Synthesis of Chlorambucil-Tempol Adduct and its Delivery using Fluoroalkyl Double-Ended Poly (Ethylene Glycol) Micelles

Figures & data

FIG. 1 Route for the synthesis of chlorambucil-tempol.

FIG. 2 EPR spectra of tempol (a) and CT (b) in methylene chloride solvents and (c) 0.5% CT in 10% 10KC8 hydrogel at 293.2 K.

FIG. 3 ¹H NMR spectrum of the nitroxyl-reduced CT in CDCl₃ solvent referenced with TMS to 0 ppm at 299.3 K.

TABLE 1 Chemical shifts in ppm of the nitroxyl-reduced CT with multiplicities in parenthesis

Chemical shift-δ ppm	Assignment of attached protons
1.3 (s)	Dimethyl groups on C3 and C7
1.75–1.93 (m)	C10
1.95–2.07 and 1.75–1.93 (m)	C4, and C6
2.2–2.3 (t)	C11
2.4–2.5 (t)	C9
3.5–3.7 (m)	C19, C20, C21, and C22
5.0–5.1 (m)	C5
6.5–6.6 (d)	C14, and C16
6.95–7.03 (d)	C13, and C17
8.0-10.0 (s)	O1

*(s) singlet, (d) doublet, (t) triplet and (m) multiplet

FIG. 4 Maldi-TOF of the CT in 2,5-dihydroxybenzoic acid matrix.

FIG. 5 ¹H NMR spectrum (a) and ¹⁹F NMR spectrum (b) of the 10KC8 hydrogel loaded with CT at 299.3 K.

TABLE 2 Comparison of T₁ relaxation times for 10KC8 hydrogel, tempol loaded 10KC8 hydrogel and CT loaded 10KC8 hydrogel

	^1H T1 times (s)	^19F T1 times (s)
10KC8	0.68 ± 0.02	0.58 ± 0.02
Tempol loaded hydrogel	0.23 ± 0.02	0.23 ± 0.02
CT adduct loaded hydrogel	0.62 ± 0.02	0.36 ± 0.02