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Synthesis of polyamidoamine dendrimer-methotrexate conjugates and in vitro characterization

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  1. Tez No: 403435
  2. Yazar: SEZEN GÜRDAĞ
  3. Danışmanlar: Dr. RANGARAMANUJAM M. KANNAN
  4. Tez Türü: Doktora
  5. Konular: Kimya Mühendisliği, Chemical Engineering
  6. Anahtar Kelimeler: Belirtilmemiş.
  7. Yıl: 2006
  8. Dil: İngilizce
  9. Üniversite: Wayne State University
  10. Enstitü: Yurtdışı Enstitü
  11. Ana Bilim Dalı: Belirtilmemiş.
  12. Bilim Dalı: Belirtilmemiş.
  13. Sayfa Sayısı: 205

Özet

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Özet (Çeviri)

Dendritic polymers have a wide array of biological applications spanning from drug and gene delivery to imaging mainly due to highly versatile densely packed end functional groups. We investigated the importance of surface charge imparted by the end groups on the in vitro activity of polyamidoamine (PAMAM)-Methotrexate (MTX) conjugates in isogenic cell lines of human acute lymphoblastoid leukemia CCRF-CEM and Chinese hamster ovary CHO cells, with drug-sensitive and -resistant sublines. Amide-bonded conjugates were prepared in a dicyclohexylcarbodiimide (DCC)-mediated coupling scheme utilizing either –NH2 or –COOH group on MTX as the linking site to afford anionic conjugate A (PAMAM-G2.5-COOH) and cationic conjugate B (PAMAM-G3-NH2), respectively. The in vitro activity tests demonstrated substantially higher activity of anionic conjugate A not only compared to cationic conjugate B but also to the free drug. This activity enhancement of the conjugated drug was more pronounced in MTX-resistant cell lines with 24-fold reduction in the IC50 value in RII cells compared to the free drug regardless of the loss of the RFC function. Exploitation of the salvage pathways by co-incubating either with the combination of adenosine and thymidine or leucovorin ensured that conjugated-drug still relies on the inhibition of dihydrofolate reductase (DHFR) activity as the sole mode of antimetabolite action. Contrarily, conjugate B did not show appreciable cytotoxicity on any of the cell lines. The significant differences in the cytotoxicities may be suggestive of the involvement of lysosomes retaining the conjugates for different periods of time determined by the surface charge of the native dendrimer to release the drug to various levels. Our preliminary drug release data suggested that an analogous anionic conjugate liberated approximately 7% of the conjugated-MTX in the presence of the enzyme, cathepsin B. Due to the precipitation of the cationic conjugate, similar experimentation could not be performed. Furthermore, to ease the accessibility of the linking site to the enzyme, we synthesized spacer-linked PAMAM-MTX conjugates with ester bonds, from which we expect to have higher drug release and eventually higher in vitro activity.

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