Determination of the Oil/ Water Distribution Coefficients of Glyceryl Trinitrate and Two Similar Nitrate Esters

Bell, Frederick K.; O’Neill, J. J.; Burgison, Raymond M.

doi:10.1002/jps.2600520706

Cited by 53 publications

(22 citation statements)

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“…Both NaCl and NaNO2 were dissolved in 10 mM pH 7.4 phosphate buffer. Samples were incubated in the dark for one week at 37 o C. Excessive salts were removed by dialysis against 10 mM PBS until the solution outside the dialysis tubes was Griess assay (Bell et al, 1963) negative for nitrite modification. Proteins in the dialysis tubes were collected and dried under argon and ready for further analysis.…”

Section: Preparation Of Nitrite-modified Collagen IVmentioning

confidence: 99%

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Tyrosine nitration site specificity identified by LC/MS in nitrite-modified collagen type IV

Wang

Paik²,

Dillon³

et al. 2007

Exp Mol Med

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Non-enzymatic nitrite induced collagen cross-linking results in changes reminiscent of age-related damage and parallels the well-known model system, non-enzymatic glycation. We have recently observed that nitrite modification of basement membrane proteins can induce deleterious effects on overlying retinal pigment epithelial cells in studies relevant to age-related macular degeneration. The present work was undertaken in order to confirm 3-nitro-tyrosine (3-NT) as a product of the reaction and to identify the site specificity of nitration in collagen IV, a major component of basement membranes. Human collagen type IV was modified via incubation with 200 mM NaNO 2 (pH = 7.38) for one week at 37 o C. The modified protein was prepared in 2 different ways, including acid hydrolysis and trypsin digestion for site specificity determination. The samples were analyzed by LC/MS using a C12 RP column. Site specificity was determined from tandem MS/MS data utilizing TurboSEQUEST software and the Swiss-Prot sequence database. 3-NT was detected in protein digests and acid hydrolysates of nitrite modified collagen IV. Positive identification with standard 3-NT was confirmed by identical Rt, λmax = 279 nm and 355 nm, and m/z = 227. Analyses of tryptic digests identified four sites of tyrosine nitration, α1(IV)Y348, α1(IV)Y534, α2(IV)Y327, and α2(IV)-Y1081. These sites are located in the triple-helical region of the protein and provide clues regarding potential sites for nitrite modification in collagen type IV.

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Section: Preparation Of Nitrite-modified Collagen IVmentioning

confidence: 99%

“…Following confirmation of complete nitrite removal using a colorimetric nitrite assay (Bell et al, 1963), modified proteins were hydrolyzed by 6 M HCl. Acid hydrolysates were analyzed by LC-MS.…”

Section: Nitrite Modified Tyrosine Residues In Collagen IVmentioning

confidence: 99%

Tyrosine nitration site specificity identified by LC/MS in nitrite-modified collagen type IV

Wang

Paik²,

Dillon³

et al. 2007

Exp Mol Med

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“…Nitric oxide activity was measured chemically following the modifications (2) of a procedure described by Bell et al (22). This method relies on the diazotization of sulfanilic acid by nitric oxide at acid pH and subsequent coupling to N-I -naphthyl)-ethylenediamine.…”

Section: Introductionmentioning

confidence: 99%

“…For these studies, a saturated solution ( 1-2 mM) ofauthentic nitric oxide solution was prepared by bubbling nitric oxide gas (Matheson Gas Products, Inc., Bridgeport, NJ) for 2 min into ice-cold, deoxygenated H20 under anaerobic conditions in sealed, gas-tight vials (2). Although the diazotization reaction is specific for nitric oxide (NO), nitrite (NOj), an oxidation product ofnitric oxide is detected at a many-fold lower sensitivity (2,22 For blood pressure studies, rats were anesthetized with 50 mg/kg i.p. Nembutal and the common carotid artery surgically exposed and cannulated with polyethylene tubing (PE 50).…”

Section: Introductionmentioning

confidence: 99%

Advanced glycosylation products quench nitric oxide and mediate defective endothelium-dependent vasodilatation in experimental diabetes.

Bucala

Tracey²,

Cerami³

1991

J. Clin. Invest.

1,109

619

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Nitric oxide (an endothelium-derived relaxing factor) induces smooth muscle relaxation and is an important mediator in the regulation of vascular tone. Advanced glycosylation end products, the glucose-derived moieties that form noncnzymatically and accumulate on long-lived tissue proteins, have been implicated in many of the complications of diabetes and normal aging. We demonstrate that advanced glycosylation products quench nitric oxide activity in vitro and in vivo. Acceleration of the advanced glycosylation process in vivo results in a time-dependent impairment in endothelium-dependent relaxation. Inhibition of advanced glycosylation with aminoguanidine prevents nitric oxide quenching, and ameliorates the vasodilatory impairment. These results implicate advanced glycosylation products as important modulators of nitric oxide activity and endothelium-dependent relaxation. (J. Clin. Invest. 1991. 87:432-438.)

