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Differentially Activated Amino Acid Coordination Polymers by Amino Acids Tien-Wen Tseng, Shruti Mendiratta, Tzuoo-Tsair Luo, Chi Chen, and Chia-Yuan Huang Cryst. Growth Des., Just Accepted Manuscript • DOI: 10.1021/acs.cgd.8b00012 • Publication Date (Web): 16 Apr 2018 Downloaded from http://pubs.acs.org on April 17, 2018

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Crystal Growth & Design

Differentially Activated Amino Acid Coordination Polymers by Amino Acids Shruti Mendiratta,† Tien-Wen Tseng,*,‡ Tzuoo-Tsair Luo,‡ Chi Chen,†,‡ and Chia-Yuan Huang† † ‡

Institute of Chemistry, Academia Sinica, Taipei 115, Taiwan Department of Chemical Engineering and Biotechnology, National Taipei University of Technology, Taipei 106, Taiwan

ABSTRACT: Two amino acid coordination polymers were synthesized using a single-step self-organization process, both of which

were found to have three-dimensional, enantiomeric structures. They could be differentially activated by four amino acids(aq), cysteine, arginine, histidine and lysine, but were inactive for the other naturally-occurring amino acids. This supramolecular reaction system provides a deep insight into the unique responses of such advanced materials. Biomaterials are substances that are derived either from nature or are synthesized in the laboratory using available chemical approaches that start from metallic components, polymers, ceramics or composite materials.1–12 Biomaterial engineering has experienced particularly strong growth and many companies are investing large amounts of money and efforts in the development of such miraculous products.13–17 We have been interested in preparing coordination polymers starting from biomolecules such as nucleosides, monosaccharides, vitamins, amino acids, and other auxiliary organic scaffolds that represent such a new category of advanced biomaterials, because their structures are amenable to bottom-up strategies and the fact that they have biomimetic functionalities with potential applications in the field of material science.18–33 As a popular aphorism“like dissolves like” goes, if natural amino acids were used as building units to form coordination polymers, some unusual biomimetic properties would be expected.34,35 As part of our ongoing efforts in the design and synthesis of functional crystalline materials,36–41 we report herein on the preparation and characterization of two mixed-ligand amino acid coordination polymers, [Cu(L-trp)(4-ptz)]n (L-1) and [Cu(D-trp)(4-ptz)]n (D-1, L-/D-trp = L-/D-tryptophanate, 4ptz = 5-(4-pyridyl)tetrazolate), which have three dimensional homochiral structures. The features of the compounds are as follows: (i) their preparation is very temperature-sensitive; (ii) these amino acid networks contain three flexible singlestranded helices along the a, b, c axes; (iii) despite the fact that these stable crystals are insoluble in pure water. When immersed in cysteine(aq) the original colorless solution turned a pale yellow color; (iv) in the presence of arginine, histidine and lysine, the solution turned blue, but all other amino acids that were tested showed no activity with respect to L-1; (v) after removing the surface layer of the crystals at least three times, the remaining material was also determined to be active. To the best of our knowledge, such coordination polymers that

can be easily and simply activated by the action of certain specific amino acids, is currently unprecedented.42–44 L-1 and D-1 were synthesized by reacting CuCl2∙2H2O, L/D-Htrp and 4-Hptz ligands at 50 °C for 7 days through a single-step, self-organization process (Scheme 1). Tryptophan, an essential amino acid, is structurally the largest of the amino acids and has an indole substituent on the β carbon. The indole nitrogen atom can act as a potential hydrogen bonding acceptor. D-/L-trp-based coordination polymers are difficult to prepare and have been rarely reported.45 The 4-Hptz ligand is a pseudo chiral species,46–49 and likely participates in

a)

b)

c)

Figure 1. Structures of L-1: a) coordination environment of the Cu 2+ center, b) a single-stranded helix [{Cu(L-trp)}+]n along the c-axis, c) a singlestranded helix [{Cu(4-ptz)}+]n along the b axis.

