Designing Dual-output Digital Logic Circuits Based on the Combination of Bovine Serum Albumin and Schiff Base

doi:10.19894/j.issn.1000-0518.220371

Chinese Journal of Applied Chemistry ›› 2023, Vol. 40 ›› Issue (6): 904-915.DOI: 10.19894/j.issn.1000-0518.220371

• Full Papers • Previous Articles Next Articles

Designing Dual-output Digital Logic Circuits Based on the Combination of Bovine Serum Albumin and Schiff Base

Xing-Mei HU, Jin-Hong ZHANG, Yu-Lin MO, Hai-Bin LIN()

College of Chemistry，Chemical Engineering and Environment，Minnan Normal University，Zhangzhou 363000，China

Received:2022-11-15 Accepted:2023-05-10 Published:2023-06-01 Online:2023-06-27
Contact: Hai-Bin LIN
About author:linhb97@mnnu.edu.cn
Supported by:
the Natural Science Foundation of Fujian Province, China(2021J01986)

1. .pdf(580KB)

Abstract

Abstract:

The ability to realize logic calculations and applications of molecules from the nanoscale is an important part of miniaturization of electronic microprocessors. Herein， a novel fluorescent probe complex （BSA@SALPHENH₂） is prepared by the interaction of bis-（salicyladehyde）-1，3-propylenedii-mine （SALPHENH₂） with bovine serum albumin（BSA）. The interaction of BSA with bis-（salicyladehyde）-1，3-propylenediimine is characterized by fluorescence titration experiment， synchronous fluorescence spectroscopy， site marker fluorescent probes and molecular docking. It is found that the conformation of BSA changes slightly in presence of bis-（salicyladehyde）-1，3-propylenediimine， the quenching type is static quenching， and there is van der Waals forces and hydrogen bonding in Subdomain ⅢA （Site Ⅱ） of BSA. Additionally， the experiment results show that the complex has two fluorescence emission bands under the excitation of 280 nm due to hybrid fluorescence resonance energy transfer and electron exchange energy transfer between BSA and Zn²⁺-bis-（salicyladehyde）-1，3-propylenediimine Schiff base. Then， Modulating the system using different ions as the input signal to design a half subtractor and a binary molecular logic circuit containing one OR gate， one NAND gate， two NOT gates and three AND gates. Simultaneously， this combination provides a good reference model in exploring Dexter energy transfer in fluorescent experiments.

Key words: Molecular logic devices, Energy transfer, Fluorescence, Dual-output, Bovine serum albumin

CLC Number:

O644.1

Xing-Mei HU, Jin-Hong ZHANG, Yu-Lin MO, Hai-Bin LIN. Designing Dual-output Digital Logic Circuits Based on the Combination of Bovine Serum Albumin and Schiff Base[J]. Chinese Journal of Applied Chemistry, 2023, 40(6): 904-915.

Figures/Tables 11

Fig. 1 （A） FT-IR spectra of BSA and the complex of BSA@SALPHENH2；（B） 1H NMR spectra of BSA， the complex of BSA@SALPHENH2 and SALPHENH2

Fig.2 Representation of the interaction model with （A） Stern-Volmer plots of BSA interacted with different concentrations of SALPHENH2；（B） Double-logarithm plots of BSA interacted with different concentrations of SALPHENH2； SFS of BSA and the different concentration of SALPHENH2 （C） ?λ=15 nm；（D） ?λ=60 nm

Table 1 Constants of the interaction between BSA and SALPHENH2

T/K	K_SV/（L·mol^-1）	K_q/（L·mol^-1·s^-1）	lg K_a	n
308	1.08×10⁵	1.08×10¹³	4.63	0.910
313	9.93×10⁴	9.93×10¹²	4.58	0.910
318	9.47×10⁴	9.47×10¹²	4.29	0.850

Table 2 Thermodynamic constants of the interaction between BSA and SALPHENH2

T/K	$Δ H θ$ /（kJ·mol^-1）	$Δ S θ$ /（J·K^-1·mol^-1）	$Δ G θ$ /（kJ·mol^-1）
308	-63.9	-118	-27.5
313	-63.9	-118	-26.9
318	-63.9	-118	-26.3

Table 2 Thermodynamic constants of the interaction between BSA and SALPHENH2

T/K	$Δ H θ$ /（kJ·mol^-1）	$Δ S θ$ /（J·K^-1·mol^-1）	$Δ G θ$ /（kJ·mol^-1）
308	-63.9	-118	-27.5
313	-63.9	-118	-26.9
318	-63.9	-118	-26.3

