(+)-Usnic acid enamines with remarkable cicatrizing properties

Bioorganic and Medicinal Chemistry

Volumn 21, Issue 7, 2013, Pages 1834-1843

  Bruno, Michela ^a,b   Trucchi, Beatrice ^a,b   Burlando, Bruno ^c   Ranzato, Elia ^c   Martinotti, Simona ^c   Akkol, Esra Küpeli ^d   Süntar, Ipek ^d   Keleş, Hikmet ^e   Verotta, Luisella ^a,b  

^a UNIVERSITY OF MILAN   (Italy)

^b Consorzio Interuniversitario Nazionale Metodologie e Processi Innovativi di Sintesi ^*  (Italy)

^c UNIVERSITY OF EASTERN PIEDMONT   (Italy)

^d GAZI UNIVERSITY   (Turkey)

^e AFYON KOCATEPE UNIVERSITY   (Turkey)

Author keywords

(+) Usnic acid; In vivo wound healing assays; Mannich bases; Scratch wound assay; Wound healing therapy

Indexed keywords

2 [1 [[2 (1H INDOL 3 YL)ETHYL]AMINO]ETHYLIDENE] 6 ACETYL 7,9 DIHYDROXY 8,9B DIMETHYLDIBENZO[B,D]FURAN 1,3(2H,9BH) DIONE; 2 [[1 (6 ACETYL 7,9 DIHYDROXY 8,9B DIMETHYL 1,3 DIOXO 1,9B DIHYDRODIBENZO[B,D]FURAN 2(3H) YLIDENE)ETHYL]AMINO] 3 (4 HYDROXYPHENYL)PROPANOIC ACID; 2 [[1 (6 ACETYL 7,9 DIHYDROXY 8,9B DIMETHYL 1,3 DIOXO 1,9B DIHYDRODIBENZO[B,D]FURAN 2(3H) YLIDENE)ETHYL]AMINO] 5 GUANIDINOPENTANOIC ACID; 2 [[1 (6 ACETYL 7,9 DIHYDROXY 8,9B DIMETHYL 1,3 DIOXO 1,9B DIHYDRODIBENZO[B,D]FURAN 2(3H) YLIDENE)ETHYL]AMINO]ETHANESULFONIC ACID; 4 [[1 (6 ACETYL 7,9 DIHYDROXY 8,9B DIMETHYL 1,3 DIOXO 1,9B DIHYDRODIBENZO[B,D]FURAN 2(3H) YLIDENE)ETHYL]AMINO]BUTANOIC ACID; 6 ACETYL 2 (1 AMINOETHYLIDENE) 7,9 DIHYDROXY 8,9B DIMETHYLDIBENZO[B,D]FURAN 1,3(2H,9BH) DIONE; 6 ACETYL 2 [1 [[2 [[2 [[1 (6 ACETYL 7,9 DIHYDROXY 8,9B DIMETHYL 1,3 DIOXO 1,9B DIHYDRODIBENZO[B,D]FURAN 2(3H)YLIDENE)ETHYL]AMINO]ETHYL]DISULFANYL]ETHYL]AMINO]ETHYLIDENE] 7,9 DIHYDROXY 8,9B DIMETHYLDIBENZO[B,D]FURAN 1,3(2H,9BH) DIONE; 6 ACETYL 7,9 DIHYDROXY 2 [1 [(2 MERCAPTOETHYL)AMINO]ETHYLIDENE] 8,9B DIMETHYLDIBENZO[B,D]FURAN 1,3(2H,9BH) DIONE; ASIATICOSIDE; COLLAGENASE; DIBENZOFURAN DERIVATIVE; ELASTASE; HYALURONIDASE; HYDROXYPROLINE; NUCLEOPHILE; TRIETHYLAMMONIUM 2 [[1 (6 ACETYL 7,9 DIHYDROXY 8,9B DIMETHYL 1,3 DIOXO 1,9B DIHYDRODIBENZO[B,D]FURAN 2(3H) YLIDENE)ETHYL]AMINO]ACETATE; TRIETHYLAMMONIUM 2 [[1(6 ACETYL 7,9 DIHYDROXY 8,9B DIMETHYL 1,3 DIOXO 1,9B DIHYDRODIBENZO[B,D]FURAN 2(3H) YLIDENE)ETHYL]AMINO] 3 (1H IMIDAZOL 4 YL)PROPANOATE; UNCLASSIFIED DRUG; USNIC ACID;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; KERATINOCYTE; MALE; MOUSE; NONHUMAN; RAT; TENSILE STRENGTH; WOUND; WOUND CONTRACTION; WOUND HEALING;

ANIMALS; ANTI-INFECTIVE AGENTS; ANTIOXIDANTS; BENZOFURANS; CELL LINE; CELL SURVIVAL; HUMANS; KERATINOCYTES; LICHENS; MALE; MICE; RATS; RATS, SPRAGUE-DAWLEY; WOUND HEALING;

EID: 84875227149     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2013.01.045     Document Type: Article

References (46)

