Synthesis, cytotoxic evaluation, and DNA binding of novel thiazolo[5,4-b]quinoline derivatives

Loza-Mejía, Marco A.; Maldonado-Hernández, Karina; Rodríguez-Hernández, Fernando; Rodríguez‐Sotres, Rogelio; González-Sánchez, Ignacio; Quintero, Angelina; Solano, José D.; Lira‐Rocha, Alfonso

doi:10.1016/j.bmc.2007.10.084

Cited by 22 publications

(15 citation statements)

References 10 publications

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“…These observations are in agreement with NOESY experiments performed for 6b and 6f, which suggest that the anilino ring in these compounds is not orthogonal to tricyclic nucleus but slightly oblique [14]. In addition, a good correlation between the Hammet parameter of the substituent present in the anilino ring and ta was observed as indicated in Fig.…”

Section: Molecular Modeling Of Isolated Moleculessupporting

confidence: 90%

“…LUMO energy values are lower in acridines and benzonaphthyridines (Table 1), suggesting these should be better intercalators than the other compounds. This is true, at least, for thiazoloquinolines which exhibited lower DNA binding affinity than did acridines, as shown in a previous study [14]. However, intercalation properties do not always correlate with cytotoxic activity; for instance, o-AMSA possesses a high affinity for DNA but lower cytotoxic activity than its isomer amsacrine (m-AMSA) [27].…”

Section: Molecular Modeling Of Isolated Moleculesmentioning

confidence: 78%

“…In the analyzed compounds with non-substituent or electron-releasing groups in the aniline ring, the dipole vector is oriented towards the tricyclic template, whereas when an electron-withdrawing group is attached, the vector is directed towards the aniline ring. Interestingly, compounds with a high dipole value have shown poor cytotoxic activity (5b, 6d and 6i) [14,30]. Although there is no agreement between dipole magnitude and cytotoxic activity, the available data suggests that compounds with a dipole value lower than 4.00 might have good cytotoxic activity [14,30].…”

Section: Molecular Modeling Of Isolated Moleculesmentioning

confidence: 96%

“…1), which have shown cytotoxic activity. Interestingly, structural requirements in the anilino ring for the improvement of cytotoxic activity differ from those of 9-anilinoacridines [14,15].…”

Section: Introductionmentioning

confidence: 95%

“…This consideration led to the synthesis of compounds such as 9-anilinothiazolo [5,4-b]quinoline 2 [13,14] and 4-anilinofuro [2,3-b]quinoline 3 [15] derivatives ( Fig. 1), which have shown cytotoxic activity.…”

Section: Introductionmentioning

confidence: 99%

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Molecular modeling of tricyclic compounds with anilino substituents and their intercalation complexes with DNA sequences

Loza-Mejía

Castillo

Lira‐Rocha

2009

Journal of Molecular Graphics and Modelling

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Section: Molecular Modeling Of Isolated Moleculessupporting

confidence: 90%

Section: Molecular Modeling Of Isolated Moleculesmentioning

confidence: 78%

Section: Molecular Modeling Of Isolated Moleculesmentioning

confidence: 96%

Section: Introductionmentioning

confidence: 95%

Section: Introductionmentioning

confidence: 99%

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Molecular modeling of tricyclic compounds with anilino substituents and their intercalation complexes with DNA sequences

Loza-Mejía

Castillo

Lira‐Rocha

2009

Journal of Molecular Graphics and Modelling

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Proteomic Profiling Reveals the Induction of UPR in Addition to DNA Damage Response in HeLa Cells Treated With the Thiazolo[5,4‐b]Quinoline Derivative D3ClP

Páez-Franco

González-Sánchez

Gutiérrez-Nájera

et al. 2016

J of Cellular Biochemistry

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9-[(3-chloro)phenylamine]-2-[3-(diethylamine)propylamine]thiazolo[5,4-b]quinolone (D3ClP) is a bioisostere of N-(4-(acridin-9-ylamino)-3-methoxyphenyl)methanesulfonamide (m-AMSA) a DNA topoisomerase II inhibitor with proven cytotoxic activity and known to induce DNA damage and apoptotic cell death in K562 cells. However, recent evidence is not consistent with DNA topoisomerase II (DNA TOP2) as the primary target of D3ClP, in contrast to m-AMSA. We provide evidence of histone γH2AX phosphorylation at Ser135 in HeLa cells treated with D3ClP, a marker of DNA double strand repair through Mre11-Rad50-Nbs1 (MRN) pathway. Using two-dimensional gel electrophoresis and mass spectrometry, the upregulation of the protein GRP78, the cleavage of Cytokeratin 18, and the downregulation of prothymosine, calumenin, and the α chain of the nascent polypeptide associated complex were observed in HeLa cells treated with D3ClP. An increase in GRP78 has been related with the onset and progression of the unfolded protein response (UPR), a process aimed to reduce endoplasmic reticulum (ER) stress and protein misfolding. The IRE1-α dependent splicing of mRNA encoding X-box binding protein 1 was detected. Microtubule-associated Proteins 1A/1B, Light Chain 3-II (LC3b-II) accumulation was observed, and suggest some involvement of autophagy. The production of the pro-apoptotic protein DNA-damage-inducible protein 153 (GADD-153) was also detected. These results, are consistent with the induction of the UPR and the DNA-Damage Response in D3ClP-treated HeLa cells, and are also consistent with a concurrent apoptotic cell death. J. Cell. Biochem. 118: 1164-1173, 2017. © 2016 Wiley Periodicals, Inc.

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Synthesis of novel 9‐amino/aryl/oxo‐2‐(het)arylthiazolo[4,5‐b]quinolines via palladium catalyzed N‐arylation‐cyclization protocol

Iniyavan

Avadhani

Kumar

et al. 2022

Journal of Heterocyclic Chem

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An efficient approach for the facile synthesis of novel hitherto unexplored 2-(het)aryl-9-amino/aryl-thiazolo [4,5-b]quinolines and the corresponding thiazolo[4,5-b]quinolin-9(4H)-ones via synthetic elaboration of 2-substituted-4-amino-5-cyano/aroyl/carboethoxy thiazoles have been developed. The overall strategy involves palladium catalyzed N-arylation of these 4-aminothiazoles to the corresponding 4-(N-aryl)thiazoles, and their subsequent triflic acid mediated intramolecular-cyclocondensation to the target compounds. This new and straightforward protocol displays broad substrate scope, and is applicable for the synthesis of 9-amino/aryl and 9-(4H)quinolones from the respective 5-cyano/aroyl/carboethoxy thiazoles in good yields.

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Synthesis, cytotoxic evaluation, and DNA binding of novel thiazolo[5,4-b]quinoline derivatives

Cited by 22 publications

References 10 publications

Molecular modeling of tricyclic compounds with anilino substituents and their intercalation complexes with DNA sequences

Molecular modeling of tricyclic compounds with anilino substituents and their intercalation complexes with DNA sequences

Proteomic Profiling Reveals the Induction of UPR in Addition to DNA Damage Response in HeLa Cells Treated With the Thiazolo[5,4‐b]Quinoline Derivative D3ClP

Synthesis of novel 9‐amino/aryl/oxo‐2‐(het)arylthiazolo[4,5‐b]quinolines via palladium catalyzed N‐arylation‐cyclization protocol

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