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1 rophenyl phosphate and diethyl p-nitrophenyl phosphorothioate.
2 otide: 1), [Rp]-phosphorothioate or 2), [Sp]-phosphorothioate.
3 Cl2(*-) with the model compound diisopropyl phosphorothioate.
4 e morpholino oligomers (PMO) and 2'-O-methyl phosphorothioate.
5 ar precursor containing a 5'-iodide and a 3'-phosphorothioate.
7 lial cell apoptosis, Bcl-2/Bcl-X(L) chimeric phosphorothioated 2'-MOE-modified antisense oligonucleot
8 ne's mRNA in human leukemia cells with fully phosphorothioated 2'F-ANA-DNA chimeras (PS-2'FANA-DNA) a
9 eous disruption of both proteins using novel phosphorothioate-2'-O-methoxyethyl antisense oligodeoxyn
11 constructs, 2'-O-methyl-1-allylinosinic acid phosphorothioate 33-mer (16) and an oligomer incorporati
14 n, the thio effect of the S(P)-isomer of the phosphorothioate analogue (k(O)/k(Sp) = 4.4 x 10(5)) app
15 bridging position of the S(p) isomer of the phosphorothioate analogue causes a dramatic (2 x 10(5)-f
16 synthesis of d(ATCCGTAGCTAAGGTCATGC) and its phosphorothioate analogue is comparable to that of comme
17 istent trend of a greater DeltaH(++) for the phosphorothioate analogue was found in all three classes
18 tion, hydrolysis of the diastereomers of the phosphorothioate analogues of 1,6-IcP, inositol cis-1,6-
23 ng group in phosphates, as compared to their phosphorothioate analogues, ruling this out as a contrib
25 early 4 A decrease in the separation between phosphorothioate and 2'F labels incorporated at A27 in t
26 s, affords two distinct products, inositol 1-phosphorothioate and inositol 6-phosphorothioate, respec
27 ite-specific 2'-deoxynucleotides, as well as phosphorothioate and methylphosphonate modifications wit
29 An efficient process for purification of phosphorothioate and native DNA sequences is described h
30 In the comparative hydrolysis reactions of phosphorothioate and phosphate esters, the sulfur substi
31 iester, phosphorothioate, and both linkages (phosphorothioate and phosphodiester) present in the same
32 amines the rates and products of cleavage of phosphorothioate and phosphorodithioate analogues of PI
33 ically injected 2'-O-methoxyethyl (2'-O-MOE)-phosphorothioate and PNA-4K oligomers (peptide nucleic a
34 ent equivalency of the transition states for phosphorothioate and sulfate hydrolysis reactions at the
37 bases were synthesized with phosphodiester, phosphorothioate, and both linkages (phosphorothioate an
38 itrophenyl phosphate and ethyl p-nitrophenyl phosphorothioate, and the triesters, diethyl p-nitrophen
39 are observed by treating donor hearts with a phosphorothioate antisense oligodeoxyribonucleotide dire
40 rization of a 5' conjugate between a 2'-O-Me phosphorothioate antisense oligonucleotide and a bivalen
43 virsen is a locked nucleic acid-modified DNA phosphorothioate antisense oligonucleotide that sequeste
44 acy and safety of drisapersen, a 2'-O-methyl-phosphorothioate antisense oligonucleotide, given for 48
47 ras-1 (KSR1) gene by continuous infusion of phosphorothioate antisense oligonucleotides (ODNs) preve
49 muscular injection of a specific 2'-O-methyl phosphorothioate antisense oligoribonucleotide (2OMeAO).
50 stering oblimersen sodium (G3139), an 18-mer phosphorothioate antisense to Bcl-2, during induction an
54 pression of Abcc8, which encodes for SUR1 by phosphorothioated antisense oligodeoxynucleotide essenti
57 transfection protocol with a 2-O-methylated phosphorothioated antisense oligoribonucleotide (2OMeAO)
58 pe 2 diabetes using 2'-methoxyethyl-modified phosphorothioate-antisense oligonucleotide (ASO) inhibit
59 rted the in vitro combinatorial selection of phosphorothioate aptamers or "thioaptamers" targeting th
65 , a diagnostic fragment originating from the phosphorothioate backbone (O2PS-: m/z 94.936) was formed
66 nucleic acids (LNA) AMOs synthesized with a phosphorothioate backbone also inhibited TLR7 sensing in
67 nucleotide [INH-ODN]) are characterized by a phosphorothioate backbone and a CC(T)XXX(3)(-)(5)GGG mot
68 ynthesized with 2' sugar modifications and a phosphorothioate backbone in a mouse model of melanoma l
70 present a unique LC/MS/MS assay for a model phosphorothioate backbone oligodeoxynucleotide (ODN) dru
71 an efficient and cost-effective manner, to a phosphorothioate backbone position at arbitrary DNA or R
73 composed of 2'-O-methyl-modified bases on a phosphorothioate backbone to treat cultured primary myob
74 olecular properties of the lipid moiety, the phosphorothioate backbone, and the presence of triplet-G
77 nse, Genta, Berkeley Heights, NJ), an 18-mer phosphorothioate Bcl-2 antisense, with fludarabine (FL),
81 ted that synthetic CpG-ODN requires backbone phosphorothioate but not TLR9 activation to render and m
82 ic HNA 'gapmer' oligonucleotide comprising a phosphorothioate central sequence flanked by 5' and 3' H
89 table nucleobase modification or significant phosphorothioate desulfurization occurs, the 3-(N-tert-b
91 rpart pNPP, while alkaline hydrolysis of the phosphorothioate diester and triester exhibits somewhat
92 tly alter DNA nucleobases or desulfurize the phosphorothioate diester model to an appreciable extent.
