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Journal articles on the topic 'Diazirina'

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Author: Grafiati

Published: 9 March 2023

Last updated: 10 March 2023

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1

Beiroth, Femke, Tomas Koudelka, Thorsten Overath, Stefan D. Knight, Andreas Tholey, and Thisbe K. Lindhorst. "Diazirine-functionalized mannosides for photoaffinity labeling: trouble with FimH." Beilstein Journal of Organic Chemistry 14 (July 24, 2018): 1890–900. http://dx.doi.org/10.3762/bjoc.14.163.

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Photoaffinity labeling is frequently employed for the investigation of ligand–receptor interactions in solution. We have employed an interdisciplinary methodology to achieve facile photolabeling of the lectin FimH, which is a bacterial protein, crucial for adhesion, colonization and infection. Following our earlier work, we have here designed and synthesized diazirine-functionalized mannosides as high-affinity FimH ligands and performed an extensive study on photo-crosslinking of the best ligand (mannoside 3) with a series of model peptides and FimH. Notably, we have employed high-performance mass spectrometry to be able to detect radiation results with the highest possible accuracy. We are concluding from this study that photolabeling of FimH with sugar diazirines has only very limited success and cannot be regarded a facile approach for covalent modification of FimH.

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2

Baldwin, J. E., J. B. Coates, J. B. Halpern, M. G. Moloney, and A. J. Pratt. "Photoaffinity labelling of isopenicillin N synthetase by laser-flash photolysis." Biochemical Journal 261, no. 1 (July 1, 1989): 197–204. http://dx.doi.org/10.1042/bj2610197.

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Isopenicillin N synthetase (IPNS) from Acremonium chrysogenum was photolabelled by laser-flash photolysis in the presence of a diazirinyl-containing substrate, 2-[3-(3-trifluoromethyl-3H-diazirin-3-yl)-phenoxy]acetyl-S- methyloxycarbonylsulphenyl-L-cysteinyl-D-valine (DCV). Labelling of IPNS by DCV is partially inhibited in the presence of an excess of L-alpha-aminoadipoyl-L-cysteinyl-D-valine (ACV), the natural substrate. In the absence of light, DCV is converted into the corresponding penicillin with comparable Km but significantly depressed Vmax relative to ACV. Selective incorporation of [14C]DCV into IPNS has been demonstrated by fluorography of IPNS analysed by SDS/polyacrylamide-gel electrophoresis. Scintillation counting of labelled IPNS purified on an ion-exchange f.p.l.c. column confirms this result. This methodology may be applicable for studies aimed at investigating the binding of substrates to IPNS.

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3

Cheng, Xiaju, Rui Sun, Huawei Xia, Jianan Ding, Ling Yin, Zhifang Chai, Haibin Shi, and Mingyuan Gao. "Light-triggered crosslinking of gold nanoparticles for remarkably improved radiation therapy and computed tomography imaging of tumors." Nanomedicine 14, no. 22 (November 2019): 2941–55. http://dx.doi.org/10.2217/nnm-2019-0015.

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Aim: We aimed to characterize the tumor-targeting and radiosensitization properties of the photo-responsive gold nanoparticles (AuNPs) decorated photolabile diazirine group and folic acid for improved radiotherapy and computed tomography imaging of tumors. Methods: Folic acid and photolabile diazirine group were covalently conjugated on the surface of AuNPs to afford the desired photo-responsive dAuNP-FA (AuNPs capped with poly(ethylene) glycol ligands bearing photolabile diazirine group and folic acid). The probes were intravenously injected into tumor-bearing mice followed by photocrosslinking upon 405 nm laser irradiation for radiotherapy and computed tomography imaging of tumors in vivo. Results: Light-triggered crosslinking of AuNPs in vivo remarkably enhanced the accumulation and retention of AuNPs within tumors. Conclusion: We have successfully developed a novel photo-responsive Au particle-based tumor theranostic probe showing remarkably improved tumor targeting ability and radiosensitization effect.

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4

Ghiassian, Sara, Mark C. Biesinger, and Mark S. Workentin. "Synthesis of small water-soluble diazirine-functionalized gold nanoparticles and their photochemical modification." Canadian Journal of Chemistry 93, no. 1 (January 2015): 98–105. http://dx.doi.org/10.1139/cjc-2014-0287.