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Scheme 1. Syntheses of compounds L-1 and D-1 HN

N

H2N

+

+ N

HO

O

L/D-Htrp

CuCl2· 2H2O

DMF/H2O 50 oC, 7d

[Cu(trp)(4-ptz)]n

NH

L-1/ D-1 N

N

4-Hptz

a)

b)

Figure 2. Structures of L-1: a) a modulated layer, b) a perspective view of 3D structure [Cu(L-trp)(4-ptz)]n.

bridging in a helical manner. It is not an easy task to prepare coordination polymers containing the flexible L- or Dtrpligands, because such materials are very temperaturesensitive. These polymers were prepared under optimum conditions using a temperature of only 50 C, except that the yields of the target products were all very low.50,51 These biopotential characteristics all reflect on the properties of amino acid coordination polymers. Single crystal X-ray diffraction analyses revealed that compounds L-1 and D-1 crystallize in the orthorhombic space group P212121. Because they are enantiomers, only the structure of L-1 is discussed in detail here. The Cu(II) center is bound to one pyridyl and one tetrazolate nitrogen atom from two different 4-ptz ligands, one nitrogen and one oxygen atoms from one L-trp ligand, and one carboxylate oxygen atom from the other L-trp ligand in a square-pyramidal geometry (Figure 1a). Each L-trp ligand linked to two Cu(II) centers in a bridging mode, yielding a left- handed singlestranded helix, [{Cu(L-trp)}+]n. This helix has a pseudo-21 screw axis with a CuCu translation distance of 7.4157 Å per turn along the c axis (Figure 1b). The indole rings of the L-trp

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ligands extend outward in an alternating orientation on both sides of the helix. Each 4-ptz ligand is bridged to two Cu(II) centers, leading to the formation of a right-handed single stranded helix, [{Cu(4-ptz)}+]n, along the b axis (Figures 1c and S3 in the ESI†). These two types of helices intersect with one another through the Cu(II) centers, yielding a modulated layer structure (Figure 2a). The CuIICuII separation distances across the syn-anti-2-COO and 2-4-ptz bridging ligands are 5.34 and 9.88 Å , respectively. These above-mentioned helices intersect with one another through the Cu(II) centers, resulting in the formation of a 3D homochiral structure, [Cu(L-trp)(4ptz)]n (Figure 2b).52,53 Thermogravimetric analyses (TGA) of L-1 and D-1 showed that the structures were stable up to a temperature of 250 °C, after which the framework decomposed (Figure S5 in the ESI†). Powder X-ray diffraction (PXRD) patterns showed that all peaks in the measured patterns were matched closely with the simulated patterns (Figure S6 in the ESI†). The Flack parameter is nearly zero, indicating that both compounds L-1 and D-1 consist of a single enantiomer. The blue crystals of L-1 are insoluble in water. However, when 0.5 mg of L-1 was immersed in an aqueous solution of cysteine (0.2 mM) at room temperature, surprisingly, the solution changed from colorless to a pale yellow color (Figure 3). We were astonished that this occurred in such an interaction system. Inspired by “amino acid transporters”, which play an important role in controlling the growth of proteins in living organisms,54–57 compound L-1 was truly activated by this amino acid. Similarly, when arginine(aq) was used instead of cysteine, the color of the solution of L-1 changed immediately from colorless to blue. In addition, we tested a series of amino acids(aq), including valine, threonine, phenylalanine, glutamine, methionine, glycine, isoleucine, proline, histidine and lysine to explore this unusual occurrence but all proved to be inactive (Figure S10 in the ESI†). In the case of histidine(aq) and lysine(aq), the color of the solution changed from colorless to blue. However, when L-1 (2.0 mg) was added to a solution of arginine(aq) (2 mL, 3.1 mM) at room temperature, some solids remained after 1h. The precipitate was then isolated on a filter and washed with water to remove the loose surface layer of the original blue crystals. Infrared spectra and PXRD patterns of the recollected crystals were identical to those of the as-synthesized material. In addition, using arginine(aq) the material could be reused in this manner at least three times (Figure S12 in the ESI†). Apparently, the crystal surface of compound L-1 is able to stoichiometrically react with specific amino acids. a)

b)

Figure 3. Comparison of the colour changes observed for solutions of L-cysteine(aq) (left) and L-arginine(aq) (right): a) without, b) on the addition of L-1 crystals, respectively.


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a)

b)

Figure 4. Fluorescent intensities of an aqueous suspension of L-1 (2.4 mg/ 2 mL) changed by the gradual addition of a) cysteine(aq), and b) arginine(aq).

