Skip to main content
Log in

Chlorophyll derivatives as visual pigments for super vision in the red

  • Paper
  • Published:
Photochemical & Photobiological Sciences Aims and scope Submit manuscript

Abstract

The primary event in vision is light-initiated activation of visual pigments. All visual pigments consist of the protein opsin bound to 11-cis-retinal and are responsible for initiating the transformation of light into an electrical signal. In a mouse model, we show that derivatives of chlorophyll can act as visual pigments initiating the transformation of light into an electrical signal and thus change the primary event in vision to initial activation of a chlorophyll derivative. Electroretinographic b-wave amplitudes recorded in response to red and blue light were two-fold greater in mice administered chlorin e6, which accumulated in photoreceptor outer segments.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. For a recent review on rhodopsin see: N. Fishkin, K. Nakanishi and N. Berova, Primary events in dim light vision: a chemical and spectroscopic approach toward understanding protein/chromophore interactions in rhodopsin, Chem. Rec., 2004, 4, 120.

    Article  CAS  Google Scholar 

  2. S. Johnsen, The red and the black: Bioluminescence and the color of animals in the deep sea, Integr. Comp. Biol., 2005, 45, 234–246.

    Article  Google Scholar 

  3. W. S. Stiles, The scattering theory of the effect of glare on the brightness difference threshold, Proc. R. Soc. London, Ser. B, 1929, 105, 131–141.

    Article  Google Scholar 

  4. V. Kefalov, Y. Fu, N. Marsh-Armstrong and K. W. Yau, Role of visual pigment properties in rod and cone phototransduction, Nature, 2003, 425, 526–31.

    Article  CAS  Google Scholar 

  5. V. J. Kefalov, M. E. Estevez, M. Kono, P. W. Goletz, R. K. Crouch, M. C. Cornwall, K.-W. Yau, Breaking the covalent bond: A pigment property that contributes to desensitization in cones, Neuron, 2005, 46, 879–890.

    Article  CAS  Google Scholar 

  6. K. Kirschfeld, N. Franceschini and B. Minke, Evidence for a sensitizing pigment in fly photoreceptors, Nature, 1977, 269, 386–390.

    Article  CAS  Google Scholar 

  7. K. Kirschfeld and K. Vogt, Does retinol serve a sensitizing function in insect photoreceptors?, Vision Res., 1986, 26, 1771–1777.

    Article  CAS  Google Scholar 

  8. S. P. Balashov, E. S. Imasheva, V. A. Boichenko, J. Antón, J. M. Wang and J. K. Lanyi, Xanthorhodopsin: A proton pump with a light-harvesting carotenoid antenna, Science, 2005, 309, 2061–2064.

    Article  CAS  Google Scholar 

  9. J. K. Bowmaker, H. J. A. Dartnall and P. J. Herring, Longwave-sensitive visual pigments in some deep-sea fishes: segregation of ‘paired’ rhodopsins and porphyropsins, J. Comp. Physiol. A, 1988, 163, 685–698.

    Article  Google Scholar 

  10. R. H. Douglas, J. C. Partridge, J. C. K. Dulai, D. Hunt, C. W. Mullineaux, A. Y. Tauber and P. H. Hynninen, Dragon fish see using chlorophyll, Nature, 1998, 393, 423.

    Article  CAS  Google Scholar 

  11. I. Washington, C. Brooks, N. J. Turro and K. Nakanishi, Porphyrins as photosensitizers to enhance night vision, J. Am. Chem. Soc., 2004, 126, 9892–9893.

    Article  CAS  Google Scholar 

  12. T. Isayama, D. Alexeev, C. L. Makino, I. Washington, K. Nakanishi and N. J. Turro, An accessory chromophore in red vision, Nature, 2006, 443, 649.

    Article  CAS  Google Scholar 

  13. S. H. D. Haddock, C. W. Dunn, P. R. Pugh and C. E. Schnitzler, Bioluminescent and red-fluorescent lures in a deep-sea siphonophore, Science, 2005, 309, 263.

    Article  CAS  Google Scholar 

  14. J. S. Levine, E. F. MacNichol, Color vision in fishes, Scient. Am., 1982, 246, 140–149.

    Article  Google Scholar 

  15. R. H. Douglas, J. C. Partridge and N. J. Marshall, The eyes of deep sea fish I. Lens pigmentation, tapeta and visual pigments, Prog. Retin Eye Res., 1998, 17, 597–636.

    Article  CAS  Google Scholar 

  16. E. J. Warrant and N. A. Locket, Vision in the deep sea, Biol. Rev., 2004, 79, 671–712.

    Article  Google Scholar 

  17. R. W. Robey, K. Steadman, O. Polgar and S. E. Bates, ABCG2-meadiated transport of photosensitizers-potential on photodynamic therapy, Cancer Biol. Therapy, 2005, 4, 187–194.