Table 3 Comparison of binding constants in site-specific labeling experiments experiments of BSA@SALPHENH2

Marker	Blank	WF	IB
K_a/（L·mol^-1）	4.34×10⁸	1.52×10⁸	4.43×10⁶

Fig.3 （A） Best conformations for SALPHENH2 docked to BSA in cartoon ribbons；（B） 2 Dimensional representation of amino acid residues surrounding SALPHENH2 in BSA；（C） The distance between SALOPHEN and Tryptophan residues；（D） The distance between SALPHENH2 and Tyrosine residues of BSA

Fig.4 （A） Fluorescence emission spectra of SALPHENH2-Zn2+@BSA at λex=280 nm；（B） Overlap spectra after normalization of the fluorescence emission curve of BSA and the UV absorption curve of SALPHENH2-Zn2+；（C） Fluorescence emission spectra of BSA@SALPHENH2-Zn2+ under different pH；（D） Fluorescence emission spectra of BSA@SALPHENH2-Zn2+ with λex=376 nm

Fig.5 （A） Fluorescence spectra of BSA and SALPHENH2 molecular system under different stimulations；（B） Changes of fluorescence intensity at 350 nm；（C） Changes of fluorescence intensity at 426 nm；（D） Combinational logic circuit equivalent to the BSA and SALPHENH2 molecular systems

Table 4 Truth table for the mono-molecular circuit based on BSA@ SALPHENH2

	Input			Output
	IN 1 Cu²⁺	IN 2 Zn²⁺	IN 3 Na₂H₂EDTA	OUT 1 at 350 nm	OUT 2 at 426 nm
a	0	0	0	1	0
b	0	0	1	1	0
c	0	1	0	0	1
d	0	1	1	1	0
e	1	0	0	0	0
f	1	0	1	1	0
g	1	1	0	0	1
h	1	1	1	1	0

Fig. 6 （A） Fluorescence spectra of BSA@ SALPHENH2-Zn2+ molecular system under different pH；（B） Changes of fluorescence intensity at 350 nm；（C） Changes of fluorescence intensity at 426 nm；（D） Combinational logic circuit equivalent to the BSA@ -SALPHENH2 molecular systems

Table 5 Truth table for the molecular logic device half-subtractor based on BSA@SALPHENH2-Zn2+

	Input		OUT
	IN 1 OH^-	IN 2 H⁺	OUT 1 at 350 nm	OUT 2 at 426 nm
a	0	0	0	0
b	1	0	0	1
c	0	1	1	1
d	1	1	0	0

