Cis Form Research Articles

The occurrence of the cis/trans geometric isomerism of myxoxanthophyll and 4-ketomyxoxanthophyll in the cyanobacterium Anabaena sp. PCC7120.

The cyanobacteria of the genus Anabaena have recently been recognized as a potential source of secondary metabolites of pharmacological and biotechnological importance. In particular, myxoxanthophylls - specific carotenoid glycosides that accumulate in cyanobacterial cells, are attracting increasing interest. Anabaena (Nostoc) sp. PCC7120, a filamentous, mesophilic, nitrogen-fixing cyanobacterium, is a model organism used in biochemical and genetic studies. The carotenoid pool of Anabaena sp. PCC7120 consists of five main species of pigments, namely β-carotene, echinenone, canthaxanthin and two derivatives of myxoxanthophyll: myxoxanthophyll ((3R,2'S)-myxol 2'-fucoside) and 4-ketomyxoxanthophyll ((3S,2'S)-4-ketomyxol 2'-fucoside). Recent findings show that the carotenoid biosynthesis pathway functions in Anabaena sp. PCC7120 cells are affected by environmental factors. Specifically, the balance between β-carotene and ketocarotenoids alters according to the temperature conditions. In this study, a new method, based on single-step liquid adsorption chromatography was developed and applied to separate a fraction containing myxoxanthophyll and 4-ketomyxoxanthophyll from Anabaena sp. PCC7120 cells. It was found that this method allowed a high purity fraction of carotenoid glycosides to be obtained from pigment pools as extracted from cyanobacterial cells. The subsequent analysis using the methods HPLC and LC/MS demonstrated that this fraction consists of a mixture of compounds with different retention times. On the basis of their fragmentation spectra and optical properties, these compounds were identified as geometrical isomers of myxoxanthophyll and 4-ketomyxoxanthophyll, including the dominant all-trans forms and less abundant cis forms. Proposals regarding the structures of myxoxanthophyll isomers are made.

Structural and vibrational investigation of Cis-Trans isomers of potent insecticide allethrin.

In this research, the optimised structural and vibrational properties of cis-trans isomers of powerful insecticide allethrin were theoretically studied in gas phase and in aqueous and ethanol solutions by using hybrid B3LYP/6-311 + + g(d,p) level of theory. The results revealed that the permittivity of solvent has influence on the properties of both isomers, thus, higher dipole moments and solvation energies are observed in water, a solvent of higher permittivity (78.355) than ethanol. Complete vibrational assignments of both isomers were done by combining the experimental IR spectrum of allethrin with the scaled quantum mechanical force field (SQMFF) methodology and the determination of corresponding scaled force constants in gas phase and aqueous solution are reported. Different signs of dihedral O2C10C6C4 angles of both isomers (negative in cis and positive in trans) support the differences in the vibrational assignments. Natural bond orbital (NBO) calculations suggest that both isomers are highly stable in gas phase and aqueous solution and that the side chains and five member's rings are involved in the n → σ* interactions. However, atoms in molecules (AIM) studies reveal a higher stability of form cis in both media than the trans one. Merz-Kollman (MK), Mulliken and natural population atomic (NPA) charges for both isomers support the higher hydration of trans isomer in aqueous media and, hence, the higher solvation energy in water (ΔGC/ZPVE = - 80.29kJ/mol). Changes in the bond orders of O and C atoms of side chain are observed in water as a consequence of hydration. The higher stability of the cis form in the above solutions could be explained by the lower solvation energy in water, as supported by AIM calculations. The studies of frontier orbital reveal that the cis form in both media is sligthly more reactive than the trans form.

Determination of Amide cis/trans Isomers in N-Acetyl-d-glucosamine: Tailored NMR Analysis of the N-Acetyl Group Conformation.

N‐Acetyl‐d‐glucosamine (GlcNAc) is one of the most common amino sugars in nature, but the conformation of its N‐acetyl group has drawn little attention. We report herein the first identification of NH protons of the amide cis forms of α‐ and β‐GlcNAc by NMR spectroscopy. Relative quantification and thermodynamic analysis of both cis and trans forms was carried out in aqueous solution. The NH protons were further utilized by adapting protein NMR experiments to measure eight J‐couplings within the N‐acetyl group, of which six are sensitive to the H2‐NH conformation and two are sensitive to the amide conformation. For amide cis and trans forms, the orientation between H2 and NH was determined as anti conformation, while a small percentage of syn conformation was predicted for the amide trans form of β‐GlcNAc. This approach holds great promise for the detailed conformational analysis of GlcNAc in larger biomolecules, such as glycoproteins and polysaccharides.

