Background

farmaec

FARMAKOEKONOMIKA. Modern Pharmacoeconomics and Pharmacoepidemiology

ФАРМАКОЭКОНОМИКА. Современная фармакоэкономика и фармакоэпидемиология

2070-49092070-4933

IRBIS LLC

10.17749/2070-4909/farmakoekonomika.2023.198

farmaec-892

Research Article

REVIEW ARTICLES

ОБЗОРНЫЕ ПУБЛИКАЦИИ

The prospects for the use of vitamin B12 derivatives in pharmacology

О перспективах применения производных витамина В12 в фармакологии

https://orcid.org/0000-0002-2659-7998

Торшин

И. Ю.

Torshin

I. Yu.

к.ф-м.н., к.х.н., старший научный сотрудник ФИЦ «Информатика и управление» РАН

ул. Вавилова, д. 44, корп. 2, Москва 119333

PhD (Phys. Math.), PhD (Chem.), Senior Researcher, Federal Research Center “Computer Science and Control”, RAS

44 corp. 2 Vavilov Str., Moscow 119333

https://orcid.org/0000-0002-7663-710X

Громова

О. А.

Gromova

O. A.

д.м.н., профессор, ведущий научный сотрудник ФИЦ «Информатика и управление» РАН

ул. Вавилова, д. 44, корп. 2, Москва 119333

Dr. Med. Sc., Professor, Leading Researcher, Federal Research Center “Computer Science and Control”, RAS

44 corp. 2 Vavilov Str., Moscow 119333

unesco.gromova@gmail.com

https://orcid.org/0000-0003-3172-5621

Майорова

Л. А.

Maiorova

L. A.

д.ф-м.н., старший научный сотудник ФИЦ «Информатика и управление»

ул. Вавилова, д. 44, корп. 2, Москва 119333

Dr. Phys. Math. Sc., Senior Researcher, Federal Research Center “Computer Science and Control”, RAS

44 corp. 2 Vavilov Str., Moscow 119333

Федеральный исследовательский центр «Информатика и управление» Российской академии наукРоссияFederal Research Center “Computer Science and Control”, Russian Academy of SciencesRussian Federation

2023

10112023

163501511

2023

Торшин И.Ю., Громова О.А., Майорова Л.А.

Torshin I.Y., Gromova O.A., Maiorova L.A.

This work is licensed under a Creative Commons Attribution 4.0 License.

https://www.pharmacoeconomics.ru/jour/article/view/892

Background

Background. The structure of corrin tetrapyrrole macrocycles (compounds similar in structure to vitamin B12) is a kind of universal chemical template for targeted drug delivery, and the development of chemical sensors and antidotes.

Objective

Objective: systematization of information on targeted modulation of certain corrins’ properties through chemical modifications.

Material and methods

Material and methods. Literature analysis using modern methods of topological and metric data analysis was carried out. All relevant publications (n=863) were extracted from the PubMed/MEDLINE database on request “(cobalamin OR Cobyrinic OR vitamin B12) AND (Molecular Conformation [MeSH Terms] OR Vitamin B 12/*analogs & derivatives/*chemistry [MeSH Terms] OR Vitamin B 12/*chemistry [MeSH Terms] OR Structure-Activity Relationship [MeSH Terms])”.

Results

Results. Information was systematized on how it is possible to regulate the properties of vitamin B12 (cobalamin) derivatives by introducing specific substitutions of groups in the corrin ring, on chemical modifications of cobalamin derivatives, biosynthetic approaches to the synthesis of cobalamin derivatives, and the effects of interactions of these modified corrins with “small” inorganic and organic molecules.

Conclusion

Conclusion. The results obtained by systematic computer analysis of publications on corrins make it possible to reasonably form samples of candidate molecules for corrin studies in silico, in vitro, and in vivo.

Актуальность

Актуальность. Структура тетрапиррольных макроциклов корринов (соединений, схожих по строению с витамином В12) представляет собой своего рода универсальный химический шаблон для таргетной доставки лекарств, разработки химических сенсоров и антидотов.

Цель

Цель: систематизация информации о таргетной модуляции свойств корринов посредством химических модификаций.

