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Cytotoxic, genotoxic and apoptotic effects of naringenin-oxime relative to naringenin on normal and cancer cell lines

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Asian Pacific Journal of Tropical Biomedicine 2016年第10期6卷 872-880页

作者： Abdurrahim Kocyigit Ismail Koyuncu Murat Dikilitas Fatemeh Bahadori Baki Turkkan Department of Medical Biochemistry Faculty of Medicine Bezmialem Vakif University Department of Biology Faculty of Arts and Sciences Harran University Department of Plant Protection Faculty of Agriculture Harran University Department of Pharmaceutical Biotechnology Faculty of Pharmacy Bezmialem Vakif University Department of Chemistry Faculty of Arts and Sciences Harran University

Objective: To assess and compare the cytotoxic, genotoxic, apoptotic and reactive oxygen species(ROS) generating effects of naringenin(NG) and its new derived compound naringenin-oxime(NG-Ox) on MCF-7, HT-29, PC-12 cancer and L-929 normal cell lines.Methods: The cells were incubated with different doses of NG-Ox and NG(50–1 000 mmol/L) for 24 h. The cell viability was assessed based on ATP cell viability assay.Intracellular accumulation of ROS was determined using the fluorescent probes 2070-dichlorodihydrofluorescin diacetate. genotoxic effects were evaluated by alkaline single cell gel electrophoresis assay(comet assay) and, the apoptotic effect was evaluated by acridine orange staining at below the IC50 levels.Results: Both NG-Ox and NG exhibited cytotoxic, genotoxic and apoptotic effects and resulted in increased ROS values in a dose-dependent manner. The effects were more pronounced on cancer cell lines. The cytotoxic, genotoxic and apoptotic effects of NG-Ox were higher than that of NG in all cell lines. Significant correlations were observed between cell viability, DNA damage, apoptosis and ROS, in all cell lines exposed to either NG-Ox or NG.Conclusions: This study showed that both NG-Ox and NG possess cytotoxic, genotoxic and apoptotic activities through the production of ROS on cells, NG-Ox being the more effective one. Therefore, derived compound of NG might be used as antiproliferative agents for the treatment of cancer.

关键词： Naringenin Naringenin-oxime Cytotoxic genotoxic Apoptosis Reactive oxygen species Comet assay

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Ultra-Sensitive LC-MS/MS Method for the Trace Level Quantification of Six Potential genotoxic Nitrosamine Impurities in Telmisartan

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American Journal of Analytical Chemistry 2021年第6期12卷 227-240页

作者： Kartheek Srinivas Chidella Vijaya Bharathi Dasari Jayashree Anireddy Center for Chemical Sciences and Technology Institute of Science and Technology Jawaharlal Nehru Technological University Hyderabad Hyderabad India Aurobindo Pharma Laboratory Research Center II Hyderabad India

Nitrosamine impurities are potentially genotoxic which are considered under cohort of concern as per ICH M7 guidelines and need to be controlled at trace levels during quantification in drug substances and drug products for safe human consumption. Recent regulatory requirements also suggest the need to have highly sensitive analytical methods for the accurate quantification of Nitrosamine impurities. In this paper we have presented simple, rapid and ultra-sensitive LC-MS/MS method for six potential genotoxic nitrosamine impurities: N-Nitroso dimethyl amine (NDMA), N-Nitroso diethyl amine (NDEA), N-Nitroso Ethyl Iso propylamine (NEIPA), N-Nitroso-N-methyl-4-aminobutyric acid (NMBA) N-Nitroso diisopropylamino (NDIPA) and N-Nitroso dibutyl amine (NDBA) with a LOQ of 0.004 ppm. Chromatographic separation is achieved using Zorbax SB C18 150 × 3.0 mm, 3.5 μ column with 0.1% formic acid in water as mobile phase A and 0.1% formic acid in methanol as mobile phase B at a flow rate of 0.3 ml/min using gradient mode of elution at a total run time of 18 minutes. Six nitrosamine impurities are successfully ionized and quantified in positive mode of atmospheric pressure chemical ionization (APCI) using multiple reaction monitoring (MRM). Method validation is performed as per ICH guidelines evaluating the limit of quantification and detection and found to give good S/N ratios with good linearity range of 0.002 - 2 ppm with regression coefficient >0.99 for all the six nitrosamine impurities. Method recoveries are established using three-step sample preparation protocol and are found to be satisfactory within 80% - 120%. The method can be used routinely applied for the detection of Nitrosamines in Telmisartan at a concentration of 1.5 ng/ml (0.03 ppm with respect to telmisartan concentration of 50 mg/ml).

