Fluorinated Carbohydrates and Their Use in Tumor Visualization, Tissue Engineering, and Cancer Chemotherapy

A compound represented by formula II:

• wherein
• RF is selected from the group consisting of fluoroalkyl, fluorocycloalkyl, fluoroheterocycloalkyl, fluoroalkenyl, fluoroalkynyl, fluoroaryl, fluoroheteroaryl, fluoroaralkyl, fluoroheteroaralkyl, fluoroacyl and fluorocarbonyl;
• W1, W2, W3, and W4 are selected independently from the group consisting of —OR2 and —OC(═O)R;
• R2 and R3 are selected independently for each occurrence from the group consisting of hydrogen, alkyl, cycloalkyl, heterocycloalkyl, alkenyl, alkynyl, aryl, heteroaryl, aralkyl and heteroaralkyl;
• or two R2 and R3 on being taken together are —(CH2)n—;
• and
• n is independently for each occurrence 1, 2, 3, 4 or 5;
• or a pharmaceutically acceptable salt thereof.

A compound represented by formula III:

• wherein
• Z is —RF or —C(═O)RF;
• RF is selected from the group consisting of fluoroalkyl, fluorocycloalkyl, fluoroheterocycloalkyl, fluoroalkenyl, fluoroalkynyl, fluoroaryl, fluoroheteroaryl, fluoroaralkyl, fluoroheteroaralkyl, fluoroacyl and fluorocarbonyl;
• M is selected from the group consisting of hydrogen, alkyl, cycloalkyl, heterocycloalkyl, alkenyl, alkynyl, aryl, heteroaryl, aralkyl and heteroaralkyl;
• W1, W2, W3, W4 and W5 are selected independently from the group consisting of —OR2 and —OC(═O)R3;
• R2 and R3 are selected independently for each occurrence from the group consisting of hydrogen, alkyl, cycloalkyl, heterocycloalkyl, alkenyl, alkynyl, aryl, heteroaryl, aralkyl and heteroaralkyl;
• or two R2 and R3 on being taken together are —(CH2)n—;
• and
• n is independently for each occurrence 1, 2, 3, 4 or 5;
• or a pharmaceutically acceptable salt thereof.

A compound represented by formula IV:

• wherein
• Z is —RF or —C(═O)R3;
• W1, W2, W3, and W4 are selected independently from the group consisting of —OR2 and —OC(═O)R3;
• M is hydrogen, alkyl, cycloalkyl, heterocycloalkyl, alkenyl, alkynyl, aryl, heteroaryl, aralkyl or heteroaralkyl;
• R2 and R3 are selected independently for each occurrence from the group consisting of hydrogen, alkyl, cycloalkyl, heterocycloalkyl, alkenyl, alkynyl, aryl, heteroaryl, aralkyl and heteroaralkyl;
• or two R2 and R3 on being taken together are —(CH2)n—;
• n is independently for each occurrence 1, 2, 3, 4 or 5;
• X is selected from the group consisting of —RF, —ORF, —OC(═O)RF, —NHRF, —NHC(═O)RF, —SRF and —SC(═O)RF;
• and
• RF is selected from the group consisting of fluoroalkyl, fluorocycloalkyl, fluoroheterocycloalkyl, fluoroalkenyl, fluoroalkynyl, fluoroaryl, fluoroheteroaryl, fluoroaralkyl, fluoroheteroaralkyl, fluoroacyl and fluorocarbonyl or a pharmaceutically acceptable salt thereof.