93 any DNA nucleobases and do not desulfurize a phosphorothioate diester model under conditions mimickin
94 cted 2'-deoxyribonucleosides or with a model phosphorothioate diester under conditions approximating
96 different phosphate diester orientations and phosphorothioate diesters highlight that the interpretat
98 tion has been achieved via backbone-modified phosphorothioate DNA and biotin- and maleimide-containin
102 the scissile phosphate blocks cleavage; the phosphorothioate effect can be rescued by the thiophilic
103 t was possible to determine that the maximal phosphorothioate effect in this system is in the range o
106 occurs spontaneously when their phosphate or phosphorothioate esters are formed during oligonucleotid
109 lysis rates of the dianions of phosphate and phosphorothioate esters are substantially accelerated by
111 rium and kinetic isotope effects for several phosphorothioate esters of p-nitrophenol (pNPPT) and com
112 Cu(I) catalyzes the allylic substitution of phosphorothioate esters with excellent alpha-regioselect
114 tion of a single phosphodiester group with a phosphorothioate, followed by selective functionalizatio
115 RNA and rRNA binding sites appear different, phosphorothioate footprinting of the L4-RNA complexes re
117 e HNA antisense oligonucleotide (lacking the phosphorothioate 'gap') was ineffective, indicating that
119 inase was used to enzymatically substitute a phosphorothioate group at the 5' terminus of a nucleic a
121 ed DNA featuring a hydrophobic belt of ethyl phosphorothioate groups insert into bilayer membranes an
125 e receptor-9 (TLR-9) vaccines using cytosine phosphorothioate guanosine (CpG)-allergen conjugates, an
126 ligomer length-dependent, and the ability of phosphorothioate homopolymers of thymidine of variable l
127 ients for AP-catalyzed aryl sulfate and aryl phosphorothioate hydrolysis (-0.76 +/- 0.14 and -0.77 +/
131 Mouse erythroleukemia cells treated with the phosphorothioate inhibitor show a significant decrease i
133 ional switching assay was used to select for phosphorothioate interference, and identifies potential
134 ant MB containing 2'-O-methyl RNA bases with phosphorothioate internucleotide linkages was designed t
137 (R,R) and (S,S) enantiomers of both LBPA and phosphorothioate LBPA were synthesized from (S)- and (R)
139 s containing tetrahydrofuran (THF) with a 5'-phosphorothioate linkage as the abasic site substrate.
141 either phosphodiester or varying numbers of phosphorothioate linkages are remarkably stable during p
144 anded DNA as a substrate and digests through phosphorothioate linkages having one absolute stereochem
145 The use of DNA polymerases to incorporate phosphorothioate linkages into DNA, and the use of exonu
146 atment of cells with RNA duplexes containing phosphorothioate linkages leads to selective inhibition
148 or two 2'-fluoro-2'-deoxyriboses and/or bis-phosphorothioate linkages, are more potent than 2',3'-cG
149 ouble-stranded DNA substrates terminating in phosphorothioate linkages, we suggest that the rate of t
153 ased immune adjuvants to plasmid by 'hybrid' phosphorothioate-LNA ODNs induces tumour necrosis factor
155 taining a single radioactive phosphate and a phosphorothioate modification at the cleavage site.
