Liquid secondary ionization mass spectrometry and collision-induced dissociation study of 2-chloro-N10-substituted phenoxazines

Chhabil Dass, K. N. Thimmaiah, B. S. Jayashree, Peter J. Houghton

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Positive-ion liquid secondary ionization mass spectrometry in combination with 3-nitrobenzyl alcohol as the liquid matrix was used to investigate the mass spectral features of a set of 21 N10-substituted derivatives of 2-chlorophenoxazine. The N-10 substitution included propyl, butyl and acetyl groups containing various secondary amines (N,N- diethylamine, N,N-diethanolamine, morpholine, piperidine, pyrrolidone or β- hydroxyethylpiperazine) or a chloro group. These compounds are potent multi- drug resistance modulators. The molecular ions are observed as M+. and [M + H]+ ions. In general, the fragmentation pathways of these molecules are similar and very straightforward. The phenoxazine ring system remains stable under the Cs+ ion beam bombardment conditions, while fragmentations are observed along the length of the alkyl and acetyl side-chains. The fragmentation reactions were corroborated by acquiring product ion and constant neutral loss tandem mass spectrometric scans of the pertinent ions.

Original languageEnglish
Pages (from-to)1279-1289
Number of pages11
JournalJournal of Mass Spectrometry
Volume32
Issue number12
DOIs
Publication statusPublished - 01-12-1997

Fingerprint

Ionization
Mass spectrometry
Ions
diethanolamine
Liquids
Pyrrolidinones
Ion beams
Modulators
Amines
Byproducts
Substitution reactions
Positive ions
Derivatives
Molecules
phenoxazine
Pharmaceutical Preparations

All Science Journal Classification (ASJC) codes

  • Spectroscopy

Cite this

@article{e0a7e7f109f04004ac4b3a42eb4a2dcc,
title = "Liquid secondary ionization mass spectrometry and collision-induced dissociation study of 2-chloro-N10-substituted phenoxazines",
abstract = "Positive-ion liquid secondary ionization mass spectrometry in combination with 3-nitrobenzyl alcohol as the liquid matrix was used to investigate the mass spectral features of a set of 21 N10-substituted derivatives of 2-chlorophenoxazine. The N-10 substitution included propyl, butyl and acetyl groups containing various secondary amines (N,N- diethylamine, N,N-diethanolamine, morpholine, piperidine, pyrrolidone or β- hydroxyethylpiperazine) or a chloro group. These compounds are potent multi- drug resistance modulators. The molecular ions are observed as M+. and [M + H]+ ions. In general, the fragmentation pathways of these molecules are similar and very straightforward. The phenoxazine ring system remains stable under the Cs+ ion beam bombardment conditions, while fragmentations are observed along the length of the alkyl and acetyl side-chains. The fragmentation reactions were corroborated by acquiring product ion and constant neutral loss tandem mass spectrometric scans of the pertinent ions.",
author = "Chhabil Dass and Thimmaiah, {K. N.} and Jayashree, {B. S.} and Houghton, {Peter J.}",
year = "1997",
month = "12",
day = "1",
doi = "10.1002/(SICI)1096-9888(199712)32:12<1279::AID-JMS586>3.0.CO;2-#",
language = "English",
volume = "32",
pages = "1279--1289",
journal = "Journal of Mass Spectrometry",
issn = "1076-5174",
publisher = "John Wiley and Sons Ltd",
number = "12",

}

Liquid secondary ionization mass spectrometry and collision-induced dissociation study of 2-chloro-N10-substituted phenoxazines. / Dass, Chhabil; Thimmaiah, K. N.; Jayashree, B. S.; Houghton, Peter J.

In: Journal of Mass Spectrometry, Vol. 32, No. 12, 01.12.1997, p. 1279-1289.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Liquid secondary ionization mass spectrometry and collision-induced dissociation study of 2-chloro-N10-substituted phenoxazines

AU - Dass, Chhabil

AU - Thimmaiah, K. N.

AU - Jayashree, B. S.

AU - Houghton, Peter J.

PY - 1997/12/1

Y1 - 1997/12/1

N2 - Positive-ion liquid secondary ionization mass spectrometry in combination with 3-nitrobenzyl alcohol as the liquid matrix was used to investigate the mass spectral features of a set of 21 N10-substituted derivatives of 2-chlorophenoxazine. The N-10 substitution included propyl, butyl and acetyl groups containing various secondary amines (N,N- diethylamine, N,N-diethanolamine, morpholine, piperidine, pyrrolidone or β- hydroxyethylpiperazine) or a chloro group. These compounds are potent multi- drug resistance modulators. The molecular ions are observed as M+. and [M + H]+ ions. In general, the fragmentation pathways of these molecules are similar and very straightforward. The phenoxazine ring system remains stable under the Cs+ ion beam bombardment conditions, while fragmentations are observed along the length of the alkyl and acetyl side-chains. The fragmentation reactions were corroborated by acquiring product ion and constant neutral loss tandem mass spectrometric scans of the pertinent ions.

AB - Positive-ion liquid secondary ionization mass spectrometry in combination with 3-nitrobenzyl alcohol as the liquid matrix was used to investigate the mass spectral features of a set of 21 N10-substituted derivatives of 2-chlorophenoxazine. The N-10 substitution included propyl, butyl and acetyl groups containing various secondary amines (N,N- diethylamine, N,N-diethanolamine, morpholine, piperidine, pyrrolidone or β- hydroxyethylpiperazine) or a chloro group. These compounds are potent multi- drug resistance modulators. The molecular ions are observed as M+. and [M + H]+ ions. In general, the fragmentation pathways of these molecules are similar and very straightforward. The phenoxazine ring system remains stable under the Cs+ ion beam bombardment conditions, while fragmentations are observed along the length of the alkyl and acetyl side-chains. The fragmentation reactions were corroborated by acquiring product ion and constant neutral loss tandem mass spectrometric scans of the pertinent ions.

UR - http://www.scopus.com/inward/record.url?scp=0031472643&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0031472643&partnerID=8YFLogxK

U2 - 10.1002/(SICI)1096-9888(199712)32:12<1279::AID-JMS586>3.0.CO;2-#

DO - 10.1002/(SICI)1096-9888(199712)32:12<1279::AID-JMS586>3.0.CO;2-#

M3 - Article

C2 - 9423281

AN - SCOPUS:0031472643

VL - 32

SP - 1279

EP - 1289

JO - Journal of Mass Spectrometry

JF - Journal of Mass Spectrometry

SN - 1076-5174

IS - 12

ER -