Audit of Molecular Mechanisms of Primary and Secondary Resistance to Various Generations of Tyrosine Kinase Inhibitors in Known Epidermal Growth Factor Receptor-Mutant Non-small Cell Lung Cancer Patients in a Tertiary Centre

AimsPresently, three generations of epidermal growth factor receptor (EGFR) tyrosine kinase inhibitors (TKIs) are approved against oncogene addicted EGFR-mutant non-small cell lung cancer (NSCLC). Patients with actionable EGFR mutations invariably develop resistance. This resistance can be intrinsic (primary) or acquired (secondary). Materials and methodsThis was a retrospective study carried out between January 2016 and April 2021 analysing 486 samples of NSCLC for primary and secondary resistance to first- (erlotinib, gefitinb), second- (afatinib) and/or third-generation (osimertinib) TKIs in EGFR-mutant NSCLCs by next generation sequencing (NGS). Tissue NGS was carried out using the Thermofischer Ion Torrent™ Oncomine™ Focus 52 gene assay; liquid biopsy NGS was carried out using the Oncomine Lung Cell-Free Total Nucleic Acid assay. All cases were previously tested for a single EGFR gene with the Therascreen® EGFR RGQ PCR kit. ResultsThe results were divided into four groups: (i) group 1: primary resistance to first- and/or second-generation TKIs. This group, with 21 cases, showed EGFR exon 20 insertions, dual, complex mutations and variant of unknown significance, de novo MET gene amplification besides other mutations. (ii) Group 2: primary resistance to third-generation TKIs. This group showed two cases, with one showing dual EGFR mutation (L858R and E709A) and EGFR gene amplification. (iii) Group 3: secondary resistance to first- and second-generation TKIs. This group had 27 cases, which were previously reported negative for EGFR T790M by single gene testing. Significant findings were MET gene amplification in four cases, with one also showing MET exon 14 skipping mutation. Three cases showed small cell change and one showed loss of primary mutation. (iv) Group 4: secondary resistance to third-generation TKIs. The latter group was further subgrouped into group 4A: secondary resistance to osimertinib (third-generation TKI) when offered as second-line therapy after first- and second-generation TKIs on detection of T790M mutation. This group had 15 cases. EGFR T790M mutation was lost in 10 (10/15; 67%) cases and was retained in five cases. Patients with T790M loss experienced early resistance (6.9 months versus 12.6 months mean, P = 0.0024) compared with cases that retained T790M. Two cases gained MET amplification as the resistance mechanisms. Other mutations that were found when EGFR T790M was lost were in FGFR3, KRAS, PIK3CA, CTNNB1, BRAF genes. One case had EML4-ALK translocation. Two cases showed driver EGFR deletion 19, retained T790M and C797S mutation in Cis form. Group 4B: secondary resistance to osimertinib (when given as first-line therapy) in EGFR-mutant NSCLC. This group had three cases. The duration of osimertinib treatment ranged from 11 to 17 months. Two patients showed additional C797S mutation along with primary EGFR mutation. ConclusionThis study shows the wide spectrum of primary and secondary EGFR resistance mechanisms to first, second and third generation of TKIs and helps us to identify newer therapeutic targets that could carry forward the initial advantage offered by EGFR TKIs.

Investigation of Barrier Potential, Structure (Monomer & Dimer), Chemical Reactivity, NLO, MEP, and NPA Analysis of Pyrrole-2- Carboxaldehyde Using Quantum Chemical Calculations

In this work, the structural conformation of pyrrole-2-carboxaldehyde was evaluated using potential energy surface (PES) scan employing DFT computations using B3LYP method with 6-311++G(d,p) level of basis set. The molecule assumed cis form in conformational ground state being more stable than the trans by 15.21 kJ mol−1 due to the orientation of the N–C–C = O dihedral angle. Existence of hydrogen bonds due to intra- and inter-molecular interactions was envisaged. The geometrical parameters of optimized monomeric and dimeric forms have been computed. The computational structural parameters of monomer are in good agreement with its experimental counterparts. The HOMO-LUMO energies were employed for determination of chemical reactivity descriptors. The electronic properties such as frontier molecular orbitals and Global reactivity descriptors were predicted using TD-DFT method. The local reactivity descriptors such as Fukui functions were investigated to determine the electrophilic and nucleophilic attacks within the molecule. The calculated first order hyperpolarizability value exhibited its suitability for non-linear optical applications. Furthermore, the electrophilic and nucleophilic regions of the molecule were studied by molecular electrostatic potential and Fukui functions. 1H and 13C NMR chemical shifts were evaluated using GIAO method employing the same level of theory. NPA analysis and thermodynamic parameters were also calculated.