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Dual water and organic solvent soluble 3-aryl-3-(trifluormethyl) diazirine-functionalized gold nanoparticles (AuNPs) were prepared through a place exchange reaction from triethylene glycol monomethyl ether (EG3-Me) capped AuNPs. These nanoparticles were fully characterized using 1H and 19F nuclear magnetic resonance (NMR) spectroscopy, transmission electron microscopy (TEM), thermogravimetric analysis (TGA), and X-ray photoelectron spectroscopy (XPS). TGA along with 1H NMR data allowed the determination of 15% incorporation of diazirine (Diaz) ligands onto mixed monolayer AuNPs, while TEM images showed an average diameter of 2.3 ± 0.5 nm. This information led to the estimated molecular formula of Au400 (S-EG4-Diaz)40 (S-EG3-Me)230 for these AuNPs. It is noteworthy that high-resolution XPS was a powerful tool for quantitative analysis. Irradiation of the diazirine capped AuNPs resulted in nitrogen extrusion and the formation of a highly reactive carbene with evidence of a portion of the reaction proceeding via the diazo intermediate and thus requiring a second photon for activation. The carbene species generated was utilized to tether the attached AuNPs via insertion into C=C or O–H functionality inherent on various substrates. Here, we demonstrated that photolysis of the diazirine modified AuNPs in the presence of a variety of model carbene scavengers led to clean and efficient insertion products while maintaining their solubility in polar solvents.

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5

Puzzarini, Cristina, and Alberto Gambi. "A theoretical study of diazirine (H2CN2), diazirinyl radical (HCN2) and their related cations (H2CN2+,HCN2+): molecular structure, energetics and ionization potential." Chemical Physics 306, no. 1-3 (November 2004): 131–41. http://dx.doi.org/10.1016/j.chemphys.2004.07.024.

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6

Walko, Martin, Eric Hewitt, Sheena E. Radford, and Andrew J. Wilson. "Design and synthesis of cysteine-specific labels for photo-crosslinking studies." RSC Advances 9, no. 14 (2019): 7610–14. http://dx.doi.org/10.1039/c8ra10436k.

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7

Verma, Udai P., Klaus Möller, Jürgen Vogt, Manfred Winnewisser, and Jørn Johs Christiansen. "Microwave and millimetre wave spectra of diazirine-d2: Rotational and hyperfine structure analysis and molecular structure." Canadian Journal of Physics 63, no. 9 (September 1, 1985): 1173–83. http://dx.doi.org/10.1139/p85-191.

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The rotational spectrum of diazirine-d2, [Formula: see text], has been recorded in the ranges 8–40 and 100–400 GHz. The hyperfine structure of the measured rotational lines has been analyzed. The analysis required the treatment of two pairs of equivalent nuclei, which is discussed in detail. The deduced deuterium nuclear-quadrupole coupling constants are[Formula: see text]The quadrupole coupling constants of the nitrogen nuclei[Formula: see text]are taken from the parent species, and the spin-rotation coupling constants are[Formula: see text]The rotational and centrifugal distortion constants have been obtained for the ground vibrational state from the analysis of the unperturbed line positions. The complete rs structure of diazirine has been determined using the rotational constants of all available isotopomers of diazirine. The internuclear distances are rs(C—N) = 148.13(24) pm, rs(C—H) = 108.03(29) pm, and rs(N—N) = 122.80(25) pm, and the bond angles are [Formula: see text] and [Formula: see text], with the HCH plane perpendicular to the NCN plane.

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8

Russell, AJ, AP Scott, and L. Radom. "Ab initio Predictions of the Gas-Phase Acidities of Diazirine and Diazomethane." Australian Journal of Chemistry 48, no. 2 (1995): 401. http://dx.doi.org/10.1071/ch9950401.

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Absolute gas-phase acidities of diazirine, diazomethane, dimethylamine, ethylamine and methylamine have been obtained with ab initio molecular orbital calculations at the G2 and G2(MP2) levels of theory. Values at the G2 and G2(MP2) levels are all within 1 kJ mol-1 of one another. The calculated gas-phase acidities for diazomethane, dimethylamine, ethylamine and methylamine (and other reference molecules considered) are all within 3 kJ mol-1 of experiment. For diazirine the calculated result, although consistent with experiment, would suggest an acidity towards the lower end of the range of possible experimental values.

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9

Dubinsky, Luba, Bastiaan P. Krom, and Michael M. Meijler. "Diazirine based photoaffinity labeling." Bioorganic & Medicinal Chemistry 20, no. 2 (January 2012): 554–70. http://dx.doi.org/10.1016/j.bmc.2011.06.066.

