Carbohydrate based anti-bacterials
A method of inhibiting bacterial growth by contacting a bacteria with at least one disaccharide compound of General Formula I,
1. A method of inhibiting bacterial growth comprising contacting a bacteria with at least one disaccharide compound of
wherein
U and Z are independently selected from the group consisting of —OR, —NHR, —NR(R),
wherein R may be the same or different, R is a moiety of not more than 20 carbon atoms independently selected from the group consisting of; alkyl, alkenyl, alkynyl, heteroalkyl, aryl, heteroaryl, arylalkyl and heteroarylalkyl;
W is independently selected from the group consisting of —OR L , —NHR L , —NR L R,
wherein R L is a substituted or unsubstituted, linear or branched moiety of between 3 and 55 carbon atoms selected from the group consisting of: alkyl, heteroalkyl, arylalkyl, and alkylaryl chain.
2. The method of claim 1 , wherein R L is substituted by a moiety selected from the group consisting of: carboxylic acids, sulfonic acids, phosphoric acids, tetrazoles, amines, guanidiniums, amidines, imidazoles, and oxazoles.
3. The method of claim 1 , wherein one or more R groups is substituted by a moiety selected from the group consisting of: —OH, —NO, —NO 2 , —NH 2 , —N 3 , halogen, —CF 3 , —CHF 2 , —CH 2 F, nitrile, alkoxy, aryloxy, amidine, guanidiniums, carboxylic acid, carboxylic acid ester, carboxylic acid amide, aryl, cycloalkyl, heteroalkyl, heteroaryl, aminoalkyl, aminodialkyl, aminotrialkyl, aminoacyl, carbonyl, substituted or unsubstituted imine, sulfate, sulfonamide, phosphate, phosphoramide, hydrazide, hydroxamate, hydroxamic acid, heteroaryloxy, carbamoyl, aminoaryl, aminoheteroaryl, thioalkyl, thioaryl and thioheteroaryl.
4. The method of claim 1 , wherein the compound is of
5. The method of claim 1 , wherein the bacteria is a Gram+bacteria.
6. The method of claim 1 , wherein the bacteria is a Gram−bacteria.
7. The method of claim 1 , wherein the bacteria is selected from the group consisting of an Escherichia coli ( E. coli ), Micrococcus luteus, Staphylococcus aureus , Methicillin-resistant Staphylococcus aurcus (MRSA), Enterococcus faecalis, Enterococcus faecalis Vancomycin resistant and Streptococcus pyogenes.
8. The method of claim 1 , wherein the bacteria is Staphylococcus aureus and the compound is
9. The method of claim 1 , wherein the bacteria is Staphylococcus aureus and the compound is
wherein:
n
X
Y
R2
R3
1
H
CF 3
1
H
CF 3
0
H
CF 3
0
H
CF 3
0
H
CF 3
1
CF 3
H
10. The method of claim 1 , wherein the bacteria is Staphylococcus aureus and the compound is
wherein:
R2
R3
11. The method of claim 1 , wherein the bacteria is Staphylococcus aureus and the compound is
wherein:
X
Y
R2
R3
H
CF 3
H
CF 3
H
CF 3
H
CF 3
H
H
CF 3
H
CF 3
H
CF 3
H
CF 3
H
CF 3
H
CF 3
H
CF 3
H
CF 3
H
CF 3
H
CF 3
H
CF 3
F
H
F
H
F
H
F
H
F
H
12. The method of claim 1 , wherein the bacteria is Staphylococcus aureus and the compound is
wherein:
X
Y
R2
R3
CF 3
H
CF 3
H
H
CH 3
H
CH 3
H
CH 3
13. The method of claim 1 , wherein the bacteria is Staphylococcus aureus and the compound is selected from the group consisting of:
wherein
R1
R2
R3
H
H
H
H
n-decyl
and
14. The method of claim 1 , wherein the bacteria is E. coli and the compound is
wherein:
X
Y
R2
R3
H
CF 3
H
CF 3
H
CF 3
H
CF 3
H
CF 3
H
CF 3
H
CF 3
H
CF 3
H
CF 3
H
CF 3
H
CF 3
H
CF 3
H
CF 3
H
CF 3
H
CF 3
H
CF 3
H
CF 3
15. The method of claim 1 , wherein the compound is
wherein:
Compound
R1
R2
R3
42
51
56
n-decyl
65
67
68
69
70
73
74
75
76
77
and the bacteria is Micrococcus luteus.
16. The method of claim 1 , wherein the compound is
wherein:
Compound
R1
R2
R3
42
51
56
n-decyl
65
67
68
69
70
73
74
75
76
77
and the bacteria is Staphylococcus aureus.
17. The method of claim 1 , wherein the compound is
wherein:
Compound
R1
R2
R3
42
51
56
n-decyl
67
68
69
73
74
75
76
77
and wherein the bacteria is Staphylococcus aureus MRSA.
18. The method of claim 1 , wherein the compound is
wherein:
Compound
R1
R2
R3
42
51
56
n-decyl
65
67
68
69
70
73
74
75
76
77
and the bacteria is Enterococcus faecalis.
19. The method of claim 1 , wherein the compound is
wherein
Compound
R1
R2
R3
42
51
56
n-decyl
65
67
68
69
70
73
74
75
76
77
and wherein the bacteria is Enterococcus faecalis Vancomycin resistant.
20. The method of claim 1 , wherein the compound is
wherein:
Compound
R1
R2
R3
42
51
56
n-decyl
65
67
68
69
70
73
74
75
76
77
and the bacteria is Streptococcus pyogenes.
21. A method of inhibiting a bacterial infection in a mammal comprising administering to said mammal an effective amount of a compound of General Formula (I),
wherein
U and Z are independently selected from the group consisting of: —OR, —NHR, and —NR(R),
wherein R may be the same or different, R is a moiety of not more than 20 carbon atoms independently selected from the group consisting of alkyl, alkenyl, alkynyl, heteroalkyl, aryl, heteroaryl, arylalkyl and heteroarylalkyl;
W is independently selected from the group consisting of —OR L , —NHR L , —NR L R,
wherein R L is a substituted or unsubstituted, linear or branched moiety of between 3 and 55 carbon atoms selected from the group consisting of: alkyl, heteroalkyl, arylalkyl, and alkylaryl chain.
22. The method of claim 1 , wherein the bacterium is a resistant or susceptible strain of a Micrococcus, Streptococcus, Enterococcus or Staphylococcus.