ライフサイエンスコーパス: diazeniumdiolate

1 of their reactivity in comparison to sodium diazeniumdiolate.

2 ith very little, if any, photorelease of the diazeniumdiolate.

3 standing of the chemistry of the acyclic (E)-diazeniumdiolates.

4 itrosamines were detected in some samples of diazeniumdiolates.

5 ) products: potassium 4-heptanone-3,3,5-tris(diazeniumdiolate) (1), potassium butanoate 2,2-bis(diaze

6 iumdiolate) (1), potassium butanoate 2,2-bis(diazeniumdiolate) (2), and potassium butanoate 2-diazeni

7 trosamine radical anion 5 upon photolysis of diazeniumdiolate 3 is confirmed by low-temperature EPR s

8 eniumdiolate) (2), and potassium butanoate 2-diazeniumdiolate (3).

9 e(4)(+) salts of methyl and ethylbutenoate-2-diazeniumdiolate-3-hydroxylate (3(2-) and 4(2-)), are is

10 oducts, namely, potassium propanoate 2,2-bis(diazeniumdiolate), 8b, all are stable in neutral and bas

11 ase of NO from previously known carbon-bound diazeniumdiolates also suggest that analogues of these c

12 As NO-releasing drug candidates, diazeniumdiolated amides would have the advantage of gen

13 These diazeniumdiolated amidines are shown to be useful NO don

14 diolate ion, H2N-N(O) horizontal lineNO(-) ("diazeniumdiolated ammonia"), might be stable enough to b

15 to the challenges inherent to the pursuit of diazeniumdiolated ammonia.

16 doped with N,N'-dibutylhexamethylenediamine diazeniumdiolate and a tetraphenylborate derivative are

17 I)-binding metabolite that contains a C-type diazeniumdiolate and N-hydroxypyrrole.

18 port the facile preparation of O2-sulfonated diazeniumdiolates and mechanistic investigation of their

19 Here we show that such diazeniumdiolate anions can readily displace halide from

20 hods for the detection and quantification of diazeniumdiolates are described.

21 The four Fe-O bond lengths in the two diazeniumdiolates are quite similar, ranging from 1.978

22 Diazeniumdiolates are valuable NO donors; however, synth

23 ber (SR) containing NO-generating compounds (diazeniumdiolates) are shown to release NO for extended

24 ered significant interest, as it added the C-diazeniumdiolate as a new Fe(III)-binding group in sider

25 potencies of JS-K and 41 other O(2)-arylated diazeniumdiolates as inhibitors of HL-60 human leukemia

26 te data for five representative glycosylated diazeniumdiolates at pH 14, 7.4, and 3.8-4.6 as backgrou

27 ompounds extends the range of O2-substituted diazeniumdiolates available for potential applications i

28 nhances contractility led us to synthesize a diazeniumdiolate-based HNO-releasing aspirin and to comp

29 Diazeniumdiolated bovine serum albumin (D-BSA; molecular

30 reaction in which it hydrolyzes to an alpha-diazeniumdiolated carbonyl compound and the parent amine

31 tulated to occur via an intermediate O-bound diazeniumdiolate [CH3O-N(O)=NO-] that decomposes to form

32 assium cis-2,6-dimethylcyclohexanone-2,6-bis(diazeniumdiolate), cis-14b, reveal that the N(2)O(2-) su

33 acterization and few structures of synthetic diazeniumdiolate complexes are reported.

34 We have found O(2)-substituted diazeniumdiolates, compounds of structure R(2)N-N(O)=NOR

35 ylase, and a key step in the assembly of the diazeniumdiolate-containing amino acid graminine.