162 demonstrate that antagomirs harbor optimized phosphorothioate modifications, require >19-nt length fo
163 arget (5ECdsRan) as a control, was partially phosphorothioate modified and tagged with superparamagne
164 to play a role in the uptake of unconjugated phosphorothioate modified ASOs in the liver as evidenced
166 growth factors, we characterized a specific phosphorothioate-modified 21-mer antisense PKCalpha (AS-
167 evaluated, we determined that a 2'-O-methyl phosphorothioate-modified anti-miR-221 oligonucleotide w
169 ntified a potent 2'-O-(2-methoxyethyl) (MOE) phosphorothioate-modified antisense oligonucleotide (ASO
170 ting EGFR via intratumoral administration of phosphorothioate-modified antisense oligonucleotides has
172 e contained an arylazido moiety coupled to a phosphorothioate-modified backbone of an oligonucleotide
174 apeutic mechanisms of systemically delivered phosphorothioate-modified EGFR antisense oligonucleotide
175 re composed of 2'-O-methyl RNAs with a fully phosphorothioate-modified loop domain (2Me/PSLOOP MBs),
176 agnetic iron oxide nanoparticles (SPIONs) to phosphorothioate-modified micro-DNA that targets actin o
177 age, the addition of 2'-O-methyl groups to a phosphorothioate-modified ODN is advantageous because of
178 ntisense effects of two types of 20mer ODNs, phosphorothioate-modified ODNs (S-ODNs) and S-ODNs with
179 PION, a T2 susceptibility agent) linked to a phosphorothioate-modified oligodeoxynucleotide (sODN) co
180 e exposure using antisense (AS) or sense (S) phosphorothioate-modified oligodeoxynucleotide (sODN) se
181 short DNA that targets mmp-9 mRNA activity [phosphorothioate-modified oligodeoxynucleotide (sODN)-mm
182 otides, a methylated oligodeoxynucleotide, a phosphorothioate-modified oligodeoxynucleotide, and an e
183 n oxide nanoparticles (SPIONs) (15-20 nm) to phosphorothioate-modified oligodeoxynucleotides (sODNs)
184 ed the effect of sequence-specific antisense phosphorothioate-modified oligodeoxyribonucleotides (PS-
186 llected from more than 1000 experiments with phosphorothioate-modified oligonucleotides revealed that
187 erentiation step, antisense inhibition using phosphorothioate-modified oligonucleotides, and overexpr
188 tions occurred even without incorporation of phosphorothioate moieties into the RNA and DNA target mo
189 eptible to fragmentation at sites containing phosphorothioate moieties, labeling and cleavage reactio
190 g(2+) was added to the hybrid complexes, the phosphorothioate moiety at one DNA-binding cleft prevent
192 ly perturbed through random incorporation of phosphorothioate nucleotide analogues, and RNA molecules
193 therapeutic benefit in treating sepsis with phosphorothioate ODN sequences containing the CpG motif.
195 developed for the quantitation of antisense phosphorothioate oligodeoxynucleotides in plasma using a
198 1, a ragweed-pollen antigen, conjugated to a phosphorothioate oligodeoxyribonucleotide immunostimulat
199 fficacy of modifying gene-specific antisense phosphorothioate oligodeoxyribonucleotides (PS-ODNs) by
200 molecules used in these studies consisted of phosphorothioate oligomers linked to the Antennapedia (A
202 poteichoic acid (LTA), thymidine homopolymer phosphorothioate oligonucleotide [Poly(dT)], and polyino
203 letion of DNA methyltransferase 1 (DNMT1) by phosphorothioate oligonucleotide antisense (DNMT1 AS) we
204 mice with locked nucleic acid (LNA)-modified phosphorothioate oligonucleotide complementary to miR 14
205 suppression by G3139 (oblimersen sodium), a phosphorothioate oligonucleotide complementary to the bc
206 d for their gene, mRNA, siRNA and 2'O-methyl phosphorothioate oligonucleotide in vitro transfection a
207 gapmer was substantially more potent than a phosphorothioate oligonucleotide of the same sequence in
208 o test this hypothesis, we used an antisense phosphorothioate oligonucleotide to effect a 50% reducti
209 ve investigated the antiviral mechanism of a phosphorothioate oligonucleotide, ISIS 5652, which has a
210 antisense chimeric 2'-O-(2-methoxy)ethyl/DNA phosphorothioate oligonucleotides (ONs) to affect cell g
211 re systems were used to study the effects of phosphorothioate oligonucleotides (PS-ONs), as amphipath
213 d by 5' and 3' HNA sequences to conventional phosphorothioate oligonucleotides and to a 2'-O-methoxye
214 we report that transfection of 2'-F-modified phosphorothioate oligonucleotides into cells can reduce
215 on of RLIP76 using either siRNA or antisense phosphorothioate oligonucleotides preferentially caused
217 e demonstrate the ability of G3139 and other phosphorothioate oligonucleotides to bind directly to mi
218 important degradation pathway for antisense phosphorothioate oligonucleotides under conditions of th
221 found to enhance triplex formation, whereas phosphorothioate or phosphotriester substitutions abroga
222 on of all four nucleotide triphosphates with phosphorothioates or the substitution of one with the eq
223 uanine-containing S-oligomers containing one phosphorothioate, -P-S-Cl results in one-electron oxidat
224 ld change in (31)P NMR chemical shift of the phosphorothioate peak (Delta approximately 3 ppm with 6
225 tives with thiols, beta-thioglycosyl thiols, phosphorothioates, phosphates, and amines to afford comp
227 trophenyl phosphate (pNPP) and p-nitrophenyl phosphorothioate (pNPPT), from water to 0.6 (mol) aq DMS
231 e probe pairs consisted of a nucleophilic 3'-phosphorothioate probe carrying a Cy5 FRET acceptor, and
238 uction of beta-chemokines by non-CpG-ODN was phosphorothioate (PS) chemistry dependent and inhibited
240 isense oligonucleotides (ASOs) modified with phosphorothioate (PS) linkages and different 2' modifica
243 tion studies of HHRz constructs containing a phosphorothioate (PS) modification at the cleavage site.
