Structural optimization and evaluation of butenolides as potent antifouling agents: Modification of the side chain affects the biological activities of compounds

Biofouling

Volumn 28, Issue 8, 2012, Pages 857-864

  Li, Yongxin ^a   Zhang, Fengying ^b   Xu, Ying ^a   Matsumura, Kiyotaka ^a   Han, Zhuang ^a   Liu, Lingli ^b   Lin, Wenhan ^b   Jia, Yanxing ^b   Qian, Pei Yuan ^a  

^a HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

^b PEKING UNIVERSITY   (China)

Author keywords

anti larval settlement; antifouling; barnacle; butenolides; lipophilicity; side chain modification; structural optimization

Indexed keywords

ANTIFOULING; ANTIFOULING AGENT; BIOACTIVITY; BUTYLTIN; CRUSTACEAN; LARVAL SETTLEMENT; OPTIMIZATION; PHYSICOCHEMICAL PROPERTY;

BALANUS AMPHITRITE; THORACICA;

EID: 84865540117     PISSN: 08927014     EISSN: 10292454     Source Type: Journal    
DOI: 10.1080/08927014.2012.717071     Document Type: Article

References (43)

1. Bellas, J. 2006. Comparative toxicity of alternative antifouling biocides on embryos and larvae of marine invertebrates. Sci Total Environ, 367: 573-585.
2. Blakemore, PR, Cole, WJ, Kocienski, PJ and Morley, A. 1998. A stereoselective synthesis of trans-1,2-disubstituted alkenes based on the condensation of aldehydes with metallated 1-phenyl-1H-tetrazol-5-yl sulfones. Synlett, 1: 26-28.
3. Blakemore, PR, Kocienski, PJ, Morley, A and Muir, K. 1999. A synthesis of herboxidiene. J Chem Soc Perk T, 1: 955-968.
4. Blihoghe, D, Manzo, E, Villela, A, Cutignano, A, Picariello, G, Faimali, M and Fontana, A. 2011. Evaluation of the antifouling properties of 3-alyklpyridine compounds. Biofouling, 27: 99-109.
5. Camp, D, Davis, RA, Campitelli, M, Ebdon, J and Quinn, RJ. 2012. Drug-like properties: Guiding principles for the design of natural product libraries. J Nat Prod, 75: 72-81.
6. Champ, MA. 2000. A review of organotin regulatory strategies pending actions, related costs and benefits. Sci Total Environ, 258: 21-71.
7. Clare, AS. 1996. Marine natural product antifoulants: status and potential. Biofouling, 9: 211-229.
8. Cronin, DMT. 2006. The role of hydrophobicity in toxicity prediction. Curr Comp Aided Drug Des, 2: 405-413.
9. Dobretsov, S, Dahms, HU and Qian, PY. 2006. Inhibition of biofouling by marine microorganisms and their metabolites. Biofouling, 22: 43-54.
10. Dobretsov, S, Xiong, HR, Xu, Y, Levin, LA and Qian, PY. 2007. Novel antifoulants: inhibition of larval attachment by proteases. Mar Biotechnol, 9: 388-397.
11. Eberhard, A, Burlingame, AL, Eberhard, C, Kenyon, GL, Nealson, KH and Oppenheimer, NJ. 1981. Structural identification of autoinducer of Photobacterium fischeri luciferase. Biochemistry, 20: 2444-2449.
12. Fusetani, N. 2004. Biofouling and antifouling. Nat Prod Rep, 21: 94-104.
13. Fusetani, N. 2011. Antifouling marine natural products. Nat Prod Rep, 28: 400-410.
14. Jefford, CW, Sledeski, AW and Boukouvalas, J. 1988. Regioselective alkylation of 2-trimethylsiloxyfuran: direct access to 4-substituted but-2-en-4-olides. J Chem Soc Chem Commun, 5: 364-365.
15. Kahns, AH and Bundgaard, H. 1991. N-Acyl derivatives as prodrug forms for amides: chemical-stability and enzymatic-hydrolysis of various N-acyl and N-alkoxycarbonyl amide derivatives. Int J Pharm, 71: 31-43.
16. Khandeparker, L and Anil, AC. 2007. Underwater adhesion the barnacle way. Int J Adhes Adhes, 27: 165-172.
17. Kitano, Y, Akima, C, Yoshimura, E and Nogata, Y. 2011. Anti-barnacle activity of novel simple alkyl isocyanides derived from citronellol. Biofouling, 27: 201-205.
18. Kitano, Y, Yokoyama, A, Nogata, Y, Shinshima, K, Yoshimura, E, Chiba, K, Tada, M and Sakaguchi, I. 2003. Synthesis and anti-barnacle activities of novel 3-isocyanotheonellin analogues. Biofouling, 19: 187-192.
19. Konstantinou, IK and Albanis, TA. 2004. Worldwide occurrence and effects of antifouling paint booster biocides in the aquatic environment: a review. Environ Int, 30: 235-248.
20. Kubinyi, H. 1979. Nonlinear dependence of biological activity on hydrophobic character: the bilinear model. Farmaco Sci, 34: 248-276.