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10

Fan, Chen-Yo, Yi-Ren Hou, Avijit K. Adak, Juanilita T. Waniwan, Mira Anne C. dela Rosa, Penk Yeir Low, Takashi Angata, Kuo-Chu Hwang, Yu-Ju Chen, and Chun-Cheng Lin. "Boronate affinity-based photoactivatable magnetic nanoparticles for the oriented and irreversible conjugation of Fc-fused lectins and antibodies." Chemical Science 10, no. 37 (2019): 8600–8609. http://dx.doi.org/10.1039/c9sc01613a.

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11

Šumanovac, Tatjana, Marija Alešković, Marina Šekutor, Marija Matković, Thibaut Baron, Kata Mlinarić-Majerski, Cornelia Bohne, and Nikola Basarić. "Photoelimination of nitrogen from adamantane and pentacycloundecane (PCU) diazirines: a spectroscopic study and supramolecular control." Photochemical & Photobiological Sciences 18, no. 7 (2019): 1806–22. http://dx.doi.org/10.1039/c9pp00124g.

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Nitrogen photoelimination delivers carbenes from diazirines. Protonation of singlet carbenes was detected based on the PCU skeleton rearrangement. Complexation of diazirines changes the relative singlet/triplet ratio of carbene products.

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12

Dey, Kaustav, S. Roy Chowdhury, Erik Dykstra, Aleksandr Koronatov, H. Peter Lu, Ruth Shinar, Joseph Shinar, and Pavel Anzenbacher. "Diazirine-based photo-crosslinkers for defect free fabrication of solution processed organic light-emitting diodes." Journal of Materials Chemistry C 8, no. 34 (2020): 11988–96. http://dx.doi.org/10.1039/d0tc02317e.

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Diazirine mediated photocross-linking (365 nm, 15 mins) of organic semiconductor films dramatically reduces the inter-layer surface roughness which results in significant improvement in OLED efficiency.

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13

Tan, Kristine Y., Surbhi Desai, Erum Raja, Chris Etienne, Brian Webb, and Amy E. Herr. "Comparison of photoactivatable crosslinkers for in-gel immunoassays." Analyst 146, no. 21 (2021): 6621–30. http://dx.doi.org/10.1039/d1an01309b.

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Diazirine-functionalized hydrogels have lower fluorescence background signal compared to benzophenone-functionalized hydrogels for in-gel immunoassays and can improve the lower limit of detection of fluorescence immunoassays.

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14

Simon, Binto, Xuexia Huang, Huangxian Ju, Guoxuan Sun, and Min Yang. "Synthesis and characterization of photoaffinity labelling reagents towards the Hsp90 C-terminal domain." Organic & Biomolecular Chemistry 15, no. 7 (2017): 1597–605. http://dx.doi.org/10.1039/c6ob02097f.

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The synthesis of diazirine type photoaffinity labelling reagents to probe the Hsp90 C-terminal domain binding pocket and the structure–activity relationship. The structure illustrates probe positions only.

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15

Murai, Yuta, and Makoto Hashimoto. "Heteroaromatic Diazirines Are Essential Building Blocks for Material and Medicinal Chemistry." Molecules 28, no. 3 (February 1, 2023): 1408. http://dx.doi.org/10.3390/molecules28031408.

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In materials (polymer) science and medicinal chemistry, heteroaromatic derivatives play the role of the central skeleton in development of novel devices and discovery of new drugs. On the other hand, (3-trifluoromethyl)phenyldiazirine (TPD) is a crucial chemical method for understanding biological processes such as ligand–receptor, nucleic acid–protein, lipid–protein, and protein–protein interactions. In particular, use of TPD has increased in recent materials science to create novel electric and polymer devices with comparative ease and reduced costs. Therefore, a combination of heteroaromatics and (3-trifluoromethyl)diazirine is a promising option for creating better materials and elucidating the unknown mechanisms of action of bioactive heteroaromatic compounds. In this review, a comprehensive synthesis of (3-trifluoromethyl)diazirine-substituted heteroaromatics is described.

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16

Khan, Md Arif, Ramy W. Ghanim, Maelyn R. Kiser, Mahsa Moradipour, Dennis T. Rogers, John M. Littleton, Luke H. Bradley, Bert C. Lynn, Stephen E. Rankin, and Barbara L. Knutson. "Strategy for Conjugating Oligopeptides to Mesoporous Silica Nanoparticles Using Diazirine-Based Heterobifunctional Linkers." Nanomaterials 12, no. 4 (February 11, 2022): 608. http://dx.doi.org/10.3390/nano12040608.