Материал и методы

Материал и методы. Проведен анализ литературы с использованием современных методов топологического и метрического анализа данных. Из базы данных PubMed/MEDLINE были извлечены все релевантные публикации (n=863) по запросу “(cobalamin OR Cobyrinic OR vitamin B12) AND (Molecular Conformation [MeSH Terms] OR Vitamin B 12/*analogs & derivatives/*chemistry [MeSH Terms] OR Vitamin B 12/*chemistry [MeSH Terms] OR Structure-Activity Relationship [MeSH Terms])”.

Результаты

Результаты. Систематизирована информация о том, каким образом можно регулировать свойства производных витамина В12 (кобаламина) путем введения специфических замещений групп в корриновом кольце, о химических модификациях производных кобаламина, биосинтетических подходах к синтезу его производных и эффектах взаимодействий этих модифицированных корринов с «малыми» неорганическими и органическими молекулами.

Заключение

Заключение. Полученные результаты систематического компьютерного анализа публикаций о корринах позволяет обоснованно формировать выборки молекул – кандидатов для исследований корринов in silico, in vitro и in vivo.

Корриноидыцианокобаламинметаболиты витамина В12хемоинформатиказадача «структура – свойство»

Corrinoidscyanocobalaminvitamin B12 metaboliteschemoinformaticsstructure-property problem

Работа выполнена при поддержке гранта Российского научного фонда № 20-12-00175-п на базе ФГБОУ ВО «Ивановский государственный химико-технологический университет».

This work was supported by the grant of the Russian Science Foundation No. 20-12-00175-p on the base of Ivanovo State University of Chemistry and Technology.

References1

Rashka C., Hergalant S., Dreumont N., et al. Analysis of fibroblasts from patients with cblC and cblG genetic defects of cobalamin metabolism reveals global dysregulation of alternative splicing. Hum Mol Genet. 2020; 29 (12): 1969–85. https://doi.org/10.1093/hmg/ddaa027.

Vu T.T., Kharitonova N.V., Maiorova L.A., et al. Compression speed as a parameter changing the dimensionality of corrole nanostructures in layers at the air-water interface. Macroheterocycles. 2018; 11 (3): 286–92. https://doi.org/10.6060/mhc171260m.

Gromova O.A., Maiorova L.A., Torshin I.Y., et al. Vitamin B12 hydrophobic derivative exhibits bioactivity: biomedical and photophysical study. BioNanoSci. 2022; 12 (7): 74–82. https://doi.org/10.1007/s12668-021-00916-4.

Maiorova L.A., Vu T.T., Gromova O.A. Nanostructured stable floating m-monoand bilayers and langmuir-schaefer films of 5,10,15triphenylcorrole. BioNanoSci. 2018; 8 (1): 81–9. https://doi.org/10.1007/s12668-017-0424-0.

Maiorova L.A., Erokhina S.I., Pisani M., et al. Encapsulation of vitamin B12 into nanoengineered capsules and soft matter nanosystems for targeted delivery. Colloids Surf B Biointerfaces. 2019; 182: 110366. https://doi.org/10.1016/j.colsurfb.2019.110366.

Russell-Jones G.J., Westwood S.W., Habberfield A.D. Vitamin B12 mediated oral delivery systems for granulocyte-colony stimulating factor and erythropoietin. Bioconjug Chem. 1995; 6 (4): 459–65. https://doi.org/10.1021/bc00034a016.

Valkova L.A., Glibin A.S., Valli L. Quantitative analysis of compression isotherms of fullerene C60 Langmuir layers. Colloid J. 2008; 70: 6–11. https://doi.org/10.1134/S1061933X0801002X.

Valkova L.A., Glibin A.S., Koifman O.I. Influence of the solvent nature on the structure of two-dimensional nanoaggregates in langmuir layers of copper tetra-tert-butyltetrabenzotriazaporphyrin. Macroheterocycles. 2011; 4: 222–6.

Valkova L.A., Erokhin V.V., Glibin A.S., Koifman O.I. The influence of molecular structure and π-system extent on nanoand microstructure of Langmuir layers of copper azaporphyrins. J Porphyr Phthalocyanines. 2011; 15 (09n10): 1044–51. https://doi.org/10.1142/S1088424611004026.

Valkova L., Borovkov N., Maccioni E., et al. Influence of molecular and supramolecular factors on sensor properties of Langmuir–Blodgett films of tert-butyl-substituted copper azaporphyrines towards hydrocarbons. Colloids and Surfaces A: Physicochemical and Engineering Aspects. 2002; 198–200: 891–6. https://doi.org/10.1016/S0927-7757(01)01016-0.

