Design and cellular kinetics of dansyl-labeled CADA derivatives with anti-HIV and CD4 receptor down-modulating activity

A new class of anti-retrovirals, cyclotriazadisulfonamide (CADA) and its derivatives, specifically down-regulate CD4, the main receptor of HIV, and prevent HIV infection in vitro. In this work, several CADA derivatives, chemically labeled with a fluorescent dansyl group, were evaluated for their bio...

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Veröffentlicht in:Biochemical pharmacology 2007-08, Vol.74 (4), p.566-578
Hauptverfasser: Vermeire, Kurt, Lisco, Andrea, Grivel, Jean-Charles, Scarbrough, Emily, Dey, Kaka, Duffy, Noah, Margolis, Leonid, Bell, Thomas W., Schols, Dominique
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container_end_page 578
container_issue 4
container_start_page 566
container_title Biochemical pharmacology
container_volume 74
creator Vermeire, Kurt
Lisco, Andrea
Grivel, Jean-Charles
Scarbrough, Emily
Dey, Kaka
Duffy, Noah
Margolis, Leonid
Bell, Thomas W.
Schols, Dominique
description A new class of anti-retrovirals, cyclotriazadisulfonamide (CADA) and its derivatives, specifically down-regulate CD4, the main receptor of HIV, and prevent HIV infection in vitro. In this work, several CADA derivatives, chemically labeled with a fluorescent dansyl group, were evaluated for their biological features and cellular uptake kinetics. We identified a derivative KKD-016 with antiviral and CD4 down-modulating capabilities similar to those of the parental compound CADA. By using flow cytometry, we demonstrated that the dose-dependent cellular uptake of this derivative correlated with CD4 down-modulation. The uptake and activity of the dansyl-labeled compounds were not dependent on the level of expression of CD4 at the cell surface. Removal of the CADA compounds from the cell culture medium resulted in their release from the cells followed by a complete restoration of CD4 expression. The inability of several fluorescent CADA derivatives to down-modulate CD4 was not associated with their lower cellular uptake and was not reversed by facilitating their cell penetration by a surfactant. These results prove the successful integration of the dansyl fluorophore into the chemical structure of a CD4 down-modulating anti-HIV compound, and show the feasibility of tracking a receptor and its down-modulator simultaneously. These fluorescent CADA analogs with reversible CD4 down-regulating potency can now be applied in further studies on receptor modulation, and in the exploration of their potentials as preventive and therapeutic anti-HIV drugs.
doi_str_mv 10.1016/j.bcp.2007.05.018
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In this work, several CADA derivatives, chemically labeled with a fluorescent dansyl group, were evaluated for their biological features and cellular uptake kinetics. We identified a derivative KKD-016 with antiviral and CD4 down-modulating capabilities similar to those of the parental compound CADA. By using flow cytometry, we demonstrated that the dose-dependent cellular uptake of this derivative correlated with CD4 down-modulation. The uptake and activity of the dansyl-labeled compounds were not dependent on the level of expression of CD4 at the cell surface. Removal of the CADA compounds from the cell culture medium resulted in their release from the cells followed by a complete restoration of CD4 expression. The inability of several fluorescent CADA derivatives to down-modulate CD4 was not associated with their lower cellular uptake and was not reversed by facilitating their cell penetration by a surfactant. These results prove the successful integration of the dansyl fluorophore into the chemical structure of a CD4 down-modulating anti-HIV compound, and show the feasibility of tracking a receptor and its down-modulator simultaneously. These fluorescent CADA analogs with reversible CD4 down-regulating potency can now be applied in further studies on receptor modulation, and in the exploration of their potentials as preventive and therapeutic anti-HIV drugs.</abstract><cop>New York, NY</cop><pub>Elsevier Inc</pub><pmid>17603023</pmid><doi>10.1016/j.bcp.2007.05.018</doi><tpages>13</tpages></addata></record>
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subjects Anti-HIV
Anti-HIV Agents - chemical synthesis
Anti-HIV Agents - metabolism
Anti-HIV Agents - pharmacology
Biological and medical sciences
CADA
CD4 Antigens - genetics
CD4 Antigens - metabolism
CD4 receptor
CD4-Positive T-Lymphocytes - cytology
CD4-Positive T-Lymphocytes - drug effects
CD4-Positive T-Lymphocytes - metabolism
Cell Line
Cell Line, Tumor
Cell Survival - drug effects
Cellular kinetics
Dansyl
Dansyl Compounds - chemical synthesis
Dansyl Compounds - chemistry
Dansyl Compounds - metabolism
Dansyl Compounds - pharmacology
Dimethyl Sulfoxide - chemistry
Dose-Response Relationship, Drug
Down-Regulation - drug effects
Drug Design
Flow Cytometry
Heterocyclic Compounds - chemical synthesis
Heterocyclic Compounds - metabolism
Heterocyclic Compounds - pharmacology
HIV-1 - drug effects
HIV-1 - growth & development
Human immunodeficiency virus
Humans
Immunohistochemistry
Kinetics
Medical sciences
Molecular Structure
Pharmacology. Drug treatments
Poloxamer - chemistry
Reversible Down-modulation
Solvents - chemistry
Spectrometry, Fluorescence
Sulfonamides - chemical synthesis
Sulfonamides - chemistry
Sulfonamides - pharmacology
Surface-Active Agents - chemistry
Transfection
title Design and cellular kinetics of dansyl-labeled CADA derivatives with anti-HIV and CD4 receptor down-modulating activity
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