Dendritic Polyglutamic Porphyrins: Probing Porphyrin Protection by Oxygen-Dependent Quenching of Phosphorescence

Vinogradov, Sergei A.; Lo, Leu‐Wei; Wilson, David F.

doi:10.1002/(sici)1521-3765(19990401)5:4<1338::aid-chem1338>3.0.co;2-n

Cited by 121 publications

(145 citation statements)

References 9 publications

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“…Microvascular Brain PO 2 . Microvascular brain O 2 tension was measured by using Oxyphor G2 phosphorescence as described (25).…”

Section: Methodsmentioning

confidence: 99%

“…Despite recent advances in brain O 2 imaging (24), a paucity of studies have assessed brain tissue O 2 delivery in acute anemia. We measured microvascular brain PO 2 by using phosphorescence quenching: a method that is highly selective for O 2 in biological systems but not affected by CO, NO, CO 2 , H 2 S, or by changes in cerebral blood flow (25,26). When arterial blood O 2 content was reduced by these two independent methods (anemia: Hb ∼ 50 g/L, 21% O 2; and hypoxia: Hb ∼ 130 g/L, 15% O 2 ), microvascular brain tissue PO 2 fell to comparable levels in WT and nNOS −/− mice (Table S1).…”

Section: Nnos Contributes To Adaptive Cardiovascular Responses Duringmentioning

confidence: 99%

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Priming of hypoxia-inducible factor by neuronal nitric oxide synthase is essential for adaptive responses to severe anemia

Tsui

Marsden²,

Mazer³

et al. 2011

Proc. Natl. Acad. Sci. U.S.A.

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103

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Cells sense and respond to changes in oxygen concentration through gene regulatory processes that are fundamental to survival. Surprisingly, little is known about how anemia affects hypoxia signaling. Because nitric oxide synthases (NOSs) figure prominently in the cellular responses to acute hypoxia, we defined the effects of NOS deficiency in acute anemia. In contrast to endothelial NOS or inducible NOS deficiency, neuronal NOS (nNOS) −/− mice demonstrated increased mortality during anemia. Unlike wild-type (WT) animals, anemia did not increase cardiac output (CO) or reduce systemic vascular resistance (SVR) in nNOS −/− mice. At the cellular level, anemia increased expression of HIF-1α protein and HIF-responsive mRNA levels (EPO, VEGF, GLUT1, PDK1) in the brain of WT, but not nNOS −/− mice, despite comparable reductions in tissue PO 2 . Paradoxically, nNOS −/− mice survived longer during hypoxia, retained the ability to regulate CO and SVR, and increased brain HIF-α protein levels and HIF-responsive mRNA transcripts. Real-time imaging of transgenic animals expressing a reporter HIF-α(ODD)-luciferase chimeric protein confirmed that nNOS was essential for anemia-mediated increases in HIF-α protein stability in vivo. S -nitrosylation effects the functional interaction between HIF and pVHL. We found that anemia led to nNOS-dependent S -nitrosylation of pVHL in vivo and, of interest, led to decreased expression of GSNO reductase. These findings identify nNOS effects on the HIF/pVHL signaling pathway as critically important in the physiological responses to anemia in vivo and provide essential mechanistic insight into the differences between anemia and hypoxia.

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“…Microvascular Brain PO 2 . Microvascular brain O 2 tension was measured by using Oxyphor G2 phosphorescence as described (25).…”

Section: Methodsmentioning

confidence: 99%

Section: Nnos Contributes To Adaptive Cardiovascular Responses Duringmentioning

confidence: 99%

Priming of hypoxia-inducible factor by neuronal nitric oxide synthase is essential for adaptive responses to severe anemia

Tsui

Marsden²,

Mazer³

et al. 2011

Proc. Natl. Acad. Sci. U.S.A.

Self Cite

103

View full text Add to dashboard Cite

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“…Dendrimers containing photoactive units [7][8][9][10][11][12][13][14][15][16][17] are particularly interesting for two reasons: (1) cooperation among the photoactive components can allow the dendrimer to perform specific functions, and (2) changes in the properties of photoactive components can be exploited to monitor the participation of dendrimers in chemical processes.…”

Section: -6mentioning

confidence: 99%

Synthesis of Poly(3,4,5-trihydroxybenzoate amide) and Poly(3,4,5-trihydroxybenzoate ester) Dendrimers from Polyphenols and Their Chemiluminescence

