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Details for Patent: 6,297,222

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Details for Patent: 6,297,222

Title: Acyl deoxyribonucleoside derivatives and uses thereof
Abstract:The invention relates to compositions comprising acyl derivatives of 2'-deoxyribonucleosides. The invention also relates to methods of treating or preventing radiation, mutagen and sunlight-induced biological damage, and methods for improving wound healing and tissue repair, comprising administering the compositions of the present invention to an animal.
Inventor(s): von Borstel; Reid Warren (Darnestown, MD), Bamat; Michael Kevin (Darnestown, MD)
Assignee: Pro-Neuron, Inc. (Gaithersburg, MD)
Filing Date:Jun 06, 1995
Application Number:08/466,379
Claims:1. An acyl derivative of 2'-deoxyadenosine, having the formula ##STR19##

wherein R.sub.1, R.sub.2, and R.sub.3 are the same or different and each is hydrogen or an acyl group derived from

(a) an unbranched fatty acid with 3 to 22 carbon atoms,

(b) an amino acid selected from the group consisting of glycine, the L forms of alanine, valine, leucine, isoleucine, tyrosine, proline, hydroxyproline, serine, threonine, cysteine, aspartic acid, glutamic acid, arginine, lysine, histidine, carnitine, and ornithine, provided that R.sub.2 is not derived from leucine and that R.sub.3 is not derived from glycine or threonine,

(c) nicotinic acid, or

(d) a dicarboxylic acid having 3 to 22 carbon atoms,

provided that not all of R.sub.1, R.sub.2, and R.sub.3 are H, and where R.sub.3 is not H, then R.sub.1 and/or R.sub.2 may also be acetyl, or a pharmaceutically acceptable salt thereof.

2. An acyl derivative of 2'-deoxyadenosine as recited in claim 1 wherein R.sub.1 is derived from an unbranched fatty acid with 6 to 16 carbon atoms, R.sub.2 is H or derived from an unbranched fatty acid wish 6 to 16 carbon atoms, and R.sub.3 is H or derived from an amino acid with an acidic or basic side chain.

3. An acyl derivative of 2'-deoxyguanosine having the formula ##STR20##

wherein R.sub.1, R.sub.2, and R.sub.3 are the same or different and each is hydrogen or an acyl group derived from

(a) an unbranched fatty acid with 3 to 22 carbon atoms, provided that when R.sub.3 is H, R.sub.1 and R.sub.2 are not both derived from butyryl,

(b) an amino acid selected from the group consisting of glycine, the L forms of alanine, valine, leucine, isoleucine, tyrosine, proline, hydroxyproline, serine, threonine, cysteine, aspartic acid, glutamic acid, arginine, lysine, histidine, phenylalanine, carnitine, and ornithine,

(c) nicotinic acid, or

(d) a dicarboxylic acid having 3 to 22 carbon atoms,

provided that not all of R.sub.1, R.sub.2, and R.sub.3 are H, and where R.sub.3 is not H, then R.sub.1 and/or R.sub.2 may also be acetyl, or a pharmaceutically acceptable salt thereof.

4. An acyl derivative of 2'-deoxyguanosine as recited in claim 3 wherein R.sub.1 is an acyl group derived from an unbranched fatty acid with 6 to 16 carbon atoms, R.sub.2 is H or an acyl group derived from an unbranched fatty acid with 6 to 16 carbon atoms or an amino acid with an acidic or basic side chain, and R.sub.3 is H or an acyl group derived from an amino acid with an acidic or basic side chain.

5. An acyl derivative of 2'-deoxycytidine, having the formula ##STR21##

wherein R.sub.1, R.sub.2, and R.sub.3 are the same or different and each is hydrogen or an acyl group derived from

(a) an unbranched fatty acid with 3 to 22 carbon atoms,

(b) an amino acid selected from the group consisting of glycine, the L forms of alanine, valine, leucine, isoleucine, tyrosine, proline, hydroxyproline, serine, threonine, cysteine, aspartic acid, glutamic acid, arginine, lysine, histidine, carnitine, and ornithine,

(c) nicotinic acid, or

(d) a dicarboxylic acid having 3 to 22 carbon atoms,

provided that not all of R.sub.1, R.sub.2, and R.sub.3 are H, and where R.sub.3 is not H, then R.sub.1 and/or R.sub.2 may also be acetyl, or a pharmaceutically acceptable salt thereof.

6. An acyl derivative of 2'-deoxycytidine as recited in claim 5 wherein R.sub.1 is an acyl group derived from an unbranched fatty acid with 6 to 16 carbon atoms, R.sub.2 is H or an acyl group derived from an unbranched fatty acid with 6 to 16 carbon atoms, and R.sub.3 is H or an acyl group derived from an amino acid with an acidic or basic side chain.

