Celogentin C
Overview
Description
Celogentin C is a natural product found in Celosia argentea with data available.
Scientific Research Applications
Anti-Cancer Activity
Celogentin C exhibits potent anti-cancer properties through its ability to inhibit tubulin polymerization. Tubulin is a crucial protein involved in cell division, and its inhibition leads to disrupted mitotic processes, ultimately resulting in cancer cell death.
- Mechanism of Action : The compound binds to tubulin similarly to established anti-cancer agents like vincristine and paclitaxel. In studies conducted on human lung cancer cell lines, this compound demonstrated significant cytotoxicity, with an IC50 value of 0.8 µM, surpassing that of vinblastine (IC50 3.0 µM) .
- Research Findings : A study by Weng and Kersten highlighted that this compound not only inhibits tubulin polymerization but also suggests novel mechanisms specific to lung cancer cells . This dual action makes it a promising candidate for further cancer therapy development.
Synthetic Chemistry
The total synthesis of this compound has been a focal point for chemists aiming to explore its structure-activity relationships and develop analogs with enhanced potency or reduced toxicity.
- Synthesis Techniques : Various synthetic methodologies have been employed to create this compound and its analogs. Notably, a left-to-right synthetic strategy was developed that involved intricate chemical reactions such as intermolecular Knoevenagel condensation and radical conjugate addition .
- Analog Development : Researchers have synthesized bicyclic analogs of this compound with modifications in their side chains to explore their efficacy as tubulin inhibitors . These analogs are crucial for understanding the structure-activity relationship of the compound and optimizing its therapeutic potential.
Pain Research
Beyond its anti-cancer applications, this compound serves as a valuable chemical probe for studying pain receptors. The compound's origin from the stinging tree (Dendrocnide moroides), known for causing intense pain upon contact, provides insights into pain perception mechanisms.
- Pain Mechanism Exploration : The unique structural features of this compound may help identify unknown pain receptors and elucidate the biochemical pathways involved in pain sensation . This research could lead to novel analgesics targeting specific pain pathways.
Traditional Medicine Context
Historically, Celosia argentea, from which this compound is derived, has been used in traditional medicine for treating various ailments, including liver and eye diseases . Understanding these traditional uses can guide modern therapeutic applications and enhance the compound's profile in integrative medicine.
Data Table: Summary of Key Studies on this compound
Properties
Molecular Formula |
C50H70N14O10 |
|---|---|
Molecular Weight |
1027.2 g/mol |
IUPAC Name |
(7S,10S,13S,19S,22S,25S,28S,29R)-10-[3-(diaminomethylideneamino)propyl]-25-(2-methylpropyl)-9,12,18,21,24,27-hexaoxo-28-[[(2S)-5-oxopyrrolidine-2-carbonyl]amino]-22,29-di(propan-2-yl)-2,4,8,11,17,20,23,26,35-nonazahexacyclo[17.16.2.12,5.130,34.013,17.033,36]nonatriaconta-1(36),3,5(39),30(38),31,33-hexaene-7-carboxylic acid |
InChI |
InChI=1S/C50H70N14O10/c1-23(2)17-33-44(68)61-39(25(5)6)46(70)59-34-20-29-28-12-11-26(38(24(3)4)40(47(71)58-33)62-43(67)31-13-14-37(65)55-31)18-32(28)56-41(29)63-21-27(54-22-63)19-35(49(73)74)60-42(66)30(9-7-15-53-50(51)52)57-45(69)36-10-8-16-64(36)48(34)72/h11-12,18,21-25,30-31,33-36,38-40,56H,7-10,13-17,19-20H2,1-6H3,(H,55,65)(H,57,69)(H,58,71)(H,59,70)(H,60,66)(H,61,68)(H,62,67)(H,73,74)(H4,51,52,53)/t30-,31-,33-,34-,35-,36-,38+,39-,40-/m0/s1 |
InChI Key |
ZIUCJBZUJCNMSJ-WYHXJWKRSA-N |
SMILES |
CC(C)CC1C(=O)NC(C(=O)NC2CC3=C(NC4=C3C=CC(=C4)C(C(C(=O)N1)NC(=O)C5CCC(=O)N5)C(C)C)N6C=C(CC(NC(=O)C(NC(=O)C7CCCN7C2=O)CCCN=C(N)N)C(=O)O)N=C6)C(C)C |
Isomeric SMILES |
CC(C)C[C@H]1C(=O)N[C@H](C(=O)N[C@H]2CC3=C(NC4=C3C=CC(=C4)[C@H]([C@@H](C(=O)N1)NC(=O)[C@@H]5CCC(=O)N5)C(C)C)N6C=C(C[C@H](NC(=O)[C@@H](NC(=O)[C@@H]7CCCN7C2=O)CCCN=C(N)N)C(=O)O)N=C6)C(C)C |
Canonical SMILES |
CC(C)CC1C(=O)NC(C(=O)NC2CC3=C(NC4=C3C=CC(=C4)C(C(C(=O)N1)NC(=O)C5CCC(=O)N5)C(C)C)N6C=C(CC(NC(=O)C(NC(=O)C7CCCN7C2=O)CCCN=C(N)N)C(=O)O)N=C6)C(C)C |
Synonyms |
celogentin C |
Origin of Product |
United States |
Retrosynthesis Analysis
AI-Powered Synthesis Planning: Our tool employs the Template_relevance Pistachio, Template_relevance Bkms_metabolic, Template_relevance Pistachio_ringbreaker, Template_relevance Reaxys, Template_relevance Reaxys_biocatalysis model, leveraging a vast database of chemical reactions to predict feasible synthetic routes.
One-Step Synthesis Focus: Specifically designed for one-step synthesis, it provides concise and direct routes for your target compounds, streamlining the synthesis process.
Accurate Predictions: Utilizing the extensive PISTACHIO, BKMS_METABOLIC, PISTACHIO_RINGBREAKER, REAXYS, REAXYS_BIOCATALYSIS database, our tool offers high-accuracy predictions, reflecting the latest in chemical research and data.
Strategy Settings
| Precursor scoring | Relevance Heuristic |
|---|---|
| Min. plausibility | 0.01 |
| Model | Template_relevance |
| Template Set | Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis |
| Top-N result to add to graph | 6 |
Feasible Synthetic Routes
Disclaimer and Information on In-Vitro Research Products
Please be aware that all articles and product information presented on BenchChem are intended solely for informational purposes. The products available for purchase on BenchChem are specifically designed for in-vitro studies, which are conducted outside of living organisms. In-vitro studies, derived from the Latin term "in glass," involve experiments performed in controlled laboratory settings using cells or tissues. It is important to note that these products are not categorized as medicines or drugs, and they have not received approval from the FDA for the prevention, treatment, or cure of any medical condition, ailment, or disease. We must emphasize that any form of bodily introduction of these products into humans or animals is strictly prohibited by law. It is essential to adhere to these guidelines to ensure compliance with legal and ethical standards in research and experimentation.
