Fragmentation study of simvastatin and lovastatin using electrospray ionization tandem mass spectrometry

Wang, Hong; Wu, Yunhui; Zhao, Zhongxi

doi:10.1002/jms.104

Cited by 40 publications

(25 citation statements)

References 31 publications

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“…, m/z 419) is studied in detail using triple-quadrupole, ion-trap and Q-TOF instruments (Wang, Wu, & Zhao, 2001;Vuletić, Cindrić, & Koruznjak, 2005) (Wang, Wu, & Zhao, 2001), although an alternative structure has been suggested, involving a cleavage of the C-C bond at the hexahydronaphthalene ring with charge retention at the lactone ring (C 7 H 11 O 3 þ ; see Scheme 24). Interestingly, accurate-mass data indicate that both structure are observed, that is, the ion with C 7 H 11 O 3 þ at low collision energy, and the ion with C 11 H 11 þ at higher collision energy, which is in agreement with expectation based on the fragmentation pathways of both ions.…”

Section: Statinsmentioning

confidence: 99%

Fragmentation of toxicologically relevant drugs in positive‐ion liquid chromatography–tandem mass spectrometry

Niessen¹

2011

Mass Spectrometry Reviews

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The identification of drugs and related compounds by LC-MS-MS is an important analytical challenge in several application areas, including clinical and forensic toxicology, doping control analysis, and environmental analysis. Although target-compound based analytical strategies are most frequently applied, at some point the information content of the MS-MS spectra becomes relevant. In this article, the positive-ion MS-MS spectra of a wide variety of drugs and related substances are discussed. Starting point was an MS-MS mass spectral library of toxicologically relevant compounds, available on the internet. The positive-ion MS-MS spectra of ∼570 compounds were interpreted by chemical and therapeutic class, thus involving a wide variety of drug compound classes, such benzodiazepines, beta-blockers, angiotensin-converting enzyme inhibitors, phenothiazines, dihydropyridine calcium channel blockers, diuretics, local anesthetics, vasodilators, as well as various subclasses of anti-diabetic, antidepressant, analgesic, and antihistaminic drugs. In addition, the scientific literature was searched for available MS-MS data of these compound classes and the interpretation thereof. The results of this elaborate study are presented in this article. For each individual compound class, the emphasis is on class-specific fragmentation, as discussing fragmentation of all individual compounds would take far too much space. The recognition of class-specific fragmentation may be quite informative in determining the compound class of a specific unknown, which may further help in the identification. In addition, knowledge on (class-specific) fragmentation may further help in the optimization of the selectivity in targeted analytical approaches of compounds of one particular class.

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Section: Statinsmentioning

confidence: 99%

Fragmentation of toxicologically relevant drugs in positive‐ion liquid chromatography–tandem mass spectrometry

Niessen¹

2011

Mass Spectrometry Reviews

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“…[13][14][15] Briefly, 300 mL 100 mM ammonium acetate, pH 4.5, with acetic acid glacial was added to each 500 mL sample of plasma. Each plasma sample was spiked with 50 mL of internal standard simvastatin in 100% acetonitrile.…”

Section: Lovastatin Plasma Measurementsmentioning

confidence: 99%

Locally delivered lovastatin nanoparticles enhance fracture healing in rats

Garrett

Gutiérrez

Rossini

et al. 2007

Journal Orthopaedic Research

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Statins stimulate bone formation in vitro and in vivo and, when given in large doses or by prolonged infusions, stimulate biomechanical strength of murine long bones with healing fractures. However, administration of statins by large oral doses or prolonged infusions to a fracture site is not a feasible therapeutic approach to hasten healing of human fractures. We administered lovastatin in biodegradable polymer nanobeads of poly(lactic-co-glycolide acid) to determine if lovastatin delivered in low doses in nanoparticles of a therapeutically acceptable scaffold could increase rates of healing in a standard preclinical model of femoral fracture. We found that these nanobeads: (1) stimulated bone formation in vitro at 5 ng/mL, (2) increased rates of healing in femoral fractures when administered as a single injection into the fracture site, and (3) decreased cortical fracture gap at 4 weeks as assessed by microcomputed tomography. These preclinical results suggest that lovastatin administered in a nanobead preparation may be therapeutically useful in hastening repair of human fractures. ß

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“…This is generally considered to obscure the structural detail that results from charge-remote processes [12,[32][33][34]. The proposed mechanism for the formation of the cyclopropene cation in 2E,6Z-unsaturated amides (1-9, 11 and 14) is postulated to be chargedinduced and involves initial formation of a bicyclic intermediate followed by hydrogen/deuterium transfer from the amide alkyl group and subsequent loss of an alkene to form a resonance stabilized product ion.…”

Section: Charge-induced Mechanismmentioning

confidence: 99%

Proposed mechanisms for the fragmentation of doubly allylic alkenamides (tingle compounds) by low energy collisional activation in a triple quadrupole mass spectrometer

Hiserodt

Pope

Cossette

et al. 2004

J. Am. Soc. Mass Spectrom.

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Tingle compounds are a class of alkenamides with organoleptic properties that include a numbing or a pins and needles effect that is generally perceived on the lips and in the mouth when consumed. They occur in nature in a number of botanical species. Spilanthol and Pellitorine are important examples of tingle compounds. A number of homologs and analogs were synthesized to study the effect of chain length, double bond location, and amide moiety on the tingle effect. This also provided the opportunity to study the behavior of these compounds in the collision cell of a triple quadrupole mass spectrometer. The doubly allylic 2E,6Z-alkenamides, which made up the largest class studied, fragmented in a characteristic way to produce a distonic radical cation and a cyclopropene cation. Mechanisms for the formation of these ions are proposed. The mechanisms are supported by energy-resolved mass spectrometric data, the analysis of deuterated analogs and homologs that are not doubly allylic, and exact mass measurements. Exceptions to the proposed mechanisms are also presented. These data represent the first attempt to apply mechanistic principles to the product ions observed in the MS/MS spectra of these compounds. The authors believe the results of this study will facilitate the identification of these and similar compounds and contribute to the fundamental understanding of the behavior of alkenamides in the collision cell of a triple quadrupole mass

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Fragmentation study of simvastatin and lovastatin using electrospray ionization tandem mass spectrometry

Cited by 40 publications

References 31 publications

Fragmentation of toxicologically relevant drugs in positive‐ion liquid chromatography–tandem mass spectrometry

Fragmentation of toxicologically relevant drugs in positive‐ion liquid chromatography–tandem mass spectrometry

Locally delivered lovastatin nanoparticles enhance fracture healing in rats

Proposed mechanisms for the fragmentation of doubly allylic alkenamides (tingle compounds) by low energy collisional activation in a triple quadrupole mass spectrometer

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