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Improved uptake and retention of lipophilic prodrug to improve treatment of HIV.

Advanced drug delivery reviews

Yatvin MB, Li W, Meredith MJ, Shenoy MA.
PMID: 10837773
Adv Drug Deliv Rev. 1999 Oct 18;39(1):165-182. doi: 10.1016/s0169-409x(99)00025-3.

Dideoxynucleosides currently in use for anti-HIV therapy have been found to be inefficient in passing through the blood-brain barrier to enter and maintain therapeutic drug levels in brain, a very significant reservoir of HIV. The low bioavailability of these...

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Yatvin MB, Li W, Meredith MJ, et al. Improved uptake and retention of lipophilic prodrug to improve treatment of HIV. Adv Drug Deliv Rev. 1999;39(1):165-182doi: 10.1016/s0169-409x(99)00025-3.
Yatvin, M. B., Li, W., Meredith, M. J., & Shenoy, M. A. (1999). Improved uptake and retention of lipophilic prodrug to improve treatment of HIV. Advanced drug delivery reviews, 39(1), 165-182. https://doi.org/10.1016/s0169-409x(99)00025-3
Yatvin, et al. "Improved uptake and retention of lipophilic prodrug to improve treatment of HIV." Advanced drug delivery reviews vol. 39,1 (1999): 165-182. doi: https://doi.org/10.1016/s0169-409x(99)00025-3
Yatvin MB, Li W, Meredith MJ, Shenoy MA. Improved uptake and retention of lipophilic prodrug to improve treatment of HIV. Adv Drug Deliv Rev. 1999 Oct 18;39(1):165-182. doi: 10.1016/s0169-409x(99)00025-3. PMID: 10837773.
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Stereoselective Synthesis of 2'-Amino-2',3'-dideoxynucleosides by Nitrone 1,3-Dipolar Cycloaddition: A New Efficient Entry Toward d4T and Its 2-Methyl Analogue.

The Journal of organic chemistry

Chiacchio U, Rescifina A, Iannazzo D, Romeo G.
PMID: 11674081
J Org Chem. 1999 Jan 08;64(1):28-36. doi: 10.1021/jo972264i.

An efficient access to 2'-(dimethylamino)-2',3'-dideoxynucleosides is reported. The synthetic strategy relies on the 1,3-dipolar cycloaddition of C-alkoxycarbonyl nitrones to allyl acetate, followed by reductive ring opening to substituted lactones, DIBALH reduction to the corresponding 3-(dimethylamino)tetrahydro-2-furanols, and coupling with silylated...

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Chiacchio U, Rescifina A, Iannazzo D, et al. Stereoselective Synthesis of 2'-Amino-2',3'-dideoxynucleosides by Nitrone 1,3-Dipolar Cycloaddition: A New Efficient Entry Toward d4T and Its 2-Methyl Analogue. J Org Chem. 1999;64(1):28-36doi: 10.1021/jo972264i.
Chiacchio, U., Rescifina, A., Iannazzo, D., & Romeo, G. (1999). Stereoselective Synthesis of 2'-Amino-2',3'-dideoxynucleosides by Nitrone 1,3-Dipolar Cycloaddition: A New Efficient Entry Toward d4T and Its 2-Methyl Analogue. The Journal of organic chemistry, 64(1), 28-36. https://doi.org/10.1021/jo972264i
Chiacchio, Ugo, et al. "Stereoselective Synthesis of 2'-Amino-2',3'-dideoxynucleosides by Nitrone 1,3-Dipolar Cycloaddition: A New Efficient Entry Toward d4T and Its 2-Methyl Analogue." The Journal of organic chemistry vol. 64,1 (1999): 28-36. doi: https://doi.org/10.1021/jo972264i
Chiacchio U, Rescifina A, Iannazzo D, Romeo G. Stereoselective Synthesis of 2'-Amino-2',3'-dideoxynucleosides by Nitrone 1,3-Dipolar Cycloaddition: A New Efficient Entry Toward d4T and Its 2-Methyl Analogue. J Org Chem. 1999 Jan 08;64(1):28-36. doi: 10.1021/jo972264i. PMID: 11674081.
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Nucleic Acid Related Compounds. 105. Synthesis of 2',3'-Didehydro-2',3'-dideoxynucleosides from Ribonucleoside Cyclic 2',3'-(Sulfates or Phosphates) or 2',3'-Dimesylates via Reductive Elimination with Sodium Naphthalenide(1).

The Journal of organic chemistry

Robins MJ, Lewandowska E, Wnuk SF.
PMID: 11672386
J Org Chem. 1998 Oct 16;63(21):7375-7381. doi: 10.1021/jo981013m.

Treatment of purine ribonucleosides with thionyl fluoride resulted in formation of cyclic 2',3'-sulfite esters. Acetylation of the 5'-hydroxy group and Sharpless oxidation (NaIO(4)/RuCl(3)) gave the cyclic 2',3'-sulfate ester derivatives. Treatment of 5'-O-silyl-protected ribonucleosides with thionyl chloride followed by oxidation...

