1. “CTP” cinnamyltriphenylphosphonium chloride
Cytotoxin
Molecular Weight: g/mol
Structure: Three benzene rings and cinnamyl group attached to phosphorous central atom. Chloride anion.
Physical Properties:
Melting Point: 225 º – 227 º C
Appearance: White to Off-White Powder or
Crystalline Powder

2. IR Spectrum of CTP
If a  is being absorbed, it means that energy (E = h) is being absorbed by the cmpd.
Energies in the IR region correspond to the energies involved in bond vibrations (stretches/bends).
=C-H (aryl) stretch C-H (alkyl) stretch
weak overtones of aromatic C-H (alkyl) bend
, C=C stretch (in ring)
=C-H (alkene) bend

3. DNA Melting Curve dsDNA 2 ssDNA = Melting Point of DNA
Half of DNA has uncoiled and remains single-stranded when the melting temperature is reached Tm
A shift in Melting Temperature is a strong indicator of the presence of an interaction between the DNA and any small molecule, such as any arylphosphonium salt.
Sample
Native Salmon DNA
Salmon DNA + 3µL
(15.2µg/150µL DMSO) CTP
Salmon DNA + 5µL
Melting Temp. (ºC)
64.6
67.2
67.8

6. Gel Electrophoresis Lane 2: (Control) Digested DNA
Lane 3: (Experimental) Digested DNA w/ 1ml CTP

8. HyperChem Predictions
CTP would bind effectively with the DNA through intercalation. This was based upon the flat, characteristic structure of the cinnamyl group.
CTP might also bind with DNA in its major groove, based on the relative size of the benzene groups and the electrostatic attraction of the phosphorous backbone of DNA.

9. HyperChem Computations
Minor groove interactions were most favorable with cinnamyl group in closest proximity to DNA: Distance of two closest atoms = Å E = kcal Gd =

10. HyperChem Predictions

11. HyperChem Computations
Intercalation and Major Groove Interactions of CTP and DNA were of greater energy:
Major Groove -
Triphenyl group of closest proximity to DNA
E = kcal
Cinnamyl group
E = kcal
Intercalation – (Interaction optimized with CTP passing through nitrogen base of cytosine)
E = kcal
Cinnamyl group through base pairs in major groove
E = kcal

13. Further Research
Nature of DNA Cooling after denaturation and possible restructuring of DNA
DNA Structure effects on Movement through gel
Potential Applications of the CTP Molecule in DNA of organisms
Further HyperChem Computations
Ultimate objective: X-ray crystallography (orientation and type of interaction)