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Successful strategies for the attachment of oligopeptides to mesoporous silica with pores large enough to load biomolecules should utilize the high surface area of pores to provide an accessible, protective environment. A two-step oligopeptide functionalization strategy is examined here using diazirine-based heterobifunctional linkers. Mesoporous silica nanoparticles (MSNPs) with average pore diameter of ~8 nm and surface area of ~730 m2/g were synthesized and amine-functionalized. Tetrapeptides Gly-Gly-Gly-Gly (GGGG) and Arg-Ser-Ser-Val (RSSV), and a peptide comprised of four copies of RSSV (4RSSV), were covalently attached via their N-terminus to the amine groups on the particle surface by a heterobifunctional linker, sulfo-succinimidyl 6-(4,4′-azipentanamido)hexanoate (sulfo-NHS-LC-diazirine, or SNLD). SNLD consists of an amine-reactive NHS ester group and UV-activable diazirine group, providing precise control over the sequence of attachment steps. Attachment efficiency of RSSV was measured using fluorescein isothiocyanate (FITC)-tagged RSSV (RSSV-FITC). TGA analysis shows similar efficiency (0.29, 0.31 and 0.26 mol peptide/mol amine, respectively) for 4G, RSSV and 4RSSV, suggesting a generalizable method of peptide conjugation. The technique developed here for the conjugation of peptides to MSNPs provides for their attachment in pores and can be translated to selective peptide-based separation and concentration of therapeutics from aqueous process and waste streams.

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17

Conway, Louis P., Appaso M. Jadhav, Rick A. Homan, Weichao Li, Juanita Sanchez Rubiano, Richard Hawkins, R. Michael Lawrence, and Christopher G. Parker. "Evaluation of fully-functionalized diazirine tags for chemical proteomic applications." Chemical Science 12, no. 22 (2021): 7839–47. http://dx.doi.org/10.1039/d1sc01360b.

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The chemical proteomic properties of five diazirine-based, fully-functionalized photoaffinity tags, including a newly developed, minimal tag, were compared. This study provides guidance for the development of new photoaffinity probes.

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18

Smith, Christine C., Marcel Hollenstein, and Christian J. Leumann. "The synthesis and application of a diazirine-modified uridine analogue for investigating RNA–protein interactions." RSC Adv. 4, no. 89 (2014): 48228–35. http://dx.doi.org/10.1039/c4ra08682a.

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A uridine analogue equipped with a photoactive diazirine unit was generated and incorporated into RNA either syntheticallyviaphosphoramidite chemistry or by enzymatic polymerization. The new analogue was developed to identify and investigate RNA–protein interactions.

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19

Bexis, Panagiotis, Maria C. Arno, Craig A. Bell, Anthony W. Thomas, and Andrew P. Dove. "Thermally-induced hyperbranching of bromine-containing polyesters by insertion of in situ generated chain-end carbenes." Chemical Communications 57, no. 35 (2021): 4275–78. http://dx.doi.org/10.1039/d1cc00821h.

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Thermolysis of a diazirine end group of a Br-functional PCL leads to carbene generation and subsequent hyperbranched polymers. Grafting of a hydrophilic PEG yields amphiphilic polymers which self-assemble into spherical core–shell nanoparticles.

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20

Bauer, Claudia C., Aisling Minard, Isabelle B. Pickles, Katie J. Simmons, Eulashini Chuntharpursat-Bon, Matthew P. Burnham, Nikil Kapur, et al. "Xanthine-based photoaffinity probes allow assessment of ligand engagement by TRPC5 channels." RSC Chemical Biology 1, no. 5 (2020): 436–48. http://dx.doi.org/10.1039/d0cb00126k.

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Diazirine-containing photoaffinity probes, based on the potent and selective TRPC1/4/5 channel inhibitor Pico145, allowed the development of an assay to probe cellular interactions between TRPC5 protein and xanthine-based TRPC5 channel modulators.

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21

Zhang, Huimin, Yanling Song, Yuan Zou, Yun Ge, Yuan An, Yanli Ma, Zhi Zhu, and Chaoyong James Yang. "A diazirine-based photoaffinity probe for facile and efficient aptamer–protein covalent conjugation." Chem. Commun. 50, no. 38 (2014): 4891–94. http://dx.doi.org/10.1039/c4cc01528b.

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A photo-reactive functional labelling reagent was designed and synthesized for site-specific labelling of oligonucleotide with the diazirine moiety for facile and efficient photo-crosslinking of the resulting oligonucleotide with its interacting partner for a variety of applications.

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22

Nakamoto, Kosuke, Koichiro Minami, Yukihiro Akao, and Yoshihito Ueno. "Labeling of target mRNAs using a photo-reactive microRNA probe." Chemical Communications 52, no. 40 (2016): 6720–22. http://dx.doi.org/10.1039/c6cc01360k.