Valkova L.A., Betrencourt C., Hochapfel A., et al. Monolayer study of monensin and lasalocid in the gas state. Molecular Crystals and Liquid Crystals Science and Technology. 1996; 287: 269–73. https://doi.org/10.1080/10587259608038763.

Valkova L.A., Shabyshev L.S., Feigin L.A., Akopova O.B. Formation and X-ray diffraction investigation of Langmuir-Blodgett films of liquid crystalline substituted crown esters. Molecular Crystals and Liquid Crystals Science and Technology. 1996; 6: 291–8.

Maiorova L.A., Kobayashi N., Salnikov D.S., et al. Supermolecular nanoentities of vitamin B12 derivative as a link in the evolution of the parent molecules during self-assembly at the air-water interface. Langmuir. 2023; 39: 3246–54. https://doi.org/10.1021/acs.langmuir.2c02964.

Карлюк М.В., Крыгин Ю.Ю., Майорова-Валькова Л.А. и др. Формирование двумерных (M) и трехмерных (V) наноагрегатов замещенного порфирина кобальта в ленгмюровских слоях и пленках Ленгмюра–Шефера. Известия Академии наук. Серия химическая. 2013; 62 (2): 471.

Karlyuk M.V., Krygin Y.Y., Maiorova-Valkova L.A., et al. Formation of two-dimensional (M) and three-dimensional (V) nanoaggregates of substituted cobalt porphyrin in the Langmuir layers and Langmuir–Schaefer films. Russian Chemical Bulletin. 2013; 62 (2): 471 (in Russ.).

Torshin I.Yu., Rudakov K.V. On metric spaces arising during formalization of recognition and classification problems. Part 1: Properties of compactness. Pattern Recognit Image Anal. 2016; 26 (2): 274–84. https://doi.org/10.1134/S1054661816020255.

Torshin I.Yu., Rudakov K.V. Combinatorial analysis of the solvability properties of the problems of recognition and completeness of algorithmic models. Part 2: Metric approach within the framework of the theory of classification of feature values. Pattern Recognit Image Anal. 2017; 27 (2): 184–99. https://doi.org/10.1134/S1054661817020110.

Torshin I.Yu., Rudakov K.V. On metric spaces arising during formalization of problems of recognition and classification. Part 2: Density properties. Pattern Recognit Image Anal. 2016; 26 (3): 483–96. https://doi.org/10.1134/S1054661816030202.

Proinsias K., Giedyk M., Gryko D. Vitamin B12: chemical modifications. Chem Soc Rev. 2013; 42 (16): 6605–19. https://doi.org/10.1039/c3cs60062a.

Bergmann K.H., Deeg R., Gneuss K.D., et al. On the preparation of intermediates in cobyrinic acid biosynthesis by suspensions of Propionibacterium shermanii (author's transl). Hoppe Seylers Z Physiol Chem. 1977; 358 (10): 1315–23 (in German).

Kiuchi F., Leeper F.J., Battersby A.R. Biosynthesis of porphyrins and related macrocycles, Part 43. Isolation and characterization of intermediates of coenzyme B12 biosynthesis, a cobyrinic acid triamide, the a,c-diamide and their Co-(5'-deoxy-5'-adenosyl) derivatives, from Propionibacterium. Chem Biol. 1995; 2 (8): 527–32. https://doi.org/10.1016/1074-5521(95)90186-8.

Raux E., Lanois A., Rambach A., et al. Cobalamin (vitamin B12) biosynthesis: functional characterization of the Bacillus megaterium cbi genes required to convert uroporphyrinogen III into cobyrinic acid a,cdiamide. Biochem J. 1998; 335 (Pt. 1): 167–73. https://doi.org/10.1042/bj3350167.

Moore S.J., Lawrence A.D., Biedendieck R., et al. Elucidation of the anaerobic pathway for the corrin component of cobalamin (vitamin B12). Proc Natl Acad Sci U S A. 2013; 110 (37): 14906–11. https://doi.org/10.1073/pnas.1308098110.