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Robins MJ, Lewandowska E, Wnuk SF. Nucleic Acid Related Compounds. 105. Synthesis of 2',3'-Didehydro-2',3'-dideoxynucleosides from Ribonucleoside Cyclic 2',3'-(Sulfates or Phosphates) or 2',3'-Dimesylates via Reductive Elimination with Sodium Naphthalenide(1). J Org Chem. 1998;63(21):7375-7381doi: 10.1021/jo981013m.
Robins, M. J., Lewandowska, E., & Wnuk, S. F. (1998). Nucleic Acid Related Compounds. 105. Synthesis of 2',3'-Didehydro-2',3'-dideoxynucleosides from Ribonucleoside Cyclic 2',3'-(Sulfates or Phosphates) or 2',3'-Dimesylates via Reductive Elimination with Sodium Naphthalenide(1). The Journal of organic chemistry, 63(21), 7375-7381. https://doi.org/10.1021/jo981013m
Robins, Morris J., et al. "Nucleic Acid Related Compounds. 105. Synthesis of 2',3'-Didehydro-2',3'-dideoxynucleosides from Ribonucleoside Cyclic 2',3'-(Sulfates or Phosphates) or 2',3'-Dimesylates via Reductive Elimination with Sodium Naphthalenide(1)." The Journal of organic chemistry vol. 63,21 (1998): 7375-7381. doi: https://doi.org/10.1021/jo981013m
Robins MJ, Lewandowska E, Wnuk SF. Nucleic Acid Related Compounds. 105. Synthesis of 2',3'-Didehydro-2',3'-dideoxynucleosides from Ribonucleoside Cyclic 2',3'-(Sulfates or Phosphates) or 2',3'-Dimesylates via Reductive Elimination with Sodium Naphthalenide(1). J Org Chem. 1998 Oct 16;63(21):7375-7381. doi: 10.1021/jo981013m. PMID: 11672386.
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Concepts for the design of anti-HIV nucleoside prodrugs for treating cephalic HIV infection.

Advanced drug delivery reviews

Wiebe LI, Knaus EE.
PMID: 10837768
Adv Drug Deliv Rev. 1999 Oct 18;39(1):63-80. doi: 10.1016/s0169-409x(99)00020-4.

The life cycle of HIV involves nine sequential stages. Of these, the reverse transcription (RT) process is a prime target for drug therapy, using both nucleoside and non-nucleoside inhibitors of RT. There are currently five marketed 2',3'-dideoxynucleoside RT inhibitors,...

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Wiebe LI, Knaus EE. Concepts for the design of anti-HIV nucleoside prodrugs for treating cephalic HIV infection. Adv Drug Deliv Rev. 1999;39(1):63-80doi: 10.1016/s0169-409x(99)00020-4.
Wiebe, L. I., & Knaus, E. E. (1999). Concepts for the design of anti-HIV nucleoside prodrugs for treating cephalic HIV infection. Advanced drug delivery reviews, 39(1), 63-80. https://doi.org/10.1016/s0169-409x(99)00020-4
Wiebe, and Knaus. "Concepts for the design of anti-HIV nucleoside prodrugs for treating cephalic HIV infection." Advanced drug delivery reviews vol. 39,1 (1999): 63-80. doi: https://doi.org/10.1016/s0169-409x(99)00020-4
Wiebe LI, Knaus EE. Concepts for the design of anti-HIV nucleoside prodrugs for treating cephalic HIV infection. Adv Drug Deliv Rev. 1999 Oct 18;39(1):63-80. doi: 10.1016/s0169-409x(99)00020-4. PMID: 10837768.
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Synthesis of 2',3'-Didehydro-2',3'-dideoxynucleosides by Reaction of 5'-Protected Nucleoside 2',3'-Dimesylates with Telluride Dianion: A General Route from Cis Vicinal Diols to Olefins.

The Journal of organic chemistry

Clive DL, Wickens PL, Sgarbi PW.
PMID: 11667671
J Org Chem. 1996 Oct 18;61(21):7426-7437. doi: 10.1021/jo9610570.

2',3'-Dimesylates of 5'-protected nucleosides are converted into the corresponding 2',3'-didehydro-2',3'-dideoxy compounds by treatment with telluride dianion in the form of the sodium or lithium salt. The method is well-suited to the preparation of unsaturated nucleosides that can be converted...