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To identify target mRNAs of an miRNA, we synthesized photo-reactive miRNA probes, which contained a photo-reactive nucleoside analog, 1-O-[4-(3-trifluoromethyl-3H-diazirine-3-yl)]benzyl-β-d-ribofuranose, in the middle of the strand.

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23

Shustov, G. V., S. V. Varlamov, A. Rauk, and R. G. Kostyanovskii. "Chiroptical properties of the diazirine chromophore." Journal of the American Chemical Society 112, no. 9 (April 1990): 3403–8. http://dx.doi.org/10.1021/ja00165a024.

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24

Elson, Clive M., Michael T. H. Liu, and Colin Mailer. "E.s.r. studies of diazirine anion radicals." Journal of the Chemical Society, Chemical Communications, no. 7 (1986): 504. http://dx.doi.org/10.1039/c39860000504.

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25

Taranenko, M., M. Mtchedlidze, N. Sumbatyan, and G. Korshunova. "A Zero-Length Diazirine Photoactive Nucleoside." Nucleosides, Nucleotides and Nucleic Acids 22, no. 5-8 (October 2003): 715–17. http://dx.doi.org/10.1081/ncn-120022617.

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26

Ismael, Amin, Manabu Abe, Rui Fausto, and Maria L. S. Cristiano. "Insights into the photochemistry of 5-aminotetrazole derivatives with applications in coordination chemistry. Effect of the saccharyl moiety on the photostability." Pure and Applied Chemistry 92, no. 1 (January 28, 2020): 49–62. http://dx.doi.org/10.1515/pac-2019-0402.

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AbstractThe properties and applications of 2-methyl-(2H)-tetrazole-5-amino-saccharinate (2MTS) in catalysis and chelant-based chemotherapy stimulated investigations on its photostability. The photochemistry of monomeric 2MTS in solid argon (15 K) was compared with those of 2-methyl-(2H)-tetrazole-5-amine (2MT) and 1-methyl-(2H)-tetrazole-5-amine (1MT). Compounds were subjected to in situ narrowband UV-irradiation at different wavelengths. Reactions were followed by infrared spectroscopy, supported by B3LYP/6-311++G(d,p) calculations. Photochemical pathways for 2MT and 2MTS proved similar but photodegradation of 2MTS was 20× slower, unraveling the photostabilizing effect of the saccharyl moiety that extends into the nitrilimine formed from 2MTS and its antiaromatic 1H-diazirene isomer, which proved photostable at 290 nm, unlike the 1H-diazirene formed from 2MT. Analysis of the photochemistries of 2MTS/2MT (250 nm) and 1MT (222 nm), including energy trends calculated for the isomeric C2H5N3 species postulated/observed from photolysis and EPR results, enabled a deeper insight into the photodegradation mechanisms of 1,5-substituted and 2,5-substituted tetrazoles. We postulate a pivotal singlet state imidoylnitrene species, sN1, as common intermediate, which undergoes a Wolff-type isomerization to a stable carbodiimide. Photo-extrusion of N2 from 1,5-substituted tetrazoles generates sN1 directly but from 2,5-substituted tetrazoles it originates a nitrilimine, then a diazirene, which finally leads to sN1. Selective formation of cyanamide from 1MT requires photoisomerization between sN1 and sN2, accessible at 222 nm. EPR studies enabled the detection of methyl nitrene, arising from photolysis of 1H-diazirene intermediate.

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27

Murtihapsari, Murtihapsari, Amir M. Suruwaky, Kadarusman Kadarusman, Dikdik Kurnia, Tati Herlina, and Unang Supratman. "A New Antiplasmodial Compound from the Papuan Marine Sponge Xestospongia sp." Jurnal Kimia VALENSI 4, no. 1 (May 31, 2018): 1–6. http://dx.doi.org/10.15408/jkv.v4i1.6735.

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A new antiplasmodial compound, 2-(3H-diazirine-3-yl)benzaldehyde (1), has been isolated from the Papuan marine sponge Xestospongia sp. The structure elucidation of compound 1 was determined by spectroscopic evidences including UV, IR, MS, 1D and 2D-NMR analysis. Compound 1 showed moderate antiplasmodial activity against Plasmodium falciparum with IC50 value of 1.08 x 10-6 mM. DOI:http://dx.doi.org/10.15408/jkv.v4i1.6735

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28

Kolářová, Petra, Václav Čmolík, Igor Linhart, Ignacio Álvarez Martínez, and Tomáš Martinů. "Nitrenic reactivity of diazirines." Tetrahedron Letters 54, no. 49 (December 2013): 6764–67. http://dx.doi.org/10.1016/j.tetlet.2013.10.001.

