Synthetic versus natural receptors: Supramolecular control of chemical sensing in fish

ACS Chemical Biology

Volumn 9, Issue 7, 2014, Pages 1432-1436

  Da Silva, José P ^a   Choudhury, Rajib ^c   Porel, Mintu ^c   Pischel, Uwe ^d   Jockusch, Steffen ^e   Hubbard, Peter C ^b   Ramamurthy, Vaidhyanathan ^c   Canário, Adelino V M ^b  

^a Hospital CUF Infante Santo   (Portugal)

^b UNIVERSITY OF ALGARVE   (Portugal)

^c University of Miami   (United States)

^d UNIVERSITY OF HUELVA   (Spain)

^e Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADAMANTAN 1 AMINE; AMINE; ARTIFICIAL RECEPTOR; CADAVERINE; CUCURBIT[6]URIL; CUCURBIT[7]URIL; UNCLASSIFIED DRUG; ADAMANTANE; BRIDGED COMPOUND; CUCURBIT(7)URIL; IMIDAZOLE DERIVATIVE; OLFACTORY RECEPTOR;

ANIMAL BEHAVIOR; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; ELECTRO OLFACTOGRAPHY; ELECTROGRAPHY; ENCAPSULATION; FEMALE; IN VIVO STUDY; MALE; NONHUMAN; OLFACTOMETRY; OLFACTORY RECEPTOR; OREOCHROMIS MOSSAMBICUS; PREDATOR AVOIDANCE; PRIORITY JOURNAL; REDUCTION; SMELLING; SUPRAMOLECULAR CHEMISTRY; ANALOGS AND DERIVATIVES; ANIMAL; CHEMICAL STRUCTURE; CHEMISTRY; METABOLISM; ODOR; PHYSIOLOGY; TILAPIA;

ADAMANTANE; ANIMALS; BRIDGED COMPOUNDS; CADAVERINE; FEMALE; IMIDAZOLES; MALE; MODELS, MOLECULAR; RECEPTORS, ODORANT; SMELL; TILAPIA;

EID: 84904543750     PISSN: 15548929     EISSN: 15548937     Source Type: Journal    
DOI: 10.1021/cb500172u     Document Type: Article

References (26)

