Synthesis and SAR of Potential Anti-Cancer Agents of Quinoline
Analogues: A Review

Tyagi, Sonakshi; Salahuddin, Salahuddin; Mazumder, Avijit; Kumar, Raj; Datt, Vimal; Shabana, Km; Yar, Mohammad Shahar; Ahsan, Mohamed Jawed

doi:10.2174/1573406419666230228140619

Cited by 4 publications

(2 citation statements)

References 86 publications

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“…14,15 Notable medicinal applications associated with the quinoline heterocycle includes anticancer, antiviral, antitubercular and many other biological properties with significant interest in the creation of beneficial quinoline-based anticancer compounds such as Campothecin, Topotecan and Irinotecan. 16–20…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis and cytotoxic activity of molecular hybrids based on quinolin-8-yloxy and cinnamide hybrids and their apoptosis inducing property

Binjawhar,

Al-Salmi,

Abu Ali

et al. 2024

RSC Adv.

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Section: Introductionmentioning

confidence: 99%

Design, synthesis and cytotoxic activity of molecular hybrids based on quinolin-8-yloxy and cinnamide hybrids and their apoptosis inducing property

Binjawhar,

Al-Salmi,

Abu Ali

et al. 2024

RSC Adv.

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“…The chelating center of Q1 comprises the nitrogen of the quinoline part, which acts as a Schiff base, and the adjacent oxygen of the quinone. Quinoline and its derivatives have wide biological and pharmacological applications, including anticancer and antimicrobial activity [ 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 ]. Similar diverse activity has also been shown by transition and other metal complexes of quinoline and its derivatives, such as 8-hydroxyquinoline ( Figure 1 ) [ 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 ].…”

Section: Introductionmentioning

confidence: 99%

Increased Free Radical Generation during the Interaction of a Quinone-Quinoline Chelator with Metal Ions and the Enhancing Effect of Light

et al. 2023

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Schiff bases and similar molecules forming metal complexes may cause redox effects, which may also be influenced by light. Anthraquinones such as doxorubicin and idarubicin are widely used antitumor agents, which can generate reactive oxygen species (ROS), stimulated by both the presence of iron and copper ions and also by light. The generated ROS can cause DNA scission, cell membrane oxidation, and many other toxic effects. The redox activity of the quinone-quinoline chelator 2-phenyl-4-(butylamino)naphtho [2,3-h]quinoline-7,12-dione (Q1) was investigated in the presence of iron, copper, and zinc. The influence of light in these interactions was also examined. The chemically induced dynamic nuclear polarization (CIDNP), nuclear magnetic resonance (NMR), and electron paramagnetic resonance (EPR) methods were used to elucidate the molecular changes and ROS generation effects of the Q1 metal interactions. A model electron transfer reaction system between 1,4-dihydropyridine and Q1 was utilized to demonstrate that the chelate complexes of Q1 with both Fe(III) and Cu(II) ions were more redox active than Q1 itself. Similarly, CIDNP and NMR data showed that the concentration dependence of the free radicals yield is much higher in the presence of Fe(III) and Cu(II) ions, in comparison to Zn(II), and also that it increased in the presence of light. These findings underline the role of transition metal ions and Q1 in cyclic redox chain reactions and increase the prospect of the development of copper- and iron-based chelating agents, including Q1 and its derivatives, for anticancer therapy. Furthermore, these findings also signify the effect of light on enhancing ROS formation by Q1 and the prospect of utilizing such information for designing target specific anticancer drugs for photodynamic therapy.

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Molecular Hybrids of Quinoline and Sulfonamide: Design, Synthesis and in Vitro Anticancer Studies

Panduranga,

Makam,

Kumar Katari

et al. 2024

ChemistryOpen

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Molecular hybrids of diversely functionalized quinoline and sulfonamide have been designed. Multistep synthetic strategies have been used for the synthesis. The anti‐cancer properties have been evaluated against various cancer cell lines including HCT116, A549, U2OS, CCRF‐CEM, Jurkat, MOLT‐4, RAMOS, and K562. Non‐cancer cell lines MRC‐5 and BJ were also included for comparison. When examining the effects on A549, HCT116, and U2OS cells, all tested compounds exhibited limited potency with IC50 values exceeding 50 μM, indicating weak activity against these cell lines. Against the ITK high cells Viz. are Jurkat, CCRF‐CEM and MOLT‐4, 9 e, 9 p and 9 j found to the maximum potent compounds with IC50 values of 7.43±7.40 μM, 13.19±1.25 μM and 5.57±7.56 μM respectively. Similarly, in the BTK high cells screenings, 9 n and 9 e molecules with an IC50 value of 2.76±0.79 μM and 5.47±1.71 μM against RAMOS and K562 respectively are highly potent. Interestingly, all the molecules have exhibited IC50 value >50 μM against the non‐cancer cells (MRC‐5 and BJ), which indicates the promising non‐cytotoxic nature of the molecules.

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Synthesis and SAR of Potential Anti-Cancer Agents of Quinoline Analogues: A Review

Cited by 4 publications

References 86 publications

Design, synthesis and cytotoxic activity of molecular hybrids based on quinolin-8-yloxy and cinnamide hybrids and their apoptosis inducing property

Design, synthesis and cytotoxic activity of molecular hybrids based on quinolin-8-yloxy and cinnamide hybrids and their apoptosis inducing property

Increased Free Radical Generation during the Interaction of a Quinone-Quinoline Chelator with Metal Ions and the Enhancing Effect of Light

Molecular Hybrids of Quinoline and Sulfonamide: Design, Synthesis and in Vitro Anticancer Studies

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