Synthesis, Crystal Structure and Spectral Properties of Six Indole Dimethine Cyanines as Well as Their Biological Application†

doi:10.7503/cjcu20150128

Abstract

Abstract:

Six novel bis(N-alkyl) indole dimethine cyanine dyes(C1—C6) were synthesized using heterocyclic quaternary ammonium salts with active methyl and N-methyl-3-indole formaldehyde as starting materials and piperidine as catalyst. The dyes were identified by UV-Vis, ¹H NMR, IR and HRMS and the crystal structures of dyes C1 and C5 were determined by X-ray single crystal diffraction analyzer. The investigation of the spectral properties of dyes C1—C6 in different solvents showed that the maximum absorption wavelength of the dyes was in the range of 370.0—521.0 nm, the emission wavelength was located in 466.4—600.8 nm and the molar extinction coefficients was in the range of 0.80×10⁴—3.92×10⁴ L·mol^-1·cm^-1 in different solvents. The interactions of dyes C1—C6 with DNA, bovine serum albumin(BSA), muramidase, amylase, bovine hemoglobin and chymotrypsin were investigated, respectively. The results showed that the spectral properties of dyes C3, C4 and C5 were significantly changed with the addition of DNA and the quantum yields of the dyes were increased with the increase of DNA concentration. The investigation of the cytotoxicity and cell staining of the selected dyes C5 and C6 showed that the two dyes had virtually no toxicity at applications dose and time and could stain cell nucleus, suggesting that the dyes C5 and C6 could be used as potential fluorescent reagents to observe living cells.

Key words: Indole dimethine cyanine, Crystal structure, Spectral property, Biomolcule, Cytotoxicity and cell staining

CLC Number:

O626

TrendMD:

ZHANG Jianghua, LÜ Ying, JIA Hongliang, SONG Yinyin, SUN Xiaoxia, CHAI Dunxiao, WANG Lanying. Synthesis, Crystal Structure and Spectral Properties of Six Indole Dimethine Cyanines as Well as Their Biological Application^†[J]. Chem. J. Chinese Universities, 2015, 36(10): 1924.

Figures/Tables 10

Synthesis route of dyes C1—C6

Table 1 Appearance, yields, melting points, HRMS, UV-Vis and IR data for dyes C1—C6

Dye	Appearance	Yield(%)	m. p./℃	HRMS ESI(calcd.), m/z	UV-Vis (MeOH), λ_max/nm	IR(KBr), $ν ˙$ /cm^-1
C1	Orange red acicular crystal	56	236—237	305.1097 (305.1107)	472.0	3067, 2926, 2854, 1599, 1571, 1499, 1445, 1304, 1217, 1162, 1127, 1071, 973, 833, 810, 749
C2	Yellow solid	65	>300	302.1636 (302.1652)	378.0	3019, 2987, 1616, 1506, 1452, 1371, 1251, 1182, 989, 813, 736
C3	Red solid	81	275—276	299.1532 (299.1543)	506.0	3050, 2973, 1585, 1519, 1457, 1396, 1346, 1295, 1247, 1193, 1118, 993, 833, 744
C4	Dark red powder	52	246—247	333.1139 (333.1153)	493.0	3097, 3035, 1589, 1509, 1457, 1305, 1220, 1182, 1114, 964, 846, 740
C5	Red acicular crystal	77	256—257	299.1540 (299.1543)	481.0	3033, 3000, 1594, 1513, 1459, 1342, 1303, 1164, 1114, 966, 842, 744
C6	Red solid	82	245—246	365.2002 (365.2012)	490.0	3025, 2971, 1567, 1502, 1452, 1394, 1338, 1292, 1227, 1174, 1122, 971, 794, 742

Table 1 Appearance, yields, melting points, HRMS, UV-Vis and IR data for dyes C1—C6