Arginine, histidine and lysine are amino acids that all contain positively charged side chains and tryptophan is an amino acid with the largest hydrophobic side chain. Our findings clearly show that compound L-1 can be simply and easily activated by these three amino acids. All other amino acids that were tested were inactive with respective to L-1 likely because they contain no effective functional groups, especially positively charged side chains. We speculate that, when the amino acid coordination networks were partially collapsed due to stimulation by these specific amino acids, the copper(II) ions were gradually released into the aqueous solutions, and related copper(II)-amino acid complexes were then formed, as evidenced by the fact that the CuII-cysteine complex has a pale yellow color, while the others are blue.58,59 To verify the formation of this CuII-cysteine complex, we collected the PXRD and FTIR data of this complex and compared it with the products formed by directly reacting Cu(NO3)2∙3H2O with L-cysteine in a ratio of 1:1, 1:2 and 1:3, respectively. The PXRD patterns of these complexes, particularly, for 1:3 complex showed several significant peaks that are similar to that of the CuII-cysteine complex using L-1 (Figure S19 in the ESI†). The FTIR spectra of these complexes also resembled that of the CuII-cysteine complex prepared

from L-1 (Figure S20 in the ESI†) and were also similar to that reported by Masoud et. al.59 In addition, compound D-1 showed the same responses as L-1 (Figure 3b). As a consequence, compounds L-1 and D-1 can be used as visual detectors of cysteine. Motivated by these findings, we conducted further experiments aimed at a comprehensive characterization of these materials. A mixture of 2.0 mL water and 2.4 mg L-1 was subjected to extensive ultra-sonication for 10 minutes to give an aqueous suspension of L-1, and the fluorescent intensity was measured as L-1*. Aqueous solutions of various amino acids (25.0 L, 3.1 mM) were then gradually added to the suspension, followed by a further ultra-sonication for at least 3 minutes. Analogous fluorescent intensities were then measured and the data showed the following order: Cys > Val ≈ Thr ≈ Phe ≈ Glu ≈ Met ≈ Gly ≈ Iso ≈ Pro ≈ L-1* > His > Lys > Arg. As mentioned-above, those amino acids that were inactive with respect to compound L-1 showed nearly the same fluorescent intensities as a blank test. For cysteine(aq), it was enhanced because of the formation of a CuII-cysteine complex. The intensities for His(aq), Lys(aq) and Arg(aq) were all significantly quenched, because of the intrinsic properties of the CuII-amino acid complexes. Furthermore, as shown in Figure 4a, when a 25.0 L aliquot of a cysteine(aq) solution (3 mM) was progressively added to a suspension of L-1, the fluorescent intensities gradually increased because of the formation of a CuII-cysteine complex that quantitatively accumulated with time. Whereas, using arginine(aq), they were decreased (Figure 4b). The results of these experiments indicate that a selective activation assay involving fluorescence detection is possible,60–63 which agrees very well with the colorimetric findings for the series of natural amino acid molecules. Consequently, such functional materials promise to provide amazing opportunities for realizing our own molecular world as we experience the unique bio-responses involved in signal transductions in living systems.64,65 In conclusion, we report on the successful synthesis of two amino acid coordination polymers, which offer distinct advantages in terms of ease of fabrication. These amino acid networks were selectively stimulated in the presence of specific amino acids, causing them to partially collapse. Upon stimulation, these compounds gradually released copper(II) ions into the aqueous solutions, resulting in the formation of related copper(II)-amino acid complexes that could be confirmed by direct visualization or through fluorescent measurements. In addition, these synthesized materials are capable of undergoing simple, selective and sensitive responses. Finally, we offer our perspective on open challenges and future areas of interest for the field. We believe that such advanced materials will have great potential for use in various applications in the future. Further research in this area is currently underway.

■ ASSOCIATED CONTENT Supporting Information The Supporting Information is available free of charge on the


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ACS Publications website at DOI: 10.1021/acs.cgd. Experimental details, tables of bond lengths and angles, additional figures including IR spectra, TGA, and PXRD. Xray crystallographic files for L-1 and D-1 in CIF format. Accession Codes CCDC: 1538583 (L-1), 1538584 (D-1), contain all the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www. ccdc.cam.ac.uk/data_request/cif.

■ AUTHOR INFORMATION Corresponding Author *E-mail: [email protected] ORCID Tien-Wen Tseng: 0000-0003-1525-9237 Notes The authors declare no competing financial interest.

■ ACKNOWLEDGMENTS We are grateful to National Taipei University of Technology, Academia Sinica, Taiwan, and the Ministry of Science and Technology of Taiwan for financial support. Keywords: amino acids • amino acid coordination polymers • biomaterials • fluorescence sensing • molecular recognition

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Differentially Activated Amino Acid Coordination Polymers by Amino Acids Shruti Mendiratta, Tien-Wen Tseng, Tzuoo-Tsair Luo, Chi Chen and Chia-Yuan Huang

Two amino acid coordination polymers with enantiomerically three-dimensional structures were prepared. They could be differentially activated by four amino acids (aq) but were inactive for the other natural amino acids that were tested. These findings provide a deep insight into the unique amino acid-responses of such advanced materials. L-Arg/L-1 L-Arg/D-1 L-Cys/ L-1 L-Cys/D-1

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