1 research outputs found
Solid-Supported Porphyrins Useful for the Synthesis of Conjugates with Oligomeric Biomolecules
<i>meso</i>-TrisÂ(pyridin-4-yl)Â(4-carboxyphenyl)Âporphyrin
and 2-(1-hexyloxyethyl)-2-devinyl pyropheophorbide-a (Photochlor,
HPPH) were amide-coupled to 1<i>R</i>,2<i>S</i>,3<i>R</i>,4<i>R</i>-2,3-dihydroxy-4-(hydromethyl)-1-aminocyclopentane
and immobilized via an ester linkage to long chain alkyl amine-derivatized
controlled pore glass (LCAA-CPG). The applicability of these supports
(<b>5</b> and <b>6</b>) for the synthesis of porphyrin
conjugates with oligomeric biomolecules was demonstrated using an
automated phosphoramidite coupling chemistry. Cleavage from the support
with concentrated ammonia gave the products, viz., porphyrin conjugates
of oligonucleotides (<b>7</b>–<b>9</b>) and dendritic
glycoclusters (<b>10</b>–<b>13</b>) and a cyclooctyne
derivative (<b>14</b>) in 23–58% yield. In addition,
the synthesized cyclooctyne derivative of <i>meso</i>-trisÂ(pyridin-4-yl)Â(4-carboxyphenyl)Âporphyrin
(<b>14</b>) was conjugated with an azidopropyl-modified hyaluronic
acid (<b>19</b>). The hyaluronic acid–porphyrin conjugate
(<b>15</b>) was radiolabeled with <sup>64</sup>Cu and its (<b>15</b>[<sup>64</sup>Cu]) receptor binding affinity to CD44-expressing
tumor cells was evaluated