Recent advances on the stability of dietary polyphenols

Recent advances on the stability of dietary polyphenols

Nanoporous Vesicular Membranes of Amphiphilic Polymers Containing Trans / Cis Isomers

Nanoporous Vesicular Membranes of Amphiphilic Polymers Containing <i>Trans</i> / <i>Cis</i> Isomers

A refined photo‐switchable cyclic peptide scaffold for use in β‐turn activation

AbstractThe ability to reversibly modulate peptide secondary structures, such as the β‐turn, allows for precise control of biological function, including protein interactions. Herein, we describe the design of two scaffolds containing an azobenzene moiety with flanking alanine or β‐alanine residues to probe essential features for photo‐control of a β‐turn within a cyclic peptide. To efficiently cyclize the designed linear peptides, prior isomerization of the azobenzene‐containing amino acid from the trans to the cis form was necessary. The two cyclic peptides (TAp and TApβ) were found to undergo rapid photochemical conversion to the cis isomer of the azobenzene, with a more gradual thermal reversion to the trans isomer over the course of a week at 37 °C. Spectroscopic analysis and restrained molecular dynamics simulation of the cis form of TAp and TApβ revealed type II and type II' β‐turns within the cyclic peptides, respectively. The trans isomer of the TAp cyclic peptide was found to have a kink within the peptide structure, whereas the longer trans‐TApβ contained a more extended conformation. TApβ, therefore, demonstrates a clearer difference in the cyclic peptide conformations when in the cis versus trans form, a feature that may prove beneficial for use with biologically active β‐turn sequences.

Stochastic Binding Dynamics of a Photoswitchable Single Supramolecular Complex.

In this work, a real‐time precise electrical method to directly monitor the stochastic binding dynamics of a single supramolecule based on the host‐guest interaction between a cyclodextrin and an azo compound is reported. Different intermolecular binding states during the binding process are distinguished by conductance signals detected from graphene‐molecule‐graphene single‐molecule junctions. In combination with theoretical calculations, the reciprocating and unidirectional motions in the trans form as well as the restrained reciprocating motion in the cis form due to the steric hindrance is observed, which could be reversibly switched by visible and UV irradiation. The integration of individual supramolecules into nanocircuits not only offers a facile and effective strategy to probe the dynamic process of supramolecular systems, but also paves the way to construct functional molecular devices toward real applications such as switches, sensors, and logic devices.

Synthesis, X-ray Structures, and spectroscopic characterization of cis and trans-bis(O-propyldithiocarbonato)bis(pyridine)nickel(II), cis and trans-[Ni(CH3CH2CH2OC(S)S)2(C5H5N)2

Single crystals of cis and trans-bis(O-propyldithiocarbonato)bis(pyridine)nickel(II), cis and trans-[Ni(CH3CH2CH2OC(S)S)2(C5H5N)2], have been prepared and studied using single crystal X-ray diffraction method and IR spectroscopy. The crystal structure of tetracoordinated Ni(II) xanthate complex, bis(O-propyldithiocarbonato)nickel(II), [Ni(CH3CH2CH2OC(S)S)2], was also determined and compared with the previously reported structure. The existence of a cis form for a hexacoordinated species of the [NiS4N2] type is infrequent for this family of complexes.

Cyclometalated Platinum(II) Complexes in a Cis-N,N Configuration: Photophysical Properties and Isomerization to Trans Isomers.

Synthesis, isomerization, and photophysical properties of novel cis-N,N-cyclometalated complexes [Pt(C∧N)(l-Phe)] (C∧N = benzoquinolinate (1), phenylpyridinate (2), 2-(p-tolyl)pyridinate (3), and 1-phenylpyrazolate (4); l-Phe- = l-phenylalaninate) are reported herein. In solution, the cis forms of the complexes isomerize to their trans forms via an associative mechanism. This cis/trans isomerism barely influences the absorption and luminescence properties of the complexes in solution, except for a characteristic absorption at approximately 340 nm in the absorption spectra of the cis complexes that is not observed for the trans complexes. Interestingly, the cis complexes are spontaneously assembled in a crystalline phase and show bathochromic absorption and emission colors compared with those of the corresponding trans isomers, which are aggregated in an amorphous phase. cis-1 and cis-2 demonstrate hypsochromic luminescence mechanochromism. The influence of the geometrical isomerism on the photophysical properties and the isomerization mechanism are supported by density functional theory calculations.