关键词： Nitrosamine NDMA genotoxic LC-MS/MS Telmisartan Impurities

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A High Sensitive LC-MS/MS Method for the Simultaneous Determination of Potential genotoxic Impurities Carboxy Phenyl Boronic Acid and Methyl Phenyl Boronic Acid in Lumacaftor

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American Journal of Analytical Chemistry 2021年第3期12卷 74-86页

作者： Kartheek Srinivas Chidella Vijaya Bharathi Dasari A. Jayashree Center for Chemical Sciences and Technology Institute of Science and Technology Jawaharlal Nehru Technological University Hyderabad Hyderabad Telangana Aurobindo Pharma Laboratory Research Center II Hyderabad Telangana

A simple, rapid, and highly sensitive LC-MS/MS method has been developed for the simultaneous and trace level quantification of underivatized boronic acids in lumacaftor active pharmaceutical ingredient. Chromatographic separation of boronic acids and lumacaftor achieved using Agilent Poroshell HPH C18 150 × 4.6 mm 2.7 μ column with 0.1% ammonia in water as mobile phase A and 100% acetonitrile as mobile phase B at a flow rate of 0.25 ml/min. Gradient elution was used with a total method run time of 14 minutes. Boronic acids were successfully ionized and quantified without derivatization using electrospray ionization in negative mode using tandem quadrupole mass spectrometry in multiple reactions monitoring mode. Method validation was performed as per ICH guidelines with good linearity over the concentration range of 0.05 ppm to 5 ppm of Lumacaftor test concentration for both the boronic acids with a correlation coefficient of >0.99. Recoveries were found good at different concentration levels and within the range of 80% - 120%. The developed method can be successfully used for the routine quantification of boronic acids at a concentration level of 20 ng/ml (1 ppm with respect to 20 mg/ml lumacaftor).

关键词： Boronic Acid genotoxic LC-MS/MS Lumacaftor

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Low Level Determination of genotoxic Impurity in Deferasirox Formulation

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Journal of Analytical Sciences, Methods and Instrumentation 2013年第4期3卷 179-183页

作者： Pravish Kumar Tiwari Padmakar Sathe Navin Devadiga Department of Chemistry Ramnarian Ruia College Mumbai India.

4-hydrazinobenzoic acid has been highlighted as one of the potential genotoxic impurities (PGIs). A sensitive HPLC method was developed and validated for the determination of 4-hydrazino benzoic acid in Deferasirox Tablet. HPLC method on Zorbax SB C18 column (250 × 4.6 mm i.d.), 5 μm, with UV Detector was used. The proposed method was cost effective, specific, linear, accurate, rugged and precise. The calibration curves showed good linearity over the concentration range of 0.5 μg/ml to 1.5 μg/ml with respect to the sample. The correlation coefficient was 0.999. Excellent recoveries of 102% were obtained at the level 0.5 μg/ml.

关键词： Deferasirox genotoxic 4-Hydrazinobenzoic Acid HPLC

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Quantitation of Genetox Impurities Using a Surrogate Standard Approach

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Journal of Analytical Sciences, Methods and Instrumentation 2013年第3期3卷 167-172页

作者： Heather Wang Regina Nardi Yuri Bereznitski Roy Helmy David J. Waterhouse Analytical Chemistry Merck Research Laboratories Merck Sharp & Dohme Corp. Rahway USA.

