ライフサイエンスコーパス: diazeniumdiolate

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

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

3 itrosamines were detected in some samples of diazeniumdiolates.

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

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

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

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

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

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

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

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

12 These diazeniumdiolated amidines are shown to be useful NO don

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

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

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

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

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

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

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

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

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

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

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

24 Diazeniumdiolated bovine serum albumin (D-BSA; molecular

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

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

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

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

29 The mechanism of diazeniumdiolate decomposition was proton initiated, gen

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

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

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

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

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

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

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

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

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

39 The diazeniumdiolate framework in all the structures is copl

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

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

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

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

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

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

46 The N-diazeniumdiolate groups also undergo slow thermal dissoc

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

48 N-Diazeniumdiolate groups were found to form more readily

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

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

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

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

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

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

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

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

57 s a convenient protecting group strategy for diazeniumdiolate ions.

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

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

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

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

62 The N-diazeniumdiolate moieties attached on the silica surface

63 Diazeniumdiolates, more commonly referred to as NONOates

64 . -23 degrees C to give mono-, bis-, or tris-diazeniumdiolate (-N2O2(-)) products: potassium 4-heptan

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

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

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

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

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

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

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

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

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

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

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

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

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

78 condititons to give either cyclohexadienone diazeniumdiolates or oximates.

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

80 The desired diazeniumdiolate photorelease has been shown to become m

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

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

83 The diazeniumdiolate products are stable crystalline solids

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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