Oligocarbonate molecular transporters: oligomerization-based syntheses and cell-penetrating studies.
A new family of guanidinium-rich molecular transporters featuring a novel oligocarbonate backbone with 1,7-side chain spacing is described. Conjugates can be rapidly assembled irrespective of length in a one-step oligomerization strategy that can proceed with concomitant introduction of probes (or by analogy drugs). The new transporters exhibit excellent cellular entry as determined by flow cytometry and fluorescence microscopy, and the functionality of their drug delivery capabilities was confirmed by the delivery of the bioluminescent small molecule probe luciferin and turnover by its intracellular target enzyme.
Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA.
Christina B
CB
Cooley
Brian M
BM
Trantow
Fredrik
F
Nederberg
Matthew K
MK
Kiesewetter
James L
JL
Hedrick
Robert M
RM
Waymouth
Paul A
PA
Wender
D000818:Animals; D001692:Biological Transport; D002254:Carbonates / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D001517:Coleoptera / Q000201:enzymology; D004353:Drug Evaluation, Preclinical; D019791:Guanidine / Q000737:chemistry / Q000378:metabolism; D006801:Humans; D019169:Jurkat Cells; D008156:Luciferases / Q000032:analysis; D049449:Luminescence; D026901:Membrane Transport Proteins / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*
D002254:Carbonates; D026901:Membrane Transport Proteins; D008156:Luciferases; D019791:Guanidine