Synthesis and spermicidal activity of a putative nitric oxide-releasing derivative of nonoxynol-9

Matthew Ingram, R. Glantz, C.E. Hall

Research output: Contribution to journalArticle

Abstract

Objectives We report on the synthesis of a potential nitric oxide releasing derivative of nonoxynol-9 (N9). Methods This derivative was synthesised via AgNO3 mediated nitroxylation of a chloride derivative of a N9 which itself was synthesised by thionyl chloride mediated chlorination of N9. In an initial in vitro study the spermicidal efficacy of the nitric oxide derivative and the parent compound (N9) was examined using boar spermatozoa. Sperm motility and viability were examined. Results The data showed that nitroxylation of N9 did not disrupt spermicidal activity; both sperm motility and viability were comparable between N9 and its nitroxylated derivative. For both compounds, low doses (1–10 μg/mL) were sufficient to induce significant immobilization of sperm after 1 min, whereas concentrations of 10–100 μg/mL were required to achieve significant increase in membrane permeability. Conclusion The results show that a nitric oxide-releasing derivative of N9 retains the spermicidal activity of the parent compound and may have other beneficial effects associated with the release of NO.
Original languageEnglish
Pages (from-to)73-76
Number of pages4
JournalContraception
Volume70
Issue number1
DOIs
Publication statusPublished - Jul 2004

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Nonoxynol
Nitric Oxide
Derivatives
Chlorination
Chlorides
Membranes

Keywords

  • Spermicide
  • Nonoxynol-9
  • Nitric oxide
  • Boar spermatazoa

Cite this

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title = "Synthesis and spermicidal activity of a putative nitric oxide-releasing derivative of nonoxynol-9",
abstract = "Objectives We report on the synthesis of a potential nitric oxide releasing derivative of nonoxynol-9 (N9). Methods This derivative was synthesised via AgNO3 mediated nitroxylation of a chloride derivative of a N9 which itself was synthesised by thionyl chloride mediated chlorination of N9. In an initial in vitro study the spermicidal efficacy of the nitric oxide derivative and the parent compound (N9) was examined using boar spermatozoa. Sperm motility and viability were examined. Results The data showed that nitroxylation of N9 did not disrupt spermicidal activity; both sperm motility and viability were comparable between N9 and its nitroxylated derivative. For both compounds, low doses (1–10 μg/mL) were sufficient to induce significant immobilization of sperm after 1 min, whereas concentrations of 10–100 μg/mL were required to achieve significant increase in membrane permeability. Conclusion The results show that a nitric oxide-releasing derivative of N9 retains the spermicidal activity of the parent compound and may have other beneficial effects associated with the release of NO.",
keywords = "Spermicide, Nonoxynol-9, Nitric oxide, Boar spermatazoa",
author = "Matthew Ingram and R. Glantz and C.E. Hall",
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language = "English",
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Synthesis and spermicidal activity of a putative nitric oxide-releasing derivative of nonoxynol-9. / Ingram, Matthew; Glantz, R.; Hall, C.E.

In: Contraception, Vol. 70, No. 1, 07.2004, p. 73-76.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Synthesis and spermicidal activity of a putative nitric oxide-releasing derivative of nonoxynol-9

AU - Ingram, Matthew

AU - Glantz, R.

AU - Hall, C.E.

PY - 2004/7

Y1 - 2004/7

N2 - Objectives We report on the synthesis of a potential nitric oxide releasing derivative of nonoxynol-9 (N9). Methods This derivative was synthesised via AgNO3 mediated nitroxylation of a chloride derivative of a N9 which itself was synthesised by thionyl chloride mediated chlorination of N9. In an initial in vitro study the spermicidal efficacy of the nitric oxide derivative and the parent compound (N9) was examined using boar spermatozoa. Sperm motility and viability were examined. Results The data showed that nitroxylation of N9 did not disrupt spermicidal activity; both sperm motility and viability were comparable between N9 and its nitroxylated derivative. For both compounds, low doses (1–10 μg/mL) were sufficient to induce significant immobilization of sperm after 1 min, whereas concentrations of 10–100 μg/mL were required to achieve significant increase in membrane permeability. Conclusion The results show that a nitric oxide-releasing derivative of N9 retains the spermicidal activity of the parent compound and may have other beneficial effects associated with the release of NO.

AB - Objectives We report on the synthesis of a potential nitric oxide releasing derivative of nonoxynol-9 (N9). Methods This derivative was synthesised via AgNO3 mediated nitroxylation of a chloride derivative of a N9 which itself was synthesised by thionyl chloride mediated chlorination of N9. In an initial in vitro study the spermicidal efficacy of the nitric oxide derivative and the parent compound (N9) was examined using boar spermatozoa. Sperm motility and viability were examined. Results The data showed that nitroxylation of N9 did not disrupt spermicidal activity; both sperm motility and viability were comparable between N9 and its nitroxylated derivative. For both compounds, low doses (1–10 μg/mL) were sufficient to induce significant immobilization of sperm after 1 min, whereas concentrations of 10–100 μg/mL were required to achieve significant increase in membrane permeability. Conclusion The results show that a nitric oxide-releasing derivative of N9 retains the spermicidal activity of the parent compound and may have other beneficial effects associated with the release of NO.

KW - Spermicide

KW - Nonoxynol-9

KW - Nitric oxide

KW - Boar spermatazoa

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M3 - Article

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