References 36

1	DE SILVA A D， GUNARATNE N H Q， MCCOY C P. A molecular photoionic AND gate based on fluorescent signalling［J］. Nature，1993， 364（6432）： 42-44.
2	ERBAS-CAKMA S， KOLEMEN S， SEDGWICK A C. Molecular logic gates： the past， present and future［J］. Chem Soc Rev， 2018， 47（7）： 2228-2248.
3	DE SILVA A P， MCCLENAGHAN N D. Molecular-scale logic gates［J］. Chem Eur J， 2004， 10（3）： 574-86.
4	WANG H B， MAO A L， TAO B B， et al. Fabrication of multiple molecular logic gates made of fluorescent DNA-templated Au nanoclusters［J］. New J Chem， 2021， 45（9）： 4195-4201.
5	MARGULIES D， MELMAN G， SHANZER A. A molecular full-adder and full-subtractor， an additional step toward a moleculator［J］. J Am Chem Soc， 2006， 128（14）： 4865-4871.
6	ZHANG S Q， LI K B， SHI W， et al. Resettable and enzyme-free molecular logic devices for the intelligent amplification detection of multiple miRNAs via catalyzed hairpin assembly［J］. Nanoscale， 2019， 11： 5048-5057.
7	HE K Y， YANG H， WANG L， et al. A universal platform for multiple logic operations based on self-assembled a DNA tripod and graphene oxide［J］. Chem Eng J， 2019， 368： 877-883.
8	WU Q， WU P M， DUANN H， et al. Quantum dot bead-based immunochromatographic assay for the quantitative detection of triazophos［J］. Food Agr Immunol， 2019， 30（1）： 955-967.
9	HOSSEIN T， GOHAR D， NARGES M， et al. A reversible and dual responsive sensing approach for determination of ascorbate ion in fruit juice， biological， and pharmaceutical samples by use of available triaryl methane dye and its application to constructing a molecular logic gate and a set/reset memorized device［J］. Spectrochim Acta A Mol Biomol Spectrosc， 2019， 215： 276-289.
10	KHATEREH R， HAMID K， SAMIRA G D， et al. Studies on a multifunctional chromo-fluorogenic sensor for dual channel recognition of Zn²⁺ and CN^- ions in aqueous media： mimicking multiple molecular logic gates and memory devices［J］. New J Chem， 2018， 42： 2158-2166.
11	辛涵申，葛从伍，傅丽娜，等. 薁乙炔封端的萘二酰亚胺小分子的设计合成与场效应性能研究［J］. 有机化学， 2017， 37（3）： 711-719.
	XIN H S， GE C W， FU L N， et al. Naphthalene diimides endcapped with ethynylazulene： molecular design， synthesis and properties［J］. Chin J Org Chem， 2017， 37（3）： 711-719.
12	王斌，王晓红，段莉梅，等. 基于P₂Mo₁₈O626-@Tb³⁺溶液可逆变色-荧光开关性质对维生素C和H₂O₂的光谱检测［J］. 高等学校化学学报， 2019， 40（4）： 676-684.
	WANG B， WANG X H， DUAN L M， et al. Spectral detection for vitamin C and H₂O₂ based on the reversible color change and luminescent switching properties of P₂Mo₁₈O₆₂₆-@Tb³⁺ mixed solution［J］. Chem J Chin Univ， 2019， 40（4）： 676-684.
13	王志强，肖殷，金会义，等. 含三苯胺基团的二噻吩乙烯光致变色化合物的合成及性能研究［J］. 化学学报， 2014， 72（6）： 731-738.
	WANG Z Q， XIAO Y， JIN H Y， et al. Synthesis and properties of photochromic dithienylethene compounds with triphenylamine units［J］. Acta Chim Sin， 2014， 72（6）： 731-738.
14	JIMENEZ-LOPEZ J， RODRIGUES S S M， RIBEIRO D S M， et al. Exploiting the fluorescence resonance energy transfer （FRET） between CdTe quantum dots and Au nanoparticles for the determination of bioactive thiols［J］. Spectrochim Acta A： Mol Biomol Spectrosc， 2019， 212： 246-254.
15	TAHA Z A， AJLOUNI A M， AL-HASSAN K A. Syntheses， characterization， biological activity and fluorescence properties of bis-（salicylaldehyde）-1，3-propylenediimine Schiff base ligand and its lanthanide complexes［J］. Spectrochim Acta A： Mol Biomol Spectrosc， 2011， 81（1）： 317-323.
16	RAJESWARI， NATCHIMUTHU S， VEMBU B. Pharmacophore and virtual screening of JAK3 inhibitors［J］. Bioinformation， 2014， 10（3）： 157-163.
17	FAZI R， CRISTINA T， ANNALAURA B， et al. Homology model-based virtual screening for the identification of human helicase DDX3 inhibitors［J］. J Chem Inf Model， 2015， 55（11）： 2443-2454.
18	张方圆，倪永年. 日落黄和β-胡萝卜素与牛血清白蛋白相互作用的对比研究［J］. 化学学报， 2012， 70（12）： 1379-1384.
	ZHANG F Y， NI Y N. A comparison study on the interaction of Sunset Yellow and β-carotene with bovine serum albumin［J］. Acta Chim Sin， 2012， 70（12）： 1379-1384.