7. A pharmaceutical composition comprising an effective amount of each of at least two compounds selected from at least two of the groups of compounds having the formulae: ##STR22##

wherein R.sub.1, R.sub.2, and R.sub.3 are the same or different and each is H or an acyl group derived from a carboxylic acid, provided that at least one of said substituents R.sub.1, R.sub.2, and R.sub.3 on each of said groups of compounds is not hydrogen, or pharmaceutically acceptable salts thereof.

8. A composition as recited in claim 7 wherein R.sub.1, R.sub.2, and R.sub.3 are the same or different and each is H or an acyl group derived from a carboxylic acid selected from the group consisting of an amino acid, an unbranched fatty acid containing 2 to 22 carbon atoms, a dicarboxylic acid containing 3 to 22 carbon atoms, and an optionally substituted benzoyl or heterocyclic aromatic carboxylic acid that is substantially nontoxic.

9. The composition of claim 8, wherein said amino acid is selected from the group consisting of glycine, the L forms of alanine, valine, leucine, isoleucine, phenylalanine, tyrosine, proline, hydroxyproline, serine, threonine, cysteine, cystine, methionine, tryptophan, aspartic acid, glutamic acid, arginine, lysine, histidine, ornithine, carnitine, and hydroxylysine.

10. A composition as recited in claim 7 which further includes at least one compound from said groups of compounds wherein R.sub.1, R.sub.2, and R.sub.3 are all hydrogen.

11. A composition as recited in claim 7 which comprises an effective amount of at least three compounds selected from at least three of said groups of compounds.

12. A composition as recited in claim 7 which comprises an effective amount of at least four compounds selected from at least four of said groups of compounds.

13. The composition of claim 7, further comprising at least one of the radioprotective compounds selected from the group consisting of: WR-2721, NAC, DDC, cysteamine, 2-mercaptoethanol, mercaptoethylamine dithiothreitol, glutathione, 2-mercaptoethanesulfonic acid, WR-1065, nicotinamide, 5-hydroxytryptamine, 2-beta-aminoethyl-isothiouronium-Br-Hbr, glucans, GLP/B04, GLP/B05, OK-432, Biostim, PSK, Lentinan, Schizophyllan, Rhodexman, Levan, Mannozym, MVE-2, MNR, MMZ, IL-1, TNF, thymic factor TF-5, glutathione peroxidase, superoxide dismutase, catalase, glutathione reductase, glutathione transferase, selenium, CdCl.sub.2, MnCl.sub.2, Zn acetate, Vitamin A, beta carotene, prostaglandins, tocopherol, methylene blue and PABA.

14. A composition as recited in claim 7 further comprising a pharmaceutically acceptable carrier.

15. A composition comprising one or more compounds as recited in claim 14, further comprising at least one radioprotective compound selected from the group consisting of WR-2721, NAC, DDC, cysteamine, 2-mercaptoethanol, mercaptoethylamine dithiothreitol, glutathione, 2-mercaptoethanesulfonic acid, WR-1065, nicotinamine, 5-hydroxytryptamine, 2-beta-aminoethyl-isothiouronium-Br-Hbr, glucans, GLP/B04, GLP/B05, OK-432, Biostim, PSK, Lentinan, Schizophyllan, Rhodexman, Levan, Mannozym, MVE-2, MNR, MMZ, IL-1, TNF, thymic factor TF-5, glutathione peroxidase, superoxide dismutase, catalase, glutathione reductase, glutathione transferase, selenium, CdCl.sub.2, MnCl.sub.2, Zn acetate, Vitamin A, beta carotene, prostaglandins, tocopherol, methylene blue and PABA, and a pharmaceutically acceptable carrier.

16. A composition as recited in claim 14 in the form of a liquid, a suspension, a tablet, a dragee, an injectable solution, a topical solution, or a suppository.

17. A composition as recited in claim 14, comprising: 0-50 mole percent of an acyl derivative of 2'-deoxycytidine, 0-50 mole percent of an acyl derivative of 2'-deoxyguanosine, 0-50 mole percent of an acyl derivative of 2'-deoxythymidine, and 0-50 mole percent of an acyl derivative of 2'-deoxyadenosine, the total content of acyl deoxyribonucleosides adding up to 100 mole percent.

18. A composition as recited in claim 17, comprising 25 mole percent of each of the said acyl deoxyribonucleosides.

19. A skin lotion containing an effective amount of a composition as recited in claim 14.

20. The skin lotion of claim 19, wherein said composition is present in from 0.1-5% by weight.

21. A bioerodible microcapsule containing an effective amount of a composition as recited in claim 14.

22. The composition as recited in claim 21, wherein said bioerodible microcapsules comprise a polymer selected from the group consisting of polylactate and a lactate-glycolate copolymer.

23. An acyl derivative of 2'-deoxyguanosine as in claim 3 wherein R.sub.1, R.sub.2, and R.sub.3 are the same or different and each is hydrogen or an acyl group derived from an unbranched fatty acid with 3 to 22 carbon atoms.

24. An acyl derivative of 2'-deoxyguanosine as in claim 23 wherein R.sub.1 and R.sub.2 are fatty acids with 6 to 16 carbon atoms.
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