Influence of Dinitroglycerol and Nitroethyleneglycol Lipid Derivatives on Spectral Parameters of Human Hemoglobin

V. V. Bezuglov¹, G. M. Andreyuk², I. V. Serkov³, and M. A. Kisel^2*

¹Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, ul. Miklukho-Maklaya 16/10, Moscow, 117871 Russia; fax: (7-095) 335-7103; E-mail: vvbez@oxylipin.ibch.ru

²Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, ul. Akademika Kuprevicha 5/2, Minsk, 220141 Belarus; E-mail: kisel@ns.iboch.ac.by

³Institute of Physiologically Active Compounds, Russian Academy of Sciences, Chernogolovka, Moscow Region, 427000 Russia; fax: (7-095) 524-5062

^* To whom correspondence should be addressed.

Received August 30, 1999; Revision received February 2, 2000

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The interaction of organic nitrates (nitroethyleneglycol, dinitroglycerol, and their esters with arachidonic acid) with oxyhemoglobin and methemoglobin has been studied. Addition of nitroethyleneglycol and dinitroglycerol to oxyhemoglobin is accompanied by a modest but significant increase in oxidation rate of the heme protein to the high-spin ferri-form--methemoglobin. Arachidonoylglycerol dinitrate exerts a similar but more pronounced effect on hemoglobin: a molar excess of this dinitrate induces the transformation of a significant portion of oxyhemoglobin to methemoglobin, whereas arachidonoylnitroethyleneglycol is inactive. Arachidonoylglycerol dinitrate also induces changes in the spectral characteristics of methemoglobin; this may be due to disintegration of the methemoglobin with the loss of heme. The data demonstrate that some organic nitrates can interact with hemoglobin; this should be taken into account when using the oxyhemoglobin technique for measuring nitric oxide generation from these compounds.

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KEY WORDS: nitric oxide, organic nitrates, hemoglobin, lipid bioeffectors

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