Small molecules that bind selectively to guanine-rich telomeric DNA sequences (quadruplex interactive agents; QIAs) can promote folding to a four-stranded quadruplex conformation. Such quadruplexes have been shown to deactivate telomerase, a key activating enzyme in many cancers, making QIAs promising targets for development of potential cancer drugs. Porphyrin-based QIAs offer several desirable properties as they are non-toxic and found in many oxidation-reduction proteins of the cell. In this study we have examined the effects of a new fluorescent pyropheophorbide porphyrin derivative (PPP-D) on the folding of model human telomeric DNA sequences (HT4). PPP-D demonstrates enhanced lipid solubility (log P = 6.80 ± 1.62) over other quadruplexed-DNA binding porphyrins, including meso-tetrakis(4-(N-methylpyridiumyl))porphyrin (TMPyP4) and N-methyl mesoporphyrin IX (NMM), and can facilitate cellular delivery (log P = 6.80 ± 1.62) through the cell membrane. Unlike TMPyP4 and NMM, PPP-D is non fluorescent in buffer solutions and highly fluorescent in organic solvents and non-polar environments. CD studies suggest that PPP-D successfully aids in the folding of HT4 sequences in addition to stabilizing the quadruplexed DNA conformation. Furthermore, PPP-D demonstrates selectivity for the quadruplexed (q-DNA) over duplexed DNA (d-DNA) conformation. The significance of these results for anti-tumorigenesis will be discussed. Supported by NIH-SCORE grants ISCI-GM093830-01 (AG) and S06-GM076168-01 (LD).