The trans/cis ratio of formic (HCOOH) and thioformic (HC(O)SH) acids in the interstellar medium

Context. Observations of the different isomers of molecules in the interstellar medium (ISM) have revealed that both low- and high-energy isomers can be present in space despite the low temperature conditions. It has been shown that the presence of these isomers may be due to tunneling effects. Aims. We carried out a theoretical study of the cis–trans isomerization reactions of two astrophysically relevant acids, formic acid (HCOOH) and thioformic acid (HC(O)SH), where the latter has recently been discovered in space. We also searched for these molecules towards the hot core G31.41+0.31 to compare their abundances with the expected theoretical isomerization results. Methods. We employed high-level ab initio calculations to study the reaction rate constants of the isomerization reactions. We used the canonical variational transition state theory with the multidimensional small curvature tunneling approximation in the temperature range of 10–400 K. Moreover, we used the spectrum obtained from the ALMA 3mm spectral survey GUAPOS (GUAPOS: G31 Unbiased ALMA sPectral Observational Survey), with a spectral resolution of ~0.488 MHz and an angular resolution of 1.′′2×1.′′2 (~4500 au), to derive column densities of HCOOH and HC(O)SH towards G31.41+0.31. Results. Our results demonstrate that these isomerizations are viable in the conditions of the ISM due to ground-state tunneling effects, which allow the system to reach the thermodynamic equilibrium at moderately low temperatures. At very low temperatures (Tkin ~ 10 K), the reaction rate constants for the cis-to-trans isomerizations are very small, which implies that the cis isomers should not be formed under cold ISM conditions. This is in disagreement with observations of the cis/trans isomers of HCOOH in cold cores where the cis isomer is found to be ~5–6% the trans isomer. At high temperatures (~150–300 K), our theoretical data not only match the observed behavior of the trans/cis abundance ratios for HCOOH (the cis form is undetected), but they support our tentative detection of the trans and – for the first time in the insterstellar medium – the cis isomer of HC(O)SH towards the hot molecular core G31.41+0.31 (with a measured trans/cis abundance ratio of ~3.7). Conclusions. While the trans/cis ratio for HC(O)SH in the ISM depends on the relative stability of the isomers, the trans/cis ratio for HCOOH cannot be explained by isomerization, and is determined by other competitive chemical processes.

Optical Control of Mitosis with a Photoswitchable Eg5 Inhibitor

AbstractEg5 is a kinesin motor protein that is responsible for bipolar spindle formation and plays a crucial role during mitosis. Loss of Eg5 function leads to the formation of monopolar spindles, followed by mitotic arrest, and subsequent cell death. Several cell‐permeable small molecules have been reported to inhibit Eg5 and some have been evaluated as anticancer agents. We now describe the design, synthesis, and biological evaluation of photoswitchable variants with five different pharmacophores. Our lead compound Azo‐EMD is a cell permeable azobenzene that inhibits Eg5 more potently in its light‐induced cis form. This activity decreased the velocity of Eg5 in single‐molecule assays, promoted formation of monopolar spindles, and led to mitotic arrest in a light dependent way.

Optical Control of Mitosis with a Photoswitchable Eg5 Inhibitor.

Eg5 is a kinesin motor protein that is responsible for bipolar spindle formation and plays a crucial role during mitosis. Loss of Eg5 function leads to the formation of monopolar spindles, followed by mitotic arrest, and subsequent cell death. Several cell-permeable small molecules have been reported to inhibit Eg5 and some have been evaluated as anticancer agents. We now describe the design, synthesis, and biological evaluation of photoswitchable variants with five different pharmacophores. Our lead compound Azo-EMD is a cell permeable azobenzene that inhibits Eg5 more potently in its light-induced cis form. This activity decreased the velocity of Eg5 in single-molecule assays, promoted formation of monopolar spindles, and led to mitotic arrest in a light dependent way.

Enhancing magnetic coupling through protonation of benzylideneaniline-bridged diradicals and comparison with stilbene- and azobenzene-based diradicals.

