Luminescent Anticancer Acenaphtho[1, 2‐b]quinoxaline: Green Synthesis, DFT and Molecular Docking Studies, Live‐Cell Imaging and Reactivity towards Nucleic Acid and Protein BSA

Abstract

A series of acenaphtho[1, 2‐b]quinoxaline derivatives 3 a‐3 j were prepared using single step condensation of acenaphthoquinone with different o‐phenylene diamine derivatives on water under sonication. Interaction of 9‐fluoro acenaptho[1, 2‐b]quinoxaline (3 g) with calf‐thymus DNA has been explored by using absorption and emission techniques. The compound 3 g cleave DNA oxidatively without any exogenous additives. The protein binding ability has been observed by quenching of tryptophan emission in the presence of 3 g using bovine serum albumin (BSA) as model protein. The DNA and protein docking study suggests that most of the quinoxaline derivatives interact with DNA through the minor groove and occupies the active site of the protein favorably by hydrogen bonding. The density functional calculations carried out on 3 a‐3 j have shown that electron‐rich regions in the highest occupied orbital are localized on the quinoxaline moiety. Live‐cells imaging result showed the clear evidence of strong cellular uptake of compound 3 g in HeLa cell line. The MTT assay concluded that compounds:9,10‐dichloroacenaptho[1, 2‐b]quinoxaline (3 d), 9‐bromoacenaptho[1, 2‐b]quinoxaline (3 e), 3 g and 9‐chloro‐10‐fluroacenaptho[1, 2‐b]quinoxaline (3 j) were exhibited highly selective cytotoxicity profiles in two cancer cell lines such as MCF‐7 and HeLa with respect to normal HEK‐293. Among them, compound 3 g displayed high potency and selectivity in all the cell lines.

One pot three component synthesis of DNA targeting phototoxic Ru(ii)-p-cymene dipyrido[3,2-a:2′,3′-c]phenazine analogues

“…In this contribution we are making a point to achieve excellent yields, higher atom economy, and one pot synthesis to reduce the reaction steps, use of water as a green solvent, and implementation of ultrasonic irradiation to avoid hazardous reaction conditions, to develop a more energy efficient synthetic route. 23,24 The photodynamic effect is basically the harm or damage of living cells or tissues by visible light in the presence of a photosensitizer and oxygen. 25,26 The mechanism of PDT is really fascinating and it consists of two types, Type-I which leads to the formation of a superoxide or a hydroperoxyl radical (HO 2…”

“…In this contribution we are making a point to achieve excellent yields, higher atom economy, and one pot synthesis to reduce the reaction steps, use of water as a green solvent, and implementation of ultrasonic irradiation to avoid hazardous reaction conditions, to develop a more energy efficient synthetic route. 23,24…”

Recent Advances in the Synthesis of Hetero- and Carbocyclic Compounds­ and Complexes Based on Acenaphthylene-1,2-dione

“…Guo et al 46 reported an environmentally friendly method for the synthesis of novel spiro-2-amino-3-phenylsulfonyl-4H-pyran derivatives 91 in 88-94% yields in EtOH with a novel basic ionic liquid, 2-hydroxyethylammonium acetate [H 3 N + CH 2 CH 2 OH][AcO -] (HEAA), as the catalyst in the multicomponent reaction of phenylsulfonylacetonitrile (92) and 1,3-dicarbonyl compounds 90c-f,k with 1 (Scheme 32). The 1,3-dipolar cycloaddition reaction of 2-oxo-(2H)acenaphthylen-1-ylidene-malononitrile (72) as the dipolarophile has been reported with azomethine ylides generated in situ from N-substituted isatins 93 and sarcosine (2) for the synthesis of novel dispiropyrrolidine oxindole derivatives 94 in 73-79% yields (Scheme 33).…”

“…Some of the synthesized derivatives exhibited cytotoxic activity. 92 Scheme 66 Synthesis of arylquinoxaline derivatives 188 using a metal catalyst 2-Oxindolyl-2-hydroxyacenaphthylen-1-ones 190 were synthesized in 81-88% yields by a one-pot, three-component reaction of 3-diazooxindole 191, benzyl alcohol derivatives (192) and 1 in the presence of rhodium(II) acetate (1 mol%) as the catalyst with high chemo-and diastereoselectivity (Scheme 67). Antibacterial activities of the synthesized oxindoles and group-based quantitative structure-activity relationships (GQSAR) for all antibacterial activities were evaluated.…”

Bioactive O^N^O^ Schiff base appended homoleptic titanium(iv) complexes: DFT, BSA/CT-DNA interactions, molecular docking and antitumor activity against HeLa and A549 cell lines

“…Moreover, intercalation can result in signicant changes to the length of the DNA helix, stiffness and unwinding that have powerful impacts on DNA replication and transcription. 46,47 Human serum albumin (HSA, 66.5 kDa) is the most prevalent protein in human plasma; it binds with various ligands associated with metal complexes at various locations, and it plays a vital role in the transport and control over the bioactivity of titanium(IV) derivatives, including cytotoxic drugs. The binding interaction of BSA (75% sequence identity with HSA) with derivatives of titanium(IV) facilitates determination of the affinity constant and primary coordination sites.…”