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Volumn 15, Issue 1, 2010, Pages 198-214

Elucidating the Structure-Activity relationships of the vasorelaxation and antioxidation properties of thionicotinic acid derivatives

Author keywords

1 adamantylthionicotinic acid and derivatives; Antioxidants; Molecular modeling; Nitric oxide; Prostacyclin; Vasorelaxants

Indexed keywords

ACETYLCHOLINE; ANTIOXIDANT; DRUG DERIVATIVE; N(G) NITROARGININE METHYL ESTER; NICOTINAMIDE; NICOTINIC ACID; PROSTAGLANDIN SYNTHASE INHIBITOR; THIOL DERIVATIVE; THIONICOTINAMIDE;

EID: 75749143457     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules15010198     Document Type: Article
Times cited : (30)

References (47)
  • 3
    • 0024335924 scopus 로고
    • Release of markedly increased quantities of prostaglandin D2 in vivo in humans following the administration of nicotinic acid
    • Morrow, J. D.; Parsons, W. G.; Roberts, L. J. Release of markedly increased quantities of prostaglandin D2 in vivo in humans following the administration of nicotinic acid. Prostaglandins 1989, 38, 263-274.
    • (1989) Prostaglandins , vol.38 , pp. 263-274
    • Morrow, J.D.1    Parsons, W.G.2    Roberts, L.J.3
  • 5
    • 75749153811 scopus 로고
    • Vasodilatory effect of nicotinamide on the fluidity of erythrocyte membrane and liposomes
    • Bhattacharyya, M.; Nandy, P. Vasodilatory effect of nicotinamide on the fluidity of erythrocyte membrane and liposomes. J. Surf. Sci. Technol. 1989, 5, 13-20.
    • (1989) J. Surf. Sci. Technol. , vol.5 , pp. 13-20
    • Bhattacharyya, M.1    Nandy, P.2
  • 6
    • 9244250304 scopus 로고    scopus 로고
    • Nicotinamide relaxes vascular smooth muscle by inhibiting myosin light chain kinase-dependent signaling pathways: Implications for anticancer efficacy
    • Ruddock, M.W.; Hirst, D.G. Nicotinamide relaxes vascular smooth muscle by inhibiting myosin light chain kinase-dependent signaling pathways: implications for anticancer efficacy. Oncol. Res. 2004, 14, 483-489.
    • (2004) Oncol. Res. , vol.14 , pp. 483-489
    • Ruddock, M.W.1    Hirst, D.G.2
  • 7
    • 75749099489 scopus 로고    scopus 로고
    • Topical agent for application to the skin prior to luminous treatment
    • US Pat. 2004191278, 2004
    • Christensen, F. K. Topical agent for application to the skin prior to luminous treatment. US Pat. 2004191278, 2004; [Chem. Abstr. 2004, 141, 282850].
    • (2004) Chem. Abstr , vol.141 , pp. 282850
    • Christensen, F.K.1
  • 8
    • 75749105994 scopus 로고    scopus 로고
    • Cosmetic compositions containing vitamin B3
    • US Pat. 6455055, 2002
    • Walling, D. W.; Vatter, M. L. Cosmetic compositions containing vitamin B3. US Pat. 6455055, 2002; [Chem. Abstr. 2002, 137, 252724].
    • (2002) Chem. Abstr. , vol.137 , pp. 252724
    • Walling, D.W.1    Vatter, M.L.2
  • 9
    • 40349094705 scopus 로고    scopus 로고
    • Nicotinic acid: An old drug with a promising future
    • DOI 10.1038/sj.bjp.0707528, PII 0707528
    • 9. Bodor, E. T.; Offermanns, S. Nicotinic acid: an old drug with a promising future. Br. J. Pharmacol. 2008, 153 (Suppl. 1), S68-S75. (Pubitemid 351340990)
    • (2008) British Journal of Pharmacology , vol.153 , Issue.SUPPL. 1
    • Bodor, E.T.1    Offermanns, S.2
  • 10
    • 29144527442 scopus 로고    scopus 로고
    • Nicorandil - Review of pharmacological properties and clinical applications
    • DOI 10.1159/000089603
    • 10. Schmid, J.-P.; Schroeder, V. Nicorandil-Review of pharmacological properties and clinical applications. Heart Drug 2005, 5, 220-229 (Pubitemid 41797979)
    • (2005) HeartDrug , vol.5 , Issue.4 , pp. 220-229