Taking nitroxide radicals as spin sources, we explore the intramolecular magnetic coupling interactions of the trans- and cis-forms of benzylideneaniline (BA)-bridged diradicals, in which the central -CH[double bond, length as m-dash]N- unit can undergo single protonation to convert to its protonated counterpart or vice versa. The calculated results for these two pairs of diradicals (protonated versus unprotonated trans and cis forms) verify that the signs of their magnetic coupling constants J do not change, but the magnitudes significantly increase after protonation. In the structure, the better conjugation of the protonated trans diradical and two reduced CCNC and CCCN torsion angles of the protonated cis one make for a more efficient spin transport, promoting the spin polarization, thus leading to larger spin couplings. In terms of mechanism, the proton-induced magnetic enhancement should be attributed to strong participation of the coupler BA through its lowest unoccupied molecular orbital (LUMO) with a lower energy level after protonation, and the small HOMO-LUMO (HOMO: highest occupied molecular orbital) gap of the coupler BA through protonation is crucial in explaining such remarkable spin-coupling enhancement. Furthermore, different linking modes of the radical groups to the couplers are also considered to confirm our conclusions. In addition, we also make a comparison of the magnetic coupling strengths among their isoelectronic analogues of BA-, AB- and stilbene-bridged nitroxide diradicals before or after protonation, and find a linear correlation among them. It should be noted that the magnetic behaviors of all these diradicals obey the spin alternation rule and singly occupied molecular orbital (SOMO) effect. This work provides helpful information for the rational design of promising magnetic molecular switches.

First report on the synthesis and structural studies of trans-Phakellistatin 18: a rotamer of marine natural product phakellistatin 18

Phakellistatin peptides from marine organisms are the sources of proline-rich cyclic peptides with reported significant antitumor activities. Phakellistatin 18 (1), reported from marine sponge Phakellia fusca, contains three proline-peptide linkages in cis form. We attempted the total synthesis of natural product 1 through solution-phase macrocyclization approach, as a result, the synthetic cyclic peptide 2 was obtained as a rotamer of natural product having all three proline residues in trans-conformation. Here, we describe the synthesis, structural, and cytotoxicity studies of trans-Phakellistatin 18 (2), and its analog [Ala1,3,6]-Phakellistatin 18 (3). Detailed NMR studies were carried out to characterize the synthesized peptides, and anti-cancer screening was performed by using MTT assay. The synthetic trans-Phakellistatin 18 (2) (IC50=67.5 ± 2.938 µM) showed comparable cytotoxicity against HepG2 cancer cell line with standard drug doxorubicin (IC50=63.88 ± 6.48 µM). Here, the first synthetic and structural studies on trans-Phakellistatin 18 (2), and its anticancer screening against HepG2 cell line was reported.

Evaluation of bisphenylthiazoles as a promising class for combating multidrug-resistant fungal infections.

To minimize the intrinsic toxicity of the antibacterial agent hydrazinyloxadiazole 1, the hydrazine moiety was replaced with ethylenediamine (compound 7). This replacement generated a potent antifungal agent with no antibacterial activity. Notably, use of a 1,2-diaminocyclohexane moiety, as a conformationally-restricted isostere for ethylenediamine, potentiated the antifungal activity in both the cis and trans forms of N-(5-(2-([1,1’-biphenyl]-4-yl)-4-methylthiazol-5-yl)-1,3,4-oxadiazol-2-yl)cyclohexane-1,2-diamine (compounds 16 and 17). Both compounds 16 and 17 were void of any antibacterial activity; nonetheless, they showed equipotent antifungal activity in vitro to that of the most potent approved antifungal agent, amphotericin B. The promising antifungal effects of compounds 16 and 17 were maintained when assessed against an additional panel of 26 yeast and mold clinical isolates, including the Candida auris and C. krusei. Furthermore, compound 17 showed superior activity to amphotericin B in vitro against Candida glabrata and Cryptococcus gattii. Additionally, neither compound inhibited the normal human microbiota, and both possessed excellent safety profiles and were 16 times more tolerable than amphotericin B.

