The antitumor drug 3-nitrobenzothiazolo(3,2-a)quinolinium chloride (NBQ): effects on lens regeneration and interaction with DNA of Notophthalmus viridescens

González, Fernando; Llende, Marta; Báez, Adriana; Ortiz, José R.

doi:10.1111/j.1432-0436.1987.tb00186.x

Cited by 11 publications

(2 citation statements)

References 37 publications

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“…During the past few years, work in our laboratory has been focused in the design and synthesis of benzazolo-[3,2-a]quinolinium salts, a new family of unnatural alkaloids that have been shown to be potent antitumor agents [1][2][3][4][5][6][7][8][9][10][11][12]. Recent work has shown that these salts exert their mechanism of action by inhibition of topoisomerase II activity [10,12].…”

Section: Introductionmentioning

confidence: 99%

Regioselective photocyclization of (e)‐2‐(2,3,6‐trichlorostyryl)‐benzothiazole and synthesis of 3,4‐dichloro‐ and 4‐chlorobenzothiazolo[3,2‐α]quinolinium chlorides: A synthetic and theoretical study

Cox

García

Cordero

2008

Journal of Heterocyclic Chem

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A high degree of regioselectivity is observed in the photochemically induced cyclization of (E)‐2‐(2,3,6‐trichlorostyryl)benzothiazole (1a). According to the proposed mechanism, this compound was expected to afford two products, 3,4‐dichloro‐ and 1,4‐dichlorobenzothiazolo[3,2‐α]quinolinium chlorides (4a and 4a', respectively). However, this reaction produced 3,4‐dichlorobenzazolo[3,2‐α]quinolinium chloride (4a) as the sole product. On the other hand, irradiation of (E)‐2‐(2,3,5‐trichlorostyryl)benzothiazole (1b) failed to produce the expected 1,3‐dichlorobenzothiazolo[3,2‐α]quinolinium chloride (4b). Furthermore, (E)‐2,3‐difluorostrylbenzothiazole (1c) also failed to give the corresponding 1‐fluorobenzothiazolo[3,2‐α]quinolinium fluoride (4c). Interestingly, the irradiation of 2,6‐dichlorostyrylbenzothialole (1d) produced 4‐chlorobenzothiazolo[3,2‐α]quinolinium chloride (4d) in excellent yield. This paper presents the results of these investigations and a mechanistic rationale for the outcome of this reaction based on steric arguments and theoretical studies using a combination of molecular mechanics (MM+) and semiempirical quantum mechanical calculations (PM3/RHF/CI). Two‐dimensional high field nmr methods were employed to make complete assignments of the proton and carbon spectra of all new compounds.

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Section: Introductionmentioning

confidence: 99%

Regioselective photocyclization of (e)‐2‐(2,3,6‐trichlorostyryl)‐benzothiazole and synthesis of 3,4‐dichloro‐ and 4‐chlorobenzothiazolo[3,2‐α]quinolinium chlorides: A synthetic and theoretical study

Cox

García

Cordero

2008

Journal of Heterocyclic Chem

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“…Lens regeneration is dependent on the presence of Present address: Biochemical Toxicology Division, National Center Toxicological Research, Jellerson, AR 72079, USA Correspondence to: A. Baez the neural retina or its products such as eye-derived growth factors [7, 8, 101. Yamada and Roesel demonstrated that the formation of a new lens is inhibited by continuous exposure of animals to the antitumor drug actinomycin D, a phenomenon they associated with the inhibition of the proliferative activity of IECs [25]. On the other hand, we have recently shown that the novel antitumor drug 3nitrobenzothiazolo[3,2-a]quinolinium chloride (NBQ), stimulates lens regeneration in vivo [12]. More recently, we have demonstrated that NBQ also induces differentiation of the promyelocytic leukemia cell line HL-60 to the myeloid pathway [l].…”

Section: Introductionmentioning

confidence: 99%

Effects of 3-nitrobenzothiazolo [3,2-a] quinolinium chloride (NBQ) and doxorubicin on lens regeneration in the adult newt: a morphological study

1994

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Electrochemical and electron spin resonance studies of selected benzazolo[3,2‐a]quinolinium salts

Cox

Dumas

Rivera

et al. 1999

Journal of Heterocyclic Chem

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The electrochemical reduction of the chloride or perchlorate salts of benzazolo[3,2‐a]quinolinium ion and several of its analogues is reported. The compounds studied are the perchlorate salt of 3‐nitrobenzothiazolo‐and 3‐nitro‐9‐methoxybenzothiazolo[3,2‐a]quinolinium, and the chloride salts of 7‐ethyl‐, 3‐nitro‐7‐methyl‐, 3‐nitro‐7‐ethyl‐, 3‐nitro‐7‐isopropyl‐, 3‐nitro‐7‐butyl‐ and 3‐nitro‐7‐benzylbenzimidazolo[3,2‐a]‐quinolinium, respectively. Cyclic voltammetry of the corresponding 3‐nitrobenzothiazolo[3,2‐a]quinolinium derivatives in N,N‐dimethylformamide shows an irreversible peak potential at ‐0.6 and a quasi‐reversible peak at ‐(1.2–1.3) volts, respectively, relative to the standard calomel electrode. In contrast, the corresponding 3‐nitrobenzimidazolo[3,2‐a]quinolinium derivatives show, in general, reversible peaks at near ‐0.8 and ‐(1.2–1.4) volts, respectively. Upon electrolytic reduction, only the nitro‐substituted derivatives produced observable electron paramagnetic resonance electron spin resonance spectra. This observation is explained in terms of the stabilization of the radicals produced by the nitro group. Theoretical MM+/AM1/UHF calculations support the idea that the larger nitrogen splitting is caused by N‐12 and the minor splittings by N‐7 in the benzimidazolo[3,2‐a]quinolinium ion series.

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The antitumor drug 3-nitrobenzothiazolo(3,2-a)quinolinium chloride (NBQ): effects on lens regeneration and interaction with DNA of Notophthalmus viridescens

Cited by 11 publications

References 37 publications

Regioselective photocyclization of (e)‐2‐(2,3,6‐trichlorostyryl)‐benzothiazole and synthesis of 3,4‐dichloro‐ and 4‐chlorobenzothiazolo[3,2‐α]quinolinium chlorides: A synthetic and theoretical study

Regioselective photocyclization of (e)‐2‐(2,3,6‐trichlorostyryl)‐benzothiazole and synthesis of 3,4‐dichloro‐ and 4‐chlorobenzothiazolo[3,2‐α]quinolinium chlorides: A synthetic and theoretical study

Effects of 3-nitrobenzothiazolo [3,2-a] quinolinium chloride (NBQ) and doxorubicin on lens regeneration in the adult newt: a morphological study

Electrochemical and electron spin resonance studies of selected benzazolo[3,2‐a]quinolinium salts

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