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

Herreno-Sáenz, Diógenes; Ortiz, José R.; Báez, Adriana

doi:10.1046/j.1432-0436.1994.5530169.x

Cited by 9 publications

(2 citation statements)

References 26 publications

(13 reference statements)

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“…Herreno-Saenz et al recently revealed that the antitumour drug 3-nitrobenzothiazolo [3,2,-a] quinolium chloride (NBQ) stimulates the in vivo lens regeneration in the adult newt Notophthalmus viridescens [6]. They also showed that another antitumour drug, doxorubicin, which is an intercalating agent just like actinomycin D, strongly inhibited lens regeneration after long-term treatment.…”

Section: Discussionmentioning

confidence: 99%

Simultaneous demonstration of lens regeneration from dorsal iris and tumour production from ventral iris in the same newt eye after carcinogen administration

Okamoto

1997

Differentiation

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Section: Discussionmentioning

confidence: 99%

Simultaneous demonstration of lens regeneration from dorsal iris and tumour production from ventral iris in the same newt eye after carcinogen administration

Okamoto

1997

Differentiation

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

Cited by 9 publications

References 26 publications

Simultaneous demonstration of lens regeneration from dorsal iris and tumour production from ventral iris in the same newt eye after carcinogen administration

Simultaneous demonstration of lens regeneration from dorsal iris and tumour production from ventral iris in the same newt eye after carcinogen administration

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

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

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