19	YANG Y W， ZHANG N， SUN Y J， et al. Multispectroscopic and molecular modeling studies on the interaction of bile acids with bovine serum albumin （BSA）［J］. J Mol Struct， 2019， 1180： 89-99.
20	PENG Q， HUA L， DING X Y， et al. Spectrochim. Influences of urea and guanidine hydrochloride on the interaction of 6-thioguanine with bovine serum albumin［J］. Acta A Mol Biomol Spectrosc， 2009， 74： 1224-1228.
21	LIN H B， LIAO Z Q， DAI Y H. Design of multiple efficient molecular logic devices based on molecular systems containing bovine serum albumin and 5-sulfosalicylic acid［J］. Sens Actuators B： Chem， 2018， 273： 672-680.
22	ZHANG R J， S B KOU， HU L， et， al. Exploring binding interaction of baricitinib with bovine serum albumin （BSA）： multi-spectroscopic approaches combined with theoretical calculation［J］. J Mol Liq， 2022， 354： 1188311.
23	李悦，谷雨，何佳，等. 光谱法与分子模拟技术研究杨梅素与牛血清白蛋白的相互作用［J］. 化学学报， 2012， 70（2）： 143-150.
	LI Y， GU Y， HE J， et al. Study on interaction between myricetin and bovine serum albumin by spectroscopy and molecular modeling［J］. Acta Chim Sin， 2012， 70（2）： 143-150.
24	BAGALKOTI J T， JOSHI S D， NANDIBEWOOR S T. Spectral and molecular modelling studies of sulfadoxine interaction with bovine serum albumin［J］. J Photoch Photobio A， 2019， 382： 1118711.
25	ROSTAMNEZHAD F， HOSSEIN F M. Comprehensive investigation of binding of some polycyclic aromatic hydrocarbons with bovine serum albumin： spectroscopic and molecular docking studies［J］. Bioorg Chem， 2022， 120： 1056561.
26	ROSS P D， SUBRAMANIAN S. Thermodynamics of protein association reactions： forces contributing to stability［J］. Biochemistry-US， 1981， 20（11）： 3096-3102.
27	GAN N， SUN Q M， TANG P X， et al. Determination of interactions between human serum albumin and niraparib through multi-spectroscopic and computational methods［J］. Spectrochim Act A Mol Biomol Spectrosc，2019， 206： 126-134.
28	NI Y， ZHU R， KOKOT S. Competitive binding of small molecules with biopolymers： a fluorescence spectroscopy and chemometrics study of the interaction of aspirin and ibuprofen with BSA［J］. Analyst， 2011， 136（22）： 4794-4801.
29	NI Y， SU S， KOKOT S. Spectrofluorimetric studies on the binding of salicylic acid to bovine serum albumin using warfarin and ibuprofen as site markers with the aid of parallel factor analysis［J］. Anal Chim Acta， 2006， 580（2）： 206-215.
30	SEN P， FATIMA S， AHMAD B. Interactions of thioflavin T with serum albumins： spectroscopic analyses［J］. Spectrochim Acta A Mol Biomol Spectrosc， 2009， 74（1）： 94-99.
31	ABDELHAMEED A S， ALANAZI A M， BAKHEIT A H. Fluorescence spectroscopic and molecular docking studies of the binding interaction between the new anaplastic lymphoma kinase inhibitor crizotinib and bovine serum albumin［J］. Spectrochim Acta A Mol Biomol Spectrosc， 2017， 171： 174-182.
32	WU L， HUANG C， EMERY B P. Förster resonance energy transfer （FRET）-based small-molecule sensors and imaging agents［J］. Chem Soc Rev，2020， 49（15）： 5110-5139.
33	MENG D， ZHOU H， XU J. Studies on the interaction of salicylic acid and its monohydroxy substituted derivatives with bovine serum albumin［J］. Chem Phys， 2021， 546：1111821.
34	STAROSTA R， SANTOS F C， RFMD A. Human and bovine serum albumin time-resolved fluorescence： tryptophan and tyrosine contributions， effect of DMSO and rotational diffusion［J］. J Mol Struct， 2020， 1221： 1288051.
35	JUN S， TONG N， LIU X Q， et al. Mechanochromism， thermochromism， protonation effect and discrimination of CHCl₃ from organic solvents in a Et₂N-substituted Salicylaldehyde Schiff base［J］. Dyes Pigm， 2021， 195： 1097081.
36	LI K， FENG Q， NIU G. Benzothiazole-based AIEgen with tunable excited-state intramolecular proton transfer and restricted intramolecular rotation processes for highly sensitive physiological pH sensing［J］. ACS Sens， 2018， 3（5）： 920-928.

