亲水性1，8-萘酰亚胺类氢离子荧光探针的合成及其在活细胞成像中的应用
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摘要
以1,8-萘酐和脂肪胺为原料合成了四种氢离子荧光探针:4-((2’-N,N-二甲基氨基)乙基)氨基-N-正丁基-1,8-萘酰亚胺(MBN)、4-((2’-N,N-二乙基氨基)乙基)氨基-N-正丁基-1,8-萘酰亚胺(EBN)、4-((2’-N,N-二甲基氨基)乙基)氨基-N-(2’-N,N-二甲基氨基)乙基-1,8-萘酰亚胺(MMN)、4-((2’-N,N-二乙基氨基)乙基)氨基-N-(2’-N,N-二乙基氨基)乙基-1,8-萘酰亚胺(EEN)。通过红外光谱、核磁共振、质谱、元素分析表征了其结构。
MBN、EBN、MMN、EEN有较好的亲水性和热稳定性,其pKa值分别为8.50,9.02,8.50,8.96。5.0*10-5 mol/L的MBN和EBN乙醇水(V:V=1:19)溶液的最大吸收波长(摩尔消光系数)分别为:438 nm(1.29 M-1·cm~(-1))和436 nm(1.32 M-1·cm~(-1)),最大荧光波长(荧光量子产率)分别为:529 nm(0.599)和529 nm(0.759);5.0*10-5 mol/L的MMN和EEN水溶液的最大吸收波长(摩尔消光系数)分别为:444 nm(1.60 M-1·cm~(-1))和444 nm(1.36 M-1·cm~(-1)),最大荧光波长(荧光量子产率)分别为:534 nm(0.558)和536 nm(0.647)。
MBN、EBN、MMN、EEN能在Britton-Robinson缓冲溶液中高选择性识别H+,而Na+, K+ (200倍)、Mg~(2+), Ca~(2+) (100倍)、Cr~(3+), Mn~(2+), Fe~(3+), Fe~(2+), Co~(2+), Ni~(2+), Cu~(2+), Zn~(2+), Cd~(2+), Hg~(2+), Pb~(2+) (10倍)、Cl- (560倍), PO43- (800倍)、SO42- (10倍)、NO3- (60倍)无显著影响。结合质子后,MBN、EBN、MMN和EEN荧光分别可增强12.9、11.8、13.6、25.6倍。EEN可以用于活细胞成像,随着细胞外pH值从5.51增大到7.55,进入细胞内结合质子的EEN分子逐渐增多,细胞荧光逐渐增强。
Four fluorescent pH probes were synthesized from 1,8-naphthalic anhydride and aliphatic amines: 4-(2’-N,N-dimethylaminoethylamino)-N-n-butyl-1,8-naphthalimide (MBN), 4-(2’-N,N-diethylaminoethylamino)-N-n-butyl-1,8-naphthalimide (EBN), 4-(2’-N,N-dimethylaminoethylamino)-N-(2’-dimethylaminoethyl)-1,8-naphthalimide (MMN) and 4-(2’-N,N-diethylaminoethylamino)-N-(2’-diethylaminoethyl)-1,8- naphthalimide (EEN). Their structures were characterized by FTIR, NMR, MS and elementary analysis.
MBN, EBN, MMN, EEN have good hydrophilicity and thermal stability, their pKa values are 8.50, 9.02, 8.50 and 8.96. The maximum absorption wavelengthλmax (molar extinction coefficientε) of 5.0*10-5 mol/L MBN and EBN ethanol water (V:V=1:19) solution are 438 nm (1.29 M-1·cm~(-1)) and 436 nm (1.32 M-1·cm~(-1)), the corresponding maximum fluorescence wavelengthλFL (fluorescence quantum yieldsφ) are 529 nm (0.599) and 529 nm (0.759). Theλmax (ε) of 5.0*10-5 mol/L MMN and EEN water solution are 444 nm (1.60 M-1·cm~(-1)) and 444 nm (1.36 M-1·cm~(-1)), the correspondingλFL (φ) are 534 nm (0.558) and 536 nm (0.647).
MBN, EBN, MMN, EEN have good selectivity to H+ in Britton-Robinson buffer solution with coexisting ions Na+, K+ (200 times), Mg~(2+), Ca~(2+) (100 times), Cr~(3+), Mn~(2+), Fe~(3+), Fe~(2+), Co~(2+), Ni~(2+), Cu~(2+), Zn~(2+), Cd~(2+), Hg~(2+), Pb~(2+) (10 times), Cl- (560 times), PO43- (800 times), SO42- (10 times), NO3- (60 times), and the coexisting ions have no obvious influence on the H+ detection. The fluorescence enhancement of MBN, EBN, MMN and EEN are 12.9, 11.8, 13.6 and 25.6 times respectively after combining protons. EEN can be used for living cells imaging. When the extracellular pH value increased from 5.51 to 7.55, the fluorescence intensity of the cells increased gradually because more EEN molecules entered into the cells and bound more Intracellular H+.