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29

Vasella, Andrea, Bruno Bernet, Martin Weber, and Wolfgang Wenger. "ChemInform Abstract: Glycosylidene Diazirines." ChemInform 32, no. 12 (March 20, 2001): no. http://dx.doi.org/10.1002/chin.200112276.

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30

Albertoni, Barbara, Jeffrey S. Hannam, Damian Ackermann, Anton Schmitz, and Michael Famulok. "A trifluoromethylphenyl diazirine-based SecinH3 photoaffinity probe." Chem. Commun. 48, no. 9 (2012): 1272–74. http://dx.doi.org/10.1039/c2cc16477a.

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31

Isaev, S. D., V. P. Sherstyuk, U. F. Kozlov, V. V. Skripkin, and I. Yanku. "Photolysis of adamantane-2-spiru-3?-diazirine." Theoretical and Experimental Chemistry 27, no. 2 (March 1991): 192–99. http://dx.doi.org/10.1007/bf01372474.

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32

Hashimoto, Makoto, and Yasumaru Hatanaka. "Recent Progress in Diazirine-Based Photoaffinity Labeling." European Journal of Organic Chemistry 2008, no. 15 (May 2008): 2513–23. http://dx.doi.org/10.1002/ejoc.200701069.

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33

Tippmann, Eric M., Wenshe Liu, Daniel Summerer, Antha V. Mack, and Peter G. Schultz. "A Genetically Encoded Diazirine Photocrosslinker inEscherichia coli." ChemBioChem 8, no. 18 (December 17, 2007): 2210–14. http://dx.doi.org/10.1002/cbic.200700460.

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34

Djordjevic, Ivan, Gautama Wicaksono, Ivan Solic, and Terry W. J. Steele. "In Vitro Biocompatibility of Diazirine‐Grafted Biomaterials." Macromolecular Rapid Communications 41, no. 21 (September 22, 2020): 2000235. http://dx.doi.org/10.1002/marc.202000235.

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35

Dzichenka, Ya U., M. S. Horetski, Ya V. Faletrov, A. V. Yantsevich, V. M. Shkumatov, and S. A. Usanov. "In silico analysis of interaction of compounds, containing photoactivatable groups,with human CYP7 enzymes." Doklady of the National Academy of Sciences of Belarus 64, no. 5 (November 5, 2020): 558–66. http://dx.doi.org/10.29235/1561-8323-2020-64-5-558-566.

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In silico analysis of “protein-ligand” complexes of human CYP7 enzymes with modified borondipyrrome-tene (BODIPY) and steroids, containing photo-activated crosslinking groups, wasperformed in order to identify structural peculiarities of their interaction. It was found that BODIPY molecules and DHEA derivative with diazirine group are able to bind tightly with human steroid-hydroxylases. Binding affinity is comparable with corresponding values for essential ligands of the enzymes. Binding mode of the modified steroid corresponds to the binding mode of essential CYP7 ligands, so formation of hydroxylated products is possible. It was found that presence of both diazirine and NBD groups in a molecule significantly increases affinity of the compound in case of CYP7A1 and, especially, CYP7B1. Amino acid residues, located in a close proximity with photo-activated groups were detected, that can form covalent adducts with them. The obtained results can shed light on the mechanism of interaction of the compounds with recombinant human CYP7 enzymes in vitro. The results can also be used for the identification of modified amino acids of the proteins that are formed under photoactivation of the compounds in vitro.

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36

Wu, Guojiao, Xia Zhao, Wenzhi Ji, Yan Zhang, and Jianbo Wang. "Metal-free oxidative cross-coupling of diazirines with arylboronic acids." Chemical Communications 52, no. 9 (2016): 1961–63. http://dx.doi.org/10.1039/c5cc08855k.

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37

Vogt, Jürgen, and Alberto Gambi. "The Infrared Spectrum of Diazirine, H2C15N2 Rovibrational Analysis of the V3 Fundamental." Zeitschrift für Naturforschung A 41, no. 9 (September 1, 1986): 1159–65. http://dx.doi.org/10.1515/zna-1986-0911.

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The mid-infrared spectrum of 15N-labeled diazirine has been recorded using a Fourier transform spectrometer at a resolution of 0.08 cm-1. The v3 fundamental at 1452.49 cm-1 which essentially corresponds to a symmetric methylene deformation has been analyzed in detail. The rovibrational assignment is given and, using Watson’s A-reduced Hamiltonian, the rotational and centrifugal distortion constants for the v3 = 1 level could be determined.

