromatid exchange

Jeremy A Squire, Jane Bayani Curr Protoc Cell Biol . 2005 Jan;Chapter 22:Unit 22.7. doi: 10.1002/0471143030.cb2207s25.

Sister chromatid exchange (SCE) refers to the interchange of DNA between replication products. The technique for detecting such exchanges takes advantage of the semiconservative nature of DNA synthesis. 5'-bromodeoxyuridine (BrdU) is incorporated into the newly synthesized DNA. Using standard culturing techniques, Colcemid is added to the culture and conventional cytogenetic preparations are made. Differential staining with Hoechst dye and Giemsa allows the newly synthesized DNA within a chromatid to be recognized, since BrdU incorporation results in much weaker staining. SCEs represent a point of DNA template exchange during strand synthesis, visualized as asymmetric chromatid staining or "harlequin" chromosomes.

What is Colcemide?

Colcemide is a microtubule-disrupting cytotoxin widely used in ADC research. It binds tubulin, preventing microtubule polymerization, which disrupts mitotic spindle formation and halts cell division. This makes it an effective tool for studying targeted cytotoxicity in cancer models.

13/5/2019

Could you explain how Colcemide functions as an ADC payload?

When used in ADCs, Colcemide inhibits microtubule dynamics after cellular uptake, leading to cell cycle arrest and apoptosis. Its high potency allows researchers to design ADCs that target tumor cells specifically, maximizing efficacy while limiting systemic toxicity.

20/5/2018

We are interested in the applications of Colcemide in research. Could you advise?

Colcemide is utilized in preclinical oncology studies to evaluate ADC performance, microtubule-targeted payload delivery, and conjugation stability. It aids in optimizing antibody-linker design and assessing cytotoxic efficiency in vitro and in vivo.

14/12/2019

Could you please let me know what the chemical properties of Colcemide are?

Colcemide is a colchicine derivative that binds to tubulin at the colchicine site, preventing polymerization. Its chemical structure allows for conjugation to antibodies through linkers suitable for ADCs, maintaining cytotoxic activity while ensuring targeted delivery.

7/11/2016

Dear BOC Sciences, how should Colcemide be handled safely in the lab?

Colcemide is highly cytotoxic and requires strict laboratory safety procedures. Protective equipment, fume hoods, and careful waste management are essential to prevent exposure during ADC payload handling, storage, and experimental use.

19/7/2020

— Dr. James Parker, Lead Scientist (USA)

Colcemide from BOC Sciences arrived with high purity and enabled smooth ADC conjugation.

14/12/2019

— Dr. Anthony White, Laboratory Director (UK)

Colcemide from BOC Sciences was delivered in excellent condition, with purity levels that matched our stringent requirements.

19/7/2020

— Ms. Eva Schneider, Biomedical Scientist (Germany)

Our experiments required Colcemide for cytotoxicity studies, and the results were reproducible thanks to its consistent quality.

7/11/2016

— Mr. Lucas Martin, Senior Research Chemist (France)

The compound came with detailed COA and NMR profiles, making Colcemide easy to integrate into our workflows.