Dye	Appearance	Yield(%)	m. p./℃	HRMS ESI(calcd.), m/z	UV-Vis (MeOH), λ_max/nm	IR(KBr), $ν ˙$ /cm^-1
C1	Orange red acicular crystal	56	236—237	305.1097 (305.1107)	472.0	3067, 2926, 2854, 1599, 1571, 1499, 1445, 1304, 1217, 1162, 1127, 1071, 973, 833, 810, 749
C2	Yellow solid	65	>300	302.1636 (302.1652)	378.0	3019, 2987, 1616, 1506, 1452, 1371, 1251, 1182, 989, 813, 736
C3	Red solid	81	275—276	299.1532 (299.1543)	506.0	3050, 2973, 1585, 1519, 1457, 1396, 1346, 1295, 1247, 1193, 1118, 993, 833, 744
C4	Dark red powder	52	246—247	333.1139 (333.1153)	493.0	3097, 3035, 1589, 1509, 1457, 1305, 1220, 1182, 1114, 964, 846, 740
C5	Red acicular crystal	77	256—257	299.1540 (299.1543)	481.0	3033, 3000, 1594, 1513, 1459, 1342, 1303, 1164, 1114, 966, 842, 744
C6	Red solid	82	245—246	365.2002 (365.2012)	490.0	3025, 2971, 1567, 1502, 1452, 1394, 1338, 1292, 1227, 1174, 1122, 971, 794, 742

Table 2 1H NMR data for dyes C1—C6

Dye	¹H NMR(400 MHz, DMSO-d₆), δ
C1	3.94(s, 3H, NCH₃), 4.25(s, 3H, N⁺CH₃), 7.37—7.44(m, 2H, ArH), 7.46(d, 1H, J=16.0 Hz, CH=CH), 7.65—7.70(m, 2H, ArH), 7.76(t, 1H, J=8.0 Hz, ArH), 8.11(d, 1H, J=8.0 Hz, ArH), 8.30(t, 2H, J=8.0 Hz, ArH), 8.37(d, 1H, J=16.0 Hz, CH=CH), 8.42(s, 1H, pyrrole—H)
C2	3.92(s, 3H, NCH₃), 4.14(s, 6H, NCH₃, N⁺CH₃), 7.15(d, 1H, J=16.4 Hz, CH=CH), 7.32—7.37(m, 2H, ArH), 7.63—7.66(m, 3H, ArH), 7.99—8.04(m, 3H, ArH), 8.17—8.22(m, 2H, pyrrole—H, CH=CH)
C3	3.93(s, 3H, NCH₃), 4.44(s, 3H, N⁺CH₃), 7.33—7.37(m, 2H, ArH, CH=CH), 7.62(d, 1H, J=7.6 Hz, ArH), 7.97—8.01(m, 2H, ArH), 8.19—8.23(m, 1H, ArH), 8.27(d, 1H, J=8.0 Hz, ArH), 8.30—8.37(m, 2H, ArH, pyrrole—H), 8.42(d, 1H, J=8.0 Hz, ArH), 8.52(d, 1H, J=16.0 Hz, CH=CH), 8.94(d, 1H, J=8.0 Hz, ArH), 9.09—9.10(m, 1H, ArH)
C4	3.96(s, 3H, NCH₃), 4.42(s, 3H, N⁺CH₃), 7.36—7.38(m, 2H, ArH), 7.50(d, 1H, J=16.0 Hz, CH=CH), 7.64—7.65(m, 1H, ArH), 7.88(d, 1H, J=8.0 Hz, ArH), 8.24—8.25(m, 2H, ArH), 8.42(s, 1H, pyrrole—H), 8.57—8.69(m, 3H, ArH, CH=CH), 8.77(d, 1H, J=8.0 Hz, ArH)
C5	3.94(s, 3H, NCH₃), 4.45(s, 3H, N⁺CH₃), 7.34—7.38(m, 2H, ArH), 7.52(d, 1H, J=16.0 Hz, CH=CH), 7.62—7.63(m, 1H, ArH), 7.83—7.86(m, 1H, ArH), 8.08—8.10(m, 1H, ArH), 8.23—8.24(m, 2H, ArH), 8.38(s, 1H, pyrrole—H), 8.42(d, 1H, J=16.0 Hz, CH=CH), 8.60—8.65(m, 2H, ArH), 8.79—8.83(m, 1H, ArH)
C6	2.05[s, 6H, C(CH₃)₂], 4.00(s, 3H, NCH₃), 4.14(s, 3H, N⁺CH₃), 7.21(d, 1H, J=15.6 Hz, CH=CH), 7.46—7.48(m, 2H, ArH), 7.64—7.68(m, 1H, ArH), 7.72(d, 1H, J=8.0 Hz, ArH), 7.76—7.79(m, 1H, ArH), 8.03(d, 1H, J=8.0 Hz, ArH), 8.17(d, 1H, J=8.0 Hz, ArH), 8.23(d, 1H, J=8.0 Hz, ArH), 8.32(d, 1H, J=8.0 Hz, ArH), 8.39(d, 1H, J=8.0 Hz, ArH), 8.70(s, 1H, pyrrole—H), 8.74(d, 1H, J=15.6 Hz, CH=CH)