Photo-Triggered Chiroptical Switching of Platinum Complexes Bearing Azobenzene Moieties

l-Alanine-derived optically active trans-platinum complexes bearing azobenzene moieties, l-trans-Pt[P(Ph)2-1,4-C6H4-CONH-C*H(CH3)-CONH-1,4-C6H4-N═N-Ph]2(C≡CPh)2 (L-2a-5t) and l-cis-Pt[P(Ph)2-1,4-C6H4-CONH-C*H(CH2Ph)-CONH-1,4-C6H4-N═N-Ph]2(C≡CPh)2 (L-2a-5c) were synthesized by the ligand exchange reaction of trans-Pt(PPh3)2(C≡CPh)2 and cis-Pt(cod)(C≡CPh)2, respectively, with l-P(Ph)2-1,4-C6H4-CONH-C*H(CH2Ph)-CONH-1,4-C6H4-N═N-Ph. The trans-azobenzene moieties of the complexes isomerized to the cis form upon UV-light irradiation and returned to the trans form upon visible-light irradiation. L-2a-5t displayed weak circular dichroism (CD) signals irrespective of the trans and cis forms of the azobenzene moieties. On the other hand, L-2a-5c with trans-azobenzene moieties displayed strong CD signals, whose intensity decreased upon UV-light irradiation, accompanied by an increase in CD signals based on cis-azobenzene moieties. DFT calculations of the complexes indicated that intramolecular hydrogen bonds form between the amide moieties of two ligands in the cis-platinum complexes, resulting in retention of conformation. A noncovalent interaction plot analysis also indicated that the π–π interaction between the benzene rings of the ligands also contributes to conformational maintenance. The d-alanine-derived counterparts, D-2a-5t and D-2a-5c, exhibited mirror-image CD spectroscopic patterns in comparison to those of L-2a-5t and L-2a-5c. Solution-state IR absorption spectroscopic peaks of C═O stretching and N–H bending vibrations of L-2a-5c were observed broadly at ca. 10 cm–1 lower and higher than those of P(Ph)2-1,4-C6H4-CONH-C*H(CH3)-CONH-1,4-C6H4-N═N-Ph (L-2a), respectively, thus supporting the formation of intramolecular hydrogen bonding at the amide groups.

Bonding, Aromaticity and Isomerization of Furfuraldehyde through Off-Nucleus Isotropic Magnetic Shielding.

Off‐nucleus isotropic magnetic shielding (σ iso(r)) and multi‐points nucleus independent chemical shift (NICS(0‐2 Å)) index were utilized to find the impacts of the isomerization of gas‐phase furfuraldehyde (FD) on bonding and aromaticity of FD. Multidimensional (1D to 3D) grids of ghost atoms (bqs) were used as local magnetic probes to evaluate σ iso(r) through gauge‐including atomic orbitals (GIAO) at density functional theory (DFT) and B3LYP functional/6‐311+G(d,p) basis set level of theory. 1D σ iso(r) responses along each bond of FD were examined. Also, a σ iso(r) 2D‐scan was performed to obtain σ iso(r) behavior at vertical heights of 0–1 Å above the FD plane in its cis, transition state (TS) and trans forms. New techniques for evaluating 2D σ iso(r) cross‐sections are also included. Our findings showed that bonds in cyclic and acyclic parts of FD are dissimilar. Unlike the C−O bond of furanyl, the C=O bond of the formyl group is magnetically different. C−C and C−H bonds in furanyl are found similar to those in aromatic rings. A unique σ iso(r) trend was observed for the C2−C6 bond during FD isomerization. Based on NICS(0‐2 Å) values, the degree of aromaticity follows the order of cis FD<trans FD<furan<TS FD.

Syntheses and properties of new photo-responsive gemini surfactants containing azobenzene group

A new asymmetric gemini type of photo-responsive cationic surfactants, N,N,N-(azobenzene-4-oxy-2-hydroxypropyl)dimethyl-N′,N′,N′-(alkyloxy-2-hydroxypropyl) dimethylethylene diammonium methylsulphate (GnAZ0DA, n = 4, 8, and 12), were synthesized. The surfactants had ammoniums in both head groups, two carbons as a spacer, azobenzene in one tail group, and alkyl groups in the other tail group. A simple process was designed to conduct the synthesis under mild conditions that included atmospheric pressure, a temperature at or below 100 ℃, and the use of easy-to-remove solvents. The synthesized GnAZ0DA series showed good solubility in water solution and returned high yields ranging from 87.0% to nearly 100% throughout the experiment. 92.5% of trans-GnAZ0DA was converted to the cis form when exposed to UV light, and 73% was reversibly converted to the trans form when exposed to visible light. The critical micelle concentration (CMC) of the trans-G4AZ0DA was 1.89 × 10−3 mol/L, while the value for the 92.5% of the cis-G4AZ0DA was 4.45 × 10−3 mol/L. Light irradiation may be used to control the CMC values. Additionally, this study examined the wettability, foaming power, and emulsion stability of the surfactants and compared them to the commercialized surfactants, sodium lauryl ether sulfate (SLES) and dodecyl benzene sulfonate (DBS).