Insights into the mechanism of binding of doxorubicin and a chlorin compound with 22-mer c-Myc G quadruplex

Shukla, Aishwarya; Kumari, Soni; Sankar, Muniappan; Nair, Maya S.

doi:10.1016/j.bbagen.2023.130482

Cited by 2 publications

(1 citation statement)

References 92 publications

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“…[5,6] The functionalization of readily accessible meso-tetraphenylporphyrins is important from a synthetic standpoint since these molecules have many potential uses in domains such as chemistry, biology, medicine, etc. [7][8][9][10][11] Porphyrin chemists are interested in the unsymmetrical β-substitution since it occurs in natural systems. Compared to substitution at the meso-position, β-substitution has substantially larger electronic and stearic effects and modulates the optical and electrochemical properties.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Structural and Redox Properties of Vanadyl β‐Cyanoporphyrin and its Utilization as Efficient Catalyst for Epoxidation of Olefins and Oxidative Bromination of Phenols

Kumari,

Prakash,

et al. 2024

Eur J Inorg Chem

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2‐Cyano‐5,10,15,20‐tetraphenylporphyrin [H2TPPCN] (1) having cyano group at one of β‐pyrrolic positions using nucleophilic substitution reaction of tetrabutylammonium cyanide (TBACN) on free‐base 2‐nitro‐5,10,15,20‐tetraphenylporphyrin, and its oxidovanadium(IV) complex [VIVOTPPCN] (2) were synthesized and characterised by various spectroscopic techniques. Single crystal X‐ray crystallography revealed quasi‐planar geometry for 1. Compounds 1 and 2 exhibited a red shift (λmax = 7–9 nm) in the Soret band relative to [MTPP] owing to the electron‐withdrawing effect of the cyano group at the β‐position. The first oxidation (∆E1/2 = 110–140 mV) and reduction potentials (∆E1/2 = 220–260 mV) of [MTPPCN] are anodically shifted relative to [MTPP]. 2 has been utilized as a catalyst for two reactions: epoxidation of olefins and bromination of phenols. The bromination of phenol using KBr/H2O2/HClO4 in water resulted in 100% conversion with a TOF value as high as 19.6 s–1 in 0.5 h. Using H2O2/NaHCO3 in a CH3CN/H2O solvent mixture at 60 °C, epoxidation was carried out, and the highest conversion rate with a turnover frequency of 1.9 s–1 was achieved in the case of cyclohexene. Catalyst 2 was recovered successfully at the end of the reaction up to 5 cycles and had good thermal stability, indicating its industrial viability and applicability.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Structural and Redox Properties of Vanadyl β‐Cyanoporphyrin and its Utilization as Efficient Catalyst for Epoxidation of Olefins and Oxidative Bromination of Phenols

Kumari,

Prakash,

et al. 2024

Eur J Inorg Chem

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The synthesis of highly nonplanar oxidovanadium(IV) porphyrins as robust catalysts for oxidative bromination of phenols in aqueous medium

Kumari,

Prakash,

Maurya

et al. 2024

J. Porphyrins Phthalocyanines

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Two new complexes, oxidovanadium(IV) 2,3,5,10,12,13,15,20-octaphenyl-7,8,17,18-tetrabromoporphyrin V(IV)O(OPP)Br4 (2), and oxidovanadium(IV) 2,3,5,10,12,13,15,20-octaphenyl-7,8,17,18-tetrachloroporphyrin V(IV)O(OPP)Cl4 (3) starting from oxidovanadium(IV) 2,3,5,10,12,13,15,20-octaphenylporphyrin V(IV)O(OPP) (1) have been prepared in good yields and characterized by various spectroscopic techniques. The single-crystal and DFT-optimized structures of these porphyrins showed a highly nonplanar saddle-shape conformation of the porphyrin macrocycle. In the cyclic voltammograms, the first ring oxidation potential and the first ring reduction potential of V(IV)O(OPP)Br4 (2) and V(IV)O(OPP)Cl4 (3) showed anodic shift as compared to V(IV)O(OPP) (1), indicating the electron-deficient nature of both the porphyrins. The oxidation state of vanadium in the synthesized complexes as +4 was confirmed by EPR spectroscopy, and these porphyrins exhibited axially compressed [Formula: see text] configuration. These porphyrins were utilized as catalysts for the oxidative bromination of thymol and other phenol derivatives with excellent conversion ([Formula: see text] 99.9%), good selectivity, and high TOF value (86869 h[Formula: see text].

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Insights into the mechanism of binding of doxorubicin and a chlorin compound with 22-mer c-Myc G quadruplex

Cited by 2 publications

References 92 publications

Synthesis, Structural and Redox Properties of Vanadyl β‐Cyanoporphyrin and its Utilization as Efficient Catalyst for Epoxidation of Olefins and Oxidative Bromination of Phenols

Synthesis, Structural and Redox Properties of Vanadyl β‐Cyanoporphyrin and its Utilization as Efficient Catalyst for Epoxidation of Olefins and Oxidative Bromination of Phenols

The synthesis of highly nonplanar oxidovanadium(IV) porphyrins as robust catalysts for oxidative bromination of phenols in aqueous medium

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