1. Cram, D. J. and Cram, J. M. (1974) Host-guest chemistry Science 183, 803-809
2. Reinhoudt, D. N. and Crego-Calama, M. (2002) Synthesis beyond the molecule Science 295, 2403-2407 (Pubitemid 34270245)
3. Ma, D., Zhang, B., Hoffmann, U., Sundrup, M. G., Eikermann, M., and Isaacs, L. (2012) Acyclic cucurbit[ n ]uril-type molecular containers bind neuromuscular blocking agents in vitro and reverse neuromuscular block in vivo Angew. Chem., Int. Ed. 51, 11358-11362
4. Rekharsky, M. V. and Inoue, Y. (1998) Complexation thermodynamics of cyclodextrins Chem. Rev. 98, 1875-1917 (Pubitemid 128633440)
5. Lee, J. W., Samal, S., Selvapalam, N., Kim, H. J., and Kim, K. (2003) Cucurbituril homologues and derivatives: new opportunities in supramolecular chemistry Acc. Chem. Res. 36, 621-630
6. Lagona, J., Mukhopadhyay, P., Chakrabarti, S., and Isaacs, L. (2005) The cucurbit[ n ]uril family Angew. Chem., Int. Ed. 44, 4844-4870
7. Verboom, W., Rudkevich, D. M., and Reinhoudt, D. N. (1994) Molecular recognition by artificial receptors Pure Appl. Chem. 66, 679-686
8. Cao, L., Sekutor, M., Zavalij, P. Y., Mlinaric-Majerski, K., Glaser, R., and Isaacs, L. (2014) Cucurbit[7]uril·guest pair with an attomolar dissociation constant Angew. Chem., Int. Ed. 53, 988-993
9. Houk, K. N., Leach, A. G., Kim, S. P., and Zhang, X. (2003) Binding affinities of host-guest, protein-ligand, and protein-transition-state complexes Angew. Chem., Int. Ed. 42, 4872-4897 (Pubitemid 37345385)
10. Hennig, A., Bakirci, H., and Nau, W. M. (2007) Label-free continuous enzyme assays with macrocycle-fluorescent dye complexes Nat. Methods 4, 629-632 (Pubitemid 47202472)
11. Liu, S., Ruspic, C., Mukhopadhyay, P., Chakrabarti, S., Zavalij, P. Y., and Isaacs, L. (2005) The cucurbit[ n ]uril family: prime components for self-sorting systems J. Am. Chem. Soc. 127, 15959-15967 (Pubitemid 41643306)
12. Márquez, C., Hudgins, R. R., and Nau, W. M. (2004) Mechanism of host-guest complexation by cucurbituril J. Am. Chem. Soc. 126, 5806-5816 (Pubitemid 38621419)
13. Ghosh, S. and Isaacs, L. (2010) Biological catalysis regulated by cucurbit[7]uril molecular containers J. Am. Chem. Soc. 132, 4445-4454
14. Rekharsky, M. V., Mori, T., Yang, C., Ko, Y. H., Selvapalam, N., Kim, H., Sobransingh, D., Kaifer, A. E., Liu, S., Isaacs, L., Chen, W., Moghaddam, S., Gilson, M. K., Kim, K., and Inoue, Y. (2007) A synthetic host-guest system achieves avidin-biotin affinity by overcoming enthalpy-entropy compensation Proc. Natl. Acad. Sci. U.S.A. 104, 20737-20742
15. Isobe, H., Sato, S., Lee, J. W., Kim, H.-J., Kim, K., and Nakamura, E. (2005) Supramolecular modulation of action of polyamine on enzyme/DNA interactions Chem. Commun. 1549-1551 (Pubitemid 40543542)
16. Ngai, J., Dowling, M. M., Buck, L., Axel, R., and Chess, A. (1993) The family of genes encoding odorant receptors in the channel catfish Cell 72, 657-666 (Pubitemid 23093875)
17. Rolen, S. H., Sorensen, P. W., Mattson, D., and Caprio, J. (2003) Polyamines as olfactory stimuli in the goldfish Carassius auratus J. Exp. Biol. 206, 1683-1696 (Pubitemid 36599394)
18. Hussain, A., Saraiva, L. R., Ferrero, D. M., Ahuja, G., Krishna, V. S., Liberles, S. D., and Korsching, S. Y. (2013) High-affinity olfactory receptor for the death-associated odor cadaverine Proc. Natl. Acad. Sci. U.S.A. 110, 19579-19584
19. Oliveira, R. F., Lopes, M., Carneiro, L. A., and Canário, A. V. M (2001) Watching fights raises fish hormone levels Nature 409, 475 (Pubitemid 32144342)
20. Dulka, J. G., Stacey, N. E., Sorensen, P. W., and Van Der Kraak, G. J. (1987) A steroid sex pheromone synchronizes male-female spawning readiness in goldfish Nature 325, 251-253 (Pubitemid 17049883)
21. Li, W., Scott, A. P., Siefkes, M. J., Yan, H., Liu, Q., Yun, S.-S., and Gage, D. A. (2002) Bile acid secreted by male sea lamprey that acts as a sex pheromone Science 296, 138-141 (Pubitemid 34280072)
22. Schild, D. and Restrepo, D. (1998) Transduction mechanisms in vertebrate olfactory receptor cells Physiol. Rev. 78, 429-466 (Pubitemid 28182900)
23. Scott, J. W. and Scott-Johnson, P. (2002) The Electroolfactogram: a review of its history and uses Microsc. Res. Tech. 58, 152-160 (Pubitemid 34832820)
24. Tang, H., Fuentealba, D., Ko, Y. H., Selvapalam, N., Kim, K., and Bohne, C. (2011) Guest binding dynamics with cucurbit[7]uril in the presence of cations J. Am. Chem. Soc. 133, 20623-20633
25. Hulme, E. C. and Trevethick, M. A. (2010) Ligand binding assays at equilibrium: validation and interpretation Br. J. Pharmacol. 161, 1219-1237
26. Fried, H. U., Fuss, S. H., and Korsching, S. I. (2002) Selective imaging of presynaptic activity in the mouse olfactory bulb shows concentration and structure dependence of odor responses in identified glomeruli Proc. Natl. Acad. Sci. U.S.A. 99, 3222-3227 (Pubitemid 34240613)