Vitamin B12 Hydrophobic Derivative Exhibits Bioactivity: Biomedical and Photophysical Study

Громова, О. А.; Maiorova, Larissa A.; Salnikov, Denis S.; Демидов, В. И.; Калачева, А. Г.; Torshin, I. Yu.; Bogacheva, T. E.; Громов, А. Н.; Лиманова, О. А.; Гришина, Т. Р.; Jafari, S M; Койфман, О. И.

doi:10.1007/s12668-021-00916-4

Cited by 8 publications

(3 citation statements)

References 27 publications

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“…Vitamin B 12 , which plays an essential role in living organisms, is a porphyrin-type biomolecule containing a central cobalt ion bound to a corrin ring. Vitamin B 12 derivatives, in particular, aquacyanocobyrinic acid heptamethyl ester, which is soluble in a wide range of organic solvents, have the same corrin ring as the natural vitamin B 12 , and their Co 3+ ion is reversibly reduced to Co 2+ and Co 1+ , which allows them to catalyze a wide variety of redox reactions. , Recently, we have shown that this compound exhibits biological activity, restoring the myelin sheath of neurons, and can be encapsulated for targeted delivery . Biomolecules used in synthetic biology can be a source of natural reactivity that can be molded by directed evolution to generate efficient entities with valuable activities.…”

Section: Introductionmentioning

confidence: 99%

Supermolecular Nanoentities of Vitamin B₁₂ Derivative as a Link in the Evolution of the Parent Molecules During Self-Assembly at the Air–Water Interface

et al. 2023

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Nanoarchitectures with promising properties have now been formed from many important biomolecules. However, the preparation of nanoparticles of vitamin B 12 and its derivatives remains an ongoing research challenge. This paper describes the formation of supermolecular nanoentities (SMEs) of vitamin B 12 derivatives, unique nanoparticles with strong noncovalent intermolecular interactions, emerging properties, and activity. These were created by a nanoarchitectonic approach using directed assembly of layers at the air−water interface as a link in the chain of evolution of the parent molecules under specially created conditions. Such layers can be represented as a nanocosm, where, at a critical density, the assemblies act as nanoreactors in which the transformation of the original material occurs. The discovered SMEs not only replicate the functioning of vitamin B 12 assemblies with proteins in living organisms and act as vitamin B 12 -depended enzymes but also demonstrate important advantages over vitamin B 12 . They are more efficient in oxygen reduction/evolution reactions and in transformation into other forms. These SMEs, in performing advanced tasks, are an alternative to widely used materials based on noble metals for catalysis, medicine, and environment protection. Our findings open new perspectives both for the fabrication of novel SMEs of biomolecules and for a better understanding of the evolution of biomolecules in nature.

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Section: Introductionmentioning

confidence: 99%

Supermolecular Nanoentities of Vitamin B₁₂ Derivative as a Link in the Evolution of the Parent Molecules During Self-Assembly at the Air–Water Interface

et al. 2023

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“…These facts explain the higher efficacy of Cbis as a cyanide antidote in comparison with H 2 OCbl. − In contrast to H 2 OCbl, Cbis have been successfully employed as hydrogen sulfide antidotes as well. − The reaction between aquahydroxocobinamide and H 2 S proceeds more rapidly than that involving H 2 OCbl and results in the reduction of Co(III) ion to Co(II) and its sulfur-containing species (viz., Co(II)-S • – and Co(II)-SSH •2– ) via the transient generation of Co(III)-hydrosulfido complexes. We have shown that vitamin B 12 derivatives, in particular aquacyanocobyrinic acid heptamethyl ester (heptamethyl cobyrinate), exhibit biological activity, restoring the myelin sheath of neurons, and can be encapsulated for targeted delivery …”

