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C3915

Sigma-Aldrich

Colchicine

suitable for plant cell culture, BioReagent, ≥95% (HPLC)

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Synonym(s):
(S)-N-(5,6,7,9-Tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl)acetamide
Empirical Formula (Hill Notation):
C22H25NO6
CAS Number:
64-86-8
Molecular Weight:
399.44
Beilstein:
2228813
EC Number:
200-598-5
MDL number:
MFCD00078484
UNSPSC Code:
10171502
PubChem Substance ID:
24892656
NACRES:
NA.72

product line

BioReagent

Quality Level

200

Assay

≥95% (HPLC)

form

powder

technique(s)

cell culture | plant: suitable

mp

150-160 °C (dec.) (lit.)

application(s)

agriculture

SMILES string

COC1=CC=C2C(=CC1=O)[C@H](CCc3cc(OC)c(OC)c(OC)c23)NC(C)=O

InChI

1S/C22H25NO6/c1-12(24)23-16-8-6-13-10-19(27-3)21(28-4)22(29-5)20(13)14-7-9-18(26-2)17(25)11-15(14)16/h7,9-11,16H,6,8H2,1-5H3,(H,23,24)/t16-/m0/s1

InChI key

IAKHMKGGTNLKSZ-INIZCTEOSA-N

Gene Information

human ... ABCB1(5243) , CYP3A4(1576) , TUBA1A(7846) , TUBA1B(10376) , TUBA1C(84790) , TUBA3C(7278) , TUBA3E(112714) , TUBA4A(7277) , TUBB(203068) , TUBB1(81027) , TUBB2A(7280) , TUBB2B(347733) , TUBB3(10381) , TUBB4A(10382) , TUBB4B(10383) , TUBB6(84617) , TUBB8(347688)
mouse ... Abcb1a(18671) , Abcb1b(18669)

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General description

Colchicine is a tricyclic alkaloid that can stay in circulation for 20 to 40 hours post intake. Leucocytes harbour maximum colchicine. It contains three hexameric rings termed A, B and C.

Application

Colchicine has been used:
  • as an inhibitor of tubulin polymerization in bone-marrow-derived macrophages
  • for the inhibition of in vitro neurite outgrowth in human neuronal cells
  • as microtubule destabilizer to induce peripheral neuropathy in induced pluripotent stem cell derived neurons (iPSC-Neurons)

Biochem/physiol Actions

Colchicine interacts with albumin and binds to tubulin. Its association with tubulin impacts autophagic vacuole fusion with lysosomes. It inhibits tyrosine kinases and phospholipases. Colchicine may be useful for treating acute coronary syndromes. It is prescribed for treating rheumatologic conditions including familial mediterranean fever (FMF) and acute gouty arthritis.
Colchicine is an inhibitor of microtubule polymerization which blocks chromosome segregation during meiosis. Consequently, Colchicine is used to induce polyploidy (tetraploid) in plant cells.

Preparation Note

Preparation and Use

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H300,H340

Hazard Classifications

Acute Tox. 2 Oral - Muta. 1B

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

监管及禁止进口产品

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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The effects of colchicine and hydroxychloroquine on the cyclo-oxygenases COX-1 and COX-2
Ben-Chetrit E, et al.
Rheumatology International, 25(5), 332-335 (2005)
NEK7 is an essential mediator of NLRP3 activation downstream of potassium efflux
He Y, et al.
Nature, 530(7590), 354-354 (2016)
Colchicine: old and new
Slobodnick A, et al.
The American Journal of Medicine, 128(5), 461-470 (2015)
Comparative Sensitivity of Human-Induced Pluripotent Stem Cell-Derived Neuronal Subtypes to Chemically Induced Neurodegeneration
Cohen JD and Tanaka Y
Applied In Vitro Toxicology, 4(4), 347-364 (2018)
Mechanism of the anti-inflammatory effect of colchicine in rheumatic diseases: a possible new outlook through microarray analysis
Ben-Chetrit E, et al.
Rheumatology (Basel), 45(3), 274-282 (2005)
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Protocols

Antibiotics in Plant Tissue Culture Protocol

Reference guide and preparation guide for antibiotic and antimycotic use in plant tissue culture.

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