Sulfated and unsulfated flavonoid oligomers as cancer therapeutics

Sulfated flavonoid dimers having the general formula of formula II:

• wherein
• R is one or more of —OH, or —OSO3−M+ or —H, each of which may be the same or different, wherein at least one −OSO3−M+ group is present on the molecule and wherein M is selected from the group consisting of Na+, K+, Li+, NH4+, NR′4+, Mg2+, Ca2+ or other metal cations, wherein R′ is H or alkyl or aryl groups;
• L is any one of linkers L1 through L9 shown below wherein n is 1-10;
• and
• the two flavonoid units are connected through either 5-2′, 5-3′, 5-4′, 6-2′, 6-3′, 6-4′, 7-2′, 7-3′, 7-4′, 8-2′, 8-3′, or 8-4′ linkages.

Sulfated flavonoid dimers having the general formula of formula III:

• wherein
• R is one or more of —OH, or —OSO3−M+ or —H, each of which may be the same or different, wherein at least one —OSO3−M+ group is present on the molecule and wherein M is selected from the group consisting of Na+, K+, Li+, NH4+, NR′4+, Mg2+, Ca2+ or other metal cations, wherein R′ is H or alkyl or aryl groups;
• L is any one of linkers L1 through L9 shown below wherein n is 1-10;
• and
• the two flavonoid units are connected through either 5-3, 6-3, 7-3, or 8-3 linkages.

Sulfated flavonoid dimers having the general formula of formula IV:

• wherein
• R is one or more of —OH, or —OSO3−M+ or —H, each of which may be the same or different, wherein at least one —OSO3−M+ group is present on the molecule and wherein M is selected from the group consisting of Na+, K+, Li+, NH4+, NR′4+, Mg2+, Ca2+ or other metal cations, wherein R′ is H or alkyl or aryl groups;
• L is any one of linkers L1 through L9 shown below wherein n is 1-10;
• and
• the two flavonoid units are connected through either 2′-3, 3′-3, or 4′-3 linkages.

Sulfated flavonoid dimers having the general formula of formula V:

• wherein
• R is one or more of —OH, or —OSO3−M+ or —H, each of which may be the same or different, wherein at least one —OSO3−M+ group is present on the molecule and wherein M is selected from the group consisting of Na+, K+, Li+, NH4+, NR′4+, Mg2+, Ca2+ or other metal cations, wherein R′ is H or alkyl or aryl groups;
• L is any one of linkers L1 through L9 shown below wherein n is 1-10;
• and
• the two flavonoid units are connected through either 2′-2′, 2′-3′, 2′-4′, 3′-3′, 3′-4′, or 4′-4′ linkages.

Sulfated flavonoid dimers having the general formula of formula VI:

• wherein
• R is one or more of —OH, or —OSO3−M+ or —H, each of which may be the same or different, wherein at least one —OSO3−M+ group is present on the molecule and wherein M is selected from the group consisting of Na+, K+, Li+, NH4+, NR′4+, Mg2+, Ca2+ or other metal cations, wherein R′ is H or alkyl or aryl groups;
• L is any one of linkers L1 through L9 shown below wherein n is 1-10;
• and
• any two flavonoid units are connected through 3-3 linkage.

Sulfated flavonoid trimers having the general formula of formula VII:

• wherein
• R is one or more of —OH, or —OSO3−M+ or —H, each of which may be the same or different, wherein at least one —OSO3−M+ group is present on the molecule and wherein M is selected from the group consisting of Na+, K+, Li+, NH4+, NR′4+, Mg2+, Ca2+ or other metal cations, wherein R′ is H or alkyl or aryl groups;
• L is any one of linkers L1 through L9 shown below wherein n is 1-10;
• and
• any two flavonoid units are connected through either 5-5, 5-6, 5-7, 5-8, 6-6, 6-7, 6-8, 7-7, 7-8, or 8-8 linkages.

Sulfated flavonoid tetramers having the general formula of formula VIII:

• wherein
• R is one or more of —OH, or —OSO3−M+ or —H each of which may be the same or different, wherein at least one —OSO3−M+ group is present on the molecule and wherein M is selected from the group consisting of Na+, K+, Li+, NH4+, NR′4+, Mg2+, Ca2+ or other metal cations, wherein R′ is H or alkyl or aryl groups;
• L is any one of linkers L1 through L9 shown below wherein n is 1-10;
• and
• any two flavonoid units are connected through either 5-5, 5-6, 5-7, 5-8, 6-6, 6-7, 6-8, 7-7, 7-8, or 8-8 linkages.