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Clive DL, Wickens PL, Sgarbi PW. Synthesis of 2',3'-Didehydro-2',3'-dideoxynucleosides by Reaction of 5'-Protected Nucleoside 2',3'-Dimesylates with Telluride Dianion: A General Route from Cis Vicinal Diols to Olefins. J Org Chem. 1996;61(21):7426-7437doi: 10.1021/jo9610570.
Clive, D. L., Wickens, P. L., & Sgarbi, P. W. (1996). Synthesis of 2',3'-Didehydro-2',3'-dideoxynucleosides by Reaction of 5'-Protected Nucleoside 2',3'-Dimesylates with Telluride Dianion: A General Route from Cis Vicinal Diols to Olefins. The Journal of organic chemistry, 61(21), 7426-7437. https://doi.org/10.1021/jo9610570
Clive, Derrick L. J., et al. "Synthesis of 2',3'-Didehydro-2',3'-dideoxynucleosides by Reaction of 5'-Protected Nucleoside 2',3'-Dimesylates with Telluride Dianion: A General Route from Cis Vicinal Diols to Olefins." The Journal of organic chemistry vol. 61,21 (1996): 7426-7437. doi: https://doi.org/10.1021/jo9610570
Clive DL, Wickens PL, Sgarbi PW. Synthesis of 2',3'-Didehydro-2',3'-dideoxynucleosides by Reaction of 5'-Protected Nucleoside 2',3'-Dimesylates with Telluride Dianion: A General Route from Cis Vicinal Diols to Olefins. J Org Chem. 1996 Oct 18;61(21):7426-7437. doi: 10.1021/jo9610570. PMID: 11667671.
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Profiling DNA Damage Induced by the Irradiation of DNA with Gold Nanoparticles.

The journal of physical chemistry letters

Huwaidi A, Kumari B, Robert G, Guérin B, Sanche L, Wagner JR.
PMID: 34617774
J Phys Chem Lett. 2021 Oct 14;12(40):9947-9954. doi: 10.1021/acs.jpclett.1c02598. Epub 2021 Oct 07.

The presence of gold nanoparticles (AuNPs) greatly enhances the formation of DNA damage when exposed to therapeutic X-rays. Three types of DNA damage are assessed in irradiated DNA by enzymatic digestion coupled to liquid chromatography tandem mass spectrometry (LC-MS/MS)...

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Huwaidi A, Kumari B, Robert G, et al. Profiling DNA Damage Induced by the Irradiation of DNA with Gold Nanoparticles. J Phys Chem Lett. 2021;12(40):9947-9954doi: 10.1021/acs.jpclett.1c02598.
Huwaidi, A., Kumari, B., Robert, G., Guérin, B., Sanche, L., & Wagner, J. R. (2021). Profiling DNA Damage Induced by the Irradiation of DNA with Gold Nanoparticles. The journal of physical chemistry letters, 12(40), 9947-9954. https://doi.org/10.1021/acs.jpclett.1c02598
Huwaidi, Alaa, et al. "Profiling DNA Damage Induced by the Irradiation of DNA with Gold Nanoparticles." The journal of physical chemistry letters vol. 12,40 (2021): 9947-9954. doi: https://doi.org/10.1021/acs.jpclett.1c02598
Huwaidi A, Kumari B, Robert G, Guérin B, Sanche L, Wagner JR. Profiling DNA Damage Induced by the Irradiation of DNA with Gold Nanoparticles. J Phys Chem Lett. 2021 Oct 14;12(40):9947-9954. doi: 10.1021/acs.jpclett.1c02598. Epub 2021 Oct 07. PMID: 34617774.
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Stereoselective Syntheses of 3'-Hydroxyamino- and 3'-Methoxyamino-2',3'-Dideoxynucleosides.

Organic letters

Bose S, Hodgson DRW.
PMID: 31668079
Org Lett. 2019 Nov 15;21(22):9084-9088. doi: 10.1021/acs.orglett.9b03474. Epub 2019 Oct 31.

Aminonucleosides are used as key motifs in medicinal and bioconjugate chemistry; however, existing strategies toward 3'-hypernucleophilic amine systems do not readily deliver

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Bose S, Hodgson DRW. Stereoselective Syntheses of 3'-Hydroxyamino- and 3'-Methoxyamino-2',3'-Dideoxynucleosides. Org Lett. 2019;21(22):9084-9088doi: 10.1021/acs.orglett.9b03474.
Bose, S., & Hodgson, D. R. W. (2019). Stereoselective Syntheses of 3'-Hydroxyamino- and 3'-Methoxyamino-2',3'-Dideoxynucleosides. Organic letters, 21(22), 9084-9088. https://doi.org/10.1021/acs.orglett.9b03474
Bose, Sritama, and Hodgson, David R W. "Stereoselective Syntheses of 3'-Hydroxyamino- and 3'-Methoxyamino-2',3'-Dideoxynucleosides." Organic letters vol. 21,22 (2019): 9084-9088. doi: https://doi.org/10.1021/acs.orglett.9b03474
Bose S, Hodgson DRW. Stereoselective Syntheses of 3'-Hydroxyamino- and 3'-Methoxyamino-2',3'-Dideoxynucleosides. Org Lett. 2019 Nov 15;21(22):9084-9088. doi: 10.1021/acs.orglett.9b03474. Epub 2019 Oct 31. PMID: 31668079; PMCID: PMC7007280.
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Showing 1 to 7 of 7 entries