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Lipid Conjugates Of Antiretroviral Agents. I. Azidothymidine-monophosphate-diglyceride: Anti-HIV Activity, Physical Properties, And Interaction With Plasma Proteins.

J. Steim, C. Camaioni Neto, P. Sarin, D. K. Sun, R. K. Sehgal, J. Turcotte
Published 1990 · Chemistry, Medicine

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3'-Azido-3'-deoxythymidine-5'-phosphate diglyceride (16:0/18:1 omega 9), a phosphatic acid conjugate of AZT, is active against HIV replication in H9 cells and syncytia formation in MOLT-3 cells. The activities rank as AZT greater than pure conjugate greater than conjugate in mixed liposomes, with the pure conjugate having about one-third the activity of free AZT. The compound binds very rapidly to serum lipoproteins, but not to serum albumin, alpha and beta globulins, or red cells. Pancreatic phospholipase A2 hydrolyzes it to the lysophosphatidic acid conjugate.
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This paper is referenced by
10.1002/cmdc.200800012
Dipeptide Derivatives of AZT: Synthesis, Chemical Stability, Activation in Human Plasma, hPEPT1 Affinity, and Antiviral Activity
Cledir Santos (2008)
10.1016/0169-409X(95)00111-J
Prodrugs of phosphates, phosphonates, and phosphinates
J. Krise (1996)
10.3109/10611869808997877
Liposomes as drug delivery system: a strategic approach for the treatment of HIV infection.
A. Désormeaux (1998)
10.3109/08923979509019748
Treatment of AIDS with drugs targeted to inhibit different stages of the HIV life cycle.
P. Sarin (1995)
10.1002/(SICI)1098-2299(199903/04)46:3/4<302::AID-DDR16>3.0.CO;2-R
Tris and the ready production of drug‐fatty acyl conjugates
X. Wells (1999)
10.1046/j.1440-1681.2000.03294.x
Tris Lipidation: A Chemically Flexible Technology For Modifying The Delivery Of Drugs and Genes
T. Lockett (2000)
10.1016/0006-291X(90)91415-O
Lipid conjugates of antiretroviral agents. II. Disodium palmityl phosphonoformate: anti-HIV activity, physical properties, and interaction with plasma proteins.
C. Camaioni Neto (1990)
10.1002/JLAC.199419940309
Synthese und Eigenschaften von N4‐Hexadecyl‐2′‐desoxycytidylyl‐(3′‐5′)‐5‐ethyl‐2′‐desoxyuridin und 2′‐Desoxythymidylyl‐(3′‐5′)‐N4‐hexadecyl‐1‐β‐D‐arabinofuranosylcytosin, zwei Vertreter einer neuen Prodrug‐Gruppe
H. Schott (1994)
10.1016/S0378-5173(96)04782-5
Solid lipid nanoparticles as drug carriers. I. Incorporation and retention of the lipophilic prodrug 3′-azido-3′-deoxythymidine palmitate
H. Heiati (1997)
10.1016/S1075-8593(96)80105-5
Comments on nucleotide delivery forms
C. Périgaud (1996)
10.1002/9781118739907.CH7
ENZYMATICALLY ACTIVATED PHOSPHATE AND PHOSPHONATE PRODRUGS
I. S. Krylov (2013)
10.1016/0005-2760(91)90074-R
Lipid conjugates of antiretroviral agents: release of antiretroviral nucleoside monophosphates by a nucleoside diphosphate diglyceride hydrolase activity from rat liver mitochondria.
G. M. van Wijk (1991)
10.1177/095632029500600506
Synthesis and in vitro Antiviral Properties of Amphiphilic Dinucleoside Phosphate Derivatives of 2′,3-dideoxycytidine (ddC)
H. Schott (1995)
10.1016/0166-3542(92)90058-D
Drug targeting systems for antiviral agents: options and limitations.
D. Meijer (1992)
10.1002/HLCA.19960790210
Nucleotides. Part XLVI. The synthesis of phospholipid conjugates of antivirally active nucleosides by the improved phosphoramidite methodology
H. Sigmund (1996)
Delivery of the anti-HIV drug azidothymidine (AZT) to T-lymphocytes with neoglycoprotein carriers
G. Molema (1992)
10.1016/S0957-4166(97)00328-5
Acyclic C-nucleosides: synthesis of chiral 1,1-diheteroaryl-alditols and X-ray crystal structure of 2,3,5-tri- O -benzyl-1,1-di-(2′-pyrryl)-1-deoxy-d-arabinitol
M. Cornia (1997)
10.1016/0169-409X(95)00106-H
Prodrugs for improved CNS delivery
Bradley D. Anderson (1996)
10.1016/0166-3542(94)90054-X
New lipophilic alkyl/acyl dinucleoside phosphates as derivatives of 3'-azido-3'-deoxythymidine: inhibition of HIV-1 replication in vitro and antiviral activity against Rauscher leukemia virus infected mice with delayed treatment regimens.
R. Schwendener (1994)
Neurologic complications of HIV disease and their treatment.
S. Letendre (2010)
10.1002/1098-1128(200011)20:6<417::AID-MED1>3.0.CO;2-Z
Pronucleotides: Toward the in vivo delivery of antiviral and anticancer nucleotides
C. Wagner (2000)
10.1016/S0378-5173(98)00236-1
Solid lipid nanoparticles as drug carriers: II. Plasma stability and biodistribution of solid lipid nanoparticles containing the lipophilic prodrug 3′-azido-3′-deoxythymidine palmitate in mice
H. Heiati (1998)
10.1016/0378-5173(93)90385-S
Drug delivery approaches for anti-HIV drugs
H. L. Mirchandani (1993)
10.1016/0378-4274(94)03171-3
Fatty acid conjugates of xenobiotics.
G. Ansari (1995)
10.1177/095632029400500606
Synthesis, and Some Properties of, Amphiphilic Dinucleoside Phosphate Derivatives of 3′-azido-2′,3′-dideoxythymidine (AZT)
H. Schott (1994)
10.1016/J.CHEMPHYSLIP.2007.05.001
Crystallization and phase behavior of fatty acid esters of 1,3-propanediol I: pure systems.
M. Abes (2007)
10.1007/978-1-4615-3340-5_15
Use of Drugs Targeted to Inhibit Different Stages of the HIV Life Cycle in the Treatment of AIDS
P. S. Sarin (1992)
10.1016/J.BMCL.2007.01.062
Synthesis and biological evaluation of two glycerolipidic prodrugs of didanosine for direct lymphatic delivery against HIV.
M. Lalanne (2007)
Part 1 Design, Synthesis and Bioactivity of a Phosphorylated Prodrug for the Inhibition of Pin1; Part 2 Conformational Specificity of Cdc25c Substrate for Cdc2 Kinase using LC-MS/MS
S. Zhao (2007)
10.1016/0163-7827(94)90028-0
Strategies for the synthesis of glycerophospholipids.
F. Paltauf (1994)
10.1080/10826079308020982
Preparative HPLC of an Experimental Anti-HIV Analogue of AZT: Azidothymidine Monophosphate Diglyceride (AZT-MP-DG)
P. Painuly (1993)
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