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. Author manuscript; available in PMC: 2008 Nov 25.
Published in final edited form as: J Med Chem. 2007 Dec 19;51(2):187–195. doi: 10.1021/jm070461w

Table 1.

Sequences and the Physicochemical Properties of the Cyclic α-MSH Analogues

m/z (M + 1)
TLC Rfb
No. Sequence calcd obsd (ESI) HPLC retention time, mina 1 2 3
4 c[CO-o-C6H4-CO-Pro-D-Phe-Arg-Trp-Lys]-NH2 862.4364 862.4345 17.27 0.68 0.45 0.75
5 c[CO-o-C6H4-CO-Pro-D-Nal(2′)-Arg-Trp-Lys]-NH2 912.4521 912.4536 19.64 0.69 0.46 0.78
6 c[CO-(CH2)3-CO-Pro-D-Phe-Arg-Trp-Lys]-NH2 828.4521 828.4544 16.97 0.61 0.35 0.72
7 c[CO-(CH2)3-CO-Pro-D-Nal(2′)-Arg-Trp-Lys]-NH2 878.4677 878.464 19.41 0.64 0.38 0.74
8 c[CO-cis-CH=CH-CO-Pro-D-Phe-Arg-Trp-Lys]-NH2 812.4208 812.4179 17.05 0.64 0.38 0.74
9 c[CO-cis-CH=CH-CO-Pro-D-Nal(2′)-Arg-Trp-Lys]-NH2 862.4364 862.4397 18.43 0.66 0.41 0.76
10 c[CO-2,6-pyridine-CO-D-Phe-Arg-Trp-Lys]-NH2 766.3789 766.3821 16.45 0.65 0.52 0.77
11 c[CO-2,6-pyridine-CO-D-Nal(2′)-Arg-Trp-Lys]-NH2 816.3946 816.393 19.10 0.67 0.49 0.78
12 c[CO-2,3-pyrazine-CO-D-Phe-Arg-Trp-Lys]-NH2 767.3742 767.3763 16.24 0.62 0.4 0.73
13 c[CO-2,3-pyrazine-CO-D-Nal(2′)-Arg-Trp-Lys]-NH2 817.3898 817.3906 19.02 0.65 0.42 0.76
14 c[CO-(CH2)2-CO-Nle-D-Phe-Arg-Trp-Lys]-NH2 830.4677 830.4704 18.80 0.68 0.45 0.78
15 c[CO-(CH2)2-CO-Nle-D-Nal(2′)-Arg-Trp-Lys]-NH2 880.4834 880.4806 21.35 0.69 0.47 0.78
a

HPLC column: Vydac 218TP104, 250 × 4.6 mm, 10 μm, 300 Å; HPLC solvent A, 0.1% TFA in water; solvent B, acetonitrile; gradient: 10–90% B in A over 40 min, flow rate 1.0 mL/min.

b

TLC system 1: n-butanol/acetic acid/water/pyridine (4:1:2:1); TLC system 2: n-butanol/acetic acid/water (4:1:1); TLC system 3: ethyl acetate/acetic acid/water/pyridine (5:1:3:5).