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Advances in the Synthesis of Oligonucleotides by the Phosphoramidite Approach

A dinucleotide analogue of formula ##STR1## where B1 and B2 are each independently a monovalent nucleoside base radical; R1 is R1 a or Z; R1 a, R2, R3 and R4 are each independently hydrogen, halogen or hydroxy; R5 is R5 a or Z; R6 is hydrogen or R6 a ; R7 is hydrogen, alkyl-N,N-dialkylphosphoramidyl or R7 a, R8 is R8 a or Z, or the indicated R7 O and R8 together denote an isopropylidenedioxy group; R5 a and R8 a are each independently hydrogen, halogen, hydroxy, --OR10, --OCOR10 or silyloxy substituted by three C1 -C15 hydrocarbyl groups; R6 a and R7 a are each independently a C1 -C10 aliphatic radical, a C6 -C15 aromatic radical, a C7 -C30 araliphatic radical, --COR11, --SO2 R11 or silyl substituted by three C1 -C15 hydrocarbyl groups; R9 is hydrogen, a C1 -C8 aliphatic radical, a C3 -C8 cycloaliphatic radical, a C6 -C15 aromatic radical, a C7 -C13 araliphatic radical, an alkali metal ion or an ammonium ion; R10 and R11 are each independently a C1 -C10 aliphatic radical, a C3 -C8 cycloaliphatic radical, a C6 -C15 aromatic radical or a C7 -C16 araliphatic radical; Rx and Ry are independently hydrogen, halogen, hydroxy, a C1 -C10 alkyl, C2 -C10 alkenyl, C3 -C8 cycloalkyl, C6 -C15 aryl, C7 -C16 aralkyl, C1 -C10 alkoxy, C2 -C10 alkenoxy, C6 -C10 aryloxy or C7 -C16 aralkyloxy group, which is substituted or unsubstituted, or --OCORz ; Rz is a substituted or unsubstituted C1 -C10 alkyl, C2 -C10 alkenyl, C3 -C8 cycloalkyl, C6 -C15 aryl or C7 -C16 aralkyl group; and Z is C6 -C10 aryloxythiocarbonyloxy, the C6 -C10 aryl group being substituted or unsubstituted.

Dinucleoside phosphinates and their pharmaceutical compositions

Regioselective manipulation of hydroxyl groups via organotin derivatives

Kinetics and Mechanisms for the Cleavage and Isomerization of the Phosphodiester Bonds of RNA by Brønsted Acids and Bases

The evolution of nucleoside analogue antivirals: A review for chemists and non-chemists. Part 1: Early structural modifications to the nucleoside scaffold

While the effects of bisphosphonates on bone-resorbing osteoclasts have been well documented, the effects of bisphosphonates on other cell types are not as well studied. Recently, we reported that bisphosphonates have direct effects on bone-forming human fetal osteoblast cells (hFOB) [1]. In this report, the role of the mevalonate pathway in the actions of bisphosphonates on hFOB, and MDA-MB-231 human breast cancer cells was examined. These studies included a novel bisphosphonate analog, the anhydride formed between arabinocytidine 5′ phosphate and etidronate (Ara-CBP). Ara-CBP was the most potent inhibitor of hFOB and MDA-MB-231 cell proliferation, and stimulator of hFOB cell mineralization compared to etidronate, the anhydride formed between AMP and etidronate (ABP), pamidronate, and zoledronate. Inhibition of hFOB cell proliferation by Ara-CBP and zoledronate was partially reversed by mevalonate pathway intermediates, and stimulation of hFOB cell mineralization was completely reversed by mevalonate pathway intermediates. These results suggest that zoledronate and Ara-CBP act, at least in part, via inhibition of the mevalonate pathway in hFOB cells. In contrast, none of the mevalonate pathway intermediates reversed the inhibition of MDA-MB-231 cell proliferation by the bisphosphonates, or the effects of pamidronate on hFOB cells. As a positive control, the effects of mevastatin on hFOB and MDA-MB-231 cells were completely reversed by mevalonate. In summary, these data suggest that zoledronate and Ara-CBP induce human osteoblast differentiation via inhibition of the mevalonate pathway. In contrast, the inhibition of MDA-MB-231 cell proliferation by the bisphosphonates appears to be through mechanisms other than inhibition of the mevalonate pathway.

Distinct mechanisms of bisphosphonate action between osteoblasts and breast cancer cells: identity of a potent new bisphosphonate analogue.

Synthesis and properties of 3′-C-methylnucleosides and their phosphoric esters

The reaction of 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane with cytosine arabinoside and 1-(6-deoxy-α-L-talofuranosyl)uracil

Synthesis of adenylyl-(2'→5')adenylyl-(2'→5')adenosine

A partir du D-glucose on prepare le desoxy-5 O-isopropylidene-1,2 α-D-xylo-hexofuranose qui permet, par addition de triethylphosphite et condensation avec l'adenine ou l'uracile proteges d'obtenir des phosphono-6' hexofuranosyl uraciles ou -adenines

Nelly Sh. Padyukova

Papers

Distinct mechanisms of bisphosphonate action between osteoblasts and breast cancer cells: identity of a potent new bisphosphonate analogue.

Synthesis and properties of 3′-C-methylnucleosides and their phosphoric esters

The reaction of 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane with cytosine arabinoside and 1-(6-deoxy-α-L-talofuranosyl)uracil

Synthesis of adenylyl-(2'→5')adenylyl-(2'→5')adenosine

Use of 5-deoxy- ribo -hexofuranose derivatives for the preparation of 5'-nucleotide phosphonates and homoribonucleosides