Structural diversity in the host–guest complexes of the antifolate pemetrexed with native cyclodextrins: gas phase, solution and solid state studies

• Magdalena Ceborska,
• Magdalena Zimnicka,
• Aneta Aniela Kowalska,
• Kajetan Dąbrowa and
• Barbara Repeć

Beilstein J. Org. Chem. 2017, 13, 2252–2263, doi:10.3762/bjoc.13.222

• /bjoc.13.222 Abstract The complexation of the antifolate pemetrexed (PTX) with native cyclodextrins was studied. This process, along with the findings gathered for the structurally related folic acid was treated as a model for exploiting host–guest interactions of this class of guest molecules in the

• equivalent – methyl α-D-glucopyranoside – was investigated for a deeper understanding of the type of host–guest interactions. Solid state studies of PTX/CDs were performed using FTIR–ATR and Raman spectroscopy techniques. Keywords: antifolate; cyclodextrin; hydrophobic interactions; inclusion complexes

• the guest molecule is located inside the CD cavity. The present study serves two purposes. The first is studying of the process of formation of the host–guest complexes of all three native CDs with PTX, an antifolate exhibiting considerable toxicity and their detailed characterization in the gas phase

Crystal engineering of analogous and homologous organic compounds: hydrogen bonding patterns in trimethoprim hydrogen phthalate and trimethoprim hydrogen adipate

• Packianathan Thomas Muthiah,
• Savarimuthu Francis,
• Urszula Rychlewska and
• Beata Warżajtis

Beilstein J. Org. Chem. 2006, 2, No. 8, doi:10.1186/1860-5397-2-8

• Trimethoprim [2,4-diamino-5-(3',4',5'-trimethoxybenzyl)pyrimidine] is an antifolate drug. It selectively inhibits the bacterial dihydrofolate reductase (DHFR) enzyme. Results In the crystal structures of trimethoprim (TMP)-hydrogen phthalate (1) and trimethoprim-hydrogen adipate (2), one of the N atoms of the

• potential. Trimethoprim [2,4-diamino-5-(3',4',5'-trimethoxybenzyl)pyrimidine] (TMP) is an antifolate drug. In the protonated form, it exerts its activity through the inhibition of the enzyme dihydrofolate reductase (DHFR) [8]. In most of the trimethoprim-carboxylate salts, one of the nitrogen atoms of the