With the ever increasing complexity of active pharmaceutical ingredient (API) preparations, more potential genotoxic impurities (PGI’s) are being observed. It is thus necessary to determine if these PGI’s are present in the final API’s, and if they are present, to ensure the levels are acceptable for any clinical uses. For PGI’s that have authentic standards available, quantitation can be accomplished in a straightforward manner. However, for PGI’s that are expected to form through rearrangements or side reactions, authentic standards may not be readily available, significantly complicating the analysis. In this study we describe a surrogate standard approach for quantifying PGI’s that allows for relative response factor calculations of PGI species utilizing both gas chromatography-mass spectrometry (GC-MS) and liquid chromatography-mass spectrometry (LC-MS).

关键词： Potential genotoxic Impurity (PGI) Active Pharmaceutical Ingredient (API) Mass Spectrometry Surrogate Standard Analyte Relative Response Factor (RRF)

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Impurity Profiling of Solid Oral Drug Products to Sail through GDUFA-II Requirements

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American Journal of Analytical Chemistry 2018年第4期9卷 187-209页

作者： Raghuram Pannala Quality Assurance and Regulatory Affairs ScieGen Pharmaceuticals Inc. Hauppauge NY USA

Defining impurity profile is key element to ensure safe, efficacious and quality human drugs. Impurity profiling changed/transformed drastically over the years. Guidelines, specifications and requirements are evolving. Initially impurity profiling was based on simple methods later by degradation studies, then to understand drug strength and efficacy chiral impurities and stereo isomers were included followed by residual solvents, polymorphic forms, genotoxic impurity studies. Currently, elemental impurities are the latest addition. As per the GDUFA II guidelines to improve review efficiency and reduce review cycles, data requirements have changed. Based on recent guidance and review points, Impurity profiling has significant importance in ANDA filing and to ensure approval within 10 months (first cycle approval) which is an exiling aspect for industries to enter into the generic market quickly. Hence, Impurity profile is a key aspect scientifically, regulatory wise and commercially also. This is a review article on impurity profiling of Solid oral drug substances and products as per GDUFA II requirements the reference documents for the review are ICH guidance, relevant FDA GDUFA guidance and common industry practices.

关键词： Impurity Profile Degradation Stereo Isomers genotoxic Polymorphic Elemental Impurities FDA GDUFA II Organic Impurities Inorganic Impurities RTR Specifications

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Is there a connection between synthetic bone grafts and sisters chromatide exchange?

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Open Journal of Stomatology 2013年第8期3卷 447-451页

作者： Banu Gurkan Koseoglu Amila Brkic Mehmet Ali Erdem Sukru Ozturk Sukru Palanduz Kivanc Cefle Department of Oral and Maxillofacial Surgery School of DentistryIstanbul UniversityIstanbulTurkey Department of Oral Surgery School of DentistrySarajevo UniversitySarajevoBosnia and Herzegovina Division of Medical Genetics Department of Internal MedicineSchool of MedicineIstanbul UniversityIstanbulTurkey

Background: In oral and maxillofacial surgery, synthetic bone grafts are most widely used as bone substitutes, due to the limited sources of autologous bone. The aim of this study was to examine the influence of three different synthetic bone grafts (Cerasorb, Fortoss and Perioglass) on sisters chromatide exchanges (SCEs) in peripheral lymphocytes. Materials and Methods: Peripheral blood samples taken from 68 patients (45 females and 23 males), who underwent oral surgery procedures, such as apical resection, cyst enucleation or periodontal curretage, were obtained for SCE a day before and two months after the surgeries. A control group included 30 patients, while the study group was made of the patients who underwent bone grafting with Cerasorb? (11 patients), Fortoss? VITAL (10 patients) or Perioglass? (17 patients). Results: Comparing with the results of the study group before and after the treatment, it was concluded that the results were statistically significant (p = 0.001). In the Perioglass? subgroup, a greater statistical significance (p = 0.003) was noted, than that in either the Cerasorb? (p = 0.620) or Fortoss? (p = 0.210) subgroups, in which there was no statistical significance. Conclusions: Although further investigations may be necessary, our results suggest that the synthetic bone grafts might have an influence on SCE in peripheral lymphocytes.

关键词： Bone Graft Sisters Chromatide Exchange genotoxic Bone Defect

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