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A coumarin-based prodrug system has been recently developed in our laboratory for the preparation of esterase-sensitive prodrugs of amines, peptides, and peptidomimetics. The drug release rates from this prodrug system were found to be dependent on the structural features of the drug moiety. In certain cases, the release can be undesirably slow for drugs that are secondary amines with relatively high pKa's. Aimed at finding ways to manipulate the release rates to suit the need of different drugs, we have examined the effect of the phenyl ring substitutions on the release kinetics of such prodrugs and found that appropriately positioned alkyl substituents on the phenyl ring could help to facilitate the release by as much as 16-fold. Therefore, introduction of alkyl substituents on the phenyl ring should allow us to manipulate the release rates and, therefore, time profiles for different drugs.
Y Liao, and
S Hendrata, and
S Y Bae, and
B Wang
April 1998,
Bioorganic & medicinal chemistry,
Y Liao, and
S Hendrata, and
S Y Bae, and
B Wang
March 2016,
Angewandte Chemie (International ed. in English),
Y Liao, and
S Hendrata, and
S Y Bae, and
B Wang
January 1999,
Methods in molecular medicine,
Y Liao, and
S Hendrata, and
S Y Bae, and
B Wang
January 1999,
Chemical & pharmaceutical bulletin,
Y Liao, and
S Hendrata, and
S Y Bae, and
B Wang
June 2001,
Archiv der Pharmazie,
Y Liao, and
S Hendrata, and
S Y Bae, and
B Wang
July 1999,
Bioorganic & medicinal chemistry letters,
Y Liao, and
S Hendrata, and
S Y Bae, and
B Wang
August 2017,
Chemical communications (Cambridge, England),
Y Liao, and
S Hendrata, and
S Y Bae, and
B Wang
August 1998,
Pharmaceutical research,
Y Liao, and
S Hendrata, and
S Y Bae, and
B Wang
September 2017,
Chemical communications (Cambridge, England),
Y Liao, and
S Hendrata, and
S Y Bae, and
B Wang
February 2017,
Organic letters,