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38

Bonneure, Eli, Amber De Baets, Sam De Decker, Koen Van den Berge, Lieven Clement, Wim Vyverman, and Sven Mangelinckx. "Altering the Sex Pheromone Cyclo(l-Pro-l-Pro) of the Diatom Seminavis robusta towards a Chemical Probe." International Journal of Molecular Sciences 22, no. 3 (January 21, 2021): 1037. http://dx.doi.org/10.3390/ijms22031037.

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As a major group of algae, diatoms are responsible for a substantial part of the primary production on the planet. Pennate diatoms have a predominantly benthic lifestyle and are the most species-rich diatom group, with members of the raphid clades being motile and generally having heterothallic sexual reproduction. It was recently shown that the model species Seminavis robusta uses multiple sexual cues during mating, including cyclo(l-Pro-l-Pro) as an attraction pheromone. Elaboration of the pheromone-detection system is a key aspect in elucidating pennate diatom life-cycle regulation that could yield novel fundamental insights into diatom speciation. This study reports the synthesis and bio-evaluation of seven novel pheromone analogs containing small structural alterations to the cyclo(l-Pro-l-Pro) pheromone. Toxicity, attraction, and interference assays were applied to assess their potential activity as a pheromone. Most of our analogs show a moderate-to-good bioactivity and low-to-no phytotoxicity. The pheromone activity of azide- and diazirine-containing analogs was unaffected and induced a similar mating behavior as the natural pheromone. These results demonstrate that the introduction of confined structural modifications can be used to develop a chemical probe based on the diazirine- and/or azide-containing analogs to study the pheromone-detection system of S. robusta.

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39

Shustov, Gennady V., Michael TH Liu, and K. N. Houk. "Facile formation of azines from reactions of singlet methylene and dimethylcarbene with precursor diazirines: theoretical explorations." Canadian Journal of Chemistry 77, no. 5-6 (June 1, 1999): 540–49. http://dx.doi.org/10.1139/v99-012.

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The reactions of the singlet methylene (1a) and dimethylcarbene (1b), with their diazirine precursors, diazirine (2a), and dimethyldiazirine (2b), have been studied theoretically using ab initio and density functional theory. The reaction has no activation barriers for the parent system (1a + 2a) and proceeds via a reactive complex and a transition state with a small negative enthalpy of activation Δ Hnot =298 = -1.1 kcal mol-1, ΔSnot =298 = -34.4 cal mol-1 K-1, ΔG°298 = 9.2 kcal mol-1) for the dimethyl derivatives (1b + 2b). The formation of N-methylene diazirinium ylides (3a,b) is exothermic by 64-80 kcal mol-1. The isomer, 1,3-diazabicyclo[1.1.0]butane (4a), is more stable (5-12 kcal mol-1) than isomer 3a, but can neither be formed by direct thermal reaction of 1a with 2a nor undergo the direct rearrangement into formaldazine (5a). The rearrangement of ylides 3a,b into azines 5a,b proceeds by conrotatory C3-N1 ring opening. The predicted activation barrier of ca. 15 kcal mol-1 for the ring opening in ylide 3b is in excellent agreement with experimental data. The formation of pyridinium ylides from carbenes and pyridine is also studied.Key words: diazirinium ylide, ab initio MO (molecular orbital) theory, density functional theory, pyridinium ylide, CIS (singles configuration interaction) transition energies.

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40

Citarella, Andrea, Davide Moi, Martina Pedrini, Helena Pérez-Peña, Stefano Pieraccini, Claudio Stagno, Nicola Micale, et al. "Discovery of a Novel Trifluoromethyl Diazirine Inhibitor of SARS-CoV-2 Mpro." Molecules 28, no. 2 (January 4, 2023): 514. http://dx.doi.org/10.3390/molecules28020514.

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SARS-CoV-2 Mpro is a chymotrypsin-like cysteine protease playing a relevant role during the replication and infectivity of SARS-CoV-2, the coronavirus responsible for COVID-19. The binding site of Mpro is characterized by the presence of a catalytic Cys145 which carries out the hydrolytic activity of the enzyme. As a consequence, several Mpro inhibitors have been proposed to date in order to fight the COVID-19 pandemic. In our work, we designed, synthesized and biologically evaluated MPD112, a novel inhibitor of SARS-CoV-2 Mpro bearing a trifluoromethyl diazirine moiety. MPD112 displayed in vitro inhibition activity against SARS-CoV-2 Mpro at a low micromolar level (IC50 = 4.1 μM) in a FRET-based assay. Moreover, an inhibition assay against PLpro revealed lack of inhibition, assuring the selectivity of the compound for the Mpro. Furthermore, the target compound MPD112 was docked within the binding site of the enzyme to predict the established intermolecular interactions in silico. MPD112 was subsequently tested on the HCT-8 cell line to evaluate its effect on human cells’ viability, displaying good tolerability, demonstrating the promising biological compatibility and activity of a trifluoromethyl diazirine moiety in the design and development of SARS-CoV-2 Mpro binders.