Roessner C.A., Huang K.X., Warren M.J., et al. Isolation and characterization of 14 additional genes specifying the anaerobic biosynthesis of cobalamin (vitamin B12) in Propionibacterium freudenreichii (P. shermanii). Microbiology (Reading). 2002; 148 (Pt. 6): 1845–53. https://doi.org/10.1099/00221287-148-6-1845.

Santander P.J., Roessner C.A., Stolowich N.J., et al. How corrinoids are synthesized without oxygen: nature's first pathway to vitamin B12. Chem Biol. 1997; 4 (9): 659–66. https://doi.org/10.1016/s10745521(97)90221-0.

Fresquet V., Williams L., Raushel F.M. Partial randomization of the four sequential amidation reactions catalyzed by cobyric acid synthetase with a single point mutation. Biochemistry. 2007; 46 (49): 13983–93. https://doi.org/10.1021/bi7016238.

Roderique J.D., Josef C.S., Newcomb A.H., et al. Preclinical evaluation of injectable reduced hydroxocobalamin as an antidote to acute carbon monoxide poisoning. J Trauma Acute Care Surg. 2015; 79 (4 Suppl. 2): S116–20. https://doi.org/10.1097/TA.0000000000000740.

Ma J., Dasgupta P.K., Zelder F.H., Boss G.R. Cobinamide chemistries for photometric cyanide determination. A merging zone liquid core waveguide cyanide analyzer using cyanoaquacobinamide. Anal Chim Acta. 2012; 736: 78–84. https://doi.org/10.1016/j.aca.2012.05.028.

Polaczek J., Subedi H., Orzeł Ł., et al. Mechanistic studies on the reaction between aquacobalamin and the HNO donor piloty's acid over a wide pH range in aqueous solution. Inorg Chem. 2021; 60 (5): 2964– 75. https://doi.org/10.1021/acs.inorgchem.0c02968.

Dassanayake R.S., Farhath M.M., Shelley J.T., et al. Kinetic studies on the reaction of cob(II)alamin with hypochlorous acid: Evidence for one electron oxidation of the metal center and corrin ring destruction. J Inorg Biochem. 2016; 163: 81–7. https://doi.org/10.1016/j. jinorgbio.2016.07.009. 30. Dereven'kov I.A., Shpagilev N.I., Valkai L., et al. Reactions of aquacobalamin and cob(II)alamin with chlorite and chlorine dioxide. J Biol Inorg Chem. 2017; 22 (4): 453–9. https://doi.org/10.1007/s00775-016-1417-0.

Dereven'kov I.A., Shpagilev N.I., Valkai L., et al. Reactions of aquacobalamin and cob(II)alamin with chlorite and chlorine dioxide. J Biol Inorg Chem. 2017; 22 (4): 453–9. https://doi.org/10.1007/s00775-016-1417-0.

Lehene M., Plesa D., Ionescu-Zinca S., et al. Adduct of aquacobalamin with hydrogen peroxide. Inorg Chem. 2021; 60 (17): 12681– 4. https://doi.org/10.1021/acs.inorgchem.1c01483.

Salnikov D.S., Makarov S.V., van Eldik R., et al. Kinetics and mechanism of the reaction of hydrogen sulfide with diaquacobinamide in aqueous solution. Eur J Inorg Chem. 2014; 2014 (25): 4123–33. https://doi.org/10.1002/ejic.201402082.

Ozturk E., Karabulut D., Akin A.T., et al. Evaluation by different mechanisms of the protective effects of vitamin B12 on methotrexate nephrotoxicity. J Mol Histol. 2022; 53 (1): 133–43. https://doi.org/10.1007/s10735-021-10027-9.

Dereven'kov I.A., Sakharova E.S., Osokin V.S., Makarov S.V. Aquacobalamin accelerates Orange II destruction by peroxymonosulfate via the transient formation of secocorrinoid: a mechanistic study. Int J Mol Sci. 2022; 23 (19): 11907. https://doi.org/10.3390/ijms231911907.

Mukherjee R., McCaddon A., Smith C.A., Brasch N.E. Synthesis, synchrotron X-ray diffraction, and kinetic studies on the formation of a novel thiolatocobalamin of captopril: evidence for cis-trans isomerization in the beta-axial ligand. Inorg Chem. 2009; 48 (19): 9526– 34. https://doi.org/10.1021/ic900891y.

