Click Glycosylation for the Synthesis of 1,2,3‐Triazole‐Linked Picropodophyllotoxin Glycoconjugates and Their Anticancer Activity
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Bibliographic record
Abstract
Abstract Cu(I)‐catalyzed azide‐alkyne cycloaddition (CuAAC) reaction was employed successfully to prepare a series 4 β ‐triazole‐linked picropodophyllotoxin glycoconjugates ( 25 – 34 ). Maltose residue, 1,6‐ β ‐D‐diglucose residue, and several triazole‐linked disaccharide and trisaccharide residues were coupled to 4 β ‐azido‐podophyllotoxin derivatives through click glycosylation strategy. The initial click glycosylation products were treated with catalytic amount of NaOCH 3 to facilitate global deacylation and epimerization at C‐2 position to yield the cis ‐γ‐lactone moiety in the picropodophyllotoxin glycoconjugates. Most of these picropodophyllotoxin glycoconjugates show weak cytotoxicity (IC 50 > 40 μ M) against a panel of five human cancer cell lines (HL‐60, SMMC‐7721, A‐549, MCF‐7, SW480) as indicated by in vitro MTT [3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyltetrazolium bromide] assay. However, compound 27 that contains a 1,6‐ β ‐D‐di‐glucose residue displays strong anticancer activity against all cancer cell lines tested, with IC 50 values ranging from 0.67 to 7.41 μ M, which is significantly more potent than the control drug etoposide against four of the five cancer cells tested. Structure activity relationship analysis suggests that the 4’‐ O ‐methyl group on the E ring of podophyllotoxin scaffold is perhaps important for the anticancer activity of glycosylated picropodophyllotoxin derivatives with a cis ‐γ‐lactone moiety.
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Full frame distilled prediction
Teacher imitationNot calibrated prevalence, not ground truth. Human validation pending. Learned from the 10,348 direct Codex labels and 10,348 direct Gemma labels. Candidate is the union of thresholded teacher heads; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels or direct frontier model labels.
Codex and Gemma teacher scores by category
| Category | Codex | Gemma |
|---|---|---|
| Metaresearch | 0.000 | 0.001 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.000 | 0.000 |
| Bibliometrics | 0.000 | 0.000 |
| Science and technology studies | 0.001 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.001 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| Insufficient payload (model declined to judge) | 0.000 | 0.000 |
Machine scores (provisional)
The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.
Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.
score_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it