36 The mechanism of diazeniumdiolate decomposition was proton initiated, gen

37 The diazeniumdiolate derived from 1-(N-morpholino)cyclohexen

38 nant of dissociation rate; (c) data for 5, a diazeniumdiolate derived from the polyamine spermine, wh

39 The rates of N-diazeniumdiolate dissociation are further related to the

40 ised of two graminine residues harboring the diazeniumdiolate donors and a beta-hydroxy-aspartate don

41 The more lipophilic diazeniumdiolates [e.g., R = (CH(2))(3)CH(3)] can be inc

42 an approach for generating pairs of Z and E diazeniumdiolates for systematic comparison of the rates

43 results illustrate the potential utility of diazeniumdiolates for targeting NO delivery in vivo and

44 O(2)-alkylation or arylation of diazeniumdiolates form stable pro-drugs which have found

45 onverted to NO release particles via in-situ diazeniumdiolate formation as carried out for the non-cr

46 layer did not have an inhibitory effect on N-diazeniumdiolate formation or NO release, and the NO-rel

47 wever, have little effect on the degree of N-diazeniumdiolate formation.

48 The diazeniumdiolate framework in all the structures is copl

49 ein, we report the expanded scope of calcium diazeniumdiolates from benzylic amines, amides, and ster

50 ease-of-handling advantages over the anionic diazeniumdiolates from which they are derived suggest th

51 uccessively cleaved to free the NO-releasing diazeniumdiolate function.

52 in the formation of compounds containing the diazeniumdiolate functional group (-[N(O)NO](-)).

53 of introducing the relatively rarely studied diazeniumdiolate functional group into organic compounds

54 h the replacement of active hydrogens by the diazeniumdiolate functional group via the Traube reactio

55 ed slow aminolysis by demonstrating that the diazeniumdiolate group greatly suppresses the electrophi

56 The N-diazeniumdiolate groups also undergo slow thermal dissoc

57 groups are then converted to corresponding N-diazeniumdiolate groups via reaction with NO(g) at high

58 N-Diazeniumdiolate groups were found to form more readily

59 The synthesis of sodium diazeniumdiolates has proven to be challenging due to ha

60 ite general and a variety of enamine-derived diazeniumdiolates have been isolated and characterized.

61 try of the previously undocumented E form of diazeniumdiolates having the structure R(1)R(2)NN(O)=NOR

62 cted for normal thermal decomposition of the diazeniumdiolate in aqueous solutions and also show the

63 isomers of 2,6-dimethylcyclohexanone-2,6-bis(diazeniumdiolate) in 12.9% and 57.6% yield.

64 strategy involved three steps: identifying a diazeniumdiolate ion (R2N[N(O)NO]-, where R2N = pyrrolid

65 the ground and excited states of the parent diazeniumdiolate ion at the CIS and B3LYP levels of theo

66 tical studies have suggested that the parent diazeniumdiolate ion, H2N-N(O) horizontal lineNO(-) ("di

67 Diazeniumdiolate ions of structure R(2)N[N(O)NO](-) (1)

68 s a convenient protecting group strategy for diazeniumdiolate ions.

69 converted into nitric oxide (NO) releasing N-diazeniumdiolates is described.

70 O produced from a small-molecule NO donor (N-diazeniumdiolated l-proline, PROLI/NO) and a NO-releasin

71 for surface measurements of NO released from diazeniumdiolate-loaded silicone rubber films (SR-DACA-6

72 The final N-diazeniumdiolated methacrylic amine polymers are shown t

73 The N-diazeniumdiolate moieties attached on the silica surface

74 Diazeniumdiolates, more commonly referred to as NONOates

75 l-Alanosine is a diazeniumdiolate (N-nitrosohydroxylamine) antibiotic tha

76 . -23 degrees C to give mono-, bis-, or tris-diazeniumdiolate (-N2O2(-)) products: potassium 4-heptan

77 The diazeniumdiolate nitric oxide donor agent 1-diethyl-2-hy

78 xysilane-based xerogel films modified with N-diazeniumdiolate NO donor precursors and the fluorescent

79 apid proton-initiated decomposition of the N-diazeniumdiolate NO donors and greater NO-release payloa

80 films formulated with two distinct types of diazeniumdiolate NO donors release NO for more than 24 h

81 nal groups in the silica were converted to N-diazeniumdiolate NO donors via exposure to high pressure

82 to store NO on a dendritic scaffold using N-diazeniumdiolate NO donors was examined via the reaction

83 bsequent conversion of secondary amines to N-diazeniumdiolate NO donors.