Lee¹,

Song²,

Lee³

et al. 2012

Bulletin of the Korean Chemical Society

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Dendrimer chemistry is rapidly expanding for fundamental reasons as well as due to requirements in technological applications.1 A recent interesting development in dendrimer chemistry concerns the coordination of metal ions by interior branches or exterior units. 2-6Dendrimers containing photoactive units 7-17 are particularly interesting for two reasons: (1) cooperation among the photoactive components can allow the dendrimer to perform specific functions, and (2) changes in the properties of photoactive components can be exploited to monitor the participation of dendrimers in chemical processes.Polyphenols such as pyrogallol and gallic acid (GA) produce a singlet oxygen in the presence of hydrogen peroxide in an alkaline medium and emit light. GA has also been utilized for selective Co 2+ detection using a chemiluminescence (CL) flow injection system. The CL intensities of polyphenols are considerably weaker than those of luminal and acridinium ester, which are representative CL compounds. Hence, trans-4-(3-propionic acid) phenylboronic acid and 4-biphenylboronic acid in the presence of peroxidase or 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide have been used as an enhancer for highly sensitive polyphenol CL determination. However, methods to derive polyphenols with strong CL intensity have not been reported yet. 18In recent times, after a new polymer, poly(amidoamine) dendrimer, was synthesized, dendrimers have been applied to material engineering based on optics in nanoscale science. The poly(propylene amine) family that was functionalized in the periphery with fluorescent dansyl units interacts with Co 2+. More recently, acridinium dendrimers have been conjugated with bovine serum albumin, and its CL was estimated to be six times that of the acridinium salt.In this paper, we report the design of new types of polyphenol dendrimers having an increased number of chemiluminophores for high CL intensity; they also have hydroxyl groups in their periphery to form hydrogen bonds with an analyte. Polyphenol dendrimers having GA in the periphery were synthesized, and their CL was measured. We synthesized first-generation polyphenol dendrimers with GA units in the periphery by employing a divergent method using phenol, pyrocatechol, resorcinol, hydroquinone, 1,2,4-trihydroxybenzene, 3,4,5-trihydroxybenzene aniline, 1,2-diaminobenzene, and 1,3-diaminobenzene as the core molecules (Supporting information, Schemes 1 and 2).Experimental methods and physical data from polyol 1a-f to first-generation esters 5a-f have been reported in our previous paper. 19The mass spectra of the zero-generation esters 3a-f and first-generation esters 5a-5f were obtained by matrix-assisted laser desorption/ionization-time-of-flight mass spectrometry (MALDI TOF MS) using 2,5-dihydroxybenzoic acid as the matrix. The amide group has a rigid, planer structure as a consequence of resonance interactions that give the amide bond ~40% double bond character. The planer conformation maximizes π-bonding overlap, which accounts for the amide group's ri...

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“…[2][3][4][5][6] Dendrimers containing photoactive units [7][8][9][10][11][12][13][14][15][16][17] are particularly interesting for two reasons: (1) cooperation among the photoactive components can allow the dendrimer to perform specific functions, and (2) changes in the properties of photoactive components can be exploited to monitor the participation of dendrimers in chemical processes.Polyphenols such as pyrogallol and gallic acid (GA) produce a singlet oxygen in the presence of hydrogen peroxide in an alkaline medium and emit light. GA has also been utilized for selective Co 2+ detection using a chemiluminescence (CL) flow injection system.…”

mentioning

confidence: 99%

Synthesis of Poly(3,4,5-trihydroxybenzoate) dendrimers from Polyphenols and Their Chemiluminescence

Jung

Song²,

Shin³

et al. 2010

Bulletin of the Korean Chemical Society

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Dendrimer chemistry is rapidly expanding both for fundamental reasons as well as due to requirements in technological applications.1 A recent interesting development in dendrimer chemistry concerns the coordination of metal ions by interior branches or exterior units. [2][3][4][5][6] Dendrimers containing photoactive units [7][8][9][10][11][12][13][14][15][16][17] are particularly interesting for two reasons: (1) cooperation among the photoactive components can allow the dendrimer to perform specific functions, and (2) changes in the properties of photoactive components can be exploited to monitor the participation of dendrimers in chemical processes.Polyphenols such as pyrogallol and gallic acid (GA) produce a singlet oxygen in the presence of hydrogen peroxide in an alkaline medium and emit light. GA has also been utilized for selective Co 2+ detection using a chemiluminescence (CL) flow injection system. The CL intensities of polyphenols are considerably weaker than those of luminal and acridinium ester, which are representative CL compounds. Hence, trans-4-(3-propionic acid)phenylboronic acid and 4-biphenylboronic acid in the presence of peroxidase or 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide have been used as an enhancer for highly sensitive polyphenol CL determination. However, methods to derive polyphenols with strong CL intensity have not been reported yet. 18In recent times, after a new polymer, poly(amidoamine) dendrimer, was synthesized, dendrimers have been applied to material engineering based on optics in nanoscale science. The poly(propylene amine) family that was functionalized in the periphery with fluorescent dansyl units interacts with Co 2+ . More recently, acridinium dendrimers have been conjugated with bovine serum albumin, and its CL was estimated to be six times that of the acridinium salt.In this paper, we report the design of new types of polyphenol dendrimers having an increased number of chemiluminophores for high CL intensity; they also have hydroxyl groups in their periphery to form hydrogen bonds with an analyst. Polyphenol dendrimers having GA in the periphery were synthesized, and their CL was measured. We synthesized first-generation polyphenol dendrimers with GA units in the periphery by employing a divergent method using phenol, pyrocatechol, resorcinol, hydroquinone, 1,2,4-trihydroxybenzene, and 3,4,5-trihydroxybenzene as the core molecules (Schemes 1-3).The esterification of 3,4,5-trihydroxybenzoyl chloride with phenol yielded 2a in 80%. After the debenzylation of 2a, we were able to separate 3a and the byproduct by chromatographic purification. Therefore, the desired zero-generation ester 3a was not isolated. Compounds 4a and 5a were synthesized by repeating this esterification and debenzylation, respectively, but the yield of the first-generation ester 5a was 91%. The esterification of 3,4,5-trihydroxybenzoyl chloride with pyrocatechol, 3,4,5-trihydroxybenzoyl chloride with resorcinol, and 3,4,5-trihydroxybenzoyl chloride with hydroquinone yielded 2b (95%), 2c (96%), a...

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Dendritic Polyglutamic Porphyrins: Probing Porphyrin Protection by Oxygen-Dependent Quenching of Phosphorescence

Cited by 121 publications

References 9 publications

Priming of hypoxia-inducible factor by neuronal nitric oxide synthase is essential for adaptive responses to severe anemia

Priming of hypoxia-inducible factor by neuronal nitric oxide synthase is essential for adaptive responses to severe anemia

Synthesis of Poly(3,4,5-trihydroxybenzoate amide) and Poly(3,4,5-trihydroxybenzoate ester) Dendrimers from Polyphenols and Their Chemiluminescence

Synthesis of Poly(3,4,5-trihydroxybenzoate) dendrimers from Polyphenols and Their Chemiluminescence

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