Section: Introductionmentioning

confidence: 99%

“…We have shown that vitamin B 12 derivatives, in particular aquacyanocobyrinic acid heptamethyl ester (heptamethyl cobyrinate), exhibit biological activity, restoring the myelin sheath of neurons, 19 and can be encapsulated for targeted delivery. 20 Cobalamins and their derivatives represent a promising platform for the development of chemosensors toward toxins as well.…”

Section: ■ Introductionmentioning

confidence: 99%

High Reactivity of Supermolecular Nanoentities of a Vitamin B₁₂ Derivative in Langmuir–Schaefer Films Toward Gaseous Toxins

Dereven’kov,

Maiorova,

Koifman

et al. 2023

Langmuir

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Effect of bovine serum albumin on the water solubility of hydrophobic corrinoids

Dereven’kov

Dzvinkas

Osokin

et al. 2023

J. Porphyrins Phthalocyanines

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Medicinal effects of hydrophobic derivatives of vitamin [Formula: see text] have been insignificantly investigated primarily due to their low solubility in aqueous solutions. One of the ways to increase their water solubility is the complexation with proteins. Here, we report the results of the studies of the reactions between aquacyano cobyrinic acid or monocyano cobesters (i.e., heptamethyl, heptaethyl, heptapropyl, and heptabutyl cobyrinates) and bovine serum albumin (BSA). The weakest binding is observed between aquacyano cobyrinic acid and BSA. In the case of monocyano heptaethyl cobyrinate, one BSA molecule is capable of binding up to six corrinoid molecules preventing its precipitation. Moreover, the pronounced effect of BSA on the solubility in water was observed in the case of monocyano heptapropyl cobyrinate. The absence of the precipitation of monocyano heptabutyl cobyrinate was observed only in the presence of high excess of BSA. BSA modification by diethyl pyrocarbonate, a chemical predominantly reactive toward imidazole motifs, indicated that a major fraction of BSA is bound with monocyano heptaethyl, heptapropyl, and heptabutyl cobyrinates via histidine residues. We showed that nitrosyl complexes of heptaethyl and heptapropyl cobyrinates can be stabilized from precipitation in aqueous solutions using BSA.

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Vitamin B12 Hydrophobic Derivative Exhibits Bioactivity: Biomedical and Photophysical Study

Cited by 8 publications

References 27 publications

Supermolecular Nanoentities of Vitamin B₁₂ Derivative as a Link in the Evolution of the Parent Molecules During Self-Assembly at the Air–Water Interface

Supermolecular Nanoentities of Vitamin B₁₂ Derivative as a Link in the Evolution of the Parent Molecules During Self-Assembly at the Air–Water Interface

High Reactivity of Supermolecular Nanoentities of a Vitamin B₁₂ Derivative in Langmuir–Schaefer Films Toward Gaseous Toxins

Effect of bovine serum albumin on the water solubility of hydrophobic corrinoids

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Vitamin B12 Hydrophobic Derivative Exhibits Bioactivity: Biomedical and Photophysical Study

Cited by 8 publications

References 27 publications

Supermolecular Nanoentities of Vitamin B12 Derivative as a Link in the Evolution of the Parent Molecules During Self-Assembly at the Air–Water Interface

Supermolecular Nanoentities of Vitamin B12 Derivative as a Link in the Evolution of the Parent Molecules During Self-Assembly at the Air–Water Interface

High Reactivity of Supermolecular Nanoentities of a Vitamin B12 Derivative in Langmuir–Schaefer Films Toward Gaseous Toxins

Effect of bovine serum albumin on the water solubility of hydrophobic corrinoids

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Supermolecular Nanoentities of Vitamin B₁₂ Derivative as a Link in the Evolution of the Parent Molecules During Self-Assembly at the Air–Water Interface

Supermolecular Nanoentities of Vitamin B₁₂ Derivative as a Link in the Evolution of the Parent Molecules During Self-Assembly at the Air–Water Interface

High Reactivity of Supermolecular Nanoentities of a Vitamin B₁₂ Derivative in Langmuir–Schaefer Films Toward Gaseous Toxins