    Article  CAS  Google Scholar 

  18. I. Izumi, S. B. Hammerman, A. N. Benz, J. Labruyere, C. F. Zorumski and J. W. Olney, Comparison of rat retinal fixation techniques: Chemical fixation and microwave irradiation, Exp. Eye Res., 2000, 70, 191–198.

    Article  CAS  Google Scholar 

  19. S. M. Saszik, J. G. Robson and L. T. Frishman, The scotopic threshold response of the dark-adapted electroretinogram of the mouse, J. Physiol., 2002, 543, 899–916.

    Article  CAS  Google Scholar 

  20. N. S. Peachey and S. L. Ball, Electrophysiological analysis of visual function in mutant mice, Doc. Ophthalmol., 2003, 107, 13–36.

    Article  Google Scholar 

  21. L. H. Pinto, M. H. Vitaterna, S. M. Siepka, K. Shimomura, S. Lumayag, M. Baker, D. Fenner, R. F. Mullins, V. C. Sheffield, E. M. Stone, E. Heffron and J. S. Takahashi, Initial results from screening over 9000 chemically-mutagenized mice for defects in the electroretinogram and appearance of the fundus, Vision Res., 2004, 44, 3335–3345.

    Article  CAS  Google Scholar 

  22. PDR for Nutritional Supplements, in Chlorophyll/Chlorophyllin, ed. S. S. Hendler and D. Rorvick, Medical Economics Company, Montvale, NJ, 2001, pp. 88–90.

    Google Scholar 

  23. N. Lane, New light on medicine, Scient. Am., 2003, 288, 38–45.

    Article  CAS  Google Scholar 

  24. J. C. Kephart, Chlorophyll derivatives—their chemistry, commercial preparation and uses, Econ. Bot., 1955, 9, 3–38.

    Article  CAS  Google Scholar 

  25. M. Sato, I. Fujimoto, S. Toshimori, A. Tachio, K. Ryohei and T. Murata, Effect of sodium copper chlorophyllin on lipid peroxidation IX. On the antioxidant components in commercial preparations of sodium copper chlorophyllin, Chem. Pharm. Bull., 1986, 34, 2428–2434.

    Article  CAS  Google Scholar 

  26. H. Inoue, H. Yamashita, K. Furuya, Y. Nonomura, N. Yashioka and S. Li, Chlorophyllin by reversed-phase high-performance liquid chromatography, J. Chromatogr., 1994, 679A, 99–104.

    Article  Google Scholar 

  27. N. E. Fishkin, J. R. Sparrow, R. Allikmets and K. Nakanishi, Isolation and characterization of a retinal pigment epithelial cell fluorophore: An all-trans-retinal dimer conjugate, Proc. Natl. Acad. Sci. USA, 2005, 102, 7091–796.

    Article  CAS  Google Scholar 

  28. R. Haimovici, T. A. Ciulla, J. W. Miller, T. Hasan, T. J. Flotte, A. G. Kenney, K. T. Schomacker and E. S. Gragoudas, Localization of rose bengal, aluminum phthalocyanine tetrasulfonate, and chlorin e6 in the rabbit eye, Retina-J. Ret. Vit. Dis., 2002, 22, 65–74.

    Google Scholar 

  29. P. A. Egner, K. H. Stansbury, E. P. Snyder, M. E. Rogers, P. A. Hintz and T. W. Kensler, Identification and characterization of chlorin e(4) ethyl ester in sera of individuals participating in the chlorophyllin chemoprevention trial, Chem. Rev. Toxicol., 2000, 13, 900–906.

    Article  CAS  Google Scholar 

  30. D. D. Perrin, The determination of phylloerythrin in blood, Biochem. J., 1958, 2, 314–318.

    Article  Google Scholar 

  31. D. Kemeri, A new porphorin component in normal human faeces, Biochem. Z., 1924, 151, 446.

    Google Scholar 

  32. H. Fischer and H. Hilmer, Information on phylloerythrin. II. Remarks on the treatise of Mr. Dr Kemeris “A new porphyrin like constituent of normal human skin”, Z. Physiol. Chem., 1925, 143, 1–8.

    Article  CAS  Google Scholar 

  33. L. D. Carter-Dawson, M. M. La Vail, Rods and cones in the mouse retina. II. Autoradiographic analysis of cell generation using tritiated thymidine, J. Comp. Neur., 1979, 188, 263–272.

    Article  CAS  Google Scholar 

  34. G. H. Jocobs, G. A. Williams and J. A. Fenwick, Influence of cone pigment coexpression on spectral sensitivity and color vision in the mouse, Vision Res., 2004, 44, 1615–162.

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Ilyas Washington.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Washington, I., Zhou, J., Jockusch, S. et al. Chlorophyll derivatives as visual pigments for super vision in the red. Photochem Photobiol Sci 6, 775–779 (2007). https://doi.org/10.1039/b618104j

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1039/b618104j

Navigation