84 ulted in a 30-50% inhibition of diethylamine diazeniumdiolate-NO-stimulated sGC activity.

85 PABA/NO is a diazeniumdiolate of structure Me(2)NN(O)=NOAr (where Ar

86 factors that govern dissociation rates among diazeniumdiolates of importance as pharmacologic progeni

87 Glycosylated diazeniumdiolates of structure R 2NN(O)NO-R' (R' = a sac

88 Diazeniumdiolates of structure R(2)N-N(O)=N-OR', in whic

89 Dialkylhexamethylenediamine diazeniumdiolates of the form RN[N(O)NO](-)(CH(2))(6)NH(

90 condititons to give either cyclohexadienone diazeniumdiolates or oximates.

91 In contrast, treatment of chondrocytes with diazeniumdiolates (or the "NOC" compounds, NOC-5 and NOC

92 The desired diazeniumdiolate photorelease has been shown to become m

93 p of 3b and the free amino group of arylated diazeniumdiolated piperazine 4.

94 line in methanolic sodium methoxide yields a diazeniumdiolate product, C5H7N3O4Na2.CH3OH (PROLI/NO),

95 The diazeniumdiolate products are stable crystalline solids

96 l scanning calorimetry data measured for the diazeniumdiolate products indicate that they decompose e

97 Except for one of the diazeniumdiolate products, namely, potassium propanoate

98 ,alpha'-dimethine ketones yield mono- or bis(diazeniumdiolate) products.

99 These O(2)-aryl diazeniumdiolates proved capable of reacting with the nu

100 produce compounds containing a carbon-bound diazeniumdiolate [R1R2R3C-N(O)=NO-] functional group (pr

101 tential photosensitive protecting groups for diazeniumdiolates (R2N-N(O)=NO-) has been initiated, and

102 the photochemistry of O2-benzyl-substituted diazeniumdiolates (R2N-N(O)=NOCH2Ar) is reported.

103 i-tert-butyl-2, 5-cyclohexadienone-4-alkyl-4-diazeniumdiolate salts (4-methyl 1a, 4-ethyl 3a, 4-metho

104 eviously disclosed that synthesis of calcium diazeniumdiolate salts are a safer and more scalable alt

105 icient means of characterizing the purity of diazeniumdiolate samples prepared for use in biomedical

106 NO-release silicone rubber coating contains diazeniumdiolated secondary amine sites covalently ancho

107 Diazeniumdiolate siderophores have so far evaded crystal

108 ur at the terminal oxygen to yield the novel diazeniumdiolate structural unit, RNHN(O)=NOMe.

109 enation reactions of methyl ketones, the bis(diazeniumdiolate)-substituted alpha-methylene and alpha-

110 Mono- and bis(diazeniumdiolate)-substituted methyl ketones are cleaved

111 e results suggest that localized delivery of diazeniumdiolates such as PROLI/NO which generate NO wit

112 pH values with those for O- and N-alkylated diazeniumdiolates suggests that protonation at the R(2)N

113 Diazeniumdiolates that have the structure RHN-N(O) horiz

114 A number of bis(diazeniumdiolates) that we designed to release up to 4 m

115 ared to small molecule alkyl secondary amine diazeniumdiolates, thus illustrating a dendritic effect

116 We report bis(diazeniumdiolates) to be a class of S-glutathionylating

117 ity compared to either aspirin or the parent diazeniumdiolate toward nonsmall cell lung carcinoma cel

118 olds: the (dihydro)pyrazine-N-oxides and the diazeniumdiolate, valdiazen.

119 d by direct observation of the photoreleased diazeniumdiolate with 1H NMR spectroscopy and by NO quan

120 salts of 1a, or treating the O(2)-protonated diazeniumdiolate with diazomethane, both yield mixtures