Imide derivatives of 3-nitro-1.8-naphthalic acid: Their inhibitory activity against DNA viruses

Gancedo, A. García; Gil-Fernández, Carmen; Vilas, Pilar; Pérez, Sara; Páez, Eduardo Ortega; Rodríguez, Francisco Javier García; Braña, Miguel F.; Roldán, C. M.

doi:10.1007/bf01314709

Cited by 8 publications

(3 citation statements)

References 5 publications

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“…The biological activity of N -substituted naphthalimides has been studied since the early 1940s. The activity of simple analogues includes antiviral [ 9 ], antibacterial [ 10 ] and antitrypanosomal properties [ 11 ]. Special attention has been devoted to the high anticancer activity of naphthalimides [ 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 ], which is due to their interactions with DNA by intercalation.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, FTIR, 13C-NMR and Temperature-Dependent 1H‑NMR Characteristics of Bis-naphthalimide Derivatives

Grzesiak

Brycki

2012

Molecules

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Chemotherapy is still the most important method of cancer treatment. To make this method more effective and safe, new drugs to destroy cancer cells are needed. Some bis-naphthalimide derivatives show potential anticancer activity via an intercalation mechanism. A higher degree of DNA intercalation corresponds to better therapeutic effects. The degree of intercalation of naphthalimides depends on their structure, molecular dynamics and intermolecular interactions with DNA. In order to apply any active substance as a drug, its molecular dynamics as well as possible interactions with target molecules have to be examined in exhaustive details. This paper describes a practical preparation of some novel bis-naphthalimide derivatives with different functional groups and their FTIR and 1H- and 13C-NMR spectral characteristics. To determine the molecular dynamics of the obtained compounds the temperature, their 1H-NMR spectra were measured. It has been clearly proven in this paper that the unusual temperature-dependent 1H-NMR behavior of the aromatic protons of phthalimide derivatives, previously described in the literature as “hypersensitivity” and explained by n-π interactions and molecular motions of aromatic amide rings, is a result of temperature driven changes of the geometry of carbonyl groups.

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Section: Introductionmentioning

confidence: 99%

Synthesis, FTIR, 13C-NMR and Temperature-Dependent 1H‑NMR Characteristics of Bis-naphthalimide Derivatives

Grzesiak

Brycki

2012

Molecules

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“…Using the human myeloid cell lines HL-60 and KBM-3, amonafide induced single strand breaks and topoisomerase-II mediated DNA cleavage, which disappeared rapidly following removal of the drug from the media [11][12][13]. In addition to these effects on DNA, amonafide has also been observed to inhibit protein and nucleotide synthesis at a concentration of 10 -5 M. At a concentration of 10-4 M, RNA and DNA synthesis was completely inhibited [15,16]. Preclinical activity of amonafide demonstrated a broad activity spectrum against 60% of the murine tumor cell lines [17,18].…”

Section: Introductionmentioning

confidence: 99%

Phase II study of amonafide in advanced pancreatic adenocarcinoma

et al. 1991

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To determine the efficacy of amonafide in patients with advanced, measurable pancreatic adenocarcinoma, 15 patients previously untreated with chemotherapy were entered on a phase II trial. The starting dose was 400 mg/m2 administered daily over 1 hr for 5 consecutive days repeated every 3 weeks. Because of grade 4 myelosuppression observed in the initial 2 patients, the daily starting dose was decreased to 350 mg/m2. Of the 15 patients, 14 were evaluable. Amonafide failed to produce clinical responses in the doses and schedule employed. Grade 4 granulocytopenia was observed in 3 of 9 courses at 400 mg/m2, 3 of 12 courses at 350 mg/m2 and in 1 of 4 courses at 300 mg/m2. Grade 4 thrombocytopenia was observed in 3 courses at 400 mg/m2. Nonhematologic toxicities included mild nausea and vomiting and skin rashes.

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“…Benzisoquinolinedione, 5-amino-2 [2-(dimethylamino) ethyl]-1H-benz [de]isoquinoline-1,3(2H)-dione (amonafide, previously named nafidamide) is one of a series of benz[de]-isoquinoline-l,3-dione compounds recently demonstrated to possess antitumor and antiviral activities [1][2][3]. Amonafide was found by the National Cancer Institute (NCI) to be active against P388 and L1210 leukemia, as well as B16 melanoma and M5076 sarcoma.…”

Section: Introductionmentioning

confidence: 99%

In vitro activity of amonafide against primary human tumors compared with the activity of standard agents

1988

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Amonafide, one of a series of benz[de]-isoquinoline-1,3-dione compounds, is now entering phase II clinical trials in this country. We tested amonafide, exposed continuously for 5 days, at four different concentrations against 56 primary human tumors in vitro. The drug concentration range used was based on amonafide's inhibitory activity against human bone marrow cells. The antitumor activity of 5-fluorouracil, mitomycin C, cisplatin, and etoposide against tumors from this panel of 56 was compared with that of amonafide at in vitro concentrations equitoxic against human bone marrow cells. Amonafide was active against only 12% of tumors compared with standard agents, which were active against more than 40% of tumors in the human bone marrow inhibitory range. Our data suggested that amonafide is less likely to be clinically active against human solid tumors than the standard agents.

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Imide derivatives of 3-nitro-1.8-naphthalic acid: Their inhibitory activity against DNA viruses

Cited by 8 publications

References 5 publications

Synthesis, FTIR, 13C-NMR and Temperature-Dependent 1H‑NMR Characteristics of Bis-naphthalimide Derivatives

Synthesis, FTIR, 13C-NMR and Temperature-Dependent 1H‑NMR Characteristics of Bis-naphthalimide Derivatives

Phase II study of amonafide in advanced pancreatic adenocarcinoma

In vitro activity of amonafide against primary human tumors compared with the activity of standard agents

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