Tandem Mass Spectrometric Analysis of the Novel Gemini Surfactant Nanoparticle Families G12-s and G18:1-s

Buse, Joshua; Badea, Ildikó; Verrall, R. E.; El‐Aneed, Anas

doi:10.1080/00387010903261206

Cited by 17 publications

(21 citation statements)

References 38 publications

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“…The MS/MS fragmentation behavior of peptide‐modified gemini surfactants showed remarkable differences compared with traditional gemini surfactants . This is mainly due to the insertion of peptide segments within the gemini surfactant spacer region, resulting in the formation of peptide‐related dissociation characteristics.…”

Section: Resultsmentioning

confidence: 99%

“…As indicated earlier, the presence of peptides within the gemini surfactants offered the compound protonated peptide characteristics, unlike conventional gemini surfactants . The dissociation of protonated peptides can be explained by the ‘mobile proton’ model: a comprehensive model that suggests a competition between charge‐remote and charge‐directed reactions to predict the fragmentation process .…”

Section: Resultsmentioning

confidence: 99%

“…Mass spectrometry (MS) is routinely used for both the quantitative and qualitative analysis of pharmaceuticals . In our group, we investigated the fragmentation pathways of different structural families of gemini surfactants establishing collision‐induced dissociation (CID)‐tandem mass spectrometric (MS/MS) fingerprints for accurate identification of gemini surfactants . This data was subsequently utilized to develop MS‐based methods for the quantification of conventional unsubstituted gemini surfactants within cells to determine the rate of cellular uptake and removal .…”

Section: Introductionmentioning

confidence: 99%

“…[19][20][21][22] In our group, we investigated the fragmentation pathways of different structural families of gemini surfactants establishing collisioninduced dissociation (CID)-tandem mass spectrometric (MS/MS) fingerprints for accurate identification of gemini surfactants. [23][24][25][26] This data was subsequently utilized to develop MS-based methods for the quantification of conventional unsubstituted gemini surfactants within cells to determine the rate of cellular uptake and removal. [27][28][29] Ongoing research employs the use of these methods to investigate subcellular localization and to identify any potential metabolites.…”

Section: Introductionmentioning

confidence: 99%

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Tandem mass spectrometric analysis of novel peptide‐modified gemini surfactants used as gene delivery vectors

Al‐Dulaymi

El‐Aneed

2017

J. Mass Spectrom.

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Diquaternary ammonium gemini surfactants have emerged as effective gene delivery vectors. A novel series of 11 peptide-modified compounds was synthesized, showing promising results in delivering genetic materials. The purpose of this work is to elucidate the tandem mass spectrometric (MS/MS) dissociation behavior of these novel molecules establishing a generalized MS/MS fingerprint. Exact mass measurements were achieved using a hybrid quadrupole orthogonal time-of-flight mass spectrometer, and a multi-stage MS/MS analysis was conducted using a triple quadrupole-linear ion trap mass spectrometer. Both instruments were operated in the positive ionization mode and are equipped with electrospray ionization. Abundant triply charged [M+H] species were observed in the single-stage analysis of all the evaluated compounds with mass accuracies of less than 8 ppm in mass error. MS/MS analysis showed that the evaluated gemini surfactants exhibited peptide-related dissociation characteristics because of the presence of amino acids within the compounds' spacer region. In particular, diagnostic product ions were originated from the neutral loss of ammonia from the amino acids' side chain resulting in the formation of pipecolic acid at the N-terminus part of the gemini surfactants. In addition, a charge-directed amide bond cleavage was initiated by the amino acids' side chain producing a protonated α-amino-ε-caprolactam ion and its complimentary C-terminus ion that contains quaternary amines. MS/MS and MS analysis revealed common fragmentation behavior among all tested compounds, resulting in the production of a universal MS/MS fragmentation pathway. Copyright © 2017 John Wiley & Sons, Ltd.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Tandem mass spectrometric analysis of novel peptide‐modified gemini surfactants used as gene delivery vectors

Al‐Dulaymi

El‐Aneed

2017

J. Mass Spectrom.

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“…The establishment of CID‐MS/MS fragmentation patterns of structurally related compounds allows confirmation of their molecular structures and identification of their diagnostic product ions to be used subsequently for qualitative and quantitative analysis. For example, our research group illustrated a universal MS/MS dissociation behavior of a series of structurally related cationic surfactants used as drug delivery agents . The data was subsequently used to develop targeted MS‐based quantification methods that were employed within cellular lysates to assess the uptake and removal of these cationic lipids .…”