[1]	Hong-Li YU, Si-Yi ZHOU, Chen HONG, Wen LUO. A Flavone-based “Off-On” Fluorescence Probe for Detecting Butyrylcholinesterase in Living Cell [J]. Chinese Journal of Applied Chemistry, 2023, 40(4): 500-508.
[2]	Yue-Xia ZHANG, Xiao-Peng FAN, Yu-Juan CAO, Xin-Tong YANG, Zhong-Ping LI, Zhen-Hua YANG, Chuan DONG. Synthesis of Oil-soluble Carbon Quantum Dots by Pyrolysis Method for the Detection of Oxytetracycline [J]. Chinese Journal of Applied Chemistry, 2023, 40(4): 509-517.
[3]	Lei WU, Ling-Yun LI, Yong-Zhen PENG. Determination of Trace Heavy Metal Elements in Sewage by Total Reflection X-Ray Fluorescence Spectrometry [J]. Chinese Journal of Applied Chemistry, 2023, 40(3): 404-412.
[4]	Jia-Mei GENG, Su-Fang MA, Wen LIU, Hai-Peng DIAO, Zhi-Fang WU, Si-Jin LI. Liver-Targeted Fluorescent Probes for Specific Detection of ONOO^- in HepG2 Cells [J]. Chinese Journal of Applied Chemistry, 2023, 40(3): 441-448.
[5]	Feng-Zhou XU, Hua-Ying TANG, Wu-Hui LIU, Yi-Feng JIANG, Wen-Kai LI, Xian-Hai LU. A Visual Semi⁃quantitative Method for Rapid Detection of Copper Ion in Water [J]. Chinese Journal of Applied Chemistry, 2022, 39(8): 1303-1311.
[6]	Chen-Yi XUE, Lin-Jia LIU, Ting WANG, Lei GONG, Long JIN, Jian-Gang HAN, Tai-Hua LI. Research Progress on Fluorescence Detection of Heavy Metal Lead Ion [J]. Chinese Journal of Applied Chemistry, 2022, 39(7): 1039-1051.
[7]	Hai-Yan QI, Chen-Qi ZHANG, Jin-Long LI, Jun LI. Synthesis of Sulfur and Nitrogen Doped Carbon Dots for Cu（Ⅱ） Detection [J]. Chinese Journal of Applied Chemistry, 2022, 39(6): 980-989.
[8]	Song-Tao ZHANG, Ying-Hui WANG, Hong-Jie ZHANG. Nd³⁺ Sensitized Fluorescent Nanoprobes for Vascular Imaging in the Second Near Infrared Window [J]. Chinese Journal of Applied Chemistry, 2022, 39(4): 685-693.
[9]	Si-Wei YU, Liang-Peng WANG, Ri-Zhe JIN, Chuan-Qing KANG. Recognition of ClO^－ and Cellular Imaging with Xanthene-based Fluorescent Probes [J]. Chinese Journal of Applied Chemistry, 2022, 39(12): 1903-1911.
[10]	Jin-Ping SONG, Qi MA, Xiao-Min LIANG, Jian-Peng SHANG, Chuan DONG. Neodymium and Nitrogen Co‑doped Carbon Dots with High Fluorescence Quantum Yield for Detection of Sulfasalazine and Hela Cell Imaging [J]. Chinese Journal of Applied Chemistry, 2022, 39(11): 1726-1734.
[11]	Chun-Mei ZHAO, Xiu-Miao ZHOU, Xi-Xi JIN, Yu-Hang WANG, Yi-Jing DANG. Preparation of Saddle-Shaped Cyclooctatetrathiophene-Based Hybrid Nanomaterials and Fluorescence Properties [J]. Chinese Journal of Applied Chemistry, 2022, 39(02): 283-288.
[12]	ZHANG Cheng-Lu, BAO Jin-Di, YU Feng-Ming, DONG Wen-Jing, ZHANG Yang, GONG Rong-Qing, ZHANG Yan-Peng, ZHANG Lu. Synthesis and Application of a Fluorescence Probe with Quinazolinone as the Core Block for Highly Selective and Sensitive Detection of Hypochlorite Ion [J]. Chinese Journal of Applied Chemistry, 2021, 38(8): 986-994.
[13]	DENG Pei-Yuan, YUAN Wei, LI Chang-Kan, CHEN Long-Xin, YANG Ying-Ying. Interaction Between Preservative Benzoic Acid and Human Serum Albumin [J]. Chinese Journal of Applied Chemistry, 2021, 38(8): 1014-1021.
[14]	HAO Li-Juan, WANG Ting, DONG Guo-Hua, ZHANG Wen-Zhi, BAI Li-Ming, DU Hai-Yao, LANG Kun, LI Xin. Preparation of Green Carbon Quantum Dots from Corn Starch and Hydrogen Ion/Hydroxyl Ion Regulated Fluorescent Switch Performance [J]. Chinese Journal of Applied Chemistry, 2021, 38(2): 202-211.
[15]	HUANG Jie-Tao, WANG Da-Peng. Analysis of the Physical Origin of the Red-Shift of Absorption Peaks of Conjugated Polymers in Solution [J]. Chinese Journal of Applied Chemistry, 2021, 38(11): 1486-1493.

Designing Dual-output Digital Logic Circuits Based on the Combination of Bovine Serum Albumin and Schiff Base

RichHTML

PDF

Supplement

Knowledge

Abstract

Cite this article

share this article

Figures/Tables 11

References 36

Related Articles 15

Recommended Articles

Metrics

Comments