JOINT PROJECT WITH RHODE ISLAND COLLEGEDEPARTMENT OF PHYSICAL SCIENCES

JULY 13- 17, 2009

Interaction of o-Xylylenebis(triphenylphosphonium bromide)

and DNA

Jennifer Andrade, Renae Miozzi, Ellen Rounds

Exeter-West Greenwich Exeter-West Greenwich Regional High SchoolRegional High School

Biotech IIIBiotech III

O-XYLYLENEBIS(TRIPHENYLPHOSPHONIUM BROMIDE)

“o-XYLY”

•Classification: Benzylic Phosphonium Salt•Molecular Weight: 788.53•Melting point: > 300 C �•Appearance

SolidOff-white or grey

•Not known to be cytotoxic in humans(Not a Hazard) •Hygroscopic

Formula: Formula: C6H4[CH2P(C6H5)3Br]2

Benzylic Phosphonium Salts

Anti-trypanonosomal effects (Trypanicide)• used to control Trypanosoma gambiense and T rhodesiense – insect vectors• work as an acetylcholinesterase inhibitor•Toxic to parasite only

Latent Thermal Indicator• used in epoxy and paint by NASA

Anti-fungal effects (Fungicide)• used to control plant fungi in agriculture

Genomic (Salmon) DNA Melting Using CARY-Bio-100 Spectrophotometer

Electrophoresis ResultsLane 5 Control (X)

BP Measurement for X

Distance (mm) BP28 5,00036 2,000

E (DNA with Hind III enzyme )Eb – with o-Xyly

X ( DNA without Hind III enzyme )Xb – with o-Xyly

Eb

10µl

Eb

15 µl

X 0µ

l

Xb

5µl

Xb

10µl

Xb

15µl

Eb

5µl

E 0 µ

l

BP Measurement for E

Distance (mm) BP31 4,000

Lane 1 Control (E)

Plasmid DNA with Hind III enzyme, with and without o-Xyly

Uncut plasmid with and without o-Xyly

Mas

s of

DN

A fr

agm

ents

(ng)

Base Pairs from Hind III Ladder (BP)

HyperChem Location Before

This is an illustration of our compound before optimization and it shows the location in the Major Groove.

The Distance between 27 C to atom 1H5M = 4.6743 ÅFrom 26 C to atom 90 C = 15 Å

From 26 C to atom 239 C = 4.6 Å

Energy Level-6675.93671Kcal/molGradient Value-285.526871

HyperChem Interactions:

• The phosphate bonds repositioned themselves to accommodate a lower energy, but the DNA molecule does not appear to be altered.

• The DNA and O-XYLY did not bond in a visible manner, but our data did prove a bond.

HyperChem(Steepest Descent) Locations After

The compound and DNA did not show any signs of physically bonding although the energy levels were decreased

The Distance between 27 C and 1H5M = 5.01036Å (increase)

Energy Level=264.62Gradient Value-0.099511

HyperChem Results:

Before Optimization After Optimization

Energy=1791.844854 Kcal/molGradient Value= 260.335489

Energy= -300.682007 Kcal/molGradient Value= 0.09384

Distance Between 28 Carbon and 57 Carbon = 20.6344Å

Distance Between 28 Carbon and 57 Carbon= 20.4114Å

Discussion

• Our Experimental results did not compare with our predictions because we went into this project hoping to see a significant reaction between the compound and Native DNA.

• Experimental changes with electrophoresis• Further Research- electrophoresis with higher

concentration and running Smart Spec™ in reverse temperatures.