Per-6-guanidino-, alkylamino-cyclodextrins, methods of their...

Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives

Reexamination Certificate

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C536S046000, C514S04400A, C514S058000, C435S455000

Reexamination Certificate

active

07834174

ABSTRACT:
The invention relates to new compounds of type hexakis(6-deoxy-6-NH(CH2)n—R1)α-cyclodextrin and heptakis(6-deoxy-6-NH(CH2)n—R1)-(β-cyclodextrin, and octakis(6-deoxy-6-NH(CH2)n—R1)-γ-cyclodextrin, where n=2-6 when R1=NH2and n=0 when R1=C(═NH)NH2and n=2-6 when R1=NH—C(═NH)NH2and their use in the compaction of DNA and in cell permeation. The invention also relates to methods of synthesis of the above compounds.

REFERENCES:
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Khan, A.R et al., “Methods for Selective Modifications of Cyclodextrins”, Chemical Reviews, American Chemical Society, vol. 98, No. 5, Jul. 1998, pp. 1977-1996.
Nozaki, T. et al., “Cycxlodextrins Modified With Polymer Chains Which Are Responsive to External Stimuli” Macromolecules, vol. 28, 1995, pp. 522-524.
Cryan, S.A et al., Cell Transfection With Polycationic Cyclodextrin Vectors, European Journal of Pharmaceutical Sciences, Elsevier, vol. 21, 2004, pp. 625-633.
Vizitiu et al., “Synthesis of Mono-Facially Functionalized Cyclodextrins Bearing Amino Pendent Groups”, Journal of Organic Chemistry, ACS, vol. 62, No. 25, 1997, pp. 8760-8766.
Cotner, E.S et al., “Phosphotyrosine Binding by Ammonium and Guanidinium-Modified Cyclodextrins”, J. Org. Chem., vol. 63, 1998, pp. 1737-1739.
Popielarski, S.R., “Structural Effect of Carbohydrate-Containing Polycations on Gene Delivery.3.Cyclodextrin . . . ”, Bioconjugate Chem., vol. 14, Mar. 22, 2003, pp. 672-678.
Ashton, P.R et al., “Amino Acid Derivatives of Beta-Cyclodextrin”, Journ. of Org. Chem., ACS, vol. 61, No. 3, Feb. 9, 1996, pp. 903-908.
Nozaki, T et al., Photo-Responsive Catalysis by Thymine-Cyclodextrin Conjugates, J. Chem. Soc., Perkin Trans 2, 1997, pp. 1217-1220.

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