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Light-Controlled Anticancer Activity and Cellular Uptake of a Photoswitchable Cisplatin Analogue
Marta Stolarek ; Kamil Kaminski ; Marta Kaczor-Kamińska , et al. JMC,2024,67(21):19103-19120. DOI: 10.1021/acs.jmedchem.4c01575 PubMed ID: 39445571
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Abstract: A photoactive analogue of cisplatin was synthesized with two arylazopyrazole ligands, able to undergo trans?cis/cis?trans photoisomerizations. The cis photoisomer showed a dark half-life of 9 days. The cytotoxicities of both photoisomers of the complex were determined in several cancer and normal cell lines and compared to that of cisplatin. The trans photoisomer of the complex was much more cytotoxic than both the cis photoisomer and cisplatin, and was more toxic for cancer (4T1) than for normal (NMuMG) murine breast cells. 4T1 cell death occurred through necrosis. Photoisomerization of the trans and cis photoisomers internalized by the 4T1 cells increased and decreased their viability, respectively. The cellular uptake of the trans photoisomer was stronger than that of both the cis photoisomer and cisplatin. Both photoisomers interacted with DNA faster than cisplatin. The trans photoisomer was bound stronger by bovine serum albumin and induced a greater decrease in cellular glutathione levels than the cis photoisomer.
Purchased from AmBeed: 298-93-1 ; 15663-27-1
CAS No. : | 15663-27-1 | MDL No. : | MFCD00011623 |
Formula : | Cl2H6N2Pt | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DQLATGHUWYMOKM-UHFFFAOYSA-L |
M.W : | 300.05 | Pubchem ID : | 2767 |
Synonyms : |
cis-Platinum;CDDP;CACP;cis-Diamminedichloroplatinum;DDP;cis DDP;cis-diamminedichloroplatinum II;NSC 119875;cis-Diaminodichloroplatinum
|
Chemical Name : | cis-Diaminodichloroplatinum(II) |
Signal Word: | Danger | Class: | 6.1 |
Precautionary Statements: | P501-P263-P260-P270-P202-P201-P264-P280-P337+P313-P305+P351+P338-P308+P311-P332+P313-P301+P310+P330-P405 | UN#: | 3288 |
Hazard Statements: | H300-H316-H319-H360-H362-H370-H372-H340-H350 | Packing Group: | Ⅱ |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | In water; for 2h;Reflux; | a solution of thiosaccharinate (0.26 g, 1.33 mmol) in hot water (30 cm3) was added to a solution of cis-[PtCl2(NH3)2] (0.20 g, 0.667 mmol) in hot water (15 cm3). The mixture was reuxed for 2 h. The light-brown solid formed was ltered off washed several times with distilled water and dried in vacuo. Yield: 89% (0.39 g). Anal. Calcd. for C14H14N4O4PtS4: C, 26.88; H, 2.26; N,8.96. Found: C, 26.33; H, 2.09; N, 8.86%. IR (KBr) (nu, cm-1): 3471 m, 3413 m, 3286 m, 1627s,1440w, 1373s, 1315s, 1236 m, 1155 m, 1126s, 1008w, 817 s, 515 m. 1H NMR (d6-DMSO): 7.96-7.90 (m, 4H), 7.82-7.75 (m, 4H), 4.54 (s, 6 H). 13C{1H} NMR (d6-DMSO): 182.8, 137.6,133.7, 133.4, 133.1, 124.3, 120.7 ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | In brief, cisplatin (0.30 g, 1 mmol), HNO3 (100 mul), andsilver nitrate (0.34 g, 2 mmol) were added into a roundbottomflask containing 50 ml pure water. The reactionmixture was stirred in the dark at room temperature for48 h. The resultant turbid solution was filtered to removewhite silver chloride. To the yellow colored solution,<strong>[2156-56-1]sodium dichloroacetate</strong> (0.36 g, 2.4 mmol) was added toform a precipitate of DCA-Pt(II). The solid was filtered and dried under vacuum. A weight of 0.42 g of the productwas obtained in an 87% yield. |