246 by directly comparing the ability of OXE and phosphorothioate (PS) ODNs to target c-myb gene expressi
252 ne monomers were used to prepare a series of phosphorothioate (PS)-modified gapmer antisense oligonuc
253 Lipofectamine 2000-mediated transfection of phosphorothioate (PS)-modified oligonucleotides (ON) on
254 t the evaluation of 20-, 18-, 16- and 14-mer phosphorothioate (PS)-modified tricycloDNA (tcDNA) gapme
255 confirmation rate during screening of fully phosphorothioated (PS)-LNA gapmer ASOs designed against
261 triction-modification (R-M) system involving phosphorothioate (PT) modification of the DNA backbone.
262 s (lipoplexes) were formulated at a nitrogen:phosphorothioate ratio (N:P) of 2 with a dose concentrat
263 dified regions and a 2'-deoxyoligonucleotide phosphorothioate region that allows RNase H digestion of
264 bstrates were synthesized, where an epimeric phosphorothioate replaces one of the phosphate diester l
267 olino phosphoroamidate (PMO) and 2'-O-methyl phosphorothioate RNA (2'Ome RNA) chemistry have been sho
268 ment of lymphoblast cells with IIS antisense phosphorothioate (S)-oligonucleotides prevents chemotact
269 icient and cost-effective manner to backbone phosphorothioate sites that are chemically substituted i
270 surface of DNA being randomly labeled at the phosphorothioate sites with this protein-cleaving reagen
271 immunostimulatory sequence (ISS)-containing phosphorothioate-stabilized oligonucleotides for antiher
272 eriments using HisRS active site mutants and phosphorothioate-substituted adenylate showed that subst
273 lease and reconstitution of the probe with a phosphorothioate-substituted oligonucleotide, an [alpha-
274 coordinated to the C208 pro-S(P) oxygen, the phosphorothioate-substituted ribozymes were also assayed
275 rates with a 3'-phosphorothiolate or an S(P) phosphorothioate substitution at the scissile phosphate.
277 are kinetically recruited and anchored to a phosphorothioate substitution embedded within a structur
280 each of these sites is supported by previous phosphorothioate substitution studies and, in the case o
281 Of the 10 ribozymes that were studied, four phosphorothioate substitutions (A207 S(P), C208 S(P), A3
283 caused recovery of the rate of reaction for phosphorothioate substitutions between A621 and A622 and
284 mbined atomic mutagenesis with site-specific phosphorothioate substitutions in the ribozyme backbone
285 m, stereospecific (R(P) or S(P)) single-site phosphorothioate substitutions were introduced at five p
287 preferences of AP endo and T4 DNA ligase for phosphorothioate substrates, we show that AP endo acts b
290 ine (R5a), was attached postsynthetically to phosphorothioates that were chemically introduced, one a
291 the solid-phase synthesis of oligonucleoside phosphorothioates, the thermolytic 2-[N-methyl-N-(2-pyri
292 AsTsAsT]2, -P-S-Cl reacts with a neighboring phosphorothioate to form the sigma(2)sigma*(1)-bonded di
293 oligonucleotide with an equivalent number of phosphorothioates to thioaptamer 97 and a scrambled cons
294 microbubble destruction-mediated delivery of phosphorothioated TRAF3IP2 antisense oligonucleotides in
295 rated site-specific delivery of antiparallel phosphorothioate triplex forming oligonucleotide (TFO) s
296 We also synthesized and evaluated the alpha-phosphorothioate variant of d5SICSTP, which provides a r
297 mechanistic difference (D(N) + A(N) for the phosphorothioate versus A(N)D(N) for the phosphate) comp
298 erminus of a nucleic acid, and the resulting phosphorothioate was then reacted with an iodomethyl der
299 s, p-nitrophenyl phosphate and p-nitrophenyl phosphorothioate, were compared to the activation parame
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