Synthesis of amphiphilic and non-agreggating chlorins from hematoporphyrin using the Diels-Alder reaction

Synthesis of amphiphilic and non-agreggating chlorins from hematoporphyrin using the Diels-Alder reaction

Santos, Fabiane A. B. dos; Pizzol, Ana F.; Brocksom, Timothy J.; Oliveira, Kleber T. de

Abstract:

Hematoporphyrin (5) (Scheme1) and its derivatives have been extensively studied since the discovery of their potential application as photosensitizers in Photodynamic Therapy (PDT). This technique is nowadays very promising for treating several diseases such as skin cancer, internal malignant tumors, viral, bacterial and dermatological diseases. Essentially, PDT treatments employ the combined action of a photosensitizer, light, and molecular oxygen to cause selective cellular damage, in which singlet oxygen, generated through a series of photoinduced processes, is believed to be the major cytotoxic agent. We are exploring the synthesis of new photosensitizers using protoporphyrin IX dimethyl ester (6) obtained from natural hematoporphyrin (5) (Scheme 1). Porphyrin 6 has been used as diene in the Diels-Alder reaction with phenylmaleimides in order to obtain amphiphilic and non-aggregating compounds.

Hematoporphyrin (5) (Scheme1) and its derivatives have been extensively studied since the discovery of their potential application as photosensitizers in Photodynamic Therapy (PDT). This technique is nowadays very promising for treating several diseases such as skin cancer, internal malignant tumors, viral, bacterial and dermatological diseases. Essentially, PDT treatments employ the combined action of a photosensitizer, light, and molecular oxygen to cause selective cellular damage, in which singlet oxygen, generated through a series of photoinduced processes, is believed to be the major cytotoxic agent. We are exploring the synthesis of new photosensitizers using protoporphyrin IX dimethyl ester (6) obtained from natural hematoporphyrin (5) (Scheme 1). Porphyrin 6 has been used as diene in the Diels-Alder reaction with phenylmaleimides in order to obtain amphiphilic and non-aggregating compounds.

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DOI: 10.5151/chempro-14bmos-R0191-1

Referências bibliográficas

• [1] 1de Oliveira, K. T. ; Silva, A. M. S. ; Tome, A. C. ; Neves, M. G. P. M. S ; Tetrahedron 2008, 64 8709.
• [2] 2Uchoa, A. F.; Baptista, M. S.; de Oliveira, K. T.; Iamamoto, Y.; Serra, O. A.; 2011, requested patent , INPI no 018110004875.
• [3] 3Jackson, H.A.; Rao, K. R. N.; Wilkins M.; J. Chem. Soc. Perkin Trans., 1987,1, 307.

Como citar:

Santos, Fabiane A. B. dos; Pizzol, Ana F.; Brocksom, Timothy J.; Oliveira, Kleber T. de; "Synthesis of amphiphilic and non-agreggating chlorins from hematoporphyrin using the Diels-Alder reaction", p-191-191. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0191-1