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• W2793065588 abstract "The self-aggregation process and its overcoming remain a barrier for the employment of many molecules as photosensitizers (PS) in photodynamic therapy (PDT). The B-ring isomer co-produced during the synthesis of the Verteporfin[Formula: see text] (A-ring) is an example. Although both isomers possess similar in vitro/in vivo efficiency, the strong and not well-understood self-aggregation process of the B-ring derivative impairs its clinical use. This paper reports the use of theoretical calculus and its correlation with experimental analysis to find the main differences between the A and B-ring isomers. For that purpose, micelles of Pluronic[Formula: see text] P-123 and Sodium Dodecyl Sulfate were chosen as simple membrane models and possible drug delivery system, as in the case of P-123. At physiological pH, the main reason for the high self-aggregation tendency is associated with the higher (22%) molecular volume of the B ring, which increases the van der Waals interactions. However, at mildly acidic conditions, the B ring possesses a shallow dihedral angle between the methyl ester group and the tetrapyrrolic macrocycle that favors the approach of units in the aggregate. These discrepancies directly affect the binding and stability of the isomers in the micelles. However, P-123 micelles were able to readily incorporate and monomerize/stabilize both PS over long periods. NOESY experiments confirmed a deep location of both PS inside P-123 micelles, which justifies their efficiency in preventing the self-aggregation process. These findings may substantiate new studies involving the marginalized B-ring isomers and encourage new development in formulations for their use in PDT." @default.
• W2793065588 created "2018-03-29" @default.
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• W2793065588 date "2018-04-01" @default.
• W2793065588 modified "2023-10-01" @default.
• W2793065588 title "New insights about the self-aggregation of benzoporphyrin derivatives: A theoretical and experimental investigation" @default.
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• W2793065588 doi "https://doi.org/10.1142/s1088424618500311" @default.
• W2793065588 hasPublicationYear "2018" @default.
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