Research output: Contribution to journal › Article › peer-review
New crystal forms for biologically active compounds. Part 1 : Noncovalent interactions in adducts of nevirapine with XB donors. / Kryukova, Mariya A.; Sapegin, Alexander V.; Novikov, Alexander S.; Krasavin, Mikhail; Ivanov, Daniil M.
In: Crystals, Vol. 9, No. 2, 71, 02.2019.Research output: Contribution to journal › Article › peer-review
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TY - JOUR
T1 - New crystal forms for biologically active compounds. Part 1
T2 - Noncovalent interactions in adducts of nevirapine with XB donors
AU - Kryukova, Mariya A.
AU - Sapegin, Alexander V.
AU - Novikov, Alexander S.
AU - Krasavin, Mikhail
AU - Ivanov, Daniil M.
PY - 2019/2
Y1 - 2019/2
N2 - Stabilization of specific crystal polymorphs of an active pharmaceutical ingredient is crucial for preventing uncontrollable interconversion of various crystalline forms, which affects physicochemical properties as well as physiological activity. Co-crystallization with various excipients is an emerging productive way of achieving such stabilization in the solid state. In this work, we identified an opportunity for co-crystallization of antiviral drug nevirapine (NVP) with a classical XB donor, 1,2,4,5-tetrafluoro-3,6-diiodobenzene (1,4-FIB), as well as 1,3-diiodobenzene (1,3-DIB), which has been seldom employed as an XB donor to date. In the X-ray structures of NVP·1,4-FIB and NVP·1,3-DIB co-crystals, different hydrogen and halogen bonding modes were detected and further investigated via DFT calculations as well as topological analysis of the electron density distribution within the framework of the QTAIM method at the M06/DZP-DKH level of theory. Estimated energies of these supramolecular contacts vary from 0.6 to 5.7 kcal/mol.
AB - Stabilization of specific crystal polymorphs of an active pharmaceutical ingredient is crucial for preventing uncontrollable interconversion of various crystalline forms, which affects physicochemical properties as well as physiological activity. Co-crystallization with various excipients is an emerging productive way of achieving such stabilization in the solid state. In this work, we identified an opportunity for co-crystallization of antiviral drug nevirapine (NVP) with a classical XB donor, 1,2,4,5-tetrafluoro-3,6-diiodobenzene (1,4-FIB), as well as 1,3-diiodobenzene (1,3-DIB), which has been seldom employed as an XB donor to date. In the X-ray structures of NVP·1,4-FIB and NVP·1,3-DIB co-crystals, different hydrogen and halogen bonding modes were detected and further investigated via DFT calculations as well as topological analysis of the electron density distribution within the framework of the QTAIM method at the M06/DZP-DKH level of theory. Estimated energies of these supramolecular contacts vary from 0.6 to 5.7 kcal/mol.
KW - Crystal engineering
KW - DFT
KW - Halogen bonding
KW - Hydrogen bonding
KW - Nevirapine
KW - Noncovalent interactions
KW - QTAIM
KW - REVERSE-TRANSCRIPTASE
KW - COMPLEXES
KW - PHARMACEUTICAL COCRYSTALS
KW - noncovalent interactions
KW - CO-CRYSTALS
KW - SOLID-STATE
KW - hydrogen bonding
KW - ANTIRETROVIRAL NEVIRAPINE
KW - nevirapine
KW - HALOGEN-BOND
KW - DISSOLUTION
KW - INCLUSION
KW - crystal engineering
KW - halogen bonding
KW - ZETA BASIS-SETS
UR - http://www.scopus.com/inward/record.url?scp=85061744710&partnerID=8YFLogxK
UR - https://elibrary.ru/item.asp?id=38639922
UR - http://www.mendeley.com/research/new-crystal-forms-biologically-active-compounds-part-1-noncovalent-interactions-adducts-nevirapine-x
U2 - 10.3390/cryst9020071
DO - 10.3390/cryst9020071
M3 - Article
AN - SCOPUS:85061744710
VL - 9
JO - Liquid Crystals Today
JF - Liquid Crystals Today
SN - 1358-314X
IS - 2
M1 - 71
ER -
ID: 39176055