Hydrolysis Studies of Chalcogenopyrylium Trimethine Dyes. 1. Product Studies in Alkaline Solution (pH ≥ 8) under Anaerobic and Aerobic Conditions

Journal of Organic Chemistry

Volumn 62, Issue 14, 1997, Pages 4692-4700

  Young, David N ^a   Detty, Michael R ^a  

^a UNIVERSITY AT BUFFALO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001064152     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970115u     Document Type: Article

References (19)

1. Balaban, A. T.; Dinculescu, A.; Dorofeenko, G. N.; Fischer, G. W.; Koblik, A. V.; Mezheritskii, V. V.; Schroth, W. Pyrylium Salts: Syntheses, Reactions, and Physical Properties; Advances in Heterocyclic Chemistry, Supplement 2, Katritzky, A. R., Ed.; Academic Press: New York, 1982; pp 66-73.
2. Williams, A. J. Am. Chem. Soc. 1971, 93, 2733-2737.
3. Salvadori, G.; Williams, A. J. Am. Chem. Soc. 1971, 93, 2727-2733.
4. Photodynamic therapy (PDT) is a recent development in the treatment of cancer in which a photochemical sensitizer produces a cytotoxic reagent (singlet oxygen, Superoxide, radicals) or reaction in the tumor upon irradiation. Dyes 3-8 in the series contain at least one heavy atom (Se or Te), which promotes higher quantum yields for singlet oxygen generation, and have been found useful in animal studies [Detty, M. R.; Powers, S. K. Photodynamic Therapy Using Seleno- or Telluropyrylium Salts. US Patent 5,047,419 (Sep, 1991) and Powers, S. K.; Detty, M. R. Photodynamic Therapy with Chalcogenapyrylium Dyes. In Photodynamic Therapy of Neoplastic Disease; Kessel, D., Ed.; CRC Press, Boca Raton, FL, 1990, pp 308-328]. The challenge to chemists in the design of sensitizers for PDT is to produce materials that (1) absorb light of ≤650 run where tissue is most transparent, (2) are photochemically efficient at producing the cytotoxic event, (3) are nontoxic in the absence of light, and (4) differentiate normal and transformed tissue, Clinical protocols using porphyrin-derived sensitizers have received FDA approval recently for the treatment of various lesions of the neck, lung, bladder, and skin.
5. Photodynamic therapy (PDT) is a recent development in the treatment of cancer in which a photochemical sensitizer produces a cytotoxic reagent (singlet oxygen, Superoxide, radicals) or reaction in the tumor upon irradiation. Dyes 3-8 in the series contain at least one heavy atom (Se or Te), which promotes higher quantum yields for singlet oxygen generation, and have been found useful in animal studies [Detty, M. R.; Powers, S. K. Photodynamic Therapy Using Seleno- or Telluropyrylium Salts. US Patent 5,047,419 (Sep, 1991) and Powers, S. K.; Detty, M. R. Photodynamic Therapy with Chalcogenapyrylium Dyes. In Photodynamic Therapy of Neoplastic Disease; Kessel, D., Ed.; CRC Press, Boca Raton, FL, 1990, pp 308-328]. The challenge to chemists in the design of sensitizers for PDT is to produce materials that (1) absorb light of ≤650 run where tissue is most transparent, (2) are photochemically efficient at producing the cytotoxic event, (3) are nontoxic in the absence of light, and (4) differentiate normal and transformed tissue, Clinical protocols using porphyrin-derived sensitizers have received FDA approval recently for the treatment of various lesions of the neck, lung, bladder, and skin.
6. For recent reviews, see: (a) Rosenthal, D. I.; Glatstein, E. Ann. Med. 1994, 26, 405. (b) Henderson, B. W.; Dougherty, T. J., Eds. Photodynamic Therapy: Basic Principles and Clinical Aspects; Marcel Dekker: New York, 1992; pp 1-459. (c) Penning, L. C.; Dubbelman, T. M. Anti-Cancer Drugs 1994, 5, 139. (d) Cannon, J. B. J. Pharmaceut. Sci. 1993, 82, 435-446. (e) Pass, H. I. J. Nat. Cancer Inst. 1993, 85, 443.
7. For recent reviews, see: (a) Rosenthal, D. I.; Glatstein, E. Ann. Med. 1994, 26, 405. (b) Henderson, B. W.; Dougherty, T. J., Eds. Photodynamic Therapy: Basic Principles and Clinical Aspects; Marcel Dekker: New York, 1992; pp 1-459. (c) Penning, L. C.; Dubbelman, T. M. Anti-Cancer Drugs 1994, 5, 139. (d) Cannon, J. B. J. Pharmaceut. Sci. 1993, 82, 435-446. (e) Pass, H. I. J. Nat. Cancer Inst. 1993, 85, 443.
8. For recent reviews, see: (a) Rosenthal, D. I.; Glatstein, E. Ann. Med. 1994, 26, 405. (b) Henderson, B. W.; Dougherty, T. J., Eds. Photodynamic Therapy: Basic Principles and Clinical Aspects; Marcel Dekker: New York, 1992; pp 1-459. (c) Penning, L. C.; Dubbelman, T. M. Anti-Cancer Drugs 1994, 5, 139. (d) Cannon, J. B. J. Pharmaceut. Sci. 1993, 82, 435-446. (e) Pass, H. I. J. Nat. Cancer Inst. 1993, 85, 443.
9. For recent reviews, see: (a) Rosenthal, D. I.; Glatstein, E. Ann. Med. 1994, 26, 405. (b) Henderson, B. W.; Dougherty, T. J., Eds. Photodynamic Therapy: Basic Principles and Clinical Aspects; Marcel Dekker: New York, 1992; pp 1-459. (c) Penning, L. C.; Dubbelman, T. M. Anti-Cancer Drugs 1994, 5, 139. (d) Cannon, J. B. J. Pharmaceut. Sci. 1993, 82, 435-446. (e) Pass, H. I. J. Nat. Cancer Inst. 1993, 85, 443.
10. For recent reviews, see: (a) Rosenthal, D. I.; Glatstein, E. Ann. Med. 1994, 26, 405. (b) Henderson, B. W.; Dougherty, T. J., Eds. Photodynamic Therapy: Basic Principles and Clinical Aspects; Marcel Dekker: New York, 1992; pp 1-459. (c) Penning, L. C.; Dubbelman, T. M. Anti-Cancer Drugs 1994, 5, 139. (d) Cannon, J. B. J. Pharmaceut. Sci. 1993, 82, 435-446. (e) Pass, H. I. J. Nat. Cancer Inst. 1993, 85, 443.
11. Detty, M. R.; Merkel, P. B.; Hilf, R.; Gibson, S. L.; Powers, S. K. J. Med. Chem. 1990, 33, 1108-1116.
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