MBN、EBN、MMN、EEN有较好的亲水性和热稳定性,其pKa值分别为8.50,9.02,8.50,8.96。5.0*10-5 mol/L的MBN和EBN乙醇水(V:V=1:19)溶液的最大吸收波长(摩尔消光系数)分别为:438 nm(1.29 M-1·cm~(-1))和436 nm(1.32 M-1·cm~(-1)),最大荧光波长(荧光量子产率)分别为:529 nm(0.599)和529 nm(0.759);5.0*10-5 mol/L的MMN和EEN水溶液的最大吸收波长(摩尔消光系数)分别为:444 nm(1.60 M-1·cm~(-1))和444 nm(1.36 M-1·cm~(-1)),最大荧光波长(荧光量子产率)分别为:534 nm(0.558)和536 nm(0.647)。
MBN、EBN、MMN、EEN能在Britton-Robinson缓冲溶液中高选择性识别H+,而Na+, K+ (200倍)、Mg~(2+), Ca~(2+) (100倍)、Cr~(3+), Mn~(2+), Fe~(3+), Fe~(2+), Co~(2+), Ni~(2+), Cu~(2+), Zn~(2+), Cd~(2+), Hg~(2+), Pb~(2+) (10倍)、Cl- (560倍), PO43- (800倍)、SO42- (10倍)、NO3- (60倍)无显著影响。结合质子后,MBN、EBN、MMN和EEN荧光分别可增强12.9、11.8、13.6、25.6倍。EEN可以用于活细胞成像,随着细胞外pH值从5.51增大到7.55,进入细胞内结合质子的EEN分子逐渐增多,细胞荧光逐渐增强。
Four fluorescent pH probes were synthesized from 1,8-naphthalic anhydride and aliphatic amines: 4-(2’-N,N-dimethylaminoethylamino)-N-n-butyl-1,8-naphthalimide (MBN), 4-(2’-N,N-diethylaminoethylamino)-N-n-butyl-1,8-naphthalimide (EBN), 4-(2’-N,N-dimethylaminoethylamino)-N-(2’-dimethylaminoethyl)-1,8-naphthalimide (MMN) and 4-(2’-N,N-diethylaminoethylamino)-N-(2’-diethylaminoethyl)-1,8- naphthalimide (EEN). Their structures were characterized by FTIR, NMR, MS and elementary analysis.
MBN, EBN, MMN, EEN have good hydrophilicity and thermal stability, their pKa values are 8.50, 9.02, 8.50 and 8.96. The maximum absorption wavelengthλmax (molar extinction coefficientε) of 5.0*10-5 mol/L MBN and EBN ethanol water (V:V=1:19) solution are 438 nm (1.29 M-1·cm~(-1)) and 436 nm (1.32 M-1·cm~(-1)), the corresponding maximum fluorescence wavelengthλFL (fluorescence quantum yieldsφ) are 529 nm (0.599) and 529 nm (0.759). Theλmax (ε) of 5.0*10-5 mol/L MMN and EEN water solution are 444 nm (1.60 M-1·cm~(-1)) and 444 nm (1.36 M-1·cm~(-1)), the correspondingλFL (φ) are 534 nm (0.558) and 536 nm (0.647).
MBN, EBN, MMN, EEN have good selectivity to H+ in Britton-Robinson buffer solution with coexisting ions Na+, K+ (200 times), Mg~(2+), Ca~(2+) (100 times), Cr~(3+), Mn~(2+), Fe~(3+), Fe~(2+), Co~(2+), Ni~(2+), Cu~(2+), Zn~(2+), Cd~(2+), Hg~(2+), Pb~(2+) (10 times), Cl- (560 times), PO43- (800 times), SO42- (10 times), NO3- (60 times), and the coexisting ions have no obvious influence on the H+ detection. The fluorescence enhancement of MBN, EBN, MMN and EEN are 12.9, 11.8, 13.6 and 25.6 times respectively after combining protons. EEN can be used for living cells imaging. When the extracellular pH value increased from 5.51 to 7.55, the fluorescence intensity of the cells increased gradually because more EEN molecules entered into the cells and bound more Intracellular H+.
引文
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