Hannibal L., Bunge S.D., van Eldik R., et al. X-ray structural characterization of imidazolylcobalamin and histidinylcobalamin: cobalamin models for aquacobalamin bound to the B12 transporter protein transcobalamin. Inorg Chem. 2007; 46 (9): 3613–8. https://doi.org/10.1021/ic070022n.

Dereven'kov I.A., Hannibal L., Makarov S.V., Molodtsov P.A. Catalytic effect of riboflavin on electron transfer from NADH to aquacobalamin. J Biol Inorg Chem. 2020; 25 (1): 125–33. https://doi.org/10.1007/s00775-019-01745-3.

Chemaly S.M., Brown K.L., Fernandes M.A., et al. Probing the nature of the Co(III) ion in corrins: the structural and electronic properties of dicyanoand aquacyanocobyrinic acid heptamethyl ester and a stable yellow dicyanoand aquacyanocobyrinic acid heptamethyl ester. Inorg Chem. 2011; 50 (18): 8700–18. https://doi.org/10.1021/ic200285k.

Chemaly S.M., Florczak M., Dirr H., Marques H.M. Probing the nature of the Co(III) ion in corrins: a comparison of the thermodynamics and kinetics of the ligand substitution reactions of aquacyanocobyrinic acid heptamethyl ester and stable yellow aquacyanocobyrinic acid heptamethyl ester. Inorg Chem. 2011; 50 (18): 8719–27. https://doi.org/10.1021/ic200288b.

Chemaly S.M., Kendall L., Nowakowska M., et al. Probing the nature of the Co(III) ion in corrins: comparison of reactions of aquacyanocobyrinic acid heptamethyl ester and aquacyano-stable yellow cobyrinic acid hexamethyl ester with neutral N-donor ligands. Inorg Chem. 2013; 52 (2): 1077–83. https://doi.org/10.1021/ic302386u.

Dereven'kov I.A., Hannibal L., Makarov S.V., et al. Characterization of the complex between native and reduced bovine serum albumin with aquacobalamin and evidence of dual tetrapyrrole binding. J Biol Inorg Chem. 2018; 23 (5): 725–38. https://doi.org/10.1007/s00775-0181562-8.

Alam A., Woo J.S., Schmitz J., et al. Structural basis of transcobalamin recognition by human CD320 receptor. Nat Commun. 2016; 7: 12100. https://doi.org/10.1038/ncomms12100.

Seetharam B., Yammani R.R. Cobalamin transport proteins and their cell-surface receptors. Expert Rev Mol Med. 2003; 5 (18): 1–18. https://doi.org/10.1017/S1462399403006422.

Furger E., Frei D.C., Schibli R., et al. Structural basis for universal corrinoid recognition by the cobalamin transport protein haptocorrin. J Biol Chem. 2013; 288 (35): 25466–76. https://doi.org/10.1074/jbc.M113.483271.

Giedyk M., ó Proinsias K., Kurcoń S., et al. Small alterations in cobinamide structure significantly influence sGC activation. ChemMedChem. 2014; 9 (10): 2344–50. https://doi.org/10.1002/cmdc.201402209.

Gromova O.A., Torshin I.Yu., Maiorova L.A., et al. Bioinformatic and chemoneurocytological analysis of the pharmacological properties of vitamin B12 and some of its derivatives. Journal of Porphyrins and Phthalocyanines. 2021; 25 (9): 835–42. https://doi.org/10.1142/S1088424621500644.

Zhong L., Zhou J., Chen X., et al. Quantitative proteomics study of the neuroprotective effects of B12 on hydrogen peroxide-induced apoptosis in SH-SY5Y cells. Sci Rep. 2016; 6: 22635. https://doi.org/10.1038/srep22635.

Bucca C.B., Culla B., Guida G., et al. Unexplained chronic cough and vitamin B-12 deficiency. Am J Clin Nutr. 2011; 93 (3): 542–8. https://doi.org/10.3945/ajcn.110.000802.

Takahata Y., Nishizawa A., Kojima I., et al. Synthesis, properties and microbiological activity of hydrophobic derivatives of vitamin B12. J Nutr Sci Vitaminol (Tokyo). 1995; 41 (5): 515–26. https://doi.org/10.3177/jnsv.41.515.

The authors declare that there are no conflicts of interest present.