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41

Oettmeier, Walter, Hans-Joachim Soli, and Ellen Olschewski. "Photoaffinity Labeling of Spinach Thylakoids and Cytochrome b6/f-Complex by the Hydrophobic Reagent 3-(Trifluoromethyl)-3-(m-[125I]iodophenyl)-diazirine." Zeitschrift für Naturforschung C 40, no. 5-6 (June 1, 1985): 454–56. http://dx.doi.org/10.1515/znc-1985-5-629.

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Abstract In isolated spinach thylakoids the hydrophobic photoreactive probe 3-(trifluoromethyl)-3-(m-[125I]iodophenyl-diazirine almost exclusively labels the photosystem I reaction center and the light-harvesting chlorophyll a/b protein. In isolated cytochrome b6/f-complex, all four components of the complex get labeled, but to a different extent. The amount of labeling in the protein components is correlated to the number of polypeptide segments embedded in the membrane system.

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42

Chou, Chungjung, Rajendra Uprety, Lloyd Davis, Jason W. Chin, and Alexander Deiters. "Genetically encoding an aliphatic diazirine for protein photocrosslinking." Chem. Sci. 2, no. 3 (2011): 480–83. http://dx.doi.org/10.1039/c0sc00373e.

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43

Bonneau, Roland, and Michael T. H. Liu. "Kinetic and Spectroscopic Properties of Carbene−Diazirine Ylides." Journal of Physical Chemistry A 104, no. 17 (May 2000): 4115–20. http://dx.doi.org/10.1021/jp993711w.

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44

Hosu, Oana, Kamal Elouarzaki, Karine Gorgy, Cecilia Cristea, Robert Sandulescu, Robert S. Marks, and Serge Cosnier. "Nanostructured photoactivatable electrode surface based on pyrene diazirine." Electrochemistry Communications 80 (July 2017): 5–8. http://dx.doi.org/10.1016/j.elecom.2017.05.002.

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45

Liu, M. T. H., and J. E. Chateauneuf. "Self quenching reaction of (Phenoxymethyl)chlorocarbene with diazirine." Research on Chemical Intermediates 20, no. 2 (January 1994): 195–99. http://dx.doi.org/10.1163/156856794x00199.

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46

Hashimoto, Makoto, Shun'ji Okamoto, Kensuke Nabeta, and Yasumaru Hatanaka. "Enzyme cleavable and biotinylated photoaffinity ligand with diazirine." Bioorganic & Medicinal Chemistry Letters 14, no. 10 (May 2004): 2447–50. http://dx.doi.org/10.1016/j.bmcl.2004.03.011.

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Hentschel, Fabia, Björn Raimer, Gerhard Kelter, Heinz-Herbert Fiebig, Florenz Sasse, and Thomas Lindel. "Synthesis and Cytotoxicity of a Diazirine-Based Photopsammaplin." European Journal of Organic Chemistry 2014, no. 10 (January 31, 2014): 2120–27. http://dx.doi.org/10.1002/ejoc.201301717.

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Moss, Robert A. "Diazirines: Carbene Precursors Par Excellence." Accounts of Chemical Research 39, no. 4 (April 2006): 267–72. http://dx.doi.org/10.1021/ar050155h.

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Zeng, Xiaoqing, Helmut Beckers, Helge Willner, and John F. Stanton. "Das schwer fassbare Diazirinon, N2CO." Angewandte Chemie 123, no. 7 (January 11, 2011): 1758–61. http://dx.doi.org/10.1002/ange.201006745.

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Tachrim, Zetryana Puteri, Lei Wang, Yuta Murai, and Makoto Hashimoto. "New Trends in Diaziridine Formation and Transformation (a Review)." Molecules 26, no. 15 (July 26, 2021): 4496. http://dx.doi.org/10.3390/molecules26154496.

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This review focuses on diaziridine, a high strained three-membered heterocycle with two nitrogen atoms that plays an important role as one of the most important precursors of diazirine photoaffinity probes, as well as their formation and transformation. Recent research trends can be grouped into three categories, based on whether they have examined non-substituted, N-monosubstituted, or N,N-disubstituted diaziridines. The discussion expands on the conventional methods for recent applications, the current spread of studies, and the unconventional synthesis approaches arising over the last decade of publications.

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