Fig.1 Molecular structures of dyes C1(A) and C5(B)

Table 3 Absorption and fluorescence spectra data of dyes C1—C6 in different solvents

Solvent	Dye	λ_max/nm	λ_ex/nm	λ_em/nm	Stokes shift/nm	10⁴ε/(L·mol^-1·cm^-1)	Ф
H₂O	C1	461.0	461.0	522.0	61.0	2.40	0.0666
	C2	370.0	370.0	475.4	105.4	0.94	0.0037
	C3	475.0	475.0	576.6	101.6	2.14	0.0175
	C4	468.0	468.0	561.6	93.6	3.04	0.0089
	C5	461.0	461.0	555.8	94.8	2.85	0.0117
	C6	484.0	484.0	557.6	73.6	3.64	0.0958
DMSO	C1	474.0	474.0	528.8	54.8	2.40	0.3838
	C2	381.0	381.0	469.8	88.8	0.93	0.0105
	C3	507.0	507.0	600.8	93.8	2.45	0.3267
	C4	497.0	497.0	570.8	73.8	3.11	0.0768
	C5	484.0	484.0	565.8	81.8	3.36	0.1136
	C6	492.0	492.0	560.0	68.0	3.49	0.2939
MeOH	C1	472.0	472.0	529.4	57.4	2.58	0.1037
	C2	378.0	378.0	467.4	89.4	0.99	0.0030
	C3	506.0	506.0	580.2	74.2	2.79	0.1018
	C4	493.0	493.0	563.2	70.2	3.76	0.0311
	C5	481.0	481.0	559.2	78.2	3.13	0.0453
	C6	490.0	490.0	561.6	91.6	3.70	0.0756
EtOH	C1	476.0	476.0	526.0	50.0	3.15	0.2037
	C2	380.0	380.0	466.4	86.4	1.01	0.0036
	C3	513.0	513.0	582.4	69.4	2.88	0.2464
	C4	497.0	497.0	565.8	68.8	3.92	0.0925
	C5	485.0	485.0	558.4	73.4	3.68	0.1542
	C6	492.0	492.0	562.4	70.4	3.66	0.1043
CHCl₃	C1	496.0	496.0	552.6	56.6	2.11	0.1407
	C2	387.0	387.0	496.8	109.8	0.80	0.0024
	C3	515.0	515.0	573.2	58.2	2.87	0.2037
	C4	517.0	517.0	577.2	60.2	3.03	0.1173
	C5	505.0	505.0	568.0	63.0	3.56	0.1659
	C6	521.0	521.0	574.2	53.2	3.28	0.0667

