Oral compositions containing polyguanidinium compounds and methods of manufacture and use thereof
The invention describes the modification of polyamine-based materials to form polyguanidine compounds that are useful for their antimicrobial, anticaries, and muccoadhesive properties. The present invention also relates to methods for preventing or treating periodontal disease and caries which include delivering a therapeutically effective amount of an oral composition containing a polyguanidine compound into an oral cavity.
1. An oral composition, comprising:
a. a polyguanidine compound of Formula (I):
wherein:
X denotes an orally acceptable counterion;
Z is CH or N;
R 1 , R 2 , and R 3 are each independently a hydrogen or a linear or branched, saturated or unsaturated, optionally hydroxylated C 1 to C 16 alkyl radical;
A denotes a linear or branched, saturated or unsaturated, optionally hydroxylated C 1 to C 16 alkyl radical; or A denotes a linear or branched, saturated or unsaturated, C 1 to C 16 alkylene radical optionally substituted with at least one radical selected from the group consisting of: a hydroxyl, carboxyl, or carboxylate radical or a halogen; the alkylene radical optionally containing at least one function group selected from the group consisting of: an amine, ether, thioether, ester, amide, carbamate, urea, C 6 aryl or C 3 to C 8 cyclanyl ring optionally substituted with a C 1 -C 8 alkyl, hydroxyl or halogen; or A denotes one or more C 6 or C 7 aryl or C 5 to C 7 cyclanyl rings unsubstituted or substituted with a C 1 -C 8 alkyl, a hydroxyl group or a halogen; or A denotes a C 10 to C 14 polyaryl or C 6 to C 10 polycyclanyl chain, which may be interrupted with at least one function group selected from the group consisting of: a C 1 to C 8 alkylene radical, amine, amide, ether, thioether, hydrogen atom, carbamate or urea; and
n denotes an integer between 2 and 5,000;
b. an orally acceptable carrier;
c. a bioacceptable glass composition comprising 40-60% SiO 2 , 10-30% CaO 2 , 10-35% Na 2 O, 2-8% P 2 O 5 , 0-25% CaF 2 , and 0-10% B 2 O 3 ; and
d. a small particle silica having an average particle size of 0.01 μm-10 μm.
2. The composition of claim 1 , wherein said counterion is bicarbonate (HCO 3 − ).
3. The composition of claim 1 , further comprising a calcium salt.
4. The composition of claim 3 , wherein said calcium salt is selected from the group consisting of: calcium carbonate, monocalcium phosphate, dicalcium phosphate, tricalcium phosphate, calcium fluoride, calcium monofluorophosphate, sodium calcium pyrophosphate, calcium laurate, calcium palmitate, and combinations thereof.
5. The composition of claim 4 , wherein said calcium salt is calcium carbonate.
6. The composition of claim 1 , further comprising a phosphorous source.
7. The composition of claim 6 , wherein said phosphorous source is a phytate or phytic acid selected from the group consisting of: inositol triphosphate (IP3), inositol tetraphosphate (IP4), inositol pentaphosphate (IP5), inositol hexakisphosphate (IP6), and combinations thereof.
8. The composition of claim 1 , wherein the oral composition is selected from the group consisting of: a dental care product, a food product, and chewing gum.
9. The composition of claim 2 , further comprising a calcium salt.
10. The composition of claim 9 , wherein the bioacceptable glass composition has the formula CaNaO 6 PSi.
11. The composition of claim 10 , further comprising a phosphorus source.
12. The composition of claim 1 , wherein the polyguanidine compound of Formula (I) is a compound selected from the group consisting of:
13. The composition of claim 12 , further comprising a calcium salt.
14. The composition of claim 13 , wherein the bioacceptable glass composition has the formula CaNaO 6 PSi.
15. The composition of claim 14 , further comprising a phosphorus source.
16. The composition of claim 1 , further comprising a potassium salt.
17. The composition of claim 14 , further comprising a potassium salt.