Experimental study of somatostatin analogue cyphetrylin lipophilicity

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Abstract

Background. Lipophilicity is a fundamental physicochemical property that determines the solubility and transport of a drug through biological membranes, as well as its behavior in the body. Lipophilicity also affects the ability of a drug to bind to plasma proteins and reach the corresponding receptors. The standard for drug lipophilicity experimental study is measuring the distribution between two immiscible phases – aqueous (water and buffer solutions) and hydrophobic (most often octanol).

Aim. The experimental study of somatostatin analogue cyphetrylin lipophilicity in octanol/water system distribution test.

Materials and methods. The lipophilicity of cyphetrylin, synthesized in the Laboratory of Chemical Synthesis of the N.N. Blokhin National Medical Research Center for Oncology of the Russian Ministry of Health, was studied in the octanol/water system; ethanol was used to study cyphetrylin spectral characteristics and its quantitative determination; shake flask method, UV-spectrometry.

Results. The experimental assessment of cyphetrylin lipophilicity was carried out by shake flask method in a system of mutually saturated water and octanol 1:1. Since cyphetrylin is practically insoluble in water, the concentration of the drug in the octanol phase was determined by UV-spectrometry and the concentration in water was calculated by mass balance. Lipophilicity was expressed as the decimal logarithm of the concentration of cyphetrylin in the octanol phase to its concentration in the aqueous phase (logPo/w) ratio. The experimentally determined value of logPo/w was 1.14.

Conclusion. The lipophilicity of cyphetrylin was studied experimentally by shake flask method as a parameter that determines the molecule probability to reach the biological target. The logPo/w value 1.14 in decimal logarithmic form indicates moderate lipophilicity of cyphetrylin, which exhibits antitumor activity when interacting with somatostatin receptors.

About the authors

Z. S. Shprakh

N.N. Blokhin National Medical Research Center of Oncology, Ministry of Health of Russia

Author for correspondence.
Email: z.shprakh@ronc.ru
ORCID iD: 0000-0003-3034-750X

Zoya Sergeevna Shprakh

24 Kashirskoe Shosse, Moscow 115522

Russian Federation

E. V. Ignateva

N.N. Blokhin National Medical Research Center of Oncology, Ministry of Health of Russia

ORCID iD: 0000-0002-9200-4492

Elena V. Ignateva

24 Kashirskoe Shosse, Moscow 115522

Russian Federation

M. N. Kraeva

N.N. Blokhin National Medical Research Center of Oncology, Ministry of Health of Russia

ORCID iD: 0000-0001-7845-1651

Marina N. Kraeva

24 Kashirskoe Shosse, Moscow 115522

Russian Federation

I. V. Yartseva

N.N. Blokhin National Medical Research Center of Oncology, Ministry of Health of Russia

ORCID iD: 0000-0002-8818-7812

Irina V. Yartseva

24 Kashirskoe Shosse, Moscow 115522

Russian Federation

D. V. Gusev

N.N. Blokhin National Medical Research Center of Oncology, Ministry of Health of Russia

ORCID iD: 0000-0003-0218-8265

Dmitriy V. Gusev

24 Kashirskoe Shosse, Moscow 115522

Russian Federation

M. V. Dmitrieva

N.N. Blokhin National Medical Research Center of Oncology, Ministry of Health of Russia

ORCID iD: 0000-0001-6740-5692

Maria V. Dmitrieva

24 Kashirskoe Shosse, Moscow 115522

Russian Federation

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