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“…Prior to incubation and at various time intervals, the concentrations of nitrite were determined by diazotization. To 0.05 ml of PB solution or plasma containing each drug, 3.95 ml of HCI (0.5 N for PB solution and 0.05 N for plasma), 0.5 ml of 0.2010 sulfanilic acid and 0.5 ml of 0.1010 N-(1-naphthyl)ethylenediamine were added subsequently (11). Absorbance of a purple dye at 548 nm was measured with a spectrophotometer (UV-2200; Shimadzu Co., Kyoto).…”

Section: Nitrite Analysismentioning

confidence: 99%

Close Correlation between Nitric Oxide (NO) Formation from NO Releasers and the Biological Activities of These Agents in Rats

Kita¹,

Fukuyama

Hirasawa³

1995

Japanese Journal of Pharmacology

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ABSTRACT-The aim of this study was to clarify the difference in the profiles of nitric oxide (NO) formation of three NO releasers and to examine the correlation between NO formation from these drugs and their biological activities in rats. (±)-(E)-ethyl-2-[(E)-hydroxyimino]-5-nitro-3-hexenamide (FK409) and 3-morpholinosydnonimine (SIN-1) spontaneously generated nitrite, an oxidative product of NO, in sodium phosphate buffer (PB) solution. On the other hand, sodium nitroprusside (SNP) did not generate nitrite. The rank order of the concentrations of nitrite generated was SIN-1 >FK409>SNP.In biological studies using rats, these drugs showed anti-platelet effects and in vitro vasorelaxant and hypotensive effects with potencies in the rank order of FK409 > SIN-1 > SNP and SNP > FK409 > SIN-1, respectively. These drugs generated nitrite with concentrations in the rank order of FK409 > SIN-1 > SNP and SNP > FK409 > SIN-1 in rat plasma and in PB solution with L-cysteine (Cys), respectively. In conclusion, three NO releasers liberate NO with NO-releasing rates of different rank orders under different incubation conditions, and the anti-platelet effects and vasorelaxant and hypotensive effects of these NO releasers closely correlate with NO formation from the compounds in the plasma and PB solution with Cys, respectively, but not with that in PB solution without Cys.Keywords: FK409, 3-Morpholinosydnonimine (SIN-1), Sodium nitroprusside (SNP), Nitric oxide (NO) Fig. 1) is a structurally unique vasodilator discovered from the fermentation products of Streptomyces griseosporeus (1). FK409 has produced a potent vasorelaxation mediated by the elevation of cyclic GMP in isolated dog coronary artery (2), rabbit aorta (3) and rat aorta (4). In addition, FK409 has shown a potent inhibition of platelet aggregation in human (5) and rat (6) platelet-rich plasma. Recently, we have reported that these biological actions of FK409 can be accounted for by spontaneous nitric oxide (NO) release following decomposition of the compound (5). However, the NO-releasing pathway of FK409 remains unclear.3-Morpholinosydnonimine (SIN-1, Fig. 1) and sodium nitroprusside (SNP, Fig. 1) have been also reported as NO releasers that liberate NO spontaneously (7,8). In addition, these compounds have been also suggested to show vasorelaxant and antiplatelet effects (9, 10). Three NO releasers including FK409 have different structures, so it is considered that the profiles of NO formation of the compounds are different. It has not been reported whether NO formation from different types of spontaneous NO releaser correlates with the activities of the compounds in several biological studies.The purpose of this study was to clarify the difference in the profiles of NO formation of these NO releasers under several incubation conditions by measuring the concentration of nitrite, an oxidative product of NO, and examine the correlation between NO formation from these drugs and their biological activities. In biological studies, we evaluated in vitro anti-platelet ...

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Determination of the Oil/ Water Distribution Coefficients of Glyceryl Trinitrate and Two Similar Nitrate Esters

Cited by 53 publications

References 0 publications

Tyrosine nitration site specificity identified by LC/MS in nitrite-modified collagen type IV

Tyrosine nitration site specificity identified by LC/MS in nitrite-modified collagen type IV

Advanced glycosylation products quench nitric oxide and mediate defective endothelium-dependent vasodilatation in experimental diabetes.

Close Correlation between Nitric Oxide (NO) Formation from NO Releasers and the Biological Activities of These Agents in Rats

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