Section: Methodsmentioning

confidence: 99%

Establishment of tandem mass spectrometric fingerprint of novel antineoplastic curcumin analogues using electrospray ionization

Awad

Das

Dimmock

et al. 2015

Rapid Comm Mass Spectrometry

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This is the pre-peer reviewed version of the following article: Awad, H., Das, U., Dimmock, J., and El-Aneed, A. (2015), Establishment of tandem mass spectrometric fingerprint of novel antineoplastic curcumin analogues using electrospray ionization. Rapid Commun. Mass Spectrom., 29, 1307-1316, which has been published in final form at doi: 10.1002/rcm.7222. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving. ABSTRACT RATIONALECurcumin analogues are antineoplastic agents, designed based on the structure of the spice turmeric with structural modifications aiming at enhancing potency. The goal is to identify the common tandem mass spectrometric (MS/MS) behavior of 13 novel curcumin analogues. Such knowledge is critical for their biological assessment, including metabolite identification and pharmacokinetic evaluation. METHODSBoth detection of the protonated molecules [M+H] + of the synthesized compounds and determination of their exact molecular masses were achieved with a hybrid quadrupole orthogonal time-of-flight mass spectrometer (QqTOF-MS). Low-energy collision induced dissociation (CID)-MS/MS analysis was performed using a triple quadrupole linear ion trap mass spectrometer (QqLIT-MS). Both instruments were equipped with an electrospray ionization (ESI) source. MS 3 and neutral loss experiments were performed using the QqLIT-MS to confirm the genesis of the observed product ions. RESULTSAbundant [M+H] + molecules were formed using the QqTOF-MS hybrid instrument with mass accuracies below 6 ppm. CID-MS/MS dissociation studies were centered on the piperidone ring of curcumin analogues;twelve common product ions have been identified from the fission of the various bonds within the piperidone moiety. There was a tendency for the formation of highly conjugated product ions, stabilized via resonance. The variety of the side chain substituents at the nitrogen atom resulted in side chain-specific product ions. CONCLUSIONSThe ESI-CID-MS/MS analysis of curcumin analogues revealed a common fragmentation behavior of all tested compounds, which gave diagnostic product ions identified for each molecule. The established MS/MS behavior will be applied to determine metabolic by-products of curcumin analogues as well as to develop targeted identification/quantification methods within biological extracts.

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Tandem mass spectrometric analysis of novel diquaternary ammonium gemini surfactants and their bromide adducts in electrospray‐positive ion mode ionization

et al. 2011

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Gemini surfactants are cationic lipids which are utilized for both in vitro and in vivo gene delivery. Structurally, they are comprised of two hydrophobic tail regions with polar head termini that are attached to one another through a spacer region. Structural elucidation and characterization of 29 novel diquaternary ammonium gemini surfactant molecules were achieved using a quadrupole time-of-flight mass spectrometer (QqToF-MS) and a quadrupole-hexapole-quadrupole mass spectrometer (QhQ-MS). The tested compounds were categorized into four distinct structural families based upon the composition of the spacer region. Single stage (MS), tandem stage (MS/MS) and quasimulti-stage (quasi MS(3)) mass spectrometric analysis allowed for confirmation of each gemini surfactant's molecular composition and structure through the identification of common and unique product ions. Identification of similarities in the gemini surfactants' fragmentation behaviour resulted in the production of a universal fragmentation pathway that can assist in the future MS/MS analysis of novel quaternary ammonium gemini surfactants, with unique product ions being indicative of specific structural elements. Furthermore, evidence for the association of agemini surfactant with bromine counter ion was confirmed during MS analysis of tested gemini surfactants regardless of their chemical composition; previously, evidence for bromine and gemini surfactant association was only observed with compounds bearing short alkyl spacer regions. MS/MS analysis of the bromine adducts was also confirmatory to the molecular structure.Understanding the ionization and fragmentation behaviour of gemini surfactants, including bromine adducts, will allow for future qualitative and quantitative identification of these novel drug delivery agents within biological samples.

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Tandem Mass Spectrometric Analysis of the Novel Gemini Surfactant Nanoparticle Families G12-s and G18:1-s

Cited by 17 publications

References 38 publications

Tandem mass spectrometric analysis of novel peptide‐modified gemini surfactants used as gene delivery vectors

Tandem mass spectrometric analysis of novel peptide‐modified gemini surfactants used as gene delivery vectors

Establishment of tandem mass spectrometric fingerprint of novel antineoplastic curcumin analogues using electrospray ionization

Tandem mass spectrometric analysis of novel diquaternary ammonium gemini surfactants and their bromide adducts in electrospray‐positive ion mode ionization

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