1. P. Martin Science 276 1997 75
2. L.G. Ovington Clin. Dermatol. 25 2007 33
3. S.C. Davis Clin. Dermatol. 27 2009 502
4. A. de Fátima, L.V. Modolo, A.C.C. Sanches, and R.R. Porto Mini-Rev. Med. Chem. 8 2008 879
5. W.J. Lindblad Int. J. Low. Extrem. Wounds 7 2008 75
6. B. Burlando, E. Ranzato, A. Volante, G. Appendino, F. Pollastro, and L. Verotta Planta Med. 75 2009 607
7. J.-Q. Jin, L.-C. He, Y.-l. Dong, and C.-Q. Li Zhongguo Yaoxue Zazhi (Beijing, China) 41 2006 1546
8. J. Jin, Y. Dong, and L. He Zhongyaocai 28 2005 109
9. P.S. Nunes, R.L.C. Albuquerque-Junior, D.R.R. Cavalcante, M.D.M. Dantas, J.C. Cardoso, M.S. Bezerra, J.C.C. Souza, M.R. Serafini, L.J. Quitans-Junior, L.R. Bonjardim, and A.A.S. Araujo J. Biomed. Biotechnol. 2011 761593
10. K. Ingólfsdóttir Phytochemistry 61 2002 729
11. Usnic acid: T. Kokubun, W.K.P. Shiu, and S. Gibbons Planta Med. 73 2007 176
12. M. Natić, Z. Tešić, K. Andelković, I. Brčeski, S. Radulović, S. Manić, and D. Sladić Synth. React. Inorg. Met.-Org. Chem. 34 2004 101
13. Abbott, S. J. PCT Int. Appl. WO2012131347, 2012.
14. R. Variati, R.H. Nordmann, and H. Budapest Olaj, Szappan, Kozmetika 59 2010 11
15. Davis, A.; Donoghue, G.; Eady, E. PCT Int. Appl. WO 2011055139, 2011.
16. Dees, H. C. EP 1362581, 2003.
17. V. Najdenova, K. Lisickov, and Z. Gyarmati Olaj, Szappan, Kozmetika 50 2001 158
18. B. Proksa, and A. Proksova Farmaceuticky Obzor 68 1999 139
19. P. Seifert, and C. Bertrand Cosmet. News 18 1995 168
20. P. Seifert, and C. Bertram SOFW J. 121 1995 480
21. M. Reyim, and A. Abdulla Zhongguo Niangzao 11 2010 122
22. L. Guo, Q. Shi, J.-L. Fang, N. Mei, A.A. Afshan, S.M. Lewis, J.E.A. Leakey, and V.H. Frankos Environ. Carcinog. Ecotoxicol. Rev. 26 2008 317
23. B.M. Hausen, L. Emde, and V. Marks Contact Dermatitis 28 1993 70
24. M. Takai, Y. Uehara, and J.A. Beisler J. Med Chem. 22 1979 1380
25. S. Tomasi, S. Picard, C. Lainé, V. Babonneau, A. Goujeon, J. Boustie, and P. Uriac J. Comb. Chem. 8 2006 11
26. J.K. Kutney, and I.H. Sanchez Can. J. Chem. 54 1976 2795
27. R.T. Petrussevska, and D. Breitkreutz J. Cell Biol. 106 1988 761
28. V.M. Schoop, N. Mirancea, and N.E. Fusenig J. Invest. Dermatol. 112 1999 343
29. K. Matsuura, T. Kuratani, and T. Gondo Eur. J. Pharmacol. 563 2007 83
30. E. Ranzato, M. Patrone, L. Mazzucco, and B. Burlando J. Dermatol. 159 2008 537
31. E. Ranzato, L. Mazzucco, M. Patrone, and B. Burlando J. Cell. Mol. Med. 13 2009 2030
32. R. Kumar, S.S. Katoch, and S. Sharma Indian J. Exp. Biol. 44 2006 371
33. B.S. Nayak, M. Anderson, and L.M. Pinto Pereira Fitoterapia 78 2007 540
34. A. Sahasrabudhe, and M. Deodhar Int. J. Bot. 6 2010 299
35. Verotta, L.; Bruno, M.; Trucchi, B.; Ranzato, E.; Martinotti, S.; Bonetta, S.; Carraro, E.; Burlando, B.; Akkol, E. K.; Süntar, I.; Keleş, H. 'Derivati dibenzofuranici ad attività cicatrizzante', MI2012A001082, 2012 (pending patent).
36. E. Ranzato, L. Mazzucco, and B. Burlando Platelet Derivatives: A New Horizon in Regenerative Medicine V.B. Leon, Advances in Medicine and Biology Vol. 11 2009 Nova Science Publishers, Inc Hauppauge, NY 1 16
37. D.N. Sokolov, V.V. Zarubaev, A.A. Shtro, M.P. Polovinka, O.A. Luzina, N.I. Komarova, N.F. Salakhutdinov, and O.I. Kiselev Bioorg. Med. Chem. Lett. 2012 7060
38. E. Borenfreund, H. Babich, and N. Martin-Alguacil Ecotoxicol. Environ. Saf. 17 1989 297
39. Barnes, M.; Correll, R.; Stevens, D. Program abstract book. A simple spreadsheet for estimating low-effect concentrations and associated logistic dose response curves. Solutions to pollution: The Society of Environmental Toxicology and Chemistry Asia/Pacific - Australasian Society of Ecotoxicology. SETAC ASE ASIA PACIFIC, 2003.
40. S. Lodhi, R.S. Pawar, A.P. Jain, and A.K. Singhai J. Ethnopharmacol. 108 2006 204
41. L. Suguna, S. Singh, P. Sivakumar, P. Sampath, and G. Chandrakasan Phytother. Res. 16 2002 227
42. V.A. Tramontina, M.A. Machado, R. Nogueira Filho Gda, S.H. Kim, M.R. Vizzioli, and S. Toledo Braz. Dent. J 13 2002 11
43. F. Sadaf, R. Saleem, M. Ahmed, S.I. Ahmad, and Z. Navaid-ul J. Ethnopharmacol. 107 2006 161
44. Z. Degim, N. Çelebi, H. Sayan, A. Babül, D. Erdoǧan, and G. Take Amino Acids 22 2002 187
45. K.K. Lee, and J.D. Choi Int. J. Cosmet. Sci. 21 1999 285
46. M.F. Melzig, B. Löser, and S. Ciesielski Pharmazie 56 2001 967