    • Schmid, J.-P.1    Schroeder, V.2
  • 11
    • 75749128404 scopus 로고
    • Vasodilating action of several series of pyridine derivatives
    • Trcka, V.; Vejdelek, Z. J. Vasodilating action of several series of pyridine derivatives. Pharmazie 1956, 11, 242-247.
    • (1956) Pharmazie , vol.11 , pp. 242-247
    • Trcka, V.1    Vejdelek, Z.J.2
  • 12
    • 75749148149 scopus 로고    scopus 로고
    • Nicotinamide adenine dinucleotide induces relaxation in vitro rat aortic rings by acting on adenosine receptors
    • Zhou, Z.; Walsh, M.; Hramiec, J. Nicotinamide adenine dinucleotide induces relaxation in vitro rat aortic rings by acting on adenosine receptors. Surg. Forum 1999, 50, 479-481.
    • (1999) Surg. Forum , vol.50 , pp. 479-481
    • Zhou, Z.1    Walsh, M.2    Hramiec, J.3
  • 13
    • 0018235519 scopus 로고
    • Synthesis and antihypertensive action of 5-thio-2-pyridinecarboxylic acid derivatives
    • Finch, N.; Campbell, T. R.; Gemenden, C. W.; Antonaccio, M. J.; Polvaski, H. J. Synthesis and antihypertensive action of 5-thio-2-pyridinecarboxylic acid derivatives. J. Med. Chem. 1987, 21, 1269-1274.
    • (1987) J. Med. Chem. , vol.21 , pp. 1269-1274
    • Finch, N.1    Campbell, T.R.2    Gemenden, C.W.3    Antonaccio, M.J.4    Polvaski, H.J.5
  • 14
    • 0022219686 scopus 로고
    • The deoxydative substitution reactions of nicotinamide and nicotinic acid N-oxides by 1-adamantanethiol in acetic anhydride
    • Prachayasittikul, S.; Buer, L. The deoxydative substitution reactions of nicotinamide and nicotinic acid N-oxides by 1-adamantanethiol in acetic anhydride. J. Heterocyclic Chem. 1985, 22, 771-775.
    • (1985) J. Heterocyclic Chem. , vol.22 , pp. 771-775
    • Prachayasittikul, S.1    Buer, L.2
  • 15
    • 0032938529 scopus 로고    scopus 로고
    • Potassium ions and endothelium-derived hyperpolarizing factor in guinea-pig carotid and porcine coronary arteries
    • DOI 10.1038/sj.bjp.0702493
    • 15. Quignard, J. F.; Félétou, M.; Thollon, C.; Vilaine, J. P.; Duhault, J.; Vanhoutte, P. M. Potassium ions and endothelium-derived hyperpolarizing factor in guinea-pig carotid and porcine coronary arteries. Br. J. Pharmacol. 1999, 127, 27-34. (Pubitemid 29213228)
    • (1999) British Journal of Pharmacology , vol.127 , Issue.1 , pp. 27-34
    • Quignard, J.-F.1    Feletou, M.2    Thollon, C.3    Vilaine, J.-P.4    Duhault, J.5    Vanhoutte, P.M.6
  • 16
    • 0033007361 scopus 로고    scopus 로고
    • +channels and sodium pump in the vasodilation induced by acetylcholine, nitric oxide, and cyclic GMP in the rabbit aorta
    • +channels and sodium pump in the vasodilation induced by acetylcholine, nitric oxide, and cyclic GMP in the rabbit aorta. Gen. Pharmacol. 1999, 33, 35-41.
    • (1999) Gen. Pharmacol. , vol.33 , pp. 35-41
    • Ferrer, M.1    J, M.2    Encabo, A.3    Alonso, M.J.4    Balfagón, G.5
  • 18
    • 0018728611 scopus 로고
    • Prostaglandins contribute to the vasodilation induced by nicotinic acid
    • DOI 10.1016/0090-6980(79)90055-8
    • 18. Eklund, B.; Kaijser, L.; Nowak, J.; Wennmalm, A. Prostaglandins contribute to the vasodilation induced by nicotinic acid. Prostaglandins 1979, 17, 821-830. (Pubitemid 10221950)
    • (1979) Prostaglandins , vol.17 , Issue.6 , pp. 821-830
    • Eklund, B.1    Kaijser, L.2    Nowak, J.3    Wennmalm, A.4
  • 19
    • 0018747350 scopus 로고
    • Dissociation of the effects of nicotinic acid on vasodilatation and lipolysis by a prostaglandin synthesis inhibitor, indomethacin, in man
