Kinetics of Hydrolysis of Succinimides

Yakatan, Gerald J.; Fan, Tsai-Yi

doi:10.3109/03639047709055615

Cited by 12 publications

(5 citation statements)

References 3 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The rate constant k2 (AdA3) was found to be 0.01 16 M-I s-I and K , wascalculatedfromA3witha knownvalueofK, (1.449X IO-l4M2) (21). The value thus obtained (1.41 X M) is comparable with the experimentally observed value of 3.3 X s-l) and AdA3 are considerably larger than the respective values of 6.64 X M-I s-I obtained at 8OoC in the hydrolytic cleavage of succinimide (22) and 19.1 X M-ls-l obtained at 8OoC in the hydrolysis of 3,3-methylethylsuccinimide (23).…”

Section: Discussionsupporting

confidence: 82%

Kinetics and Mechanism of the Alkaline Hydrolysis of Maleimide

Khan

1984

Journal of Pharmaceutical Sciences

View full text Add to dashboard Cite

Section: Discussionsupporting

confidence: 82%

Kinetics and Mechanism of the Alkaline Hydrolysis of Maleimide

Khan

1984

Journal of Pharmaceutical Sciences

View full text Add to dashboard Cite

“…It should be noted that the amine‐succinimide reaction is relatively efficient. Furthermore, succinimide groups are unstable in aqueous solution and hydrolyze in ∼24 h after the grafting reaction to produce carboxylic acid terminated macromers (Yakatan and Fan, 1977).…”

Section: Methodsmentioning

confidence: 99%

Effect of encapsulation or grafting on release kinetics of recombinant human bone morphogenetic protein‐2 from self‐assembled poly(lactide‐co‐glycolide ethylene oxide fumarate) nanoparticles

Mercado¹,

Jabbari²

2010

Microscopy Res & Technique

View full text Add to dashboard Cite

The objective of this work was to compare the release characteristics of Recombinant human bone morphogenetic protein-2 (rhBMP-2) encapsulated in thermally self-assembled poly(lactide ethylene oxide fumarate) (PLEOF) nanoparticles (NPs) with rhBMP-2 grafted to succinimide-terminated poly(lactide fumarate) (PLAF-NHS) or poly(lactide-co-glycolide fumarate) (PLGF-NHS) NPs. The amphiphilic PLEOF NPs had average size of 110 +/- 50 nm. The hydrophobic PLAF-NHS and PLGF-NHS NPs had average size of 242 +/- 67 and 195 +/- 42 nm, respectively. PLEOF NPs had rhBMP-2 encapsulation efficiency ranging from 65 to 93%. Grafting efficiency of rhBMP-2 to PLAF-NHS and PLGF-NHS NPs was 97% +/- 1% and 98% +/- 1%, respectively. PLEOF NPs displayed a relatively high-release rate of rhBMP-2 in the first week, which rapidly dropped to zero after 10 days. PLEOF NPs grafted with 10 and 20 microg/mL rhBMP-2 released 67 and 80% of the protein in the active conformation after degradation. PLGF-NHS NPs displayed sustained release of rhBMP-2 in the first 2 weeks but dropped to almost zero rate (< 3 ng/day) after 20 days. PLAF-NHS NPs showed the longest period of sustained release of active rhBMP-2 at two rates: a high rate of 25-35 ng/mL in the first 2 weeks followed by a low rate of 5-10 ng/mL from 2 to 6 weeks. Nearly, 25 and 50% of the rhBMP-2 released from PLGF-NHS and PLAF-NHS NPs, respectively, were enzymatically active after degradation of the NPs. PLEOF NPs provided a fast release of rhBMP-2 for 1 week, whereas PLAF-NHS NPs provided a slow release for up to 6 weeks.

show abstract

“…12) have been observed by us as by-products when performing oxidative stress testing with NMP-water in the presence of primary aniline suggesting that the NMP imide (3) was hydrolytically transformed to the corresponding anhydride (6), which then reacted with the aniline. [52][53][54] There is literature precedent for the formation of amide acids (7) from succinic acid (5) and anilines via a succinic anhydride (6) intermediate. However, products such as (7) have been observed infrequently and this is not considered a major problem for the NMP-water procedure.…”

Section: Limitationsmentioning

confidence: 99%