Thiocolchicine

Synonyms: Thiocolchicine, NSC 7578, Colchicine thio analog

Thiocolchicine is a semi-synthetic derivative of colchicine, a tropolone alkaloid isolated from plants of the genus Colchicum. The key structural modification involves the replacement of the methoxy group at the C-10 position with a thiomethyl group, which alters the electronic environment of the tropolone ring and significantly influences the compound’s biological activity. This subtle change in the molecule’s architecture not only affects its affinity for tubulin but also its metabolic stability and pharmacokinetic profile.

Thiocolchicine acts primarily by binding to the colchicine site on the β-subunit of tubulin, inhibiting microtubule polymerization. This mechanism underpins its potential as an anti-mitotic agent, making it of interest in oncology research and in the study of cell division. Unlike colchicine, thiocolchicine has a lower toxicity profile in certain models, which has prompted investigations into its use as a safer alternative or as a lead compound for further structural optimization.

In research and pharmaceutical development, thiocolchicine is utilized as a reference standard and as a starting material for the synthesis of more complex derivatives, such as thiocolchicine dimers and conjugates. Its purity and consistent quality are critical for reproducible experimental results and for the development of therapeutic candidates. LyvBio supplies thiocolchicine with a purity of ≥98% (HPLC), suitable for R&D purposes and pre-clinical studies.

Chemical Structure & Properties

Thiocolchicine possesses the characteristic fused ring system of colchicine, comprising a trimethoxyphenyl ring, a seven-membered tropolone ring, and an acetamide side chain. The substitution of the methoxy group with a thiomethyl group at C-10 introduces a sulfur atom that enhances lipophilicity and can participate in additional interactions with the binding pocket. The compound has a molecular formula of C22H25NO6S and a molecular weight of 431.5 g/mol. It appears as an off-white to pale yellow crystalline powder, sparingly soluble in water but soluble in organic solvents such as ethanol, DMSO, and chloroform.

Механизм действия

• Tubulin binding: Binds to the colchicine site on tubulin, preventing microtubule assembly and leading to mitotic arrest.
• Apoptosis induction: Disruption of microtubule dynamics triggers apoptotic pathways in rapidly dividing cells.
• Противовоспалительное действие: Modulates neutrophil activity and reduces inflammatory responses, similar to colchicine but with potentially altered potency.
• Metabolic stability: The thiomethyl group may slow hepatic metabolism, prolonging the compound’s half-life relative to colchicine.

Quality Specifications

Supply & Documentation

• Capacity: Multi-kilogram to metric ton quantities available.
• Срок выполнения заказа: Typically 2-3 weeks for standard orders.
• Документация: COA, MSDS, TDS, and analytical data provided.
• Упаковка: Sealed foil bags or HDPE drums, custom sizes on request.

Запрос Цитировать

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