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Novel asymmetric 5-(4-bromo)-10-15-20-tris-(4-morpholine)porphyrin (complex  1 ) and its Zn derivative ( 2 ) were synthesized, and the latter was quaternized to give  2Q , and their photodynamic therapy (PDT) activities were compared to those of the symmetric tetra-morpholine porphyrin ( 3 ) and its respective quaternized analogue ( 3Q ). Respective porphyrins were further conjugated to biotin-nitrogen doped graphene quantum dots (B-NGQDs) through π-π stacking. It was observed that the asymmetric complexes and their conjugates had high singlet oxygen quantum yields when compared to the symmetrical porphyrin and their conjugates. PDT studies were performed using MCF-7 breast cancer line. It was observed that all the complexes/conjugates have negligible dark toxicity, and  2Q -B-NGQDs had a highest PDT efficiency with cell viability of 14.4% and IC 50  of 1.41 µg/mL.

The effect of asymmetry and conjugation of biotin decorated nitrogen doped graphene quantum dots on morpholine porphyrin for photodynamic therapy