Persulfated molecular umbrellas as anti-HIV and anti-HSV agents.
A series of persulfated molecular umbrellas have been synthesized from putrescine, spermidine, spermine, lysine, and cholic acid (1a, 2a, 3a, 4a, and 5a) and their anti-HIV and anti-HSV activities determined. Despite it size, the most active of these conjugates (5a) was able to cross phospholipid bilayers made from 1-palmitoyl-2-oleyol-sn-glycero-3-phosphocholine (POPC) and 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphatidylglycerol (POPG). The unique combination of anti-viral activity, an ability to cross hydrophobic barriers, a lack of cytotoxicity, and a simple three-step synthesis from biogenic starting material suggests that 5a and related conjugates may be exploitable as a novel class of anti-viral agents for systemic and topical applications.
Jing
Bingwen
B
Department of Chemistry, Lehigh University, Bethlehem, Pennsylvania 18015, USA.
Janout
Vaclav
V
Herold
Betsy C
BC
Klotman
Mary E
ME
Heald
Taylor
T
Regen
Steven L
SL
D019380:Anti-HIV Agents / Q000008:administration & dosage / Q000737:chemistry / Q000493:pharmacokinetics / Q000494:pharmacology; D000998:Antiviral Agents / Q000008:administration & dosage / Q000737:chemistry* / Q000493:pharmacokinetics / Q000494:pharmacology*; D002460:Cell Line; D002462:Cell Membrane / Q000378:metabolism; D002584:Cervix Uteri / Q000821:virology; D002793:Cholic Acids / Q000737:chemistry* / Q000494:pharmacology*; D005260:Female; D015497:HIV-1 / Q000187:drug effects*; D018258:Herpesvirus 2, Human / Q000187:drug effects* / Q000378:metabolism; D006801:Humans; D057927:Hydrophobic and Hydrophilic Interactions; D008051:Lipid Bilayers / Q000737:chemistry / Q000378:metabolism; D013329:Structure-Activity Relationship; D013463:Sulfuric Acid Esters / Q000737:chemistry* / Q000494:pharmacology*
D019380:Anti-HIV Agents; D000998:Antiviral Agents; D002793:Cholic Acids; D008051:Lipid Bilayers; D013463:Sulfuric Acid Esters