PMID- 12419905
OWN - NLM
STAT- MEDLINE
DCOM- 20030421
LR  - 20190706
IS  - 0009-2363 (Print)
IS  - 0009-2363 (Linking)
VI  - 50
IP  - 11
DP  - 2002 Nov
TI  - Synthesis of water-soluble polymeric prodrugs possessing 4-methylcatechol 
      derivatives by mechanochemical solid-state copolymerization and nature of drug 
      release.
PG  - 1434-8
AB  - In this study we synthesized the water-soluble polymeric prodrugs possessing a 
      4-methylcatechol (4MC) derivative as a side chain by mechanochemical solid-state 
      copolymerization. 1-benzoyl-4-methylcatechol (Bz4MC) was selected as a model 
      compound of 4MC, and its methacryloyl derivative (1) was synthesized. 
      6-O-methacryloyl-D-galactose (2) was also prepared as a water-soluble monomer. 
      The mechanochemical solid-state copolymerization of 1 and 2 was carried out to 
      obtain the water-soluble polymeric prodrug possessing the Bz4MC as a side chain. 
      The mechanochemical copolymerization of 1 and 2 proceeded to completion, and the 
      polymeric prodrug produced possessed a narrow molecular weight distribution. 
      Three kinds of polymeric prodrugs, whose compositions were different from one 
      another, were hydrolyzed in vitro. The hydrolysis of these polymeric prodrugs 
      proceeded to completion. The rate constants of hydrolysis decreased with 
      increasing the mole fraction of 1 in polymeric prodrug. It was suggested that the 
      rate constant of hydrolysis could be controlled by the composition, the mole 
      fraction of 1 in the polymeric prodrug.
FAU - Kondo, Shin-ichi
AU  - Kondo S
AD  - Laboratory of Pharmaceutical Physical Chemistry, Gifu Pharmaceutical University, 
      Japan. skondo@gifu-pu.ac.jp
FAU - Sasai, Yasushi
AU  - Sasai Y
FAU - Kuzuya, Masayuki
AU  - Kuzuya M
FAU - Furukawa, Shoei
AU  - Furukawa S
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
PL  - Japan
TA  - Chem Pharm Bull (Tokyo)
JT  - Chemical & pharmaceutical bulletin
JID - 0377775
RN  - 0 (Catechols)
RN  - 0 (Polymers)
RN  - 0 (Prodrugs)
RN  - 059QF0KO0R (Water)
RN  - 12GLI7JGB3 (4-methylcatechol)
SB  - IM
MH  - Catechols/*chemical synthesis/pharmacokinetics
MH  - Polymers/*chemical synthesis/pharmacokinetics
MH  - Prodrugs/*chemical synthesis/pharmacokinetics
MH  - Solubility
MH  - Technology, Pharmaceutical/methods
MH  - Water/*chemistry
EDAT- 2002/11/07 04:00
MHDA- 2003/04/22 05:00
CRDT- 2002/11/07 04:00
PHST- 2002/11/07 04:00 [pubmed]
PHST- 2003/04/22 05:00 [medline]
PHST- 2002/11/07 04:00 [entrez]
AID - 10.1248/cpb.50.1434 [doi]
PST - ppublish
SO  - Chem Pharm Bull (Tokyo). 2002 Nov;50(11):1434-8. doi: 10.1248/cpb.50.1434.