21. Leeson, PD and Springthorpe, B. 2007. The influence of drug-like concepts on decision-making in medicinal chemistry. Nat Rev Drug Discov, 6: 881-889.
22. Li, YX, Wu, HX, Xu, Y, Shao, CL, Wang, CY and Qian, PY. 2012. Secondary metabolites isolated from marine organisms along Chinese coastal areas as larval settlement inhibitors of the barnacle Balanus amphitrite. Mar Biotech,
23. Lipinski, CA, Lombardo, F, Dominy, BW and Feeney, PJ. 1997. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliver Rev, 23: 3-25.
24. Lo, Y. 2003. Relationships between the hydrophilic-lipophilic balance values of pharmaceutical excipients and their multidrug resistance modulating effect in caco-2 cells and rat intestines. J Control Release, 90: 37-48.
25. Molander, GA and St Jean, DJ. 2002. Samarium(II) iodide-mediated intramolecular conjugate additions of alpha, beta-unsaturated lactones. J Org Chem, 67: 3861-3865.
26. Moore, FK, Chai, CLL, Teo, SLM, Rittschoff, D, Chen, CL and Lee, SSC. 2009. Antifouling compounds and use thereof. International Patent no: WO, 2009139729
27. Nantasenamat, C, Piacham, T, Tantimongcolwat, T, Naenna, T, Isarankura-Na-Ayudhya, C and Prachayasittikul, V. 2008. QSAR model of the quorum-quenching N-acyl-homoserine lactone lactonase activity. J Biol Syst, 16: 279-293.
28. Nogata, Y, Yoshimura, E, Shinshima, K, Kitano, Y and Sakaguchi, I. 2003. Antifouling substances against larvae of the barnacle Balanus amphitrite from the marine sponge, Acanthella cavernosa. Biofouling, 19: 193-196.
29. Omae, I. 2003. Organotin antifouling paints and their alternatives. Appl Organomet Chem, 17: 81-105.
30. Piola, RF and Johnston, EL. 2006. Differential tolerance to metals among populations of the introduced bryozoan Bugula neritina. Mar Biol, 148: 997-1010.
31. Qian, PY, Xu, Y and Fusetani, N. 2010a. Natural products as antifouling compounds: recent progress and future perspectives. Biofouling, 26: 223-234.
32. Qian, PY, Wong, YH and Zhang, Y. 2010b. Changes in the proteome and phosphoproteome expression in the bryozoan Bugula neritina larvae in response to the antifouling agent butenolide. Proteomics, 10: 3435-3446.
33. Richmond, MD and Seed, R. 1991. A review of marine macrofouling communities with special reference to animal fouling. Biofouling, 2: 151-168.
34. Schultz, MP, Bendick, JA, Holm, ER and Hertel, WM. 2011. Economic impact of biofouling on a naval surface ship. Biofouling, 27: 87-98.
35. Thomas, KV and Brooks, S. 2010. The environmental fate and effects of antifouling paint biocides. Biofouling, 26: 73-88.
36. Townsin, RL. 2003. The ship hull fouling penalty. Biofouling, 19(SUPPL.): 9-15.
37. Voulvoulis, N, Scrimshaw, MD and Lester, JN. 2002. Comparative environmental assessment of biocides used in antifouling paints. Chemosphere, 47: 789-795.
38. Wilkinson, A, Danino, V, Wisniewski-Dye, F, Lithgow, JK and Downie, JA. 2002. N-acyl-homoserine lactone inhibition of rhizobial growth is mediated by two quorum-sensing genes that regulate plasmid transfer. J Bacteriol, 184: 4510-4519.
39. Xu, Y, He, HP, Schulz, S, Liu, X, Fusetani, N, Xiong, HR, Xiao, X and Qian, PY. 2010. Potent antifouling compounds produced by marine Streptomyces. Bioresource Technol, 101: 1331-1336.
40. Zhang, Y, Xu, Y, Arellano, SM, Xiao, K and Qian, PY. 2010. Comparative proteome and phosphoproteome analyses during cyprid development of the barnacle Balanus (=Amphibalanus) amphitrite). J Proteome Res, 9: 3146-3157.
41. Zhang, YF, Wang, GC, Xu, Y, Sougrat, R and Qian, PY. 2011. The effect of butenolide on behavioral and morphological changes in two marine fouling species, the barnacle Balanus amphitrite and the bryozoan Bugula neritina. Biofouling, 27: 467-475.
42. Zhang, YF, Zhang, HM, He, LS, Liu, CD, Xu, Y and Qian, PY. 2012. Butenolide inhibits marine fouling by altering the primary metabolism of three target organisms. ACS Chem Biol, 7: 1049-1058.
43. Zhou, XJ, Okamura, H and Nagata, S. 2006. Remarkable synergistic effects in antifouling chemicals against Vibrio fischeri in a bioluminescent assay. J Health Sci, 52: 243-251.