A synthetic approach to bacteriochlorin derivatives using natural chlorophyll a pigment

A synthetic approach to bacteriochlorin derivatives using natural chlorophyll a pigment

Santos, Luna S. dos; Santos, Thais C. dos; Brocksom, Timothy J.; Oliveira, Kleber T. de

Abstract:

Bacteriochlorin derivatives are tetrapyrrolic macrocycles that differ from porphyrins and chlorins only in the reduced state of the b-pyrrolic positions. These differences are sufficient to modify the electronic spectra of the bacteriochlorins, obtaining an adequate Q-band 730 nm compared to porphyrins (last Q-band around 630 nm) and chlorins (last Q-band around 650 nm). Compounds with absorption bands greater than 700 nm have been suggested as better photosensitizers to be applied in photodynamic therapy (PDT) treatments, since they have strong absorption of penetrating light (700 nm). PDT is a very innovative technique for the treatment of skin cancer, several malignant tumors, viral, bacterial and dermatological diseases. In this work, we present studies on the extraction and synthesis of new photosensitizers based on natural models such as chlorophyll a (1) (Scheme 1).

Bacteriochlorin derivatives are tetrapyrrolic macrocycles that differ from porphyrins and chlorins only in the reduced state of the b-pyrrolic positions. These differences are sufficient to modify the electronic spectra of the bacteriochlorins, obtaining an adequate Q-band 730 nm compared to porphyrins (last Q-band around 630 nm) and chlorins (last Q-band around 650 nm). Compounds with absorption bands greater than 700 nm have been suggested as better photosensitizers to be applied in photodynamic therapy (PDT) treatments, since they have strong absorption of penetrating light (700 nm). PDT is a very innovative technique for the treatment of skin cancer, several malignant tumors, viral, bacterial and dermatological diseases. In this work, we present studies on the extraction and synthesis of new photosensitizers based on natural models such as chlorophyll a (1) (Scheme 1).

Palavras-chave:

DOI: 10.5151/chempro-14bmos-R0193-1

Referências bibliográficas

• [1] 1 Ruzié, C.; Krayer, M.; Balasubramanian, T.; Lindsey, J. S. J. Org. Chem. 2008, 73, 5806.
• [2] 2 Hargus, J. A.; Fronczek, F. R.; Vicente, M. G. H.; Smith, K. M. Photochem. Photobiol. 2007, 83, 1006.
• [3] 3 Maestrin, A. P. J.; Neri, C. R.; de Oliveira, K. T.; Serra, O. A.; Iamamoto, Y. Quim. Nova 2009, 32, 1670.
• [4] 4 Gerlach, B.; Brantley, S. E.; Smith, K. M. J. Org. Chem. 1998, 63, 2314.

Como citar:

Santos, Luna S. dos; Santos, Thais C. dos; Brocksom, Timothy J.; Oliveira, Kleber T. de; "A synthetic approach to bacteriochlorin derivatives using natural chlorophyll a pigment", p-193-193. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0193-1