Molecular design, chemical synthesis and biological evaluation of quinoxaline–carbohydrate hybrids as novel and selective photo-induced DNA cleaving and cytotoxic agents

Toshima, Kazunobu; Kimura, Tomonori; Takano, Ryusuke; Ozawa, Tomohiro; Ariga, Akiko; Shima, Yutaka; Umezawa, Kazuo; Matsumura, Shuichi

doi:10.1016/s0040-4020(03)00820-2

Cited by 20 publications

(8 citation statements)

References 20 publications

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“…rings and a groove binding cyclic peptidic chain [58]. The specifity concerning binding of the quinoxaline antibiotic depends on the peptide backbone interaction in the minor groove.…”

Section: Minor Groove Binder With Different Basic Structure and Functmentioning

confidence: 99%

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Advances in DNA-Ligands with Groove Binding, Intercalating and/or Alkylating Activity: Chemistry, DNA-Binding and Biology

Pindur¹,

Jansen²,

Lemster

2005

CMC

105

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It is known that DNA is a well-characterized intracellular target but its size and sequential characteristics make it an elusive target for selective drug action. Binding of low molecular weight ligands to DNA causes a variety of significant biological responses. In this context the main consideration is given to recent developments in DNA sequence selective binding agents bearing conjugated effectors because of their potential application in treatment of cancers, in diagnosis as well as in molecular biology. In the present review recent results about analogues of netropsins, distamycin A and of some lexitropsins and combilexins or related hybrid molecules with sequence reading, intercalating or alkylating activity are described and evaluated for prospective applications. Furthermore there exists DNA minor groove binder with different basic structures which does not possess the typical polyamide chain, including dimeric intercalating chromophores. Finally new results about peptide nucleic acids and related nucleic acid bases linked with polyamides are reported. In pronounced examples the structural chemistry, synthesis, DNA binding with several biophysical methods, molecular aspects, structure activity relationship, topoisomerase inhibition, antitumour and antibacterial effects are discussed in detail.

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“…rings and a groove binding cyclic peptidic chain [58]. The specifity concerning binding of the quinoxaline antibiotic depends on the peptide backbone interaction in the minor groove.…”

Section: Minor Groove Binder With Different Basic Structure and Functmentioning

confidence: 99%

“…For further variants of dimeric intercalators see also the following chapter. In a new study on photodynamic therapy using photosensitizing drugs the photocleaving property of novel quinoxaline-carbohydrate hybrids 64 as artificial light activatable agents is described [58] (Fig. (33), (34)).…”

Section: Minor Groove Binder With Different Basic Structure and Functmentioning

confidence: 99%

Advances in DNA-Ligands with Groove Binding, Intercalating and/or Alkylating Activity: Chemistry, DNA-Binding and Biology

Pindur¹,

Jansen²,

Lemster

2005

CMC

105

View full text Add to dashboard Cite

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“…[3] Numerous quinoxaline derivatives have been reported to produce a wide range of biologically active compounds. [4][5][6] Recently, there have been efforts to incorporate a quinoxaline unit into conjugated methinium systems.…”

mentioning

confidence: 99%

Striking Antitumor Activity of a Methinium System with Incorporated Quinoxaline Unit Obtained by Spontaneous Cyclization

et al. 2015

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“…Several quinoxaline derivatives are associated with a broad range of physiological activities such as antimalarial (Haworth and Robinson, 1948), antibacterial (Khan, 2008), antifungal (Ali et al, 2000), anticancer (Toshima et al, 2003), antidiabetic (Sarges, 1990), antitubercular (Jaso et al, 2005), and anticonvulsant (Cai et al, 1997). They are also used as fluorescent dyes and effective dyeing photo initiators for free radical polymerization (Kucybala and Paczkowski, 1999;Rangnekar and Sonawane, 2000).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel quinoxalinone derivatives by conventional and microwave methods and assessing their biological activity

et al. 2011

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In this study, twenty-one arylaminoquinoxalinone derivatives were synthesized and their antibacterial activities against Staphylococci aureus, Pseudomonas aureus, Escherichia coli, Bacillus subtilis, Salmonella typhi, and Shigella pneumoniae were evaluated relative to known antibiotics; augmentin, ampicillin, and chloramphenicol. The insecticidal activities of the prepared compounds were also investigated against Tribolium castaneum using permethrin as a standard insecticide. The derivatives were synthesized using both conventional and microwave techniques. Their structures were confirmed using spectral techniques and elemental analysis.

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Molecular design, chemical synthesis and biological evaluation of quinoxaline–carbohydrate hybrids as novel and selective photo-induced DNA cleaving and cytotoxic agents

Cited by 20 publications

References 20 publications

Advances in DNA-Ligands with Groove Binding, Intercalating and/or Alkylating Activity: Chemistry, DNA-Binding and Biology

Advances in DNA-Ligands with Groove Binding, Intercalating and/or Alkylating Activity: Chemistry, DNA-Binding and Biology

Striking Antitumor Activity of a Methinium System with Incorporated Quinoxaline Unit Obtained by Spontaneous Cyclization

Synthesis of novel quinoxalinone derivatives by conventional and microwave methods and assessing their biological activity

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