    • Kaijser, L.; Eklund, B.; Olsson, A. G.; Carlson, L. A. Dissociation of the effects of nicotinic acid on vasodilatation and lipolysis by a prostaglandin synthesis inhibitor, indomethacin, in man. Med. Biol. 1979, 57, 114-117.
    • (1979) Med. Biol. , vol.57 , pp. 114-117
    • Kaijser, L.1    Eklund, B.2    Olsson, A.G.3    Carlson, L.A.4
  • 20
    • 34250776466 scopus 로고    scopus 로고
    • Prostacyclin in liver disease: A potential therapeutic option
    • DOI 10.1517/14712598.7.6.785
    • 20. Zardi, E. M.; Dobrina, A.; Amoroso, A.; Afeltra, A. Prostacyclin in liver disease: a potential therapeutic option. Expert Opin. Biol. Ther. 2007, 7, 785-790. (Pubitemid 46954425)
    • (2007) Expert Opinion on Biological Therapy , vol.7 , Issue.6 , pp. 785-790
    • Zardi, E.M.1    Dobrina, A.2    Amoroso, A.3    Afeltra, A.4
  • 21
  • 22
    • 24344466900 scopus 로고    scopus 로고
    • Vasorelaxant and antioxidant activity of flavonols and flavones: Structure-activity relationships
    • DOI 10.1097/01.fjc.0000175431.62626.07
    • 22. Woodman, O. L.; Meeker, W. F.; Boujaoude, M. Vasorelaxant and antioxidant activity of flavonols and flavones: Structure-activity relationships. J. Cardiovasc. Pharm. 2005, 46, 302-309. (Pubitemid 41262832)
    • (2005) Journal of Cardiovascular Pharmacology , vol.46 , Issue.3 , pp. 302-309
    • Woodman, O.L.1    Meeker, W.F.2    Boujaoude, M.3
  • 23
    • 34248574742 scopus 로고    scopus 로고
    • Quantitative structure-imprinting factor relationship of molecularly imprinted polymers
    • DOI 10.1016/j.bios.2007.01.017, PII S0956566307000358, Chem and Biosensing Transistors: from materials to systems
    • 23. Nantasenamat, C.; Isarankura-Na-Ayudhya, C.; Naenna, T.; Prachayasittikul, V. Quantitative structure-imprinting factor relationship of molecularly imprinted polymers. Biosens. Bioelectron. 2007, 22, 3309-3317. (Pubitemid 46754891)
    • (2007) Biosensors and Bioelectronics , vol.22 , Issue.12 , pp. 3309-3317
    • Nantasenamat, C.1    Isarankura-Na-Ayudhya, C.2    Naenna, T.3    Prachayasittikul, V.4
  • 25
    • 31444441573 scopus 로고    scopus 로고
    • Quantitative prediction of imprinting factor of molecularly imprinted polymers by artificial neural network
    • DOI 10.1007/s10822-005-9004-4
    • 25. Nantasenamat, C.; Naenna, T.; Isarankura Na-Ayudhya, C.; Prachayasittikul, V. Quantitative prediction of imprinting factor of molecularly imprinted polymers by artificial neural network. J. Comput. Aid. Mol. Des. 2005, 19, 509-524. (Pubitemid 43150057)
    • (2005) Journal of Computer-Aided Molecular Design , vol.19 , Issue.7 , pp. 509-524
    • Nantasenamat, C.1    Naenna, T.2    Ayudhya, C.I.N.3    Prachayasittikul, V.4
  • 30
    • 33845183253 scopus 로고    scopus 로고
    • Absolute electronegativity and hardness: Applications to organic chemistry
    • Pearson, R.G. Absolute electronegativity and hardness: applications to organic chemistry. J. Org. Chem. 2002, 54, 1423-1430.
    • (2002) J. Org. Chem. , vol.54 , pp. 1423-1430
    • Pearson, R.G.1
  • 31
    • 0013602932 scopus 로고    scopus 로고
    • Activation hardness: New index for describing the orientation of electrophilic aromatic substitution
    • Zhou, Z.; Parr, R. G. Activation hardness: new index for describing the orientation of electrophilic aromatic substitution. J. Am. Chem. Soc. 2002, 112, 5720-5724.
    • (2002) J. Am. Chem. Soc. , vol.112 , pp. 5720-5724
    • Zhou, Z.1    Parr, R.G.2
  • 32
    • 0001776482 scopus 로고
    • Explosive molecular ionic crystals
    • Faust, W.L. Explosive Molecular Ionic Crystals. Science 1989, 245, 37-42.
    • (1989) Science , vol.245 , pp. 37-42
    • Faust, W.L.1
  • 33
    • 33947090337 scopus 로고    scopus 로고
    • Simple, comprehensive correlation of organic oxidation and ionization potentials
    • Miller, L. L.; Nordblom, G. D.; Mayeda, E. A. Simple, comprehensive correlation of organic oxidation and ionization potentials. J. Org. Chem. 2002, 37, 916-918.
    • (2002) J. Org. Chem. , vol.37 , pp. 916-918
    • Miller, L.L.1    Nordblom, G.D.2    Mayeda, E.A.3
  • 34
    • 0000576580 scopus 로고    scopus 로고
    • Comparison of density functional and Hartree-Fock average local ionization energies on molecular surfaces
    • Politzer, P.; Abu-Awwad, F.; Murray, J. S. Comparison of density functional and Hartree-Fock average local ionization energies on molecular surfaces. Int. J. Quantum Chem. 1998, 69, 607-613.
    • (1998) Int. J. Quantum Chem. , vol.69 , pp. 607-613
    • Politzer, P.1    Abu-Awwad, F.2    Murray, J.S.3
  • 35
    • 0038281434 scopus 로고    scopus 로고
    • Ionization potential, electron affinity, electronegativity, hardness, and electron excitation energy: Molecular properties from density functional theory orbital energies
    • Zhan, C.-G.; Nichols, J.A.; Dixon, D.A. Ionization potential, electron affinity, electronegativity, hardness, and electron excitation energy: Molecular properties from density functional theory orbital energies. J. Phys. Chem. A 2003, 107, 4184-4195.
    • (2003) J. Phys. Chem. A , vol.107 , pp. 4184-4195
    • Zhan, C.-G.1    Nichols, J.A.2    Dixon, D.A.3
  • 36
    • 0030739966 scopus 로고    scopus 로고
    • 116. Theoretical parameters to characterize antioxidants: The case of Vitamin e and analogs
    • DOI 10.1002/hlca.19970800519
    • 36. Migliavacca, E.; Carrupt, P.-A.; Testa, B. Theoretical parameters to characterize antioxidants. Part 1. The case of vitamin E and analogs. Helv. Chim. Acta 1997, 80, 1613-1626. (Pubitemid 27356284)
    • (1997) Helvetica Chimica Acta , vol.80 , Issue.5 , pp. 1613-1626
    • Migliavacca, E.1    Carrupt, P.-A.2    Testa, B.3
  • 37
    • 67549135468 scopus 로고    scopus 로고
    • Theoretical investigation on antioxidant activity of vitamins and phenolic acids for designing a novel antioxidant
    • Mohajeri, A.; Asemani, S. S. Theoretical investigation on antioxidant activity of vitamins and phenolic acids for designing a novel antioxidant. J. Mol. Struct. 2009, 930, 15-20.
    • (2009) J. Mol. Struct. , vol.930 , pp. 15-20
    • Mohajeri, A.1    Asemani, S.S.2
  • 38
    • 33749246236 scopus 로고    scopus 로고
    • Exploring a possible way to synthesize novel better antioxidants based on vitamin E: A DFT study
    • DOI 10.1016/j.bmcl.2006.08.063, PII S0960894X06009516
    • 38. Chen, W.; Song, J.; Guo, P.; Cao, W.; Bian, J. Exploring a possible way to synthesize novel better antioxidants based on vitamin E: A DFT study. Bioorg. Med. Chem. Lett. 2006, 16, 5874-5877. (Pubitemid 44486729)
    • (2006) Bioorganic and Medicinal Chemistry Letters , vol.16 , Issue.22 , pp. 5874-5877
    • Chen, W.1    Song, J.2    Guo, P.3    Cao, W.4    Bian, J.5
  • 42
    • 0033962075 scopus 로고    scopus 로고
    • Contribution of nitric oxide, cyclic GMP and K+ channels to acetylcholine-induced dilatation of rat conduit and resistance arteries
    • Woodman, O. L.; Wongsawatkul, O.; Sobey, C. G. Contribution of nitric oxide, cyclic GMP and K+ channels to acetylcholine-induced dilatation of rat conduit and resistance arteries. Clin. Exp. Pharmacol. Physiol. 2000, 27, 34-40.
    • (2000) Clin. Exp. Pharmacol. Physiol. , vol.27 , pp. 34-40
    • Woodman, O.L.1    Wongsawatkul, O.2    Sobey, C.G.3


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