Fig.2 λmax of dyes C1—C6(a—f) in different solvents

Table 4 Fluorescence quantum yield of dyes C1—C6 with different biomolecules*

Dye	c(Dye)/ (mol·L^-1)	c(Biomolecules)/ (μg·mL^-1)	Φ_DNA/ Φ_Free	Φ_BSA/ Φ_Free	Φ_Murmidase/ Φ_Free	Φ_Amylase/ Φ_Free	Φ_Chmotrypsin/ Φ_Free	Φ_{Bovine hemoglobin}/ Φ_Free
C1	1×10^-5	0	1.00	1.00	1.00	1.00	1.00	1.00
		4	2.23	1.10	1.26	1.16	1.10	1.24
		10	4.23	1.21	1.13	1.07	1.32	1.20
	5×10^-5	0	1.00	1.00	1.00	1.00	1.00	1.00
		4	1.26	0.91	0.86	0.87	0.92	0.68
		10	1.77	1.01	1.00	1.10	1.00	0.74
C2	1×10^-5	0	1.00	1.00	1.00	1.00	1.00	1.00
		4	0.20	0.56	0.36	0.12	0.13	0.29
		10	0.50	0.76	0.27	0.43	0.14	0.21
	5×10^-5	0	1.00	1.00	1.00	1.00	1.00	1.00
		4	1.20	0.85	0.85	0.35	0.98	0.57
		10	1.41	1.11	0.66	0.58	0.34	0.37
C3	1×10^-5	0	1.00	1.00	1.00	1.00	1.00	1.00
		4	3.50	0.91	0.91	0.85	0.97	0.85
		10	10.04	0.99	0.78	0.79	0.89	0.81
	5×10^-5	0	1.00	1.00	1.00	1.00	1.00	1.00
		4	2.14	1.20	1.62	1.71	1.31	1.30
		10	3.45	1.63	1.07	1.26	1.19	1.60
C4	1×10^-5	0	1.00	1.00	1.00	1.00	1.00	1.00
		4	2.82	1.14	1.48	1.07	1.16	1.14
		10	17.41	1.09	1.23	0.98	1.14	1.13
	3×10^-5	0	1.00	1.00	1.00	1.00	1.00	1.00
		4	0.55	1.00	1.01	1.04	0.94	1.04
		10	5.36	0.97	0.93	1.01	0.94	1.00
C5	1×10^-5	0	1.00	1.00	1.00	1.00	1.00	1.00
		4	5.55	0.89	0.94	0.92	0.92	0.92
		10	12.27	0.96	0.88	0.92	0.90	0.94
	3×10^-5	0	1.00	1.00	1.00	1.00	1.00	1.00
		4	1.37	1.02	1.00	1.10	1.00	1.07
		10	1.15	1.03	0.99	1.11	0.93	0.98
C6	5×10^-6	0	1.00	1.00	1.00	1.00	1.00	1.00
		4	2.22	1.22	1.14	1.08	1.14	1.09
		10	4.04	1.40	1.18	1.13	1.16	1.08
	1×10^-5	0	1.00	1.00	1.00	1.00	1.00	1.00
		4	1.85	1.15	1.12	1.07	1.06	1.09
		10	2.80	1.18	1.11	1.27	1.08	1.05

Table 5 Spectroscopic data of dyes C3—C5(1×10-5 mol/L) in presence of DNA

Dye	c(DNA)/ (μg·mL^-1)	Absorption			Fluorescence
Dye	c(DNA)/ (μg·mL^-1)	λ_max/nm	Hypochromic effect(%)	10⁴ε/ (L·mol^-1·cm^-1)	λ_ex/nm	λ_em/nm	Stokes shift/nm	Φ_DNA/Φ_Free
C3	0	477.0	0.0	2.09	475.0	572.4	97.4	1.00
	2	445.0	13.8	1.8	475.0	574.4	99.4	1.84
	4	448.0	24.9	1.57	475.0	592.8	117.8	3.50
	6	484.0	29.1	1.48	475.0	592.6	117.6	7.79
	8	478.0	15.7	1.76	475.0	593.4	118.4	8.02
	10	488.0	9.5	1.9	475.0	595.4	120.4	10.04
	12	489.0	5.3	1.98	475.0	592.6	117.6	12.22
C4	0	473.0	0.0	1.57	468.0	559.4	91.4	1.00
	2	465.0	2.7	1.14	468.0	565.2	97.2	2.14
	4	465.0	5.3	1.94	468.0	567.2	99.2	2.82
	6	473.0	19.5	1.15	468.0	567.8	99.8	11.55
	8	479.0	19.1	1.46	468.0	567.4	99.4	12.19
	10	479.0	17.8	1.33	468.0	566.6	98.6	17.41
	12	483.0	18.8	1.40	468.0	566.4	98.4	20.03
C5	0	462.0	0.0	3.98	461.0	553.8	92.8	1.00
	2	459.0	19.0	3.22	461.0	559.4	98.4	1.20
	4	461.0	23.3	3.05	461.0	564.0	103.0	5.55
	6	462.0	16.8	3.31	461.0	563.6	102.6	7.29
	8	462.0	16.6	3.32	461.0	564.4	103.4	10.17
	10	464.0	15.2	3.37	461.0	564.0	103.0	12.27
	12	465.0	15.4	3.36	461.0	563.8	102.8	15.30

Fig.3 Viability of A172 cells incubated with dyes C5 and C6 at various concentrations

Fig.4 Fluorescence images of A172 cells incubated with dyes C5(A1, A2) and C6(B1, B2)